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280 Results

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A traditional windmill with a pointed roof and wooden blades on a hill overlooking the white buildings of Patmos, Greece, with the historic Monastery of Saint John in the distance.
FREE All-Inclusive Upgrade + up to $400 Onboard Credit*
Windstar

7-night Treasures Of The Greek Isles Cruise From Piraeus (Athens), Greece

Athens (Piraeus)
Delos
Mykonos
Kusadasi (Ephesus)
Patmos
+3 more

Aboard

Wind Spirit

From

Piraeus (Athens), Greece

1 Sailing

Oct 8, 2026

1 Sailing

Oct 8, 2026

Published prices from

$5,363

per person*

taxes & fees included

A breathtaking landscape of Raiatea Island, French Polynesia, showcasing lush, green volcanic mountains covered in tropical foliage descending into a tranquil turquoise lagoon.
FREE All-Inclusive Upgrade + up to $400 Onboard Credit*
Windstar

10-night Overwater Bungalow & Tahitian Paradises Cruise/Land Package From Papeete, Tahiti, French Polynesia

Papeete
Moorea
Raiatea
Taha'a
Bora Bora

Aboard

Star Breeze

From

Papeete, Tahiti, French Polynesia

6 Sailings

Oct 8 - Dec 10, 2026

6 Sailings

Oct 8 - Dec 10, 2026

A beautiful panoramic view of the island of Taha'a, French Polynesia, with lush green hills and a large, puffy white cloud formation reflecting in the calm, deep blue water under a clear blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

14-night Star Collector: Extended Tahiti & Tuamotu Adventures Cruise From Papeete, Tahiti, French Polynesia

Papeete
Moorea
Raiatea
Taha'a
Bora Bora
+4 more

Aboard

Star Breeze

From

Papeete, Tahiti, French Polynesia

8 Sailings

Oct 8, 2026 - Oct 28, 2027

8 Sailings

Oct 8, 2026 - Oct 28, 2027

Published prices from

$4,964

per person*

taxes & fees included

Overwater bungalows in Tahiti, French Polynesia.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

7-night Dreams Of Tahiti Cruise From Papeete, Tahiti, French Polynesia

Papeete
Moorea
Raiatea
Motu Mahaea
Bora Bora

Aboard

Star Breeze

From

Papeete, Tahiti, French Polynesia

36 Sailings

Oct 8, 2026 - Dec 28, 2028

36 Sailings

Oct 8, 2026 - Dec 28, 2028

Published prices from

$2,606

per person*

taxes & fees included

A breathtaking view of the unique, rocky coastline of St. George's, Bermuda, with a tall rock formation rising from the shallow, clear turquoise waters.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

19-night Star Collector: Fall Leaves & Caribbean Breezes Cruise From Montreal, Quebec

Montreal
Quebec City
Gaspe
Cap-aux-Meules
Sydney (Nova Scotia)
+8 more

Aboard

Star Pride

From

Montreal, Quebec

1 Sailing

Oct 9, 2026

1 Sailing

Oct 9, 2026

Published prices from

$6,991

per person*

taxes & fees included

A historic castle fortress illuminated at night, located on a small island surrounded by calm water under a deep blue evening sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

11-night Southeast Canadian Explorations Cruise From Montreal, Quebec

Montreal
Quebec City
Gaspe
Cap-aux-Meules
Sydney (Nova Scotia)
+5 more

Aboard

Star Pride

From

Montreal, Quebec

3 Sailings

Oct 9, 2026 - Oct 9, 2028

3 Sailings

Oct 9, 2026 - Oct 9, 2028

Published prices from

$4,427

per person*

taxes & fees included

Blue Mosque and historic Istanbul skyline with Bosphorus Strait.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

11-night Istanbul Icons & Aegean Artifacts Cruise/Land Package From Piraeus (Athens), Greece

Athens (Piraeus)
Corinth Canal
Delphi
Santorini
Bodrum
+5 more

Aboard

Star Legend

From

Piraeus (Athens), Greece

6 Sailings

Oct 11, 2026 - Sep 27, 2028

6 Sailings

Oct 11, 2026 - Sep 27, 2028

Published prices from

$6,883

per person*

taxes & fees included

The iconic Library of Celsus in the ancient city of Ephesus, Turkey, with its magnificent, two-story facade and marble columns standing against a backdrop of cypress trees and green hills.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

11-night Cappadocia & Aegean Rhapsody Cruise Tour Via The Corinth Canal Cruise/Land Package From Piraeus (Athens), Greece

