Philipsburg, Sint Maarten
One of the places included in this itinerary.
○ = last seen (sold out or delisted).
Lowest fares with no residency, age, or service requirement — verify eligibility at booking. How our pricing works
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 30, 2027, the voyage visits 12 ports including Road Bay, Soper's Hole, Tortola, British, Jost Van Dyke. Fares start from $7,330 per person.
- Length
- 14 nights
- Departs
- Jan 30, 2027
- Returns
- Feb 13, 2027
- Ports of call
- 12
Voyage code SU20270130-14D
14 nights · Caribbean
Why this route stands out
A closer look at the journey
Price tracking
Today’s fare, in context
Price history
Cheaper than 68%All
Current prices
Per person · 2 guests
Tax and fee inclusion varies by fare source. Confirm the total, including any additional charges, before booking.
Inside
No recorded fare
Oceanview
No recorded fare
Balcony
No recorded fare
Suite
from $7,330
$523 / night
Fare rows
Deluxe Stateroom
Cabin grade
from $7,330
$523 / night
per person
Observed 14 Oct 2026, 08:16 UTC
Rate details
Rate name not supplied
Rate code not supplied
Rate conditions not supplied. Confirm the rate and its terms before booking.
This sailing
Catch the next fare drop
We’ll email you if this sailing drops below today’s $7,330 fare.
Check your email to finish
We sent a confirmation link to your inbox. Your alert is not on yet — click that link to switch it on.
The journey
14 nights, in order
Philipsburg, Sint Maarten
Explore Philipsburg, Sint MaartenDay by day
The full itinerary
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
Wind Surf
Deck plans
Scroll to explore · Double-tap to zoom
Keep exploring
More ways to take this journey
Other sailing dates
Same itinerary, different departure dates.
Departs
Jan 16, 2027
Voyage SU20270116-14D
from $5,899
$421 / night
