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St. Peter's Basilica, Rome cityscape at sunset.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

7-night Vatican & Italian Riviera Cruise/Land Package From Civitavecchia, Rome, Italy

Aboard

Wind Surf

From

Civitavecchia, Rome, Italy

1 Sailing

Oct 23, 2026

1 Sailing

Oct 23, 2026

A close-up view of traditional, colorful wooden fishing boats called 'pointus' docked in the picturesque harbor of Sanary-sur-Mer, France, under a bright, sunny sky.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

10-night Yachtsman’s Mediterranean Rivieras & Madrid Cruise/Land Package From Civitavecchia, Rome, Italy

Aboard

Wind Surf

From

Civitavecchia, Rome, Italy

1 Sailing

Oct 25, 2026

1 Sailing

Oct 25, 2026

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

13-night Star Collector: Enchantment Of The Western Med Cruise From Civitavecchia, Rome, Italy

Aboard

Wind Surf

From

Civitavecchia, Rome, Italy

1 Sailing

Oct 25, 2026

1 Sailing

Oct 25, 2026

Published prices from

$4,811

per person*

taxes & fees included

A classic view of the picturesque harbor of Portofino, Italy, with its iconic, brightly painted buildings reflected on the shimmering blue water and lush green hills in the background.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

5-night Yachtsman's Harbors Of The Rivieras Cruise From Civitavecchia, Rome, Italy

Aboard

Wind Surf

From

Civitavecchia, Rome, Italy

1 Sailing

Oct 25, 2026

1 Sailing

Oct 25, 2026

Published prices from

$1,922

per person*

taxes & fees included

A historic fortress, the Castle of La Calahorra, stands on a hilltop overlooking a town with white-washed houses below, under a blue sky with scattered clouds in Almería, Spain.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

12-night Spanish Symphony & Madrid Medley Cruise/Land Package From Madrid, Spain

Aboard

Wind Surf

From

Madrid, Spain

1 Sailing

Oct 26, 2026

1 Sailing

Oct 26, 2026

FREE All-Inclusive Upgrade + up to $400 Onboard Credit*

12-night Portuguese Passages & Spanish Shorelines Cruise/Land Package From Barcelona, Spain

Aboard

Wind Surf

From

Barcelona, Spain

2 Sailings

Oct 30, 2026 - Oct 28, 2028

2 Sailings

Oct 30, 2026 - Oct 28, 2028

Published prices from

$7,864

per person*

taxes & fees included

A low-angle shot of the magnificent Palacio Consistorial, the town hall of Cartagena, Spain, showcasing its ornate, white marble facade and domed rooftops against a blue sky.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

8-night Spanish Symphony Cruise From Barcelona, Spain

Aboard

Wind Surf

From

Barcelona, Spain

3 Sailings

Oct 30, 2026 - Oct 28, 2028

3 Sailings

Oct 30, 2026 - Oct 28, 2028

Published prices from

$2,984

per person*

taxes & fees included

An aerial view of Road Bay, Anguilla, showing a pristine white sand beach, lush green vegetation, and the stunningly clear turquoise water of the Caribbean Sea.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

21-night Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing Cruise From Lisbon, Portugal

Lisbon

St. John's

St. Maarten (Philipsburg)

Falmouth Harbour

Gustavia

+5 more

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

An aerial panoramic view of a winding road overlooking Frigate Bay and the Caribbean Sea, with rolling green hills, a beach, and the town of Basseterre, St. Kitts.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

14-night Star Collector: Caribbean Explorations Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

13 Sailings

Dec 19, 2026 - Mar 13, 2027

13 Sailings

Dec 19, 2026 - Mar 13, 2027

Published prices from

$5,280

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

7 Sailings

Dec 19, 2026 - Mar 13, 2027

7 Sailings

Dec 19, 2026 - Mar 13, 2027

Published prices from

$2,901

per person*

taxes & fees included

A breathtaking panoramic view of Charlotte Amalie harbor in St. Thomas, with a cruise ship anchored in the bay, surrounded by rolling green hills and a colorful sunset.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

7-night Classic Caribbean Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

15 Sailings

Dec 26, 2026 - Mar 5, 2028

15 Sailings

Dec 26, 2026 - Mar 5, 2028

Published prices from

$2,362

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

23-night Star Collector: Atlantic Interludes & Iberian Indulgences Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Mar 27, 2027

1 Sailing

Mar 27, 2027

Published prices from

$5,398

per person*

taxes & fees included

A beautiful panoramic shot from a garden in Funchal, Madeira, Portugal, showcasing meticulously manicured flower beds in geometric patterns with the city and the Atlantic Ocean in the background.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

15-night Ocean Crossings Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Funchal (Madeira)