Athens (Piraeus)
Corinth Canal
Delphi
Santorini
Bodrum
+6 more

Aboard

Star Legend

From

Piraeus (Athens), Greece

1 Sailing

Oct 11, 2026

1 Sailing

Oct 11, 2026

A dramatic dusk shot of the historic Bodrum Castle, also known as the Castle of St. Peter, illuminated at night, with its reflection visible in the calm waters of the harbor in Turkey.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Aegean Sea Odyssey via the Corinth Canal Cruise From Piraeus (Athens), Greece

Athens (Piraeus)
Corinth Canal
Delphi
Santorini
Bodrum
+5 more

Aboard

Star Legend

From

Piraeus (Athens), Greece

1 Sailing

Oct 11, 2026

1 Sailing

Oct 11, 2026

Published prices from

$4,422

per person*

taxes & fees included

Microlimano harbor in Piraeus, Greece at sunset.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

10-night Enchanting Meteora, Greece, And Amalfi Coast Cruise/Land Package From Piraeus (Athens), Greece

Athens (Piraeus)
Delphi
Meteora
Monemvasia
Gythion
+4 more

Aboard

Wind Spirit

From

Piraeus (Athens), Greece

1 Sailing

Oct 12, 2026

1 Sailing

Oct 12, 2026

A beautiful hillside view of the colorful, clifftop houses of Sorrento, Italy, overlooking the brilliant blue Tyrrhenian Sea on a sunny day.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

13-night Lake Como & Adriatic Romance Cruise/Land Package From Milan, Italy

Milan
Lake Como
Bellagio
Venice
Rovinj
+7 more

Aboard

Wind Surf

From

Milan, Italy

1 Sailing

Oct 12, 2026

1 Sailing

Oct 12, 2026

A panoramic view of the traditional Japanese garden Ritsurin Koen in Takamatsu, Japan, with a curved wooden bridge over a large, calm pond with a small boat and traditional houses nestled in the lush green forest.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

12-night Kyoto & The Zen Of Japan Cruise/Land Package From Osaka, Japan

Osaka
Kyoto (Kobe)
Nara
Takamatsu
Hiroshima
+9 more

Aboard

Star Seeker

From

Osaka, Japan

14 Sailings

Oct 14, 2026 - May 13, 2029

14 Sailings

Oct 14, 2026 - May 13, 2029

Published prices from

$6,715

per person*

taxes & fees included

Microlimano harbor in Piraeus, Greece at sunset.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

10-night Enchanting Meteora, Greece, And Amalfi Coast Cruise/Land Package From Piraeus (Athens), Greece

Athens (Piraeus)
Delphi
Meteora
Monemvasia
Gythion
+5 more

Aboard

Wind Star

From

Piraeus (Athens), Greece

1 Sailing

Oct 14, 2026

1 Sailing

Oct 14, 2026

St. Peter's Basilica, Rome cityscape at sunset.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

7-night Enchanting Greece & The Amalfi Coast Cruise From Piraeus (Athens), Greece

Athens (Piraeus)
Monemvasia
Gythion
Strait of Messina
Sorrento
+2 more

Aboard

Wind Spirit

From

Piraeus (Athens), Greece

1 Sailing

Oct 15, 2026

1 Sailing

Oct 15, 2026

Published prices from

$2,934

per person*

taxes & fees included

Gondolas on a canal in Venice.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

12-night Vatican & Croatian Coastlines Cruise/Land Package From Venice, Italy

Venice
Rovinj
Split
Dubrovnik
Kotor
+4 more

Aboard

Wind Surf

From

Venice, Italy

1 Sailing

Oct 15, 2026

1 Sailing

Oct 15, 2026

A serene tropical beach on Fakarava atoll in French Polynesia, featuring a white sandy shoreline fringed with swaying palm trees and clear turquoise waters under a sunny blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

7-night Tantalizing Tuamotu Islands & Beautiful Bora Bora Cruise From Papeete, Tahiti, French Polynesia

Papeete
Fakarava
Rangiroa
Bora Bora
Motu Mahaea

Aboard

Star Breeze

From

Papeete, Tahiti, French Polynesia

6 Sailings

Oct 15, 2026 - Nov 2, 2028

6 Sailings

Oct 15, 2026 - Nov 2, 2028

Published prices from

$2,676

per person*

taxes & fees included

Plaza Espana in Barcelona, showcasing unique architectural design and vibrant surroundings.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

23-night Star Collector: Riviera Rhapsody Cruise From Venice, Italy

Venice
Rovinj
Split
Dubrovnik
Kotor
+16 more

Aboard

Wind Surf

From

Venice, Italy

1 Sailing

Oct 15, 2026

1 Sailing

Oct 15, 2026

Published prices from

$11,451

per person*

taxes & fees included

Gondolas on a canal in Venice.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

