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 Philipsburg, St. Martin 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.

Wind Surf 14-night Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten from Philipsburg, St. Martin, Feb 20, 2027

Windstar Cruises · Wind Surf · Feb 20, 2027 – Mar 06, 2027

Visit Philipsburg, St. Martin, Charlestown, Nevis, Mayreau, Grenadines, Les Saintes, Guadeloupe, Basseterre, St. Kitts and 6 more ports

Departure Philipsburg, St. Martin

Return Philipsburg, St. Martin

Duration 14 Nights

From $6350 pp

Itinerary

Day 1

Philipsburg, St. Martin Arrives 1:00 PM · Departs 7:00 PM
Day 2

Charlestown, Nevis Arrives 8:00 AM · Departs 5:00 PM
Day 3

At Sea Arrives 8:00 AM · Departs 4:00 PM
Day 4

Mayreau, Grenadines Arrives 8:00 AM · Departs 5:00 PM
Day 5

Les Saintes, Guadeloupe Arrives 12:00 PM · Departs 6:00 PM
Day 6

Basseterre, St. Kitts Arrives 8:00 AM · Departs 10:00 PM
Day 7

Gustavia, St. Barthelemy Arrives 8:00 AM · Departs 10:00 PM
Day 8

Philipsburg, St. Martin Arrives 6:00 AM · Departs 7:00 PM
Day 9

Soper'S Hole, Tortola, B.V.I. Arrives 8:00 AM · Departs 6:00 PM
Day 9

Jost Van Dyke, Great Harbour Arrives 7:00 PM · Departs 11:59 PM
Day 10

Jost Van Dyke, Great Harbour Arrives 12:00 AM · Departs 10:00 PM
Day 11

Virgin Gorda / Prickly Pear, British Virgin Island Arrives 7:00 AM · Departs 5:00 PM
Day 12

Gustavia, St. Barthelemy Arrives 8:00 AM · Departs 10:00 PM
Day 13

Road Bay, Anguilla Arrives 8:00 AM · Departs 6:00 PM
Day 14

Falmouth Harbour, Antigua Arrives 8:00 AM · Departs 5:00 PM
Day 15

Philipsburg, St. Martin Arrives 6:00 AM · Departs 7:00 AM

Cabin Prices

Prices as of 2026-10-19.

Prices per person, based on double occupancy in USD.

Ocean View $6350

Suite $7820

Ports of Call

Philipsburg, St. Martin
Charlestown, Nevis
Mayreau, Grenadines
Les Saintes, Guadeloupe
Basseterre, St. Kitts
Gustavia, St. Barthelemy
Soper'S Hole, Tortola, B.V.I.
Jost Van Dyke, Great Harbour
Virgin Gorda / Prickly Pear, British Virgin Island
Road Bay, Anguilla
Falmouth Harbour, Antigua

About This Cruise

14-night Windstar Cruises Wind Surf cruise from Philipsburg, St. Martin to Charlestown, Nevis, Mayreau, Grenadines, Les Saintes, Guadeloupe and…

Cruise Line Windstar Cruises

Ship Wind Surf

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 Philipsburg, St. Martin 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.