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14-night Caribbean cruise from Philipsburg, Sint Maarten on Wind Surf

The Caribbean Explorations - Philipsburg, St. Maarten to Philipsburg, St. Maarten is a 14-night Caribbean cruise aboard Wind Surf, operated by Windstar Cruises. Departing Philipsburg, Sint Maarten on January 16, 2027, the voyage visits 12 ports including Road Bay, Soper's Hole, Tortola, British, Jost Van Dyke. CruiseCaptain has fare history for this sailing.

Length
14 nights
Departs
Jan 16, 2027
Returns
Jan 30, 2027
Ports of call
12

Voyage code SU20270116-14D

Philipsburg, Sint Maarten

14 nights · Caribbean

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Why this route stands out

A closer look at the journey

Philipsburg, Sint Maarten

One of the places included in this itinerary.

Road Bay

One of the places included in this itinerary.

Virgin Gorda (BVI)

One of the places included in this itinerary.

Price tracking

Today’s fare, in context

Price history

Cheaper than 91%
30 days
Fare details

Fare details

Per person
Current fares

No live fare right now.

Tracked range
Mar 26 – Oct 14
Price history by cabin type
CabinLast recordedLowestHighest
Oceanview $7,470 · Sep 21 $5,599 on Apr 6 $8,380 on Sep 11
Suite $19,090 · Sep 15 $7,296 on May 10 $19,090 on Sep 15
Cabin grades
8 total
StateroomOceanview · A
Deluxe StateroomOceanview · AX
StateroomOceanview · B
Deluxe StateroomOceanview · BX
Bridge SuiteSuite · BRS
Officers’ SuiteSuite · OS
SuiteSuite · STE
Deluxe StateroomSuite · TX

○ = last seen (sold out or delisted).

Lowest fares with no residency, age, or service requirement — verify eligibility at booking. How our pricing works

Current prices

Per person · 2 guests

Tax and fee inclusion varies by fare source. Confirm the total, including any additional charges, before booking.

Price information is not available.

This sailing

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The journey

14 nights, in order

Philipsburg, Sint Maarten

Day 1 Jan 16, 2027

Philipsburg, Sint Maarten

Explore Philipsburg, Sint Maarten

Day by day

The full itinerary

16 scheduled calls
Wind Surf

Your ship

Wind Surf

On any day, our 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 – and, appropriately, that’s only the beginning. When you return to your stateroom, the luxury gets personal. Windstar’s signature bowls of flowers and fresh fruit will still be waiting for you, along with rich tufted headboards, soft seascape colors, beautiful new upholstery, and fine count Egyptian cotton linens welcome you to an oasis of relaxing indulgence. Wind Surf recently underwent a significant renovation in November 2019 of public spaces and suites, including an expanded lounge with new lights and sound for upcoming stage performances. Relax into the destinations you’re visiting at the new World Spa by Windstar, which will offer regional spa treatments, including massage styles like Swedish, Japanese Shiatsu and Hawaiian Lomi Lomi. A new Officer’s Suite, which might be the only one of its kind, provides you the chance to stay in the heart of the officer quarters tucked right behind the Bridge. Everything about Wind Surf speaks of welcome. Come aboard and see it for yourself.

4★ 14,745 GT 342 Passengers Built 1989
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Deck plans

Wind Surf deck plan — Deck 1

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