Skip to main content
Cruise ship

28 Nights - St. Maarten (Philipsburg) To Oranjestad, Aruba

28-night Star Collector: The Best Of The Windward & Leeward Isles Cruise

Windstar Cruises Logo
Wind Surf
cruise info

28 Nights - St. Maarten (Philipsburg) To Oranjestad, Aruba

  • 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
    | 6:00 AM - 6:00 PM
  25. Day 25
    Man O'War Bay, Tobago
    | Mon Jan 26, 2026
    | 8:00 AM - 5:00 PM
  26. Day 26
    Mayreau, Grenadines
    | Tue Jan 27, 2026
    | 8:00 AM - 6:00 PM
  27. Day 27
    Soufriere
    | Wed Jan 28, 2026
    | 8:00 AM - 4:00 PM
  28. Day 28
    At Sea
    | Thu Jan 29, 2026
  29. Day 29
    Kralendijk
    | Fri Jan 30, 2026
    | 1:00 PM - 10:00 PM
  30. Day 30
    Willemstad, Curacao
    | Sat Jan 31, 2026
    | 8:00 AM - 6:00 PM
  31. Day 31
    Oranjestad, Aruba
    | Sun Feb 1, 2026
    | Arrive 6:00 AM
Sailing Features
  • 28 Nights
  • Jan 4, 2026 / Feb 1, 2026
  • St. Maarten (Philipsburg)
  • Oranjestad, Aruba
  • Wind Surf
  • 31 Land Tours

Suites

Choose the perfect room for you
Oceanview
From: $9,195
Suite
From: $11,995
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.

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
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.

Windstar Cruises Expert Advisors

Connect with an Expert to personally walk you through this Itinerary
Wind Surf cruise ship

Windstar Cruises:   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.
  • Maiden Voyage:
    1990
  • Last Refurbished:
    2019
  • Registry:
    Bahamas
  • Gross Tonnage :
    14,745
  • Beam:
    66 ft (20.1 m)
  • Maximum Speed:
    12 knots
  • Ship Length:
    535 ft (163.1 m)
  • Passenger Capacity:
    342
  • Number of Crew:
    210
  • Crew Nationality:
    International
  • Number of Staterooms:
    150
  • Number of Suites:
    21
  • Dining / Restaurants:
    5
  • Pool:
    Yes
  • Number of Decks:
    6
  • Spa:
    Yes
  • Bars / Lounges:
    4
  • Fitness Center:
    Yes
  • Wheelchair Accessible:
    Yes

Ship Information

Explore Your Cruise Ship
  • Dining

  • Bars & Lounges

  • Onboard Activities

  • Outdoor Activities

  • Wellness

The colorfully painted beach houses of Slovenia as seen from a cave
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.
A beautiful wooden foyer with luxury seating and shelves filled with fine items
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.