Small yachts/Sailboats

TREASURES OF THE GREEK ISLES

from $4,999.00 (USD)

Per Person

+ $32.00 taxes/fees

Aug 23, 2025
through Aug 30, 2025

More offers from Windstar Cruises

Nights: 7

Ship: Wind Spirit

Price Per Night:$714.14 (USD)
(based on double occupancy, for comparison only)

Aug 23, 2025 through Aug 30, 2025

Itinerary: Athens, Greece, Nafplio, Mykonos, Kusadasi, Patmos, Santorini, Monemvasia, Athens, Greece

Visit sun-drenched places as you sail the Greek Isles, discovering a world abounding with seaside scenery and ancient treasures. On such legendary islands as Santorini and Mykonos, views of azure sea and white-washed villages will take your breath away. On your Greek islands cruise, you may embrace the magic and mythology of ancient temples built to honor Greek gods and goddesses. Visit UNESCO World Heritage Sites such as the amazing hilltop Acropolis in Athens, the haunts of St.

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STAR COLLECTOR: MEDITERRANEAN MOMENTS & MONUMENTS

from $5,799.00 (USD)

Per Person

+ $55.00 taxes/fees

May 10, 2026
through May 26, 2026

More offers from Windstar Cruises

Nights: 16

Ship: Star Legend

Price Per Night:$362.44 (USD)
(based on double occupancy, for comparison only)

May 10, 2026 through May 26, 2026

Itinerary: Athens, Greece, Delphi, Corinth Canal, Corfu, Argostoli, Messina (Taormina), Trapani, Cagliari, Barcelona, Valencia...

This far-ranging 16-day southern Mediterranean cruise from Greece to Spain and gives you additional time to linger on overnight port stays in Seville and Lisbon. A small ship exclusive transit of the Corinth Canal grants extra moments to savor the hallowed ruins of the Oracle of Delphi. Ride mountain bikes to villages, Venetian ruins, and rural countryside during a scenic Corfu cycling tour.

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MYTHS & MARVELS OF THE AEGEAN

from $3,799.00 (USD)

Per Person

+ $20.00 taxes/fees

Oct 14, 2025
through Oct 22, 2025

More offers from Windstar Cruises

Nights: 8

Ship: Star Legend

Price Per Night:$474.88 (USD)
(based on double occupancy, for comparison only)

Oct 14, 2025 through Oct 22, 2025

Itinerary: Athens, Greece, Mykonos, Heraklion, Rhodes, Bodrum, Kusadasi, Patmos, Athens, Greece

Savor the enticing islands and historic wonders of Greece and Turkey on this roundtrip voyage from Athens. Watch the Aegean sun shift shadows on the white columns of the Parthenon, let your imagination soar at the Palace of Knossos with its legendary Minotaur and labyrinth, and experience a once-in-a-lifetime event as you dine under the stars at the ruins of Ephesus during Windstar’s exclusive and complimentary Destination Discovery event.

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STAR COLLECTOR: CULTURE & CHARMS OF ITALY & CROATIA

from $11,399.00 (USD)

Per Person

+ $91.00 taxes/fees

Sep 14, 2025
through Oct 03, 2025

More offers from Windstar Cruises

Nights: 19

Ship: Wind Surf

Price Per Night:$599.95 (USD)
(based on double occupancy, for comparison only)

Sep 14, 2025 through Oct 03, 2025

Itinerary: Venice, Rovinj, Split, Dubrovnik, Kotor, Giardini Naxos, Sorrento, Rome, Giardini Naxos, Syracuse, Italy...

Roam between the broken monoliths and columns in the Roman Forum, Western Civilization’s former epicenter. Gaze across Catania’s umber-hued, terracotta-tiled skyline to the steaming summit of Mount Etna as you sample authentic Sicilian dishes like densely textured handmade pasta topped with aromatic variations like sundried tomatoes, golden-brown dried grapes, fresh basil and minced garlic.

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ROME & PRIX DU MONDE OF MONACO

from $9,099.00 (USD)

Per Person

+ $33.00 taxes/fees

May 21, 2026
through May 28, 2026

More offers from Windstar Cruises

Nights: 7

Ship: Wind Surf

Price Per Night:$1,299.86 (USD)
(based on double occupancy, for comparison only)

May 21, 2026 through May 28, 2026

Itinerary: Rome, Bastia, Monte Carlo, St. Tropez, Portofino, Portoferraio, Rome

Surrounded by glitterati on the Wind Surf, the largest sailing yacht in the world, you'll fit right in. Enjoy our exclusive insider's experience at the legendary Prix du Monde of Monaco, the crown jewel of this exceptional itinerary. Stroll famous promenades, shop elite boutiques and bask on world-famous beaches of the Rivieras.

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STAR COLLECTOR: LOVELY LEEWARDS

from $6,299.00 (USD)

Per Person

+ $109.00 taxes/fees

Nov 23, 2024
through Dec 07, 2024

More offers from Windstar Cruises

Nights: 14

Ship: Star Pride

Price Per Night:$449.93 (USD)
(based on double occupancy, for comparison only)

Nov 23, 2024 through Dec 07, 2024

Itinerary: San Juan, St. George's, Bequia, Pigeon Island, Les Saintes, Philipsburg, St. Maarten, San Juan, St. Thomas, Philipsburg, St. Maarten, Basseterre...

Whether you’re passionate about swimming among rarely seen undersea wildlife or the intricate cultures and intertwined European histories of the Windward Islands, this 2-week cruise offers the best combinations of charm, island heritage and natural beauty. Shop unique designer apparel in St. Barts, where you’ll discover a fashionable confluence of high-end brands normally associated with places like Madison Avenue, but displayed in an ambiance that’s anything but intimidating.

