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- Beach Fun & Sun: A Remote Caribbean Getaway from St. Maarten with Island Stay
Beach Fun & Sun: A Remote Caribbean Getaway from St. Maarten with Island Stay, 16 December 2026
Bespoke Cruise & Stay
Handpicked cruise, hotel stays and tours pair together for more of the journey, with your Voyage Consultant shaping every detail to your taste.
11 nights
Wind Surf
16 Dec '26Cruise overview
Somewhere between the barefoot ease of Anguilla’s Road Bay and the quietly glamorous streets of Gustavia, something shifts. Wind Surf moves through these waters at a pace that feels unhurried, calling at corners of the Caribbean that bigger ships simply cannot reach. Three nights in Philipsburg give you time to settle into island life before the sailing begins, and from there the journey unfolds across some of the most quietly beautiful stretches of the Lesser Antilles. Jost Van Dyke is little more than a dot on the map, yet it lingers long in the memory, all white sand and easy afternoons. St Barts, by contrast, arrives with a certain polish, its harbour lined with superyachts and its backstreets full of good food and unhurried style. This is a part of the world that rewards those willing to slow down and look closely.
Itinerary
Fly to Philipsburg
Your journey begins today as you fly from London to Philipsburg, St. Maarten. On arrival, a private transfer takes you directly to your hotel, where you can settle in and acclimatise before the days ahead.
Philipsburg, Sint Maarten
Embarkation at Philipsburg
Gustavia, Saint Barthélemy
Falmouth Harbour, Antigua
Road Bay, Anguilla
Soper's Hole and Jost Van Dyke, British Virgin Islands
Jost Van Dyke, Great Harbour, British Virgin Islands
Virgin Gorda / Prickly Pear, British Virgin Islands
Disembarkation at Philipsburg
Arrive home
What's Included
This exclusive cruise and stay experience includes:
- Return flights from London (alternative airports available on request)
- Private overseas transfers
- Three-night pre-cruise stay at the Palm Court Residence & Hotel at Orient Beach with breakfast
- Seven-night Caribbean cruise aboard Wind Surf
- All meals onboard, including specialty restaurants
- Signature onboard & beach barbecues
- Cruise taxes, fees and port expenses
- Post-cruise beach day at Divi Little Bay Resort
Gracious Staterooms
Size (approx): ~188 sq ft
Stylish comfort and ocean views welcome you with beautifully designed comfort.
Amenities
- Queen or Twin Configuration
- Lounge Area
- Shower
- Toiletries Provided
- Room Service Available
- Suite Benefits
- TV
- Wi-Fi (Additional Cost)
- Safe
- Hair Dryer
- Desk
- Vanity Area
- Telephone
- Mini Bar (Additional Cost)
Broadmoor Suite/Sea Island Suite
Size (approx): ~495 sq ft
Flagship suite offering distinct bedroom and living room, luxury bathroom, and premium features.
- Queen or Twin Configuration
- Lounge Area
- Shower
- Toiletries Provided
- Room Service Available
- TV
- Safe
- Hair Dryer
- Telephone
- Desk
- Mini Bar (Additional Cost)
Owner's Suite
Size (approx): ~242 sq ft
The Owner’s Suite blends timeless elegance with subtle curves, leather accents, and tailored patterns.
- Lounge Area
- Room Service Available
- Queen or Twin Configuration
- Vanity Area
- Shower
- Toiletries Provided
- Mini Bar (Additional Cost)
- TV
- Wi-Fi (Additional Cost)
- Safe
- Hair Dryer
- Telephone
- Desk
Spacious Suites
Size (approx): ~376 sq ft
Spacious suite with separate sitting area, luxurious finishes and excellent views.
- Queen or Twin Configuration
- Shower
- Toiletries Provided
- Room Service Available
- TV
- Wi-Fi (Additional Cost)
- Safe
- Hair Dryer
- Desk
- Lounge Area
- Vanity Area
- Telephone
- Mini Bar (Additional Cost)
Gracious Staterooms
Size (approx): ~188 sq ft
Stylish comfort and ocean views welcome you with beautifully designed comfort.
- Queen or Twin Configuration
- Lounge Area
- Shower
- Toiletries Provided
- Room Service Available
- Suite Benefits
- TV
- Wi-Fi (Additional Cost)
- Safe
- Hair Dryer
- Desk
- Vanity Area
- Telephone
- Mini Bar (Additional Cost)
Star Deck
- Stella Bistro
- Veranda/Candles
- Fitness Centre
- Terrace Bar
Bridge Deck
- Bridge
- World Spa by Windstar
- Compass Rose Bar
- Owner’s Suite
- Broadmoor Suite
- Sea Island Suite
Main Deck
- Amphora Restaurant
- Amphora Wine Room
- Lounge
- Reception
- Yacht Club Café
- Cruise Consultant Desk
- Destination Desk
- Star Boutique
- Pool / Pool Bar / Whirlpools
Deck Three
- Suites
- TX Staterooms
Deck Two
- Watersports Platform
- A Staterooms
- AX Staterooms
Deck One
- BX Staterooms
- B Staterooms
- Medical Facility
Ship features
Wind Surf marries classic sailing romance with modern yacht comforts and upscale amenities.
- Five large sails up to 67.5 m high
- Full-service spa, fitness centre and wellness offerings
- Multiple dining outlets including AmphorA, Stella Bistro and Candles
- Open-bridge policy allowing guest visits
- Watersports platform with snorkeling, paddleboards etc.
- Indoor & outdoor lounges, bars, library, photo gallery
- Pools, two whirlpools and reclining decks
- Boutique shopping and signature shop
Accommodation
Accommodation
The ship offers a variety of staterooms and suites, all refined in style. Bridge Suites and Officer’s Suites deliver extra space and views. Amenities include plush linens, private bathrooms, in-room entertainment, climate control, and luxury toiletries.
Dining
Dining
Wind Surf’s culinary programme spans a range of refined options. AmphorA Restaurant offers elegant plated dining. Stella Bistro provides a more casual, lighter menu. Candles serves romantic dinners under the stars, and the Veranda or Yacht Club Espresso & Sandwich Bar accommodate informal bites. The Terrace Bar and Pool Bar support dining al fresco, while room service ensures flexibility. All venues reflect seasonal and local ingredients across menus.
Amenities
Amenities
Guests are pampered with a full spa, fitness centre, open decks, signature lounges (Compass Rose, The Lounge), open-bridge access and boutique shopping. The ship also features a photo gallery, watersports platform, two whirlpools, swimming pool and multiple bars.
Spa
Spa
WindSpa provides massage and beauty treatments, a sauna and wellness therapies in a tranquil setting. Guests can unwind after active days of sailing and excursions with refreshing treatments and relaxation zones.
Entertainment
Entertainment
Evening ambience is elegant and relaxed: live music in lounges, guest lectures, stargazing sessions, sail-raising ceremonies and casual gatherings. The Compass Rose and Lounge host refined social evenings.
Families
Families
Wind Surf is primarily geared toward adult travellers and couples, but families may be accommodated in certain suites. The ship’s atmosphere remains upscale and calm rather than child-centric.