7-Day Windstar Windward Islands Surf & Sunset
Luxury Small Ship Cruise on Refreshed Wind Surf
Early Booking Offer – Get up to $200 Onboard Credit per stateroom + Free upgrade to all-inclusive package on select 2026-2027 Caribbean & Latin America, Japan, Canada & New England and Southeast Asia Sailings when you book by May 31, 2025!*
- Ship: Star Pride
- Cruise Line: Windstar Cruises
- Sail Date: November 8, 2026
- From/To: Roundtrip San Juan
- Length: 7-Days
Ocean View (Deck 4 Forward) Suite From
$2,630
per person including all taxes, fees and port expenses
Ocean View (Deck 4-Midship/Aft Suite) From
$2,730
per person including all taxes, fees and port expenses
Balcony Suite (Deck 5-Midship)
$3,790
per person including all taxes, fees and port expenses
Deluxe Suite (Decks 4, 5, 6-Midship)
$5,030
per person including all taxes, fees and port expenses
Windstar Knows the Way to the Caribbean
One of the most sought-after yachting destinations in the Caribbean, the Windward Islands give you a glimpse of what the West Indies looked like in days of old. Technicolor travel posters come to life in its lush green mountains, shimmering blue waters, swaying palm trees and uncrowded beaches. Colorful fishing boats bob in the harbor next to private yachts, and resorts give way to charming boutique hotels and B&Bs.
Pastel Georgian buildings, crumbling forts, and rusting canons recall the days when pirates roamed the seas and Britain and France fought over who would rule these islands. And while each island has its unique charms, the pace of life is almost universally slow, with time to absorb the copious amounts of natural beauty and chat with people who are genuinely welcoming.
Sip a local Carib beer in the shade of sea grape trees. Dive off the Watersports Platform and snorkel above coral gardens entirely undisturbed by your passage. Stand on the ramparts of forts that have seen centuries come and go staring out at a view that never grows old. Discover islands that perfectly match your dreams.
Popular Highlights:
Tour St. Barts to find a chic collection of designer botiques, stunning beaches, and delightful restaurants.
Pigeon Island National Park features splendid beaches, relics of Arawak Indians and English fort ruins.
Discover the underwater world of Les Saintes and enjoy some of the best snorkeling around in the deep blue waters of Guadaloupe.
Shop for spices, especially nutmeg and cinnamon in St. George’s local market.
The UNESCO site Piton’s two volcanic peaks rising more than 2,400 feet in St. Lucia.
Shop the 100% duty free island of two nations, St. Maarten and St. Martin.
| Date | Day | Port | Arrive | Depart |
|---|---|---|---|---|
| Nov. 8, 2026 | Sun. | San Juan, Puerto Rico | 5:00pm | |
| Nov. 9, 2026 | Mon. | At Sea | ||
| Nov. 10, 2026 | Tues. | St. George’s | 9:00am | 10:00pm |
| Nov. 11, 2026 | Wed. | Bequia | 8:00am | 10:00pm |
| Nov. 12, 2026 | Thurs. | Mayreau | 8:00am | 5:00pm |
| Nov. 13, 2026 | Fri. | Les Saintes | 10:00am | 5:00pm |
| Nov. 14, 2026 | Sat. | Marigot, Saint Martin | 8:00am | 3:00pm |
| Nov 15, 2026 | Sun. | San Juan, Puerto Rico | 7:00am |
Windstar’s Flagship Sailing Ship
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 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.
Always Included Complimentary:
- Open dining with no reservation fees required
- Non-alcoholic beverages, including coffee, tea and soda
- Beautifully appointed ocean-view suites
- Plush bathrobes and slippers
- Fresh flowers and fruit in your stateroom or suite
- Flat-screen TV
- Signature onboard deck barbecue*
- Onboard entertainment, including local performances in most regions
- 24-hour Room service
- Fully equipped Watersports Platform and use of all water sports equipment*
- Access to the Open Bridge
- Champagne welcome reception
- Signature Sail Away event from every port*
- Access to WorldSpa by Windstar sauna/steam room facilities, yoga and Pilates
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 the cruise line and can be removed at any time without notice. Applicable bookings: Windstar Pride: October 20, 2026 – March 21, 2027; Windstar Star October 31, 2026 – January 2, 2027. Other restrictions may apply. Ships’ registry: Bahamas