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Windward Islands 7 Nights

from $1,700.00 (USD)

Per Person

+ $235.00 taxes/fees

Mar 08, 2025
through Mar 15, 2025

More offers from Star Clippers

Nights: 7

Ship: Royal Clipper

Price Per Night:$242.86 (USD)
(based on double occupancy, for comparison only)

Mar 08, 2025 through Mar 15, 2025

Itinerary: Bridgetown, Barbados, Rodney Bay, St. Lucia, Sail with Star Flyer to Cabrits, Cabrits, Dominica, Falmouth Harbour, Antigua, Basseterre, St. Kitts (morning), South Friar's Bay (beach), St. Kitts (PM), Terre de Haut, Iles des Saintes, Beach, Martinique, Bridgetown, Barbados

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Inside

$1,700.00
Cat:Category 6
242.86 per night

Outside

$1,940.00
Cat:Category 5
277.14 per night

Balcony

N/A

Suite

$3,520.00
Cat:Deluxe Suite with Veranda
502.86 per night

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Costa Rica & Panama 7 Nights

from $1,640.00 (USD)

Per Person

+ $235.00 taxes/fees

Jan 11, 2025
through Jan 18, 2025

More offers from Star Clippers

Nights: 7

Ship: Star Clipper

Price Per Night:$234.29 (USD)
(based on double occupancy, for comparison only)

Jan 11, 2025 through Jan 18, 2025

Itinerary: Puerto Caldera, Costa Rica, Quepos, Costa Rica, Golfito, Costa Rica, Coiba National Park, Panama, Marine Park Golfo de Chiriqui - Parida Island, Pan, Islas Tortugas, Costa Rica, Puerto Caldera, Costa Rica

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$1,640.00
Cat:Category 6
234.29 per night

Outside

$1,930.00
Cat:Category 5
275.71 per night

Balcony

N/A

Suite

N/A

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STAR COLLECTOR: CLASSIC CROSSING TO SPAIN & MORE

from $4,899.00 (USD)

Per Person

+ $91.00 taxes/fees

Oct 25, 2025
through Nov 18, 2025

More offers from Windstar Cruises

Nights: 24

Ship: Wind Spirit

Price Per Night:$204.13 (USD)
(based on double occupancy, for comparison only)

Oct 25, 2025 through Nov 18, 2025

Itinerary: Barcelona, Tarragona, Palma de Mallorca, Valencia, Cartagena, Málaga, Tangier, Lisbon, Bridgetown

Ideal for anyone seeking equal portions of relaxing time at sea and port visits, this transatlantic crossing features a combination of leisurely, uninterrupted sea crossing time balanced with the best ports in the Western Mediterranean. Spend time crossing the Atlantic and enjoying the romance of sailing as you make your way to your ultimate destination.

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STAR COLLECTOR: WINDWARD TREASURES: AN ANTILLES ODYSSEY

from $4,099.00 (USD)

Per Person

+ $69.00 taxes/fees

Dec 07, 2024
through Dec 21, 2024

More offers from Windstar Cruises

Nights: 14

Ship: Wind Spirit

Price Per Night:$292.79 (USD)
(based on double occupancy, for comparison only)

Dec 07, 2024 through Dec 21, 2024

Itinerary: Bridgetown, Pigeon Island, The Pitons, Castries, Kingstown, Mayreau, St. George's, Bequia, Bridgetown, Basseterre...

Indulge in exquisite white-sand delights and delicious regional cuisine during this voyage to the Lesser Antilles’ Windward Islands, a journey rich in exclusive excursions seldom experienced by others. Trek through a private nature reserve inhabited by lyrical thrushes, curious macaws, and radiant tropical birds to Mount Pimard’s summit views above Pigeon Island. Sample local St. Lucian bites and Trinidadian culinary delights during a walking food tour at Rodney Bay.

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Leeward Islands 7 Nights

from $1,640.00 (USD)

Per Person

+ $235.00 taxes/fees

Feb 08, 2025
through Feb 15, 2025

More offers from Star Clippers

Nights: 7

Ship: Star Flyer

Price Per Night:$234.29 (USD)
(based on double occupancy, for comparison only)

Feb 08, 2025 through Feb 15, 2025

Itinerary: Philipsburg, St. Maarten, River Bay, Barbuda, Sail with Royal Clipper South of Iles des Saintes, Cabrits, Dominica, Terre-de-Haut, Iles des Saintes, Deshaies, Guadeloupe, Falmouth Harbour, Antigua, Gustavia, St. Barts, Philipsburg, St. Maarten

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Inside

$1,640.00
Cat:Category 6
234.29 per night

Outside

$1,930.00
Cat:Category 5
275.71 per night

Balcony

N/A

Suite

N/A

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Royal Clipper - Windward Islands 7 Nights

from $1,790.00 (USD)

Per Person

+ $235.00 taxes/fees

Jan 24, 2026
through Jan 31, 2026

More offers from Star Clippers

Nights: 7

Ship: Royal Clipper

Price Per Night:$255.71 (USD)
(based on double occupancy, for comparison only)

Jan 24, 2026 through Jan 31, 2026

Itinerary: Bridgetown, Barbados, Rodney Bay, St. Lucia, Sail with Star Flyer to Cabrits, Cabrits, Dominica, Falmouth Harbour, Antigua, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), Terre de Haut, Iles des Saintes, Beach, Martinique, Bridgetown, Barbados

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Inside

$1,790.00
Cat:Category 6
255.71 per night

Outside

$2,040.00
Cat:Category 5
291.43 per night

Balcony

N/A

Suite

$3,880.00
Cat:Deluxe Suite with Veranda
554.29 per night

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Star Clipper - Grand Voyage: Athens to Athens 14 Nights

from $3,420.00 (USD)

Per Person

+ $550.00 taxes/fees

Jul 05, 2025
through Jul 19, 2025

More offers from Star Clippers

Nights: 14

Ship: Star Clipper

Price Per Night:$244.29 (USD)
(based on double occupancy, for comparison only)

Jul 05, 2025 through Jul 19, 2025

Itinerary: Piraeus (Port of Athens), Greece, Morning sailing through Samos Strait, Kusadasi, Turkey (Optional Tour Ephesus), Patmos, Greece, Amorgos, Greece, Mykonos, Greece, Spetses, Greece, Piraeus (Port of Athens), Greece, Rhodes, Greece, Bodrum, Turkey...

