Sail to fascinating destinations on The World's Best Small Ship Cruise Line
From £3,068 per person
All fares are displayed in Great British Pound, and pricing is per person based on twin share occupancy unless stated otherwise. Although all due care is taken to keep information as up-to-date as possible, pricing and availability are subject to change without notice: due to varying timing schedules of supplier automated update processes; currency fluctuations; fuel surcharges or government tax & fee changes and may not be guaranteed until paid in full. Gratuities may be an additional onboard charge depending on particular cruise line selected. Please ask your cruise consultant for any clarification of Terms & Conditions.
Pricing is based on departure date 06th Feb 2027
Itinerary Highlights
Philipsburg, St. Maarten – Begin your Caribbean adventure in Philipsburg, known for its beautiful beaches, duty-free shopping, colorful waterfront and lively island atmosphere.
Charlestown, Nevis – Discover the charming historic town of Charlestown and the relaxed beauty of Nevis, with opportunities to explore colonial heritage, tropical scenery and local culture.
Roseau, Dominica – Explore the “Nature Island” of the Caribbean, famous for lush rainforests, waterfalls, volcanic landscapes, hot springs and spectacular natural scenery.
Mayreau – Escape to the tranquil island of Mayreau, known for its secluded beaches, turquoise waters and peaceful Caribbean atmosphere.
Les Saintes – Visit this picturesque French Caribbean archipelago, featuring colorful waterfronts, beautiful bays, charming villages and stunning coastal views. Marina access is available at this stop.
Basse-Terre, Guadeloupe – Discover the lush natural beauty of Guadeloupe, with tropical forests, waterfalls, volcanic landscapes and opportunities to experience authentic French-Caribbean culture.
Gustavia, St. Barthélemy – Finish your island journey in glamorous Gustavia, famous for upscale boutiques, waterfront restaurants, beautiful beaches and spectacular harbor scenery. Marina access is available.
Cruise Overview

From the lush volcanic landscapes of Nevis Peak to the captivating charm of Les Saintes; hidden coves and secret beaches to exotic markets and lively cafés, you’ll discover the best of this region on a single Caribbean voyage. Sandy beaches, turquoise waters, verdant hills, and beautiful waterfalls blend seamlessly with the music, flavors, and joie de vivre that define Caribbean life.
Itinerary Highlights
Ship: Wind Surf
Cabin: Category B
Sail Date: 06th Feb 2027
Duration: 07 Nights

| Day | Date | Destination | Arrive | Depart |
| 1 | 6-Feb-27 | Philipsburg, St. Maarten | - | 07:00pm |
| 2 | 7-Feb-27 | Charlestown | 08:00am | 5:00pm |
| 3 | 8-Feb-27 | Roseau | 08:00am | 04:00pm |
| 4 | 9-Feb-27 | Mayreau | 08:00am | 5:00pm |
| 5 | 10-Feb-27 | Les Saintes | 12:00pm | 06:00pm |
| 6 | 11-Feb-27 | Basseterre | 8:00am | 10:00pm |
| 7 | 12-Feb-27 | Gustavia | 8:00am | 10:00pm |
| 8 | 13-Feb-27 | Philipsburg, St. Maarten | 06:00am |
The World's Best Small Ship Cruise Line
All cruise ships let you see the world. Only Windstar’s private yacht style cruises bring's you close enough so you can truly experience it. Each of our Windstar Cruises yachts serves between 148 and 342 guests. This intimacy provides you with the luxuries of time, space and freedom to immerse yourself in both the journey and the destination — in ways you may never have imagined possible.
Your Ship: Wind Surf
As part of our Wind Class, our 342-guest Wind Surf offers a sailing experience like no other — one with real working sails.
Newly upgraded under our Setting Sails initiative, Wind Surf features redesigned common areas that include lounge, the pool deck and bar, the Yacht Club Café, a newly minted wine room and much more.
Our flagship sailing yacht features stylish staterooms and multiple suites, including opulent Bridge Suites, an Officer’s Suite, and brand-new versions of the Broadmoor and Sea Island Suites currently on our Star Class yachts.
And did we mention all dining is included? From gourmet bites at our Yacht Club Café to specialty restaurants like Stella Bistro, our award-winning cuisine is always complimentary, so you can indulge freely.
Enquire Now!
All fares are displayed in Great British Pound, and pricing is per person based on twin share occupancy unless stated otherwise. Although all due care is taken to keep information as up-to-date as possible, pricing and availability are subject to change without notice: due to varying timing schedules of supplier automated update processes; currency fluctuations; fuel surcharges or government tax & fee changes and may not be guaranteed until paid in full. Gratuities may be an additional onboard charge depending on particular cruise line selected. Please ask your cruise consultant for any clarification of Terms & Conditions.