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Wind Surf Cruise Itineraries & Ship Specs

Windstar Cruises
Wind Surf from Windstar Cruises

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Wind Surf Overview

The largest sailing cruise ship in the world, Wind Surf impresses with five masts and elegant interiors.

About the Wind Surf
  • Total Passengers: 342 guests
  • Total Crew: 210 staff
  • Year Built: 1990
  • Last Renovation: 2019
  • Gross Tonnage: 14745 tonnes
  • Length: 617 ft (188 m)
  • Beam (width): 66 ft (20 m)
  • Speed: 12 knots (under sail)
  • Draft: 16 ft (4.9 m)
  • Ship Class: Wind Class
  • Ship Registry: Bahamas
View Sailing Dates

Wind Surf Sailing Dates

Jan 25, 2026 (Sun - Mon)
15 Nt Caribbean Cruise
From Bridgetown
Ports of Call:
Bridgetown | Bequia | Mayreau | Soufriere | Kralendijk | Willemstad | Oranjestad | Cartagena | Cartagena | San Blas, Panama | Bocas Del Toro | Colon | Colon
Special Offers:
  • Reduced Deposits
  • Signature Collection
$7,766 pp
Jan 25, 2026 (Sun - Sun)
7 Nt Caribbean Cruise
From Bridgetown
Ports of Call:
Bridgetown | Bequia | Mayreau | Soufriere | Kralendijk | Willemstad | Oranjestad
Special Offers:
  • Signature Collection
$4,424 pp
Jan 25, 2026 (Sun - Sun)
7 Nt Caribbean Cruise
From Bridgetown
Ports of Call:
Bridgetown | Bequia | Mayreau | Soufriere | Kralendijk | Willemstad | Oranjestad
Special Offers:
  • Reduced Deposits
  • Signature Collection
$4,424 pp
Feb 1, 2026 (Sun - Tue)
16 Nt Caribbean Cruise
From Oranjestad
Ports of Call:
Oranjestad | Cartagena | Cartagena | San Blas, Panama | Bocas Del Toro | Colon | Colon | Bocas Del Toro | Isla San Andres | Roatan | Belize City | Costa Maya | Cozumel
Special Offers:
  • Reduced Deposits
  • Signature Collection
$4,565 pp
Feb 1, 2026 (Sun - Mon)
8 Nt Caribbean Cruise
From Oranjestad
Ports of Call:
Oranjestad | Cartagena | Cartagena | San Blas, Panama | Bocas Del Toro | Colon | Colon
Special Offers:
  • Reduced Deposits
  • Signature Collection
$2,630 pp
Feb 9, 2026 (Mon - Tue)
8 Nt Mexico Cruise
From Colon
Ports of Call:
Colon | Bocas Del Toro | Isla San Andres | Roatan | Belize City | Costa Maya | Cozumel
Special Offers:
  • Reduced Deposits
  • Signature Collection
$3,083 pp
Feb 9, 2026 (Mon - Sat)
19 Nt Caribbean Cruise
From Colon
Ports of Call:
Colon | Bocas Del Toro | Isla San Andres | Roatan | Belize City | Costa Maya | Cozumel | Grand Cayman | Cayman Brac | Ocho Rios, Jamaica | Santo Domingo | La Romana | Jost Van Dyke, Great Harbour | Virgin Gorda / Prickly Pear, British Virgin Islands | Philipsburg, St Maarten
Special Offers:
  • Reduced Deposits
  • Signature Collection
$6,373 pp
Feb 17, 2026 (Tue - Sat)
18 Nt Caribbean Cruise
From Cozumel
Ports of Call:
Cozumel | Grand Cayman | Cayman Brac | Ocho Rios, Jamaica | Santo Domingo | La Romana | Jost Van Dyke, Great Harbour | Virgin Gorda / Prickly Pear, British Virgin Islands | Philipsburg, St Maarten | Charlestown | Roseau | Mayreau | Deshaies | Basseterre | Gustavia | Philipsburg, St Maarten