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Inside

$3,420.00
Cat:Category 6
244.29 per night

Outside

$3,700.00
Cat:Category 5
264.29 per night

Balcony

N/A

Suite

N/A

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STAR COLLECTOR: WINDWARD ISLANDS & SPANISH NEW WORLD

from $4,999.00 (USD)

Per Person

+ $67.00 taxes/fees

Jan 25, 2026
through Feb 09, 2026

More offers from Windstar Cruises

Nights: 15

Ship: Wind Surf

Price Per Night:$333.27 (USD)
(based on double occupancy, for comparison only)

Jan 25, 2026 through Feb 09, 2026

Itinerary: Bridgetown, Man-O-War Bay, Mayreau, Soufriere, Kralendijk, Willemstad, Oranjestad, Santa Marta, Cartagena, Bocas del Toro...

Your journey begins in Bridgetown, a city with Jolly Ole England flavor and two UNESCO sites before an opportunity to swim with sea turtles in Tobago Cays Marine Park. Save your appetite for the exclusive Signature Beach Party on Mayreau and feel the heart and soul of St. Lucia in Soufriere as you wander the vendor-filled streets. Savor a day at sea before bird watching for flamingos and parrots in Bonaire.

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CLASSIC ITALY & DALMATIAN COAST

from $4,199.00 (USD)

Per Person

+ $50.00 taxes/fees

Oct 15, 2026
through Oct 25, 2026

More offers from Windstar Cruises

Nights: 10

Ship: Wind Surf

Price Per Night:$419.90 (USD)
(based on double occupancy, for comparison only)

Oct 15, 2026 through Oct 25, 2026

Itinerary: Venice, Rovinj, Split, Dubrovnik, Kotor, Giardini Naxos, Sorrento, Rome

Explore the shores of Italy, Croatia and Montenegro, discovering the charm of Venice, the magnificence of Rome, and the vast beauty of the Dalmatian Coast. Wander down the ancient cobblestone streets of Taormina, travel up the sparking fjord to Kotor and bask in the allure of small ship cruising as your small ship anchors in the heart of Old Town Dubrovnik while larger ships only pass by.

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STAR COLLECTOR: TWICE THE TAHITI

from $6,699.00 (USD)

Per Person

+ $34.00 taxes/fees

Feb 05, 2026
through Feb 23, 2026

More offers from Windstar Cruises

Nights: 18

Ship: Star Breeze

Price Per Night:$372.17 (USD)
(based on double occupancy, for comparison only)

Feb 05, 2026 through Feb 23, 2026

Itinerary: Papeete, Moorea, Raiatea, Motu Mahaea (Tahaa), Bora Bora, Huahine, Papeete, Fakarava, Rangiroa, Raiatea...

Ideal for anyone who can’t get enough of Tahiti, this unique cruise features twice the visits to ports, so you have double the opportunities to see and experience what you love, and you can do all the things you passed up during your previous stop. It’s a top tropical pick among romantic couples, active divers and anyone in love with everything under the sun among countless blue Pacific lagoons.

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BEACH FUN & SUN: A REMOTE CARIBBEAN GETAWAY

from $3,199.00 (USD)

Per Person

+ $68.00 taxes/fees

Jan 11, 2025
through Jan 18, 2025

More offers from Windstar Cruises

Nights: 7

Ship: Wind Surf

Price Per Night:$457.00 (USD)
(based on double occupancy, for comparison only)

Jan 11, 2025 through Jan 18, 2025

Itinerary: Philipsburg, St. Maarten, Falmouth Harbour, Gustavia, Jost Van Dyke, Great Harbour, Soper's Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Road Bay, Philipsburg, St. Maarten

Bask on remote beaches resplendent in natural beauty during this relaxing, unrushed, and uncrowded 7-day getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke.

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STAR COLLECTOR: GREEK MYTHS & RIVIERA MAGIC

from $9,699.00 (USD)

Per Person

+ $76.00 taxes/fees

Sep 11, 2026
through Oct 03, 2026

More offers from Windstar Cruises

Nights: 22

Ship: Star Legend

Price Per Night:$440.86 (USD)
(based on double occupancy, for comparison only)

Sep 11, 2026 through Oct 03, 2026

Itinerary: Barcelona, Palamos, Sanary-sur-Mer, Monte Carlo, Cannes, Portofino, Portoferraio, Porto Ercole, Rome, Sorrento...

Immerse yourself in the tiniest details of ancient Mediterranean culture on a 22-night cruise of Greece, the French and Italian Riveiras. Swim the serene blue waters of Spain’s Costa Brava near Palamós, exploring an 11th century fortified castle that protected medieval villagers against pirates. Behold the natural beauty of the French Riviera from the sunbaked beaches of Sanary-sur-Mer to the inimitable limestone cliffs of Cassis.

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STAR COLLECTOR: WINTER MEDITERRANEAN ADVENTURE

from $7,099.00 (USD)

Per Person

+ $185.00 taxes/fees

Jan 19, 2026
through Feb 12, 2026

More offers from Windstar Cruises

Nights: 24

Ship: Star Legend

Price Per Night:$295.79 (USD)
(based on double occupancy, for comparison only)

Jan 19, 2026 through Feb 12, 2026

Itinerary: Barcelona, Valencia, Cartagena, Gibraltar, Málaga, Palma de Mallorca, Barcelona, Nice , Genoa, Italy, Livorno...

