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26 Results

Taxes and fees included in all prices shown

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BelƩm Tower on Tagus River.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night The Colorful Canary Islands Cruise From Lisbon, Portugal

Lisbon
Funchal (Madeira)
San Sebastian (Spain)
Santa Cruz de La Palma
Las Palmas (Gran Canaria)
+2 more

Aboard

Wind Spirit

From

Lisbon, Portugal

1 Sailing

Nov 9, 2026

1 Sailing

Nov 9, 2026

Published prices from

$3,364

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

14-night Ocean Crossings Cruise From Lisbon, Portugal

Lisbon
Bridgetown (Barbados)

Aboard

Wind Star

From

Lisbon, Portugal

1 Sailing

Nov 10, 2026

1 Sailing

Nov 10, 2026

Published prices from

$3,622

per person*

taxes & fees included

An aerial view of the colorful waterfront of St. George's, Grenada, with the town's buildings nestled on a hillside and a long, rocky breakwater extending into the calm, turquoise water.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

25-night Star Collector: Southern Caribbean Thanksgiving Jubilee Cruise From Lisbon, Portugal

Lisbon
Bridgetown (Barbados)
Bequia
St. George's
Kralendijk
+6 more

Aboard

Wind Star

From

Lisbon, Portugal

1 Sailing

Nov 10, 2026

1 Sailing

Nov 10, 2026

Published prices from

$7,989

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
Windstar

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

A panoramic view of the colorful city of Coimbra, Portugal, with its historic buildings and university perched on a hill, overlooking the Mondego River and a bridge.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

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

Lisbon
Fatima
Porto (Oporto)
Oporto (Leixoes)
Douro Valley
+11 more

Aboard

Star Legend

From

Lisbon, Portugal

2 Sailings

Mar 13 - Jun 12, 2027

2 Sailings

Mar 13 - Jun 12, 2027

Published prices from

$6,120

per person*

taxes & fees included

A scenic view of the iconic Plaza de EspaƱa in Seville, Spain, featuring its grand arcade of arches and columns, a main building with a clock tower, and a bright blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

15-night Star Collector: Iberian Charm, Italian Elegance & Riviera Nights Cruise From Lisbon, Portugal

Lisbon
Seville (Cadiz)
Gibraltar
Malaga
Almeria
+8 more

Aboard

Star Legend

From

Lisbon, Portugal

1 Sailing

Mar 17, 2027

1 Sailing

Mar 17, 2027

Published prices from

$5,658

per person*

taxes & fees included

BelƩm Tower on Tagus River.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Spanish Symphony Cruise From Lisbon, Portugal

Lisbon
Seville (Cadiz)
Gibraltar
Malaga
Almeria
+4 more

Aboard

Star Legend

From

Lisbon, Portugal

4 Sailings

Mar 17, 2027 - Jul 3, 2028

4 Sailings

Mar 17, 2027 - Jul 3, 2028

Published prices from

$3,110

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

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

Lisbon
Fatima
Porto (Oporto)
Douro Valley
Coimbra
+10 more

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

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 AlmerĆ­a, Spain.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

8-night Spanish Symphony Cruise From Lisbon, Portugal

Lisbon
Seville (Cadiz)
Gibraltar
Malaga
Almeria
+4 more

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
Windstar

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

Lisbon
Seville (Cadiz)
Gibraltar
Malaga
Almeria
+12 more

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

White Cliffs of Dover.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

18-night Star Collector Cruise: The Flavors Of France From Lisbon, Portugal

Lisbon
Oporto (Leixoes)
Vigo
Gijon
Bilbao
+11 more

Aboard

Star Explorer

From

Lisbon, Portugal

1 Sailing

May 13, 2027

1 Sailing

May 13, 2027

Published prices from

$13,434

per person*

taxes & fees included

Bordeaux vineyard with a windmill.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Connoisseur’s Delight: Northern Spain & Portugal Cruise From Lisbon, Portugal

Lisbon
Oporto (Leixoes)
Vigo
Gijon
Bilbao
+3 more

Aboard

Star Explorer

From

Lisbon, Portugal

2 Sailings

May 13, 2027 - May 7, 2028

2 Sailings

May 13, 2027 - May 7, 2028

Published prices from

$5,526

per person*

taxes & fees included

A sunlit, narrow street scene in Alcudia, Mallorca, with an arched stone doorway, potted plants, and a rustic wooden bench.
FREE All-Inclusive Upgrade + up to $400 Onboard Credit*
Windstar

19-night Star Collector: Spanish Spectacular & Riviera Reveries Cruise From Lisbon, Portugal

Lisbon
Seville (Cadiz)
Gibraltar
Malaga
Almeria
+14 more

Aboard

Star Legend

From

Lisbon, Portugal

1 Sailing

Jun 16, 2027

1 Sailing

Jun 16, 2027

Published prices from

$7,200

per person*

taxes & fees included

Alcazaba fortress in Malaga.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

12-night Star Collector Cruise: Moorish Legacies & Island Escapes From Lisbon, Portugal

