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STAR COLLECTOR: CARIBBEAN EXPLORATIONS on Wind Surf

Wind Surf Capri
Exterior view of Wind Surf sailing near Capri, Italy
Photo Credit: Roger Paperno
  • Exterior view of Wind Surf sailing near Capri, Italy - Photo Credit: Roger Paperno
  • Exterior view of Wind Surf
  • Exterior view of Wind Surf - Photo Credit: Jeff Zaruba
  • Close-up exterior view of Wind Surf bow - Photo Credit: Roger Paperno
  • Exterior view of Wind Surf - Photo Credit: Roger Paperno
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
About Wind Surf
About Windstar Cruises
Windstar Cruises logo
THE WORLD'S BEST SMALL SHIP CRUISE LINE

NO ONE ELSE GOES SO FAR TO GET TRAVELERS SO CLOSE …
You’re closer to secluded coves, tiny villages, misty fjords. To ancient ruins, medieval alleyways, quaint marinas. To unspoiled beaches, unfamiliar cultures, undiscovered atolls. To enlivening your curiosity and awakening your sense of wonder. You’re closer than ever to the kind of authentic and unforgettable experiences that you travel to find in the first ...
Dec 07, 2025 through
Dec 21, 2025
Dec 1, 2025 7:00 PM
14 Nights from
$3,699.00 (USD)
Per Person
+ $265.00 taxes/fees
Category b
Inside
N/A
Outside
$3,699.00
Cat:B
$264.21 per night
Balcony
N/A
Suite
$9,799.00
Cat:OS
$699.93 per night
Special Offer!
Exclusive Benefits
8313792
Jan 18, 2025 through
Feb 01, 2025
Jan 12, 2025 7:00 PM
14 Nights from
$4,299.00 (USD)
Per Person
+ $265.00 taxes/fees
Category bx
Inside
N/A
Outside
$4,299.00
Cat:BX
$307.07 per night
Balcony
N/A
Suite
$10,099.00
Cat:OS
$721.36 per night
8278797
Dec 21, 2025 through
Jan 04, 2026
Dec 15, 2025 7:00 PM
14 Nights from
$4,299.00 (USD)
Per Person
+ $265.00 taxes/fees
Category b
Inside
N/A
Outside
$4,299.00
Cat:B
$307.07 per night
Balcony
N/A
Suite
$10,399.00
Cat:OS
$742.79 per night
8313793
More Departure Dates

Itinerary

Day Port Arrive Depart
1 St. Maarten 7:00 PM
2 Charlestown 8:00 AM 5:00 PM
3 Roseau 8:00 AM 5:00 PM
4 Pigeon Island 8:00 AM 5:00 PM
5 Les Saintes 8:00 AM 5:00 PM
6 Gustavia 8:00 AM 10:00 PM
7 Basseterre 8:00 AM 9:00 PM
8 St. Maarten 6:00 AM 7:00 PM
9 Falmouth Harbour 8:00 AM 6:00 PM
10 Road Bay 8:00 AM 6:00 PM
11 Jost Van Dyke, Great Harbour 7:00 PM
11 Soper's Hole 8:00 AM 6:00 PM
12 Jost Van Dyke, Great Harbour 10:00 PM
13 Virgin Gorda / Prickly Pear 8:00 AM 5:00 PM
14 Gustavia 8:00 AM 10:00 PM
15 St. Maarten 6:00 AM
Prices are per-person based on double occupancy, unless otherwise noted.