Embark on a quiet-season adventure along the Mediterranean's southern shores as you sail through the Adriatic to Gibraltar. This 24-day cruise sails between Venice’s Grand Canal to Barcelona's hallmark baroque and gothic architecture. Linger late during overnight port stays in Venice, Florence, Dubrovnik, Malaga, and Barcelona . Take in the beauty of Croatia in the winter and enjoy stunning landscapes dusted with snow, seasonal markets, and authentic and tranquil old towns.

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STAR COLLECTOR: ITALIAN TRIO

from $5,399.00 (USD)

Per Person

+ $95.00 taxes/fees

Oct 26, 2025
through Nov 10, 2025

More offers from Windstar Cruises

Nights: 15

Ship: Wind Surf

Price Per Night:$359.93 (USD)
(based on double occupancy, for comparison only)

Oct 26, 2025 through Nov 10, 2025

Itinerary: Venice, Rovinj, Split, Dubrovnik, Kotor, Giardini Naxos, Sorrento, Rome, Portoferraio, Portofino...

Discover the culture, history and cuisine on both sides of the Italian peninsula during this 15-day cruise of the Adriatic, Ionian, Ligurian and Tyrrhenian seas. This back-to-back cruise is ideal for optimizing shore excursion time in Italy, Croatia, Montenegro, Monaco, France, and Spain.

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Star Flyer - Grand Voyage: Nice to Las Palmas 16 Nights

from $3,880.00 (USD)

Per Person

+ $620.00 taxes/fees

Oct 22, 2025
through Nov 07, 2025

More offers from Star Clippers

Nights: 16

Ship: Star Flyer

Price Per Night:$242.50 (USD)
(based on double occupancy, for comparison only)

Oct 22, 2025 through Nov 07, 2025

Itinerary: Nice, France, Mahon, Menorca - Balearic Islands, Spain, Palma de Mallorca, Mallorca - Balearic Islands, Sp, Ibiza - Balearic Islands, Spain, Cartagena, Spain, Motril, Spain, Malaga, Spain, Gibraltar, British Overseas Territory, Tangier, Morocco, Cadiz, Spain...

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Inside

$3,880.00
Cat:Category 6
242.50 per night

Outside

$4,210.00
Cat:Category 5
263.13 per night

Balcony

N/A

Suite

N/A

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STAR COLLECTOR: WINDWARD ISLANDS & SPANISH NEW WORLD

from $4,399.00 (USD)

Per Person

+ $386.00 taxes/fees

Dec 14, 2024
through Dec 28, 2024

More offers from Windstar Cruises

Nights: 14

Ship: Star Pride

Price Per Night:$314.21 (USD)
(based on double occupancy, for comparison only)

Dec 14, 2024 through Dec 28, 2024

Itinerary: Bridgetown, Man-O-War Bay, Mayreau, Soufriere, St. George's, Willemstad, Oranjestad, Cartagena, San Blas, Bocas del Toro...

Your journey begins in Bridgetown, a city with Jolly Ole England flavor and two UNESCO sites before an opportunity to swim with sea turtles in Tobago Cays Marine Park. Save your appetite for the exclusive Signature Beach Party on Mayreau and feel the heart and soul of St. Lucia in Soufriere as you wander the vendor-filled streets. Savor a day at sea before bird watching for flamingos and parrots in Bonaire.

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TREASURES OF SOUTHERN SPAIN & MOROCCO

from $4,439.00 (USD)

Per Person

+ $65.00 taxes/fees

Apr 10, 2025
through Apr 20, 2025

More offers from Windstar Cruises

Nights: 10

Ship: Wind Star

Price Per Night:$443.90 (USD)
(based on double occupancy, for comparison only)

Apr 10, 2025 through Apr 20, 2025

Itinerary: Lisbon, Tangier, Málaga, Cartagena, Valencia, Palma de Mallorca, Tarragona, Barcelona

Dazzle your senses with Spanish treasure - golden Costa del Sol beaches, Picasso’s genius in Málaga, the Roman ruins of Cartagena and Tarragona. Sit at a café in Tangier’s medina sipping mint tea and watching old men play backgammon. Nestle up to the other exclusive yachts in Ibiza’s harbor with some 80 blissful beaches calling your name. Celebrate a dream come true.

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STAR COLLECTOR: CLASSIC CROSSING TO SPAIN & MORE

from $6,199.00 (USD)

Per Person

+ $91.00 taxes/fees

Mar 26, 2025
through Apr 20, 2025

More offers from Windstar Cruises

Nights: 25

Ship: Wind Star

Price Per Night:$247.96 (USD)
(based on double occupancy, for comparison only)

Mar 26, 2025 through Apr 20, 2025

Itinerary: Bridgetown, Lisbon, Tangier, Málaga, Cartagena, Valencia, Palma de Mallorca, Tarragona, Barcelona

Ideal for anyone seeking equal portions of relaxing time at sea and port visits, this transatlantic crossing features a combination of leisurely, uninterrupted sea crossing time balanced with the best ports in the Western Mediterranean. Spend time crossing the Atlantic and enjoying the romance of sailing as you make your way to your ultimate destination.

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Star Flyer - Treasure Islands 7 Nights

from $1,730.00 (USD)

Per Person

+ $235.00 taxes/fees

Feb 14, 2026
through Feb 21, 2026

More offers from Star Clippers

Nights: 7

Ship: Star Flyer

Price Per Night:$247.14 (USD)
(based on double occupancy, for comparison only)

Feb 14, 2026 through Feb 21, 2026

Itinerary: Philipsburg, St. Maarten, Road Bay, Anguilla, White Bay, Jost van Dyke (B.V.I.), Sopers Hole - Tortola, British Virgin Islands (BVI, Sailing Sir Francis Drake Channel, The Bight - Norman Island, British Virgin Islands, Spanish Town - Virgin Gorda, British Virgin Island, Beach, Captain's Best, British Virgin Islands (B.V, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon)...

