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 27, 2027

Windstar Cruises · Wind Surf · Feb 27, 2027 – Mar 13, 2027

Visit Philipsburg, St. Martin, Soper'S Hole, Tortola, B.V.I. , Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Island, Gustavia, St. Barthelemy and 6 more ports

Departure Philipsburg, St. Martin

Return Philipsburg, St. Martin

Duration 14 Nights

From $6770 pp

Itinerary

Day 1

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

Soper'S Hole, Tortola, B.V.I. Arrives 8:00 AM · Departs 6:00 PM
Day 2

Jost Van Dyke, Great Harbour Arrives 7:00 PM · Departs 12:00 AM
Day 3

Jost Van Dyke, Great Harbour Arrives 12:00 AM · Departs 10:00 PM
Day 4

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

Gustavia, St. Barthelemy Arrives 8:00 AM · Departs 10:00 PM
Day 6

Road Bay, Anguilla Arrives 8:00 AM · Departs 6:00 PM
Day 7

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

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

Charlestown, Nevis Arrives 8:00 AM · Departs 5:00 PM
Day 10

At Sea Arrives 8:00 AM · Departs 4:00 PM
Day 11

Mayreau, Grenadines Arrives 8:00 AM · Departs 5:00 PM
Day 12

Les Saintes, Guadeloupe Arrives 12:00 PM · Departs 6:00 PM
Day 13

Basseterre, St. Kitts Arrives 8:00 AM · Departs 10:00 PM
Day 14

Gustavia, St. Barthelemy Arrives 8:00 AM · Departs 10:00 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 $6770

Suite $11110

Ports of Call

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

About This Cruise

14-night Windstar Cruises Wind Surf cruise from Philipsburg, St. Martin to Soper'S Hole, Tortola, B.V.I. , Jost Van Dyke, Great Harbour, Virgin Gorda /…

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.