Porto Santo

Lisbon

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

2 Sailings

Mar 27, 2027 - Mar 19, 2028

2 Sailings

Mar 27, 2027 - Mar 19, 2028

Published prices from

$2,580

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

12-night Portuguese Passages & Spanish Shorelines Cruise/Land Package From Lisbon, Portugal

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Apr 7, 2027

1 Sailing

Apr 7, 2027

Published prices from

$5,508

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

8-night Spanish Symphony Cruise From Lisbon, Portugal

Aboard

Wind Surf

From

Lisbon, Portugal

2 Sailings

Apr 11, 2027 - Apr 3, 2028

2 Sailings

Apr 11, 2027 - Apr 3, 2028

Published prices from

$3,008

per person*

taxes & fees included

A panoramic sunset shot of the beautiful harbor in Palma de Mallorca, Spain, with a marina full of boats and buildings on the surrounding hills.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

16-night Star Collector: Enchantment Of The Western Med Cruise From Lisbon, Portugal

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Apr 11, 2027

1 Sailing

Apr 11, 2027

Published prices from

$5,574

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

10-night Vatican & Italian Riviera Cruise/Land Package From Tarragona, Spain

Barcelona (Tarragona)

Aboard

Wind Surf

From

Tarragona, Spain

1 Sailing

Apr 19, 2027

1 Sailing

Apr 19, 2027

Published prices from

$4,946

per person*

taxes & fees included

Microlimano harbor in Piraeus, Greece at sunset.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

15-night Star Collector: Riches Of The Rivieras, Romans, And Greeks Cruise From Barcelona, Spain

Aboard

Wind Surf

From

Barcelona, Spain

1 Sailing

Apr 19, 2027

1 Sailing

Apr 19, 2027

Published prices from

$4,936

per person*

taxes & fees included

A wide-angle, twilight shot of the famous La Croisette promenade in Cannes, France, with its luxurious hotels, sandy beaches, and beautiful ocean views lit up at dusk.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

8-night Yachtsman's Harbors Of The Rivieras Cruise From Barcelona, Spain

Aboard

Wind Surf

From

Barcelona, Spain

1 Sailing

Apr 19, 2027

1 Sailing

Apr 19, 2027

Published prices from

$3,046

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.

FREE All-Inclusive Upgrade + up to $400 Onboard Credit*

10-night Enchanting Meteora, Greece, And Amalfi Coast Cruise/Land Package From Civitavecchia, Rome, Italy

Aboard

Wind Surf

From

Civitavecchia, Rome, Italy

1 Sailing

Apr 27, 2027

1 Sailing

Apr 27, 2027

Published prices from

$4,470

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

7-night Enchanting Greece & The Amalfi Coast Cruise From Civitavecchia, Rome, Italy

Aboard

Wind Surf

From

Civitavecchia, Rome, Italy

2 Sailings

Apr 27, 2027 - Apr 18, 2028

2 Sailings

Apr 27, 2027 - Apr 18, 2028

Published prices from

$2,570

per person*

taxes & fees included

The ancient Greek ruins of Delphi, Greece, featuring a large column fragment in the foreground with a dramatic mountain and valley backdrop.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

10-night Delphi & Meteora: Grecian Treasures Cruise/Land Package From Athens, Greece

Aboard

Wind Surf

From

Athens, Greece

41 Sailings

May 1, 2027 - Oct 4, 2028

41 Sailings

May 1, 2027 - Oct 4, 2028

Published prices from

$5,669

per person*

taxes & fees included

A beautiful daytime view of the iconic windmills of Mykonos, Greece, with their white-washed walls and thatched roofs against a vivid blue sky.

Up to $500 FREE Onboard Credit*+ 2 more offers

TCW EXCLUSIVE

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

Aboard

Wind Surf

From

Piraeus (Athens), Greece

41 Sailings

May 4, 2027 - Oct 7, 2028

41 Sailings

May 4, 2027 - Oct 7, 2028

Published prices from

$3,769

per person*

taxes & fees included

A breathtaking view of Ermoupolis on the island of Syros, Greece, showcasing beautiful neoclassical buildings perched on the rocky coastline, with vibrant turquoise water and rolling hills in the background.

Up to $500 FREE Onboard Credit*

TCW EXCLUSIVE

7-night Off The Beaten Path Greek Islands Cruise From Piraeus (Athens), Greece

Aboard

Wind Surf

From

Piraeus (Athens), Greece

2 Sailings

Jul 6 - Aug 19, 2027

2 Sailings

Jul 6 - Aug 19, 2027

Published prices from

$3,760

per person*

taxes & fees included

A colorful image of a traditional Greek boat moored in the turquoise water of a fishing village. The village features charming whitewashed houses with brightly painted doors, built at the base of a cliff.

