7-Day Windstar Classic Caribbean Cruise

Windstar Flagship 342-Guest Sailing Ship: Wind Surf

From the chic harborfront of Gustavia to the captivating charm of Les Saintes. From hidden coves and secret beaches to exotic markets and lively cafes. Discover the best of this region with one single Caribbean cruise. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre to the Caribbean life.

Get up to $200 Onboard Credit per stateroom + All-inclusive experience on select 2026/2027 Caribbean & Latin America Voyages when you book by October 31, 2025.

Ship: Wind Surf | Cruise Line: Windstar| Sail Date: December 26, 2026 | From/To: Roundtrip Philipsburg, St. Maarten | Length: 7-Nights

Window Stateroom (Cat. B/Deck 1/Forward or Aft) From

$2,751

Per person including all taxes, fees and port expenses

Window stateroom (Cat BX Deluxe/Deck 1/Midship) From

$2,951

Per person including all taxes, fees and port expenses

Window stateroom (Cat. A/Deck 2/Forward or Aft) From

$3,051

Per person including all taxes, fees and port expenses

Window Suite (Suite/Deck 3/Forward, Midship or Aft) From

$5,651

Per person including all taxes, fees and port expenses

All-Inclusive Package Includes:

~Wi-Fi

~Unlimited beer, wine and cocktails

~All gratuities

Popular Highlights:

  • Let yourself go - at Windstar's Signature Beach Party, where the Caribbean spirit is in full swing
  • Savor the distinctive French charm of enchanting Les Saintes
  • Enjoy the unspoiled paradise of Pinney's Beach where Nevis volunteers tag sea turtles at night.
  • Embrace the island life on St. Kitt's one-of-a-kind Shipwreck Beach.
  • Shop Gustavia's duty-free boutiques or grab a glass of the island's signature ti punch at a beachside bar.
Date Day Port Arrive Depart
Dec. 26, 2026 Sat. Philipsburg, St. Maarten 7:00pm
Dec. 27, 2026 Sun. Gustavia 8:00am 10:00pm
Dec. 28, 2026 Mon. Charlestown 8:00am 5:00pm
Dec. 29, 2026 Tues. Roseau 8:00am 4:00pm
Dec. 30, 2026 Wed. Mayreau 8:00am 5:00pm
Dec. 31, 2026 Thurs. Les Saintes 12:00pm 6:00pm
Jan. 1, 2026 Fri. Basseterre 8:00am 10:00pm
Jan. 2, 2026 Sat. Philipsburg, St. Maarten 6:00am

Windstar's Flagship Sailing Ship: Wind Surf

On any day, our 342-guest flagship, Wind Surf, 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 bowl of 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 underwent a significant renovation 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. An Officer’s Suite, which might be the only one of its kind, provides you with 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.

Windstar has always been known for our iconic sailing ships, and now we are embarking on a multi-year refresh of the Wind Class ships. The initiative, Setting Sails: A Wind Class Refresh, brings the tight-knit connection of the Windstar community to the forefront through the redesign of public spaces and staterooms. From a revamped lobby to a new pool and larger pool bar, new World Spa by Windstar to a redesigned lounge, this initiative also includes intricate details like new teak decks and décor for a timeless and welcoming experience. Wind Surf will complete her redesign in 2026.

*Prices are in USD, per person based on double occupancy, availability and subject to change without notice. All taxes, fees and port expenses are included in the above pricing. All promotions are capacity controlled by Windstar and can be eliminated at any time without notice. Other restrictions may apply. Ships’ registry: Bahamas