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A scenic view of the white sand beach and lush palm trees of Mystery Island, Aneityum, with calm, turquoise water under a clear blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

23-night Star Collector Cruise: Spanish Mystery & Atlantic Crossing From Barcelona, Spain

Barcelona
Mystery Island (Aneityum)
Malaga
Tangier
Casablanca
+3 more

Aboard

Star Legend

From

Barcelona, Spain

1 Sailing

Nov 4, 2026

1 Sailing

Nov 4, 2026

Published prices from

$7,472

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

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

22-night Star Collector Cruise: Caribbean Beats & Transatlantic Treats From Malaga, Spain

Malaga
Tangier
Casablanca
Funchal (Madeira)
Bridgetown (Barbados)
+8 more

Aboard

Star Legend

From

Malaga, Spain

1 Sailing

Nov 12, 2026

1 Sailing

Nov 12, 2026

Published prices from

$7,458

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*+ 2 more offers
TCW EXCLUSIVE
Windstar

13-night Ocean Crossings Cruise From Malaga, Spain

Malaga
Tangier
Casablanca
Funchal (Madeira)
Bridgetown (Barbados)

Aboard

Star Legend

From

Malaga, Spain

1 Sailing

Nov 12, 2026

1 Sailing

Nov 12, 2026

Published prices from

$5,710

per person*

taxes & fees included

A beautiful Porto Santo beach landscape with a long stretch of golden sand, a wicker bench, a wooden fence, and the distinctive mountains of Madeira in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

15-night Ocean Crossings Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Funchal (Madeira)
Porto Santo
Casablanca
Lisbon

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Mar 2, 2027

1 Sailing

Mar 2, 2027

Published prices from

$2,592

per person*

taxes & fees included

A scenic view of the iconic Plaza de España 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

23-night Star Collector Cruise: Spanish Shores Transatlantic Crossing From Bridgetown, Barbados

Bridgetown (Barbados)
Funchal (Madeira)
Porto Santo
Casablanca
Lisbon
+8 more

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Mar 2, 2027

1 Sailing

Mar 2, 2027

Published prices from

$5,162

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
Windstar

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

Tulip fields with traditional windmills, showcasing the beauty of the Netherlands in springtime.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

16-night Ocean Crossings Cruise From San Juan, Puerto Rico

San Juan
Lisbon
Brest
Amsterdam

Aboard

Star Pride

From

San Juan, Puerto Rico

2 Sailings

Mar 30, 2027 - Apr 3, 2028

2 Sailings

Mar 30, 2027 - Apr 3, 2028

Published prices from

$2,760

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

Belém 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

$5,220

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

$6,193

per person*

taxes & fees included

A picturesque view of a small town nestled at the base of a lush, green mountain on Iles des Saintes, Guadeloupe, with boats moored in the deep blue water and fluffy clouds in the sky.
Windstar

22-night Star Collector Cruise: Caribbean Charms To Iberian Shores From San Juan, Puerto Rico

San Juan
St. George's
Bequia
Mayreau
Iles des Saintes
+5 more

Aboard

Star Legend

From

San Juan, Puerto Rico

1 Sailing

Feb 21, 2028

1 Sailing

Feb 21, 2028

Published prices from

$4,271

per person*

taxes & fees included

An aerial view of Agadir, Morocco, showcasing the city's long sandy beach and curving coastline, with a busy marina and port in the foreground.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

15-night Ocean Crossings Cruise From San Juan, Puerto Rico

San Juan
Agadir
Casablanca
Lisbon

Aboard

Star Legend

From

San Juan, Puerto Rico

1 Sailing

Feb 28, 2028

1 Sailing

Feb 28, 2028

An aerial view of the colorful waterfront of St. John's, Antigua, with a long pier extending into the calm, blue sea and the town's charming buildings and marina in the background.
Up to $500 FREE Onboard Credit*
TCW EXCLUSIVE
Windstar

22-night Star Collector Cruise: Hearty Ports & Rum Punches - A Transatlantic Crossing From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
St. John's
Road Bay
Sopers Hole
Jost Van Dyke
+6 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Mar 12, 2028

1 Sailing

Mar 12, 2028

Published prices from

$4,388

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.
Windstar

23-night Star Collector: Spanish Shores Transatlantic Crossing Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Porto Santo
Funchal (Madeira)
Lisbon
Seville (Cadiz)
+7 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Mar 19, 2028

1 Sailing

Mar 19, 2028

Published prices from

$5,689

per person*

taxes & fees included

A scenic landscape view of Admiralty Bay in Bequia, St. Vincent and the Grenadines, with dozens of sailboats moored on the vibrant turquoise water, surrounded by lush green hills.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

23-night Star Collector Cruise: Tropical Horizons To Historic Amsterdam From San Juan, Puerto Rico

San Juan
St. George's
Bequia
Mayreau
Iles des Saintes
+5 more

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2028

1 Sailing

Mar 27, 2028

Published prices from

$4,211

per person*

taxes & fees included

Belém Tower on Tagus River.
Windstar

14-night Ocean Crossing Cruise From Lisbon, Portugal

Lisbon
St. John's
St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Nov 5, 2028

1 Sailing

Nov 5, 2028

Published prices from

$2,839

per person*

taxes & fees included

*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.