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$1,730.00
Cat:Category 6
247.14 per night

Outside

$2,030.00
Cat:Category 5
290.00 per night

Balcony

N/A

Suite

N/A

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STAR COLLECTOR: HEARTY PORTS & RUM PUNCHES - A TRANSATLANTIC CROSSING

from $3,599.00 (USD)

Per Person

+ $81.00 taxes/fees

Nov 18, 2025
through Dec 07, 2025

More offers from Windstar Cruises

Nights: 19

Ship: Wind Surf

Price Per Night:$189.42 (USD)
(based on double occupancy, for comparison only)

Nov 18, 2025 through Dec 07, 2025

Itinerary: Lisbon, St. John's, Philipsburg, St. Maarten, Jost Van Dyke, Great Harbour, Soper's Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St. Maarten

Caribbean beaches, vibrant tropical fish, and savory West Indies cuisine during this 19-day transatlantic crossing. Relax, unwind and refocus with back-to-back spa days throughout your ocean crossing and dine on award-winning meals paired with the company of your new Windstar family. Relive history while sailing aboard a former America's Cup competition sailboat or cook up delicious French meals with a certified chef in Grand Case outside Philipsburg, St. Maarten.

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TREASURES OF SOUTHERN SPAIN & MOROCCO

from $3,499.00 (USD)

Per Person

+ $65.00 taxes/fees

Nov 02, 2025
through Nov 12, 2025

More offers from Windstar Cruises

Nights: 10

Ship: Wind Star

Price Per Night:$349.90 (USD)
(based on double occupancy, for comparison only)

Nov 02, 2025 through Nov 12, 2025

Itinerary: Barcelona, Tarragona, Palma de Mallorca, Valencia, Cartagena, Málaga, Tangier, Lisbon

Dazzle your senses with Spanish treasure - golden Costa del Sol beaches, Picasso’s genius in Málaga, the Roman ruins of Cartagena and Tarragona. Sit at a café in Tangier’s medina sipping mint tea and watching old men play backgammon. Nestle up to the other exclusive yachts in Ibiza’s harbor with some 80 blissful beaches calling your name. Celebrate a dream come true.

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STAR COLLECTOR: TWICE THE TAHITI

from $6,099.00 (USD)

Per Person

+ $34.00 taxes/fees

Dec 11, 2025
through Dec 29, 2025

More offers from Windstar Cruises

Nights: 18

Ship: Star Breeze

Price Per Night:$338.83 (USD)
(based on double occupancy, for comparison only)

Dec 11, 2025 through Dec 29, 2025

Itinerary: Papeete, Moorea, Raiatea, Motu Mahaea (Tahaa), Bora Bora, Huahine, Papeete, Fakarava, Rangiroa, Raiatea...

Ideal for anyone who can’t get enough of Tahiti, this unique cruise features twice the visits to ports, so you have double the opportunities to see and experience what you love, and you can do all the things you passed up during your previous stop. It’s a top tropical pick among romantic couples, active divers and anyone in love with everything under the sun among countless blue Pacific lagoons.

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Royal Clipper - Las Palmas to Malaga 6 Nights

from $1,880.00 (USD)

Per Person

+ $240.00 taxes/fees

May 12, 2025
through May 18, 2025

More offers from Star Clippers

Nights: 6

Ship: Royal Clipper

Price Per Night:$313.33 (USD)
(based on double occupancy, for comparison only)

May 12, 2025 through May 18, 2025

Itinerary: Las Palmas, Gran Canaria - Canary Islands, Spain, Puerto del Rosario, Fuertaventura - Canary Isl. -, Safi, Morocco, Casablanca, Morocco, Gibraltar, British Overseas Territory, Malaga, Spain

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Inside

$1,880.00
Cat:Category 6
313.33 per night

Outside

$1,980.00
Cat:Category 5
330.00 per night

Balcony

N/A

Suite

$3,720.00
Cat:Deluxe Suite with Veranda
620.00 per night

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PORTUGUESE PASSAGES & SPANISH SHORELINES CRUISE TOUR

from $5,799.00 (USD)

Per Person

+ $62.00 taxes/fees

Jul 31, 2025
through Aug 08, 2025

More offers from Windstar Cruises

Nights: 8

Ship: Wind Surf

Price Per Night:$724.88 (USD)
(based on double occupancy, for comparison only)

Jul 31, 2025 through Aug 08, 2025

Itinerary: Lisbon, Portugal, Lisbon, Cádiz, Gibraltar, Málaga, Almeria, Spain, Cartagena, Palma de Mallorca, Barcelona

Combine a culturally immersive inland journey throughout Portugal with a scenic and insightful tracing of Spain’s iconic coastlines during this remarkable 12-day combination cruise and land tour. Inhale intermingled aromas of seafood and spicy bean soup on Porto’s glowing twilight streets as melancholic fado lyrics and guitarra strings reverberate across stone walls from a more modest skyline. Light a white candle amid prayerful pilgrims in the silence of Fátima’s most sacred sites.

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THE COLORFUL CANARY ISLANDS

from $2,999.00 (USD)

Per Person

+ $42.00 taxes/fees

Nov 12, 2025
through Nov 20, 2025

More offers from Windstar Cruises

Nights: 8

Ship: Wind Star

Price Per Night:$374.88 (USD)
(based on double occupancy, for comparison only)

Nov 12, 2025 through Nov 20, 2025

Itinerary: Lisbon, Funchal, San Sebastian, Santa Cruz de Palma, Las Palmas, Santa Cruz de Tenerife

Volcanoes have left their mark everywhere here – on snow-capped Mount Teide, on black sand beaches, in rich soils and natural sea pools – yet each island is unique. Palms, pines, vineyards, and banana plantations each offer their own shade of green. On some islands you’ll see terraced farms clinging to valley walls. On others, trails trace the cliffs and reward hikers with breathtaking ocean views. And there’s always something new to do.