15-night Star Collector: Italian Trio Cruise From Venice, Italy

Venice
Rovinj
Split
Dubrovnik
Kotor
+9 more

Aboard

Wind Surf

From

Venice, Italy

1 Sailing

Oct 15, 2026

1 Sailing

Oct 15, 2026

Published prices from

$6,172

per person*

taxes & fees included

Gondolas on a canal in Venice.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

10-night Classic Italy & Dalmatian Coast Cruise From Venice, Italy

Venice
Rovinj
Split
Dubrovnik
Kotor
+4 more

Aboard

Wind Surf

From

Venice, Italy

1 Sailing

Oct 15, 2026

1 Sailing

Oct 15, 2026

Published prices from

$4,000

per person*

taxes & fees included

A stunning landscape of Cappadocia, Turkey, featuring unique rock formations and fairy chimneys under a bright blue sky with scattered clouds.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

11-night Cappadocia & Aegean Rhapsody Via The Corinth Canal Cruise/Land Package From Istanbul, Turkey

Istanbul
Cappadocia
Myrina
Mykonos
Kusadasi (Ephesus)
+6 more

Aboard

Star Legend

From

Istanbul, Turkey

5 Sailings

Oct 16, 2026 - Oct 7, 2027

5 Sailings

Oct 16, 2026 - Oct 7, 2027

The iconic Library of Celsus in the ancient city of Ephesus, Turkey, with its magnificent, two-story facade and marble columns standing against a backdrop of cypress trees and green hills.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

11-night Istanbul Icons & Aegean Artifacts Cruise/Land Package From Istanbul, Turkey

Istanbul
Myrina
Mykonos
Kusadasi (Ephesus)
Bodrum
+5 more

Aboard

Star Legend

From

Istanbul, Turkey

1 Sailing

Oct 16, 2026

1 Sailing

Oct 16, 2026

A striking view of the active Sakurajima volcano and its peaks, rising behind a foreground of green trees, in the bay of Kagoshima, Japan.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

10-night Grand Japan Cruise From Osaka, Japan

Osaka
Takamatsu
Hiroshima
Karatsu
Pusan (Busan)
+7 more

Aboard

Star Seeker

From

Osaka, Japan

15 Sailings

Oct 16, 2026 - May 15, 2029

15 Sailings

Oct 16, 2026 - May 15, 2029

Published prices from

$4,415

per person*

taxes & fees included

A beautiful wide shot of the Port of Portoferraio on Elba Island, Italy, showcasing the historic town's terracotta-roofed buildings and fortifications sprawling up the hillside from the blue sea.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

14-night Star Collector: Ancient To Avant-Garde Mediterranean Cruise From Piraeus (Athens), Greece

Athens (Piraeus)
Monemvasia
Gythion
Strait of Messina
Sorrento
+9 more

Aboard

Wind Star

From

Piraeus (Athens), Greece

1 Sailing

Oct 17, 2026

1 Sailing

Oct 17, 2026

Published prices from

$5,452

per person*

taxes & fees included

A beautiful hillside view of the colorful, clifftop houses of Sorrento, Italy, overlooking the brilliant blue Tyrrhenian Sea on a sunny day.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

7-night Enchanting Greece & The Amalfi Coast Cruise From Piraeus (Athens), Greece

Athens (Piraeus)
Monemvasia
Gythion
Strait of Messina
Sorrento
+3 more

Aboard

Wind Star

From

Piraeus (Athens), Greece

1 Sailing

Oct 17, 2026

1 Sailing

Oct 17, 2026

Published prices from

$2,829

per person*

taxes & fees included

Overwater bungalows in Tahiti, French Polynesia.
FREE All-Inclusive Upgrade + up to $400 Onboard Credit*
Windstar

10-night Golden Days In Bora Bora Cruise/Land Package From Papeete, Tahiti, French Polynesia

Papeete
Bora Bora
Moorea
Raiatea
Motu Mahaea

Aboard

Star Breeze

From

Papeete, Tahiti, French Polynesia

4 Sailings

Oct 19 - Dec 7, 2026

4 Sailings

Oct 19 - Dec 7, 2026

    • Showing results 1 - 24 of 280

*Rates and offers are per person, in US Dollars, based on double occupancy, capacity controlled, subject to availability and confirmation, and may change without notice. Government taxes and fees are included. Rates and offers are available for select dates and categories only. Additional restrictions may apply. Call 1-800-377-9383 for full terms and conditions.