Classic Caribbean

Was SG$3,700 per person

SG$3,030 per person

With RCI Exchange (7TP or 20,000 Points) - Inclusive of RCI Exchange Fee*

Duration: 7 Nights

Region: Caribbean

Cruise Line: Windstar Cruises

Cabin: Oceanview

Deal Code: DC194SR1

1300 301 022

Deal Description

Pricing is based on departure date 28th Feb 2026

Embarkation from Philipsburg, St. Maarten

Itinerary Highlights

Philipsburg, St. Maarten

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.

Charlestown

This capital of Nevis with its narrow streets and brightly painted Victorian and Georgian stone buildings is full of colonial history. Alexander Hamilton lived here as a child and you can see the ruins of the Hamilton Estate. Lovely Pinney’s Beach is nearby and a group of volunteers work at night tagging sea turtles here and on the other beautiful beaches. Walk the main street and check out the Museum of Nevis History, St. Thomas Lowland Church and the Nevisian Heritage Village to name a few of the historic sites here.

Roseau

Get ready for a full day with plenty to do. Snorkel alongside brilliant parrot fish in the bubbly waters of Champagne Beach. Take a break to enjoy more than 150 species of plants and brilliant red-necked Jaco parrots at the botanical gardens. If you’re up for an optional hike, don’t miss Boiling Lake and the Valley of Desolation at Dominica’s Morne Trois Pitons National Park, a UNESCO World Heritage Site.

Mayreau