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STAR COLLECTOR: LEEWARD & WINDWARD CARIBBEAN HAVENS

from $4,099.00 (USD)

Per Person

+ $48.00 taxes/fees

Jan 04, 2026
through Jan 18, 2026

More offers from Windstar Cruises

Nights: 14

Ship: Wind Surf

Price Per Night:$292.79 (USD)
(based on double occupancy, for comparison only)

Jan 04, 2026 through Jan 18, 2026

Itinerary: Philipsburg, St. Maarten, Falmouth Harbour, Road Bay, Jost Van Dyke, Great Harbour, Soper's Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St. Maarten, Basseterre...

Little ports, remote reaches and sincere island pleasures exclusive to small-ship cruising beckon during this two-week exploration of the Caribbean’s Windward and Leeward Islands. Take the wheel of a 4x4 buggy and follow dirt roads along the rural outskirts of Falmouth Harbour on Antigua. Sail from Gustavia to remote Colombier Bay and swim or sunbathe among anchored mega yachts prior to elegant snacks and cocktails.

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STAR COLLECTOR: CRUISING ON THE RIVIERAS

from $6,099.00 (USD)

Per Person

+ $85.00 taxes/fees

May 28, 2026
through Jun 14, 2026

More offers from Windstar Cruises

Nights: 17

Ship: Wind Surf

Price Per Night:$358.76 (USD)
(based on double occupancy, for comparison only)

May 28, 2026 through Jun 14, 2026

Itinerary: Rome, Syracuse, Italy, Gozo, Valletta, Porto Empedocle, Trapani, Lipari, Sorrento, Amalfi, Rome...

Indulge in unhurried pleasures among steep coastal cliffs, tiny vineyards and romantic villages throughout the Rivieras and Western Italy during this 17-day, autumn cruise. During the fall winemakers are racking fresh wine into barrels, and new olive oils are sampled for the first time.

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OCEAN CROSSINGS + PONTA DELGADA, AZORES

from $2,499.00 (USD)

Per Person

+ $27.00 taxes/fees

Mar 29, 2025
through Apr 12, 2025

More offers from Windstar Cruises

Nights: 14

Ship: Wind Surf

Price Per Night:$178.50 (USD)
(based on double occupancy, for comparison only)

Mar 29, 2025 through Apr 12, 2025

Itinerary: Philipsburg, St. Maarten, Ponta Delgada, Lisbon

This is a place where dreams really do come true. The place where nothing comes between you and your fondest wishes. Where no schedules intrude, where day-to-day annoyances can’t reach you, where every moment of every hour of every day is yours alone. This is your place – at sea under an open sky – the one place in which you truly can get away from it all. Simply step on board and we’ll take it from there. Meals so delicious they might be sinful are served when, where, and any way you choose.

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WINDWARD ISLANDS SURF & SUNSETS

from $4,599.00 (USD)

Per Person

+ $40.00 taxes/fees

Nov 09, 2024
through Nov 16, 2024

More offers from Windstar Cruises

Nights: 7

Ship: Star Pride

Price Per Night:$657.00 (USD)
(based on double occupancy, for comparison only)

Nov 09, 2024 through Nov 16, 2024

Itinerary: San Juan, St. George's, Bequia, Pigeon Island, Les Saintes, Philipsburg, St. Maarten, San Juan

Revel in seven days of surf, sand and sunsets during this leisurely cruise up and down the Caribbean’s Windward Islands. It’s a perfect vacation getaway for anyone craving a quick escape from life’s everyday obligations. Clip into a zipline and hang on as moss-covered limbs and colorful wild birds rush by your head as you glide through St. Lucia’s rainforest canopy.

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Star Flyer - Treasure Islands 7 Nights

from $1,730.00 (USD)

Per Person

+ $235.00 taxes/fees

Mar 14, 2026
through Mar 21, 2026

More offers from Star Clippers

Nights: 7

Ship: Star Flyer

Price Per Night:$247.14 (USD)
(based on double occupancy, for comparison only)

Mar 14, 2026 through Mar 21, 2026

Itinerary: Philipsburg, St. Maarten, Road Bay, Anguilla, White Bay, Jost van Dyke (B.V.I.), Sopers Hole - Tortola, British Virgin Islands (BVI, Sailing Sir Francis Drake Channel, The Bight - Norman Island, British Virgin Islands, Spanish Town - Virgin Gorda, British Virgin Island, Beach, Captain's Best, British Virgin Islands (B.V, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon)...

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Inside

$1,730.00
Cat:Category 6
247.14 per night

Outside

$2,030.00
Cat:Category 5
290.00 per night

Balcony

N/A

Suite

N/A

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OCEAN CROSSINGS

from $2,499.00 (USD)

Per Person

+ $26.00 taxes/fees

Nov 13, 2024
through Nov 27, 2024

More offers from Windstar Cruises

Nights: 14

Ship: Wind Spirit

Price Per Night:$178.50 (USD)
(based on double occupancy, for comparison only)

Nov 13, 2024 through Nov 27, 2024

Itinerary: Lisbon, Bridgetown

This is a place where dreams really do come true. The place where nothing comes between you and your fondest wishes. Where no schedules intrude, where day-to-day annoyances can’t reach you, where every moment of every hour of every day is yours alone. This is your place – at sea under an open sky – the one place in which you truly can get away from it all. Simply step on board and we’ll take it from there. Meals so delicious they might be sinful are served when, where, and any way you choose.