Up to $500 FREE Onboard Credit*+ 1 more offer

TCW EXCLUSIVE

14-night Star Collector: Greek Classics & Hidden Gems Unveiled Cruise From Piraeus (Athens), Greece

Aboard

Wind Surf

From

Piraeus (Athens), Greece

7 Sailings

Jul 6, 2027 - Aug 19, 2028

7 Sailings

Jul 6, 2027 - Aug 19, 2028

Published prices from

$6,619

per person*

taxes & fees included

7-night Vatican & Italian Riviera Cruise/Land Package From Civitavecchia, Rome, Italy

10-night Yachtsman’s Mediterranean Rivieras & Madrid Cruise/Land Package From Civitavecchia, Rome, Italy

13-night Star Collector: Enchantment Of The Western Med Cruise From Civitavecchia, Rome, Italy

$4,811

5-night Yachtsman's Harbors Of The Rivieras Cruise From Civitavecchia, Rome, Italy

$1,922

12-night Spanish Symphony & Madrid Medley Cruise/Land Package From Madrid, Spain

12-night Portuguese Passages & Spanish Shorelines Cruise/Land Package From Barcelona, Spain

$7,864

8-night Spanish Symphony Cruise From Barcelona, Spain

$2,984

21-night Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing Cruise From Lisbon, Portugal

14-night Star Collector: Caribbean Explorations Cruise From Philipsburg, St. Maarten, The Netherlands

$5,280

7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise From Philipsburg, St. Maarten, The Netherlands

$2,901

7-night Classic Caribbean Cruise From Philipsburg, St. Maarten, The Netherlands

$2,362

23-night Star Collector: Atlantic Interludes & Iberian Indulgences Cruise From Philipsburg, St. Maarten, The Netherlands

$5,398

15-night Ocean Crossings Cruise From Philipsburg, St. Maarten, The Netherlands

$2,580

12-night Portuguese Passages & Spanish Shorelines Cruise/Land Package From Lisbon, Portugal

$5,508

8-night Spanish Symphony Cruise From Lisbon, Portugal

$3,008

16-night Star Collector: Enchantment Of The Western Med Cruise From Lisbon, Portugal

$5,574

10-night Vatican & Italian Riviera Cruise/Land Package From Tarragona, Spain

$4,946

15-night Star Collector: Riches Of The Rivieras, Romans, And Greeks Cruise From Barcelona, Spain

$4,936

8-night Yachtsman's Harbors Of The Rivieras Cruise From Barcelona, Spain

$3,046

10-night Enchanting Meteora, Greece, And Amalfi Coast Cruise/Land Package From Civitavecchia, Rome, Italy

$4,470

7-night Enchanting Greece & The Amalfi Coast Cruise From Civitavecchia, Rome, Italy

$2,570

10-night Delphi & Meteora: Grecian Treasures Cruise/Land Package From Athens, Greece

$5,669

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

$3,769

7-night Off The Beaten Path Greek Islands Cruise From Piraeus (Athens), Greece

$3,760

14-night Star Collector: Greek Classics & Hidden Gems Unveiled Cruise From Piraeus (Athens), Greece

$6,619

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7-night Vatican & Italian Riviera Cruise/Land Package From Civitavecchia, Rome, Italy

10-night Yachtsman’s Mediterranean Rivieras & Madrid Cruise/Land Package From Civitavecchia, Rome, Italy

13-night Star Collector: Enchantment Of The Western Med Cruise From Civitavecchia, Rome, Italy

$4,811

5-night Yachtsman's Harbors Of The Rivieras Cruise From Civitavecchia, Rome, Italy

$1,922

12-night Spanish Symphony & Madrid Medley Cruise/Land Package From Madrid, Spain

12-night Portuguese Passages & Spanish Shorelines Cruise/Land Package From Barcelona, Spain

$7,864

8-night Spanish Symphony Cruise From Barcelona, Spain

$2,984

21-night Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing Cruise From Lisbon, Portugal

14-night Star Collector: Caribbean Explorations Cruise From Philipsburg, St. Maarten, The Netherlands

$5,280

7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise From Philipsburg, St. Maarten, The Netherlands

$2,901

7-night Classic Caribbean Cruise From Philipsburg, St. Maarten, The Netherlands

$2,362

23-night Star Collector: Atlantic Interludes & Iberian Indulgences Cruise From Philipsburg, St. Maarten, The Netherlands

$5,398

15-night Ocean Crossings Cruise From Philipsburg, St. Maarten, The Netherlands

$2,580

12-night Portuguese Passages & Spanish Shorelines Cruise/Land Package From Lisbon, Portugal

$5,508

8-night Spanish Symphony Cruise From Lisbon, Portugal

$3,008

16-night Star Collector: Enchantment Of The Western Med Cruise From Lisbon, Portugal

$5,574