Special Offers:
  • Non-Refundable Rate
  • Reduced Deposits
  • Signature Collection
$10,115 pp
Feb 17, 2026 (Tue - Sat)
11 Nt Caribbean Cruise
From Cozumel
Ports of Call:
Cozumel | Grand Cayman | Cayman Brac | Ocho Rios, Jamaica | Santo Domingo | La Romana | Jost Van Dyke, Great Harbour | Virgin Gorda / Prickly Pear, British Virgin Islands | Philipsburg, St Maarten
Special Offers:
  • Additional Savings
  • Signature Collection
$2,703 pp
Feb 28, 2026 (Sat - Sat)
14 Nt Caribbean Cruise
From St Maarten
Ports of Call:
Philipsburg, St Maarten | Charlestown | Roseau | Mayreau | Deshaies | Basseterre | Gustavia | Philipsburg, St Maarten | Falmouth Harbour | Road Bay | Virgin Gorda / Prickly Pear, British Virgin Islands | Sopers Hole | Sopers Hole | Jost Van Dyke, Great Harbour | Gustavia | Philipsburg, St Maarten
Special Offers:
  • Signature Collection
View Price
Feb 28, 2026 (Sat - Sat)
7 Nt Caribbean Cruise
From St Maarten
Ports of Call:
Philipsburg, St Maarten | Charlestown | Roseau | Mayreau | Deshaies | Basseterre | Gustavia | Philipsburg, St Maarten
Special Offers:
  • Signature Collection
$4,351 pp
Mar 7, 2026 (Sat - Sat)
7 Nt Caribbean Cruise
From St Maarten
Ports of Call:
Philipsburg, St Maarten | Falmouth Harbour | Road Bay | Virgin Gorda / Prickly Pear, British Virgin Islands | Sopers Hole | Sopers Hole | Jost Van Dyke, Great Harbour | Gustavia | Philipsburg, St Maarten
Special Offers:
  • Reduced Deposits
  • Signature Collection
$3,867 pp
Mar 14, 2026 (Sat - Sat)
14 Nt Caribbean Cruise
From St Maarten
Ports of Call:
Philipsburg, St Maarten | Falmouth Harbour | Road Bay | Sopers Hole | Jost Van Dyke, Great Harbour | Jost Van Dyke, Great Harbour | Virgin Gorda / Prickly Pear, British Virgin Islands | Gustavia | Philipsburg, St Maarten | Charlestown | Roseau | Mayreau | Les Saintes | Basseterre | Gustavia | Philipsburg, St Maarten
Special Offers:
  • Reduced Deposits
  • Signature Collection
$6,819 pp
Mar 14, 2026 (Sat - Sat)
7 Nt Eastern Caribbean Cruise
From St Maarten
Ports of Call:
Philipsburg, St Maarten | Falmouth Harbour | Road Bay | Sopers Hole | Jost Van Dyke, Great Harbour | Jost Van Dyke, Great Harbour | Virgin Gorda / Prickly Pear, British Virgin Islands | Gustavia | Philipsburg, St Maarten
Special Offers:
  • Reduced Deposits
  • Signature Collection
$3,767 pp
Mar 21, 2026 (Sat - Sat)
7 Nt Caribbean Cruise
From St Maarten
Ports of Call:
Philipsburg, St Maarten | Charlestown | Roseau | Mayreau | Les Saintes | Basseterre | Gustavia | Philipsburg, St Maarten
Special Offers:
  • Reduced Deposits
  • Signature Collection
$3,851 pp
Mar 21, 2026 (Sat - Sat)
14 Nt Caribbean Cruise
From St Maarten
Ports of Call:
Philipsburg, St Maarten | Charlestown | Roseau | Mayreau | Les Saintes | Basseterre | Gustavia | Philipsburg, St Maarten | St Johns | Road Bay | Sopers Hole | Jost Van Dyke, Great Harbour | Jost Van Dyke, Great Harbour | Virgin Gorda / Prickly Pear, British Virgin Islands | Gustavia | Philipsburg, St Maarten
Special Offers:
