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 15-night cruise like?

A 15-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 15-night Star Collector: Caribbean Explorations from Philipsburg, St. Martin, Nov 20, 2027

Windstar Cruises · Wind Surf · Nov 20, 2027 – Dec 05, 2027

Visit Philipsburg, St. Martin, Gustavia, St. Barthelemy , St. John's, Antigua, Deshaies, Guadeloupe, Road Bay, Anguilla and 7 more ports

Departure Philipsburg, St. Martin

Return Philipsburg, St. Martin

Duration 15 Nights

From $4770 pp

Itinerary

Day 1

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

Gustavia, St. Barthelemy Arrives 8:00 AM · Departs 10:00 PM
Day 3

St. John's, Antigua Arrives 8:00 AM · Departs 10:00 PM
Day 4

Deshaies, Guadeloupe Arrives 7:00 AM · Departs 5:00 PM
Day 5

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

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

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

Jost Van Dyke, Great Harbour Arrives 12:00 AM · Departs 10:00 PM
Day 8

Virgin Gorda / Prickly Pear, British Virgin Island Arrives 8:00 AM · Departs 5:00 PM
Day 9

Philipsburg, St. Martin Arrives 6:00 AM · Departs 7:00 PM
Day 10

Charlestown, Nevis Arrives 8:00 AM · Departs 5:00 PM
Day 11

At Sea Arrives 8:00 AM · Departs 4:00 PM
Day 12

Mayreau, Grenadines Arrives 8:00 AM · Departs 5:00 PM
Day 13

Les Saintes, Guadeloupe Arrives 12:00 PM · Departs 6:00 PM
Day 14

Gustavia, St. Barthelemy Arrives 8:00 AM · Departs 10:00 PM
Day 15

Basseterre, St. Kitts Arrives 8:00 AM · Departs 5:00 PM
Day 16

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 $4770

Suite $6270

Ports of Call

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

About This Cruise

15-night Windstar Cruises Wind Surf cruise from Philipsburg, St. Martin to Gustavia, St. Barthelemy , St. John's, Antigua, Deshaies, 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 15-night cruise like?: A 15-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.