Philipsburg, Sint Maarten
One of the places included in this itinerary.
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7-night Caribbean cruise from Philipsburg, Sint Maarten on Wind Surf
The Classic Caribbean is a 7-night Caribbean cruise aboard Wind Surf, operated by Windstar Cruises. Departing Philipsburg, Sint Maarten on January 23, 2028, the voyage visits 7 ports including Charlestown, Nevis, Roseau, Mayreau. Fares start from $2,362 per person.
- Length
- 7 nights
- Departs
- Jan 23, 2028
- Returns
- Jan 30, 2028
- Ports of call
- 7
Voyage code SU20280123-7D
7 nights · Caribbean
Why this route stands out
A closer look at the journey
Price tracking
Today’s fare, in context
Price history
30 days
Current prices
Per person · 2 guests · incl. taxes & fees
Inside
Not available
Oceanview
from $2,362
$337 / night
Fare rows
Stateroom
Cabin grade
from $2,362
$337 / night
per person · incl. taxes & fees
Deluxe Stateroom
Cabin grade
from $2,537
$362 / night
per person · incl. taxes & fees
Stateroom
Cabin grade
from $2,677
$382 / night
per person · incl. taxes & fees
Deluxe Stateroom
Cabin grade
from $2,922
$417 / night
per person · incl. taxes & fees
Balcony
Not available
Suite
from $3,202
$457 / night
Fare rows
Deluxe Stateroom
Cabin grade
from $3,202
$457 / night
per person · incl. taxes & fees
Suite
Cabin grade
from $5,267
$752 / night
per person · incl. taxes & fees
Officers’ Suite
Cabin grade
from $7,017
$1,002 / night
per person · incl. taxes & fees
Bridge Suite
Cabin grade
from $8,767
$1,252 / night
per person · incl. taxes & fees
Prices verified Sep 7, 2026
This sailing
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The journey
7 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
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