14-Night St. Maarten to St. Maarten

Windstar Cruises · Wind Surf

Visit St. Maarten, Charlestown, Nevis, Pigeon Island, St.Lucia, Les Saintes, Guadeloupe, Gustavia, St. Barthelemy and 6 more ports

Departure St. Maarten
Return St. Maarten
Duration 14 Nights

Itinerary

  1. Day 1
    St. Maarten Arrives 12:00 AM · Departs 7:00 PM
  2. Day 2
    Charlestown, Nevis Arrives 8:00 AM · Departs 5:00 PM
  3. Day 3
    At Sea Arrives 8:00 AM · Departs 5:00 PM
  4. Day 4
    Pigeon Island, St.Lucia Arrives 8:00 AM · Departs 5:00 PM
  5. Day 5
    Les Saintes, Guadeloupe Arrives 8:00 AM · Departs 6:00 PM
  6. Day 6
    Gustavia, St. Barthelemy Arrives 8:00 AM · Departs 10:00 PM
  7. Day 7
    Basseterre, St. Kitts Arrives 8:00 AM · Departs 10:00 PM
  8. Day 8
    St. Maarten Arrives 6:00 AM · Departs 12:00 AM
  9. Day 9
    Falmouth, Antigua Arrives 8:00 AM · Departs 6:00 PM
  10. Day 10
    Road Bay, Anguilla Arrives 8:00 AM · Departs 6:00 PM
  11. Day 11
    Soper'S Hole, Tortola, B.V.I. Arrives 8:00 AM · Departs 6:00 PM
  12. Day 11
    Jost Van Dyke, B.V.I Arrives 7:00 PM · Departs 12:00 AM
  13. Day 12
    Jost Van Dyke, B.V.I Arrives 12:00 AM · Departs 10:00 PM
  14. Day 13
    Virgin Gorda, B.V.I Arrives 8:00 AM · Departs 5:00 PM
  15. Day 14
    Gustavia, St. Barthelemy Arrives 8:00 AM · Departs 5:00 PM
  16. Day 15
    St. Maarten Arrives 6:00 AM · Departs 12:00 AM

Ports of Call

  • St. Maarten
  • Charlestown, Nevis
  • Pigeon Island, St.Lucia
  • Les Saintes, Guadeloupe
  • Gustavia, St. Barthelemy
  • Basseterre, St. Kitts
  • Falmouth, Antigua
  • Road Bay, Anguilla
  • Soper'S Hole, Tortola, B.V.I.
  • Jost Van Dyke, B.V.I
  • Virgin Gorda, B.V.I

About This Cruise

14-night Windstar Cruises Wind Surf cruise from St. Maarten to Charlestown, Nevis, Pigeon Island, St.Lucia, Les Saintes, Guadeloupe and Gustavia, St.…

Cruise Line Windstar Cruises
Ship Wind Surf

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Frequently asked questions

What is included in the cruise fare?
Standard cruise fares include your cabin, onboard meals at main dining venues, most non-specialty entertainment, use of pools and common facilities, and transport between ports of call. Gratuities, specialty dining, alcoholic drinks, shore excursions and onboard spa services are typically billed separately.
How far in advance should I book this cruise?
For popular sailings, booking 6–12 months ahead typically gives the best cabin selection and fares. Last-minute discounts can appear 30–60 days before departure when the cruise line wants to fill remaining cabins on Wind Surf.
What documents do I need to board?
Most international itineraries require a passport valid for at least six months beyond your return date. Closed-loop sailings that depart and return to the same U.S. port from St. Maarten may accept a government-issued photo ID plus a certified birth certificate for U.S. citizens — always verify with the cruise line.
Can I change or cancel my booking?
Change and cancellation policies depend on Windstar Cruises's fare type and how close you are to departure. Refundable deposits typically allow changes up to the final-payment date without penalty; closer to sailing, cancellation fees scale up. Review the specific fare rules before booking.
What is a 14-night cruise like?
A 14-night cruise balances relaxing sea days with active port days. You can expect a mix of onboard programming — dining, entertainment, spa and fitness — and multiple shore excursions from Wind Surf. Pack for both formal nights and casual deck days.