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COSTA RICA & PANAMA CANAL

from $3,199.00 (USD)

Per Person

+ $370.00 taxes/fees

Dec 07, 2024
through Dec 14, 2024

More offers from Windstar Cruises

Nights: 7

Ship: Wind Star

Price Per Night:$457.00 (USD)
(based on double occupancy, for comparison only)

Dec 07, 2024 through Dec 14, 2024

Itinerary: Puerto Caldera, Quepos, Golfo Dulce, Isla Parida, Balboa / Fuerte Amador, Panama Canal, Colón

Come find the natural and man-made wonders combined on this exotic Costa Rican and Panama Canal cruise full of bucket list places and activities. Learn about the area from a local Naturalist on board, then take a Zodiac ashore and find rare experiences for yourself. Hike through Manuel Antonio National Park in search of its lovely beaches and abundant animal life.

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STAR COLLECTOR: GREEK BEACHES, ITALIAN ISLES & IBERIAN COASTLINES

from $8,999.00 (USD)

Per Person

+ $83.00 taxes/fees

May 10, 2026
through Jun 03, 2026

More offers from Windstar Cruises

Nights: 24

Ship: Star Legend

Price Per Night:$374.96 (USD)
(based on double occupancy, for comparison only)

May 10, 2026 through Jun 03, 2026

Itinerary: Athens, Greece, Delphi, Corinth Canal, Corfu, Argostoli, Messina (Taormina), Trapani, Cagliari, Barcelona, Valencia...

Delight in an exclusive Mediterranean adventure whisking you from the islands of Greece to the distinctive Sicilian and Sardinian regions of Italy, to southwest Europe’s Iberian Peninsula and its inimitable blend of Spanish, Portuguese and French cultures. Marvel at the towering-rock confines of the Corinth Canal before visiting the ruins of Delphi, a UNESCO World Heritage Site and once among the world’s most important religious centers.

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DREAMS OF TAHITI

from $2,699.00 (USD)

Per Person

+ $16.00 taxes/fees

Mar 05, 2026
through Mar 12, 2026

More offers from Windstar Cruises

Nights: 7

Ship: Star Breeze

Price Per Night:$385.57 (USD)
(based on double occupancy, for comparison only)

Mar 05, 2026 through Mar 12, 2026

Itinerary: Papeete, Moorea, Raiatea, Motu Mahaea (Tahaa), Bora Bora, Huahine, Papeete

A graceful yacht is the perfect way to experience the true wonder of Tahiti. We’ll let the trade winds take us to visit one legendary island after another, with plenty of casual time to swim and snorkel in crystal-clear lagoons, meander through lush rainforests, and experience the fascinating Polynesian culture from tikis to tiare flowers.

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WINDWARD WAYS & TOBAGO CAYS

from $2,799.00 (USD)

Per Person

+ $25.00 taxes/fees

Jan 25, 2026
through Feb 01, 2026

More offers from Windstar Cruises

Nights: 7

Ship: Wind Surf

Price Per Night:$399.86 (USD)
(based on double occupancy, for comparison only)

Jan 25, 2026 through Feb 01, 2026

Itinerary: Bridgetown, Man-O-War Bay, Mayreau, Soufriere, Kralendijk, Willemstad, Oranjestad

Those who love watersports, snorkeling and diving will be on Cloud 9 on this cruise through the Windward and ABC islands. Swim with vibrant fish and friendly sea turtles as you visit ports in Tobago Cays Marine Park, in Bonaire National Marine Park, and in the proposed Speyside Marine Protected Area. Paddleboard right from the Watersports Platform as we visit smaller ports and less-visited bays away from the crowds.

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WINDWARD WAYS & TOBAGO CAYS

from $3,599.00 (USD)

Per Person

+ $21.00 taxes/fees

Jan 11, 2025
through Jan 18, 2025

More offers from Windstar Cruises

Nights: 7

Ship: Star Pride

Price Per Night:$514.14 (USD)
(based on double occupancy, for comparison only)

Jan 11, 2025 through Jan 18, 2025

Itinerary: Bridgetown, Man-O-War Bay, Mayreau, Soufriere, Willemstad, Kralendijk, Oranjestad

Those who love watersports, snorkeling and diving will be on Cloud 9 on this cruise through the Windward and ABC islands. Swim with vibrant fish and friendly sea turtles as you visit ports in Tobago Cays Marine Park, in Bonaire National Marine Park, and in the proposed Speyside Marine Protected Area. Paddleboard right from the Watersports Platform as we visit smaller ports and less-visited bays away from the crowds.

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STAR COLLECTOR: WINTER RHAPSODY IN ITALY AND CROATIA

from $8,099.00 (USD)

Per Person

+ $104.00 taxes/fees

Mar 18, 2025
through Apr 03, 2025

More offers from Windstar Cruises

Nights: 16

Ship: Star Legend

Price Per Night:$506.19 (USD)
(based on double occupancy, for comparison only)

Mar 18, 2025 through Apr 03, 2025

Itinerary: Rome, Naples, Messina (Taormina), Dubrovnik, Zadar, Venice, Koper, Slovenia, Zadar, Dubrovnik, Kotor...

Discover Italy, the Adriatic and Greece from a new perspective during this 16-day winter cruise. Wander the winding medieval alleyways of Old Towns in Dubrovnik, Zadar, Koper and Kotor, where the stone pathways are worn smooth as glass by centuries of use.

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Star Flyer - Treasure Islands 7 Nights

from $1,730.00 (USD)

Per Person

+ $235.00 taxes/fees

Nov 22, 2025
through Nov 29, 2025

More offers from Star Clippers

Nights: 7

Ship: Star Flyer

Price Per Night:$247.14 (USD)
(based on double occupancy, for comparison only)

Nov 22, 2025 through Nov 29, 2025

Itinerary: Philipsburg, St. Maarten, Road Bay, Anguilla, White Bay, Jost van Dyke (B.V.I.), Sopers Hole - Tortola, British Virgin Islands (BVI, Sailing Sir Francis Drake Channel, The Bight - Norman Island, British Virgin Islands, Spanish Town - Virgin Gorda, British Virgin Island, Beach, Captain's Best, British Virgin Islands (B.V, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon)...

