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14 Nights - St. Maarten (Philipsburg) Round Trip

14-night Star Collector: Caribbean Explorations

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Wind Surf
cruise info

14 Nights - St. Maarten (Philipsburg) Round Trip

  • Windstar Cruises: Wind Surf
  • |
  • December 21, 2025

itinerary

  1. Day 1
    St. Maarten (Philipsburg)
    | Sun Dec 21, 2025
    | Depart 7:00 PM
  2. Day 2
    Charlestown
    | Mon Dec 22, 2025
    | 8:00 AM - 5:00 PM
  3. Day 3
    Roseau, Dominica
    | Tue Dec 23, 2025
    | 8:00 AM - 5:00 PM
  4. Day 4
    Pigeon Island, St. Lucia
    | Wed Dec 24, 2025
    | 8:00 AM - 5:00 PM
  5. Day 5
    Iles des Saintes
    | Thu Dec 25, 2025
    | 8:00 AM - 5:00 PM
  6. Day 6
    Gustavia
    | Fri Dec 26, 2025
    | 8:00 AM - 10:00 PM
  7. Day 7
    Basseterre, St. Kitts
    | Sat Dec 27, 2025
    | 8:00 AM - 9:00 PM
  8. Day 8
    St. Maarten (Philipsburg)
    | Sun Dec 28, 2025
    | 6:00 AM - 7:00 PM
  9. Day 9
    Falmouth Harbour, Antigua
    | Mon Dec 29, 2025
    | 8:00 AM - 6:00 PM
  10. Day 10
    Road Bay
    | Tue Dec 30, 2025
    | 8:00 AM - 6:00 PM
  11. Day 11
    Sopers Hole, Tortola
    | Wed Dec 31, 2025
    | 8:00 AM - 6:00 PM
  12. Day 12
    Jost Van Dyke
    | Wed Dec 31, 2025
    | 7:00 PM - 11:59 PM
  13. Day 13
    Jost Van Dyke
    | Thu Jan 1, 2026
    | Depart 10:00 PM
  14. Day 14
    Virgin Gorda
    | Fri Jan 2, 2026
    | 8:00 AM - 5:00 PM
  15. Day 15
    Gustavia
    | Sat Jan 3, 2026
    | 8:00 AM - 10:00 PM
  16. Day 16
    St. Maarten (Philipsburg)
    | Sun Jan 4, 2026
    | Arrive 6:00 AM
Sailing Features
  • 14 Nights
  • Dec 21, 2025 / Jan 4, 2026
  • St. Maarten (Philipsburg)
  • St. Maarten (Philipsburg)
  • Wind Surf
  • 16 Land Tours

Suites

Choose the perfect room for you
Oceanview
From: $4,419
Suite
From: $6,119
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. 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
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Debbie Welch

(520) 232-5501
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Lisa Summer

(520) 276-4085
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Danielle Doran

(520) 232-5588
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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.