Sailing Update: The March 28, 2026 departure has passed, but 22 similar active Windstar Cruises offers are open for booking below!
SIMILAR 2026 & 2027 SAILINGS AVAILABLE

21-night Star Collector: Spectacular Transatlantic Journey: Caribbean To The Azores Cruise

St. Maarten (Philipsburg)/Lisbon

Similar Active Windstar Cruises Offers

Explore comparable upcoming itineraries with exclusive Signature Travel Network amenities.

Dec 05, 2026Special Rate
Windstar Cruises • Wind Surf
14-night Ocean Crossings Cruise
14 Nights • Lisbon/St. Maarten (Philipsburg)
Dec 19, 2026From $2,693
Windstar Cruises • Wind Surf
7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise
7 Nights • Roundtrip St. Maarten (Philipsburg)
Dec 19, 2026From $5,887
Windstar Cruises • Wind Surf
14-night Star Collector: Caribbean Explorations Cruise
14 Nights • Roundtrip St. Maarten (Philipsburg)
Dec 26, 2026From $5,811
Windstar Cruises • Wind Surf
14-night Star Collector: Caribbean Explorations Cruise
14 Nights • Roundtrip St. Maarten (Philipsburg)
Dec 26, 2026From $2,817
Windstar Cruises • Wind Surf
7-night Classic Caribbean Cruise
7 Nights • Roundtrip St. Maarten (Philipsburg)
Looking for a specific departure date or custom package? Call 1 (888) 883-0460 Browse All Live Windstar Cruises Sailings →

Voyage Overview

Embarkation
St. Maarten (Philipsburg)
Disembarkation
Lisbon
About the Ship
On any day, the 342-guest flagship, Wind Surf, the world’s largest sailing ship, draws admiring glances as she glides majestically into port with her tall sails billowing and her beauty is far more than skin deep. During their cruise, you will find the perfect setting for ‘making an entrance’ in the beautiful reception area.

Stateroom Options

Deluxe Ocean View Stateroom
Deluxe Ocean View Stateroom (Cat TX)
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Size: 188 square feet (18 square meters). 
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers. Note: Staterooms with 3rd Berths: 117–139; all suites (excluding 501). Staterooms with One Queen Size Bed Only (no twin option): 101, 102, 157, 301-304.

Officer's Suite
Officer's Suite (Cat OS)
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Size: 242 square feet (22.5 square meters) and 1 bathroom.
For the ultimate in nautical experiences, reserve the new Officer’s Suite located close to the Bridge where the own ship’s officers have their quarters. With its unique “insider” location and 242 square feet of comfort, the nautically appointed Officer’s Suite offers an experience you won’t find on any other cruise line.

Suite
Suite (Cat STE)
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Size: 242-376 square feet (22.5-35 square meters). Some Suites have 2 bathrooms. 
You’ll find the perfect space for time together — and plenty of room for time to yourself. You’ll even enjoy two full separate bathrooms. All the amenities of the staterooms await you, plus a beautiful sitting area, and two flat-screen television sets with DVD players.

Bridge Suite
Bridge Suite (Cat BRS)
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Size: 495 square feet (46 square meters).
The ultimate in space and style surrounds you in 495 square feet of pure indulgence. Separate bedroom and living room with an in-suite dining area is an invitation to relaxation. And possibly best of all, your expansive bathroom features both a whirlpool spa tub and a massage shower.

Deluxe Ocean View Stateroom
Deluxe Ocean View Stateroom (Cat AX)
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Size: 188 square feet (18 square meters). 
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.

Deluxe Ocean View Stateroom
Deluxe Ocean View Stateroom (Cat BX)
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Size: 188 square feet (18 square meters). 
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers. Note: Staterooms with 3rd Berths: 117–139; all suites (excluding 501). Staterooms with One Queen Size Bed Only (no twin option): 101, 102, 157, 301-304.

Ocean View Stateroom
Ocean View Stateroom (Cat A)
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Size: 188 square feet (18 square meters). 
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers.

Ocean View Stateroom
Ocean View Stateroom (Cat B)
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Size: 188 square feet (18 square meters). 
Stylish comfort and ocean views welcome you in 188 square feet of beautifully designed comfort. Your queen bed (which can be separated as twins if you prefer) is swathed in luxurious Egyptian cotton linens. Before or after you enjoy an invigorating massage shower with soothing L’Occitane® bath products, wrap up in your waffle-weave robe, have a snack from the fresh fruit bowl, or simply stretch out and smell the flowers. Note: Staterooms with 3rd Berths: 117–139; all suites (excluding 501). Staterooms with One Queen Size Bed Only (no twin option): 101, 102, 157, 301-304.

Guarantee Stateroom
Guarantee Stateroom (Cat Y)
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With this selection, you are guaranteed to receive a stateroom within a selected category, anywhere on the ship. However, the actual room assignment and location on the ship may be determined at any time after your reservation has been completed and paid in full up to the day of sailing.

Included Amenities

Exclusive Bonus:
  • $300 Per Couple Shipboard Credit

Note: Amenities may not be combinable with fares shown. Additional restrictions apply.

  • 21-night Cruise
  • Meals
  • Entertainment
Similar Voyages From
$2,693
per person • 22 active offers

VIEW UPCOMING OFFERS (22) REQUEST A FREE QUOTE VIEW ALL WINDSTAR CRUISES OFFERS
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Trip Summary
Ship Name Wind Surf
Departure Date March 28, 2026
Duration 21 Nights
Offer ID 1559493
Call Vincent Vacations: 1 (888) 883-0460