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Inside

$1,730.00
Cat:Category 6
247.14 per night

Outside

$2,030.00
Cat:Category 5
290.00 per night

Balcony

N/A

Suite

N/A

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Star Flyer - Italy, Montenegro, Croatia 11 Nights

from $3,030.00 (USD)

Per Person

+ $420.00 taxes/fees

Jul 03, 2025
through Jul 14, 2025

More offers from Star Clippers

Nights: 11

Ship: Star Flyer

Price Per Night:$275.45 (USD)
(based on double occupancy, for comparison only)

Jul 03, 2025 through Jul 14, 2025

Itinerary: Venice, Italy, Mali Losinj, Croatia, Hvar, Croatia, Dubrovnik, Croatia, Kotor, Montenegro, Otranto, Italy, Taormina - Sicly, Italy, Lipari - Aeolian Islands, Italy, Amalfi, Italy, Ponza - Pontine Islands, Italy...

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$3,030.00
Cat:Category 6
275.45 per night

Outside

$3,320.00
Cat:Category 5
301.82 per night

Balcony

N/A

Suite

N/A

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Star Clipper - Sicily & Greece 8 Nights

from $2,280.00 (USD)

Per Person

+ $310.00 taxes/fees

Oct 18, 2025
through Oct 26, 2025

More offers from Star Clippers

Nights: 8

Ship: Star Clipper

Price Per Night:$285.00 (USD)
(based on double occupancy, for comparison only)

Oct 18, 2025 through Oct 26, 2025

Itinerary: Piraeus (Port of Athens), Greece, Nafplio, Greece, Monemvasia, Greece, Pilos, Greece, Taormina - Sicily, Italy, Syracuse - Sicily, Italy, Gozo, Malta, Valletta, Malta

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$2,280.00
Cat:Category 6
285.00 per night

Outside

$2,490.00
Cat:Category 5
311.25 per night

Balcony

N/A

Suite

N/A

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Royal Clipper - Barbados to Panama 14 Nights

from $3,830.00 (USD)

Per Person

+ $470.00 taxes/fees

Nov 01, 2025
through Nov 15, 2025

More offers from Star Clippers

Nights: 14

Ship: Royal Clipper

Price Per Night:$273.57 (USD)
(based on double occupancy, for comparison only)

Nov 01, 2025 through Nov 15, 2025

Itinerary: Bridgetown, Barbados, Soufriere Bay, St. Lucia, Tobago Cays, Grenadines, St. George's, Grenada, Kralendijk, Bonaire, Willemstad, Curacao, Oranjestad, Aruba, Santa Marta, Colombia, Cartagena de Indias, Colombia, San Blas Archipelago, Panama...

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$3,830.00
Cat:Category 6
273.57 per night

Outside

$4,440.00
Cat:Category 5
317.14 per night

Balcony

N/A

Suite

$8,230.00
Cat:Deluxe Suite with Veranda
587.86 per night

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Leeward Islands 7 Nights

from $1,640.00 (USD)

Per Person

+ $235.00 taxes/fees

Mar 08, 2025
through Mar 15, 2025

More offers from Star Clippers

Nights: 7

Ship: Star Flyer

Price Per Night:$234.29 (USD)
(based on double occupancy, for comparison only)

Mar 08, 2025 through Mar 15, 2025

Itinerary: Philipsburg, St. Maarten, River Bay, Barbuda, Sail with Royal Clipper South of Iles des Saintes, Cabrits, Dominica, Terre-de-Haut, Iles des Saintes, Deshaies, Guadeloupe, Falmouth Harbour, Antigua, Gustavia, St. Barts, Philipsburg, St. Maarten

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$1,640.00
Cat:Category 6
234.29 per night

Outside

$1,930.00
Cat:Category 5
275.71 per night

Balcony

N/A

Suite

N/A

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STAR COLLECTOR: ITALIAN TRIO

from $5,399.00 (USD)

Per Person

+ $86.00 taxes/fees

Oct 15, 2026
through Oct 30, 2026

More offers from Windstar Cruises

Nights: 15

Ship: Wind Surf

Price Per Night:$359.93 (USD)
(based on double occupancy, for comparison only)

Oct 15, 2026 through Oct 30, 2026

Itinerary: Venice, Rovinj, Split, Dubrovnik, Kotor, Giardini Naxos, Sorrento, Rome, Portofino, Monte Carlo...

Discover the culture, history and cuisine on both sides of the Italian peninsula during this 15-day cruise of the Adriatic, Ionian, Ligurian and Tyrrhenian seas. This back-to-back cruise is ideal for optimizing shore excursion time in Italy, Croatia, Montenegro, Monaco, France, and Spain.

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STAR COLLECTOR: ROMANCE OF THE WEST MED

from $6,099.00 (USD)

Per Person

+ $99.00 taxes/fees

Apr 07, 2026
through Apr 24, 2026

More offers from Windstar Cruises

Nights: 17

Ship: Wind Star

Price Per Night:$358.76 (USD)
(based on double occupancy, for comparison only)

Apr 07, 2026 through Apr 24, 2026

Itinerary: Lisbon, Tangier, Málaga, Cartagena, Valencia, Palma de Mallorca, Tarragona, Barcelona, Palma de Mallorca, Mahon...

Sip red wines and savor tapas, pastas, rich cheeses and aged hams throughout Portugal, Spain, France and Italy. You’ll spend 15 memorable days exploring tiny rustic villages, historic fortified ports and contemporary architecture in Ibiza, Barcelona, Palma, Mahon, Portoferraio, Rome and more. Kayak along the stunning coastline of Mallorca and bike from Portoferraio to Enfola, Elba in Italy.

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Small yachts/Sailboats (50 offers included)