  • Non-Refundable Rate
  • Reduced Deposits
  • Signature Collection
$6,719 pp
Mar 28, 2026 (Sat - Sat)
7 Nt Caribbean Cruise
From St Maarten
Ports of Call:
Philipsburg, St Maarten | St Johns | Road Bay | Sopers Hole | Jost Van Dyke, Great Harbour | Jost Van Dyke, Great Harbour | Virgin Gorda / Prickly Pear, British Virgin Islands | Gustavia | Philipsburg, St Maarten
Special Offers:
  • Reduced Deposits
  • Signature Collection
$3,267 pp
Mar 28, 2026 (Sat - Sat)
21 Nt Caribbean Cruise
From St Maarten
Ports of Call:
Philipsburg, St Maarten | St Johns | Road Bay | Sopers Hole | Jost Van Dyke, Great Harbour | Jost Van Dyke, Great Harbour | Virgin Gorda / Prickly Pear, British Virgin Islands | Gustavia | Philipsburg, St Maarten | Ponta Delgada | Lisbon
Special Offers:
  • Non-Refundable Rate
  • Reduced Deposits
  • Signature Collection
$6,094 pp
Apr 4, 2026 (Sat - Sat)
14 Nt TransAtlantic Cruise
From St Maarten
Ports of Call:
Philipsburg, St Maarten | Ponta Delgada | Lisbon
Special Offers:
  • Reduced Deposits
  • Signature Collection
$3,226 pp
Apr 4, 2026 (Sat - Sun)
22 Nt TransAtlantic Cruise
From St Maarten
Ports of Call:
Philipsburg, St Maarten | Ponta Delgada | Lisbon | Cadiz | Gibraltar | Malaga | Almeria, Spain | Cartagena | Palma De Mallorca | Barcelona
Special Offers:
  • Non-Refundable Rate
  • Reduced Deposits
  • Signature Collection
$6,488 pp
Apr 14, 2026 (Tue - Sun)
12 Nt Southern Europe Cruise
From Lisbon
Ports of Call:
Lisbon, Portugal | Lisbon, Portugal | Lisbon, Portugal | Lisbon, Portugal | Lisbon, Portugal | Lisbon | Cadiz | Gibraltar | Malaga | Almeria, Spain | Cartagena | Palma De Mallorca | Barcelona
Special Offers:
  • Signature Collection
$6,761 pp
Apr 18, 2026 (Sat - Thu)
12 Nt Southern Europe Cruise
From Lisbon
Ports of Call:
Lisbon | Cadiz | Gibraltar | Malaga | Almeria, Spain | Cartagena | Palma De Mallorca | Barcelona | Madrid, Spain | Madrid, Spain | Madrid, Spain | Madrid, Spain | Madrid, Spain
Special Offers:
  • Signature Collection
$8,761 pp
Apr 18, 2026 (Sat - Sun)
8 Nt Western Mediterranean Cruise
From Lisbon
Ports of Call:
Lisbon | Cadiz | Gibraltar | Malaga | Almeria, Spain | Cartagena | Palma De Mallorca | Barcelona
Special Offers:
  • Reduced Deposits
  • Signature Collection
$4,461 pp
Apr 18, 2026 (Sat - Mon)
16 Nt Western Mediterranean Cruise
From Lisbon
Ports of Call:
Lisbon | Cadiz | Gibraltar | Malaga | Almeria, Spain | Cartagena | Palma De Mallorca | Barcelona | Palamos | Port Vendres | Sanary-Sur-Mer | Monte Carlo | Cannes | Portofino | Portoferraio | Rome
Special Offers:
  • Non-Refundable Rate
  • Reduced Deposits
  • Signature Collection
$6,709 pp
Apr 22, 2026 (Wed - Mon)
12 Nt Southern Europe Cruise
From Madrid
Ports of Call:
Madrid, Spain | Madrid, Spain | Madrid, Spain | Barcelona | Barcelona | Barcelona | Palamos | Port Vendres | Sanary-Sur-Mer | Monte Carlo | Cannes | Portofino | Portoferraio | Rome
Special Offers:
  • Signature Collection
$6,746 pp

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