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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

Windstar

15-night Ocean Crossings Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Funchal (Madeira)

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Mar 2, 2027

1 Sailing

Mar 2, 2027

Published prices from

$2,946

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

Windstar

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

Bridgetown (Barbados)

Funchal (Madeira)

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Mar 2, 2027

1 Sailing

Mar 2, 2027

Published prices from

$5,847

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*+ 1 more offer

Windstar

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

St. Maarten (Philipsburg)

Funchal (Madeira)

Seville (Cadiz)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Mar 27, 2027

1 Sailing

Mar 27, 2027

Published prices from

$5,230

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

Windstar

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

St. Maarten (Philipsburg)

Funchal (Madeira)

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

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*

Windstar

28-night Star Collector: Spain, Morocco & Atlantic Archipelagos Cruise From Tarragona, Spain

Barcelona (Tarragona)

Palma de Mallorca

Cartagena (Spain)

Aboard

Wind Spirit

From

Tarragona, Spain

1 Sailing

Oct 22, 2027

1 Sailing

Oct 22, 2027

Published prices from

$14,691

per person*

taxes & fees included

Alcazaba fortress in Malaga.

Up to $500 FREE Onboard Credit*

Windstar

20-night Star Collector: Morocco, Madeira & The Canary Islands Cruise From Malaga, Spain

Seville (Cadiz)

Aboard

Wind Spirit

From

Malaga, Spain

1 Sailing

Oct 30, 2027

1 Sailing

Oct 30, 2027

Published prices from

$11,442

per person*

taxes & fees included

Anaga Mountains landscape, Tenerife.

Up to $500 FREE Onboard Credit*

Windstar

10-night Hidden Gems Of The Canary Islands & Madeira Cruise From Santa Cruz de Tenerife, Canary Islands

Santa Cruz de Tenerife

Funchal (Madeira)

Santa Cruz de La Palma

Aboard

Wind Spirit

From

Santa Cruz de Tenerife, Canary Islands

11 Sailings

Nov 9, 2027 - Feb 17, 2028

11 Sailings

Nov 9, 2027 - Feb 17, 2028

Published prices from

$3,520

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.