Lisbon
Seville (Cadiz)
Gibraltar
Malaga
Almeria
+6 more

Aboard

Star Legend

From

Lisbon, Portugal

1 Sailing

Jun 16, 2027

1 Sailing

Jun 16, 2027

Published prices from

$4,174

per person*

taxes & fees included

Plaza Espana in Barcelona, showcasing unique architectural design and vibrant surroundings.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

24-night Star Collector Cruise: Iberian Nights & Adriatic Delights From Lisbon, Portugal

Lisbon
Guadalquivir River
Seville (Cadiz)
Tangier
Cartagena (Spain)
+18 more

Aboard

Star Explorer

From

Lisbon, Portugal

1 Sailing

Sep 7, 2027

1 Sailing

Sep 7, 2027

Published prices from

$19,045

per person*

taxes & fees included

A picturesque view of the historic Cape Spartel Lighthouse on a cliff overlooking the Atlantic Ocean near Tangier, Morocco.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

16-night Star Collector: Wonders Of Andalusia, Provence & Tuscany Cruise From Lisbon, Portugal

Lisbon
Seville (Cadiz)
Tangier
Cartagena (Spain)
Valencia
+10 more

Aboard

Star Explorer

From

Lisbon, Portugal

1 Sailing

Sep 7, 2027

1 Sailing

Sep 7, 2027

Published prices from

$10,792

per person*

taxes & fees included

A scenic view of the iconic Plaza de EspaƱa in Seville, Spain, featuring its grand arcade of arches and columns, a main building with a clock tower, and a bright blue sky.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

8-night Moroccan Markets & Iberian Icons Cruise From Lisbon, Portugal

Lisbon
Seville (Cadiz)
Tangier
Cartagena (Spain)
Valencia
+2 more

Aboard

Star Explorer

From

Lisbon, Portugal

1 Sailing

Sep 7, 2027

1 Sailing

Sep 7, 2027

Published prices from

$6,382

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*
TCW EXCLUSIVE
Windstar

8-night Ocean Crossings Cruise From Lisbon, Portugal

Lisbon
Funchal (Madeira)
Jost Van Dyke
St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Nov 5, 2027

1 Sailing

Nov 5, 2027

Published prices from

$2,580

per person*

taxes & fees included

The picturesque fishing village of Deshaies, Guadeloupe, with its colorful waterfront and red-roofed church nestled on a tranquil bay.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
Windstar

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

Lisbon
Funchal (Madeira)
Jost Van Dyke
St. Maarten (Philipsburg)
Gustavia
+6 more

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Nov 5, 2027

1 Sailing

Nov 5, 2027

Published prices from

$4,813

per person*

taxes & fees included

BelƩm Tower on Tagus River.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

14-night Ocean Crossings Cruise From Lisbon, Portugal

Lisbon
Funchal (Madeira)
Jost Van Dyke
San Juan

Aboard

Star Legend

From

Lisbon, Portugal

1 Sailing

Dec 6, 2027

1 Sailing

Dec 6, 2027

Published prices from

$4,450

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

21-night Star Collector Cruise: Atlantic Crossing To The Virgin Islands From Lisbon, Portugal

Lisbon
Funchal (Madeira)
Jost Van Dyke
San Juan
Cruz Bay
+5 more

Aboard

Star Legend

From

Lisbon, Portugal

1 Sailing

Dec 6, 2027

1 Sailing

Dec 6, 2027

Published prices from

$5,668

per person*

taxes & fees included

A scenic panoramic shot from the top of the Rock of Gibraltar, overlooking the city, marina, and the Mediterranean Sea under a bright blue sky.
Windstar

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

Lisbon
Seville (Cadiz)
Gibraltar
Malaga
Almeria
+5 more

Aboard

Star Legend

From

Lisbon, Portugal

2 Sailings

Mar 13 - Jul 3, 2028

2 Sailings

Mar 13 - Jul 3, 2028

Published prices from

$8,329

per person*

taxes & fees included

A scenic view of the iconic Plaza de EspaƱa in Seville, Spain, featuring its grand arcade of arches and columns, a main building with a clock tower, and a bright blue sky.
Windstar

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

Lisbon
Seville (Cadiz)
Gibraltar
Malaga
Almeria
+5 more

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Apr 3, 2028

1 Sailing

Apr 3, 2028

Published prices from

$8,323

per person*

taxes & fees included

A scenic panoramic shot from the top of the Rock of Gibraltar, overlooking the city, marina, and the Mediterranean Sea under a bright blue sky.
Windstar

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

Lisbon
Seville (Cadiz)
Gibraltar
Malaga
Almeria
+11 more

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Apr 3, 2028

1 Sailing

Apr 3, 2028

Published prices from

$6,666

per person*

taxes & fees included

Bordeaux vineyard with a windmill.
Windstar

16-night Star Collector: The Flavors of France Cruise From Lisbon, Portugal

Lisbon
Oporto (Leixoes)
Vigo
Gijon
Bilbao
+11 more

Aboard

Star Explorer

From

Lisbon, Portugal

1 Sailing

May 7, 2028

1 Sailing

May 7, 2028

Published prices from

$8,700

per person*

taxes & fees included

  • Showing results 1 - 24 of 26


*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.