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Windstar Wind Surf

21 Nights - St. Maarten (Philipsburg) To Bridgetown (Barbados)

21-night Star Collector: A Lesser Antilles Odyssey

Wind Surf
cruise info

21 Nights - St. Maarten (Philipsburg) To Bridgetown (Barbados)

  • Windstar Cruises: Wind Surf
  • |
  • January 4, 2026

itinerary

  1. Day 1
    St. Maarten (Philipsburg)
    | Sun Jan 4, 2026
    | Depart 7:00 PM
  2. Day 2
    Falmouth Harbour, Antigua
    | Mon Jan 5, 2026
    | 8:00 AM - 6:00 PM
  3. Day 3
    Road Bay
    | Tue Jan 6, 2026
    | 8:00 AM - 6:00 PM
  4. Day 4
    Sopers Hole, Tortola
    | Wed Jan 7, 2026
    | 8:00 AM - 6:00 PM
  5. Day 5
    Jost Van Dyke
    | Wed Jan 7, 2026
    | 7:00 PM - 11:59 PM
  6. Day 6
    Jost Van Dyke
    | Thu Jan 8, 2026
    | Depart 10:00 PM
  7. Day 7
    Virgin Gorda
    | Fri Jan 9, 2026
    | 8:00 AM - 5:00 PM
  8. Day 8
    Gustavia
    | Sat Jan 10, 2026
    | 8:00 AM - 10:00 PM
  9. Day 9
    St. Maarten (Philipsburg)
    | Sun Jan 11, 2026
    | 6:00 AM - 7:00 PM
  10. Day 10
    Basseterre, St. Kitts
    | Mon Jan 12, 2026
    | 7:00 AM - 10:00 PM
  11. Day 11
    Little Bay
    | Tue Jan 13, 2026
    | 8:00 AM - 6:00 PM
  12. Day 12
    Gustavia
    | Wed Jan 14, 2026
    | 8:00 AM - 11:00 PM
  13. Day 13
    Deshaies, Guadeloupe
    | Thu Jan 15, 2026
    | 12:30 PM - 10:00 PM
  14. Day 14
    Roseau, Dominica
    | Fri Jan 16, 2026
    | 8:00 AM - 5:00 PM
  15. Day 15
    Pigeon Island, St. Lucia
    | Sat Jan 17, 2026
    | 7:00 AM - 4:00 PM
  16. Day 16
    Bridgetown (Barbados)
    | Sun Jan 18, 2026
    | 5:00 AM - 6:00 PM
  17. Day 17
    Anse Mitan
    | Mon Jan 19, 2026
    | 9:00 AM - 11:00 PM
  18. Day 18
    Castries
    | Tue Jan 20, 2026
    | 8:00 AM - 4:00 PM
  19. Day 19
    Pigeon Island, St. Lucia
    | Tue Jan 20, 2026
    | 6:00 PM - 11:59 PM
  20. Day 20
    Pigeon Island, St. Lucia
    | Wed Jan 21, 2026
    | Depart 6:00 PM
  21. Day 21
    Bequia, Grenadines
    | Thu Jan 22, 2026
    | 8:00 AM - 10:00 PM
  22. Day 22
    Mayreau, Grenadines
    | Fri Jan 23, 2026
    | 8:00 AM - 6:00 PM
  23. Day 23
    St. George's, Grenada
    | Sat Jan 24, 2026
    | 7:00 AM - 2:00 PM
  24. Day 24
    Bridgetown (Barbados)
    | Sun Jan 25, 2026
    | Arrive 6:00 AM

Promotions

  • Pick Your Perk - Up to $1,000 Onboard Credit per Suite or One Free Pre or Post Hotel Night or Free Upgrade to All-Inclusive Experience for Premium Suite Guests!
  • 21 Nights
  • Jan 4, 2026 / Jan 25, 2026
  • St. Maarten (Philipsburg)
  • Bridgetown (Barbados)
  • Wind Surf
bonus offers
  • Onboard Credit

Staterooms & Suites

Choose the perfect room for you
Oceanview
From: $6,370
Suite
From: $8,970
Oceanview
Guarantee Stateroom

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.

Oceanview
Ocean View Stateroom

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.

Oceanview
Ocean View Stateroom

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.

Oceanview
Deluxe Ocean View Stateroom

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.

Oceanview
Deluxe Ocean View Stateroom

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.

Windstar Wind Surf
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.

Ship Information

Explore Your Cruise Ship
  • Dining

  • Bars & Lounges

  • Onboard Activities

  • Outdoor Activities

  • Wellness

Couple walking arm-in-arm on dirt path next to flowering hedge
Don't Miss Out on Any Trip Enhancing Shore Excursions!
Immerse yourself in local culture with authentic cooking classes, traditional dance lessons, and unforgettable visits to historical landmarks during your cruise shore excursions.
Hotel reception area with shiny wood floors, wood paneling on walls and fancy chandeliers
Extend Your Trip with Immersive Pre-Cruise or Post-Cruise Stays
Enjoy the local culture and savor delicious cuisine with pre-cruise or post-cruise stays, ensuring a seamless transition between your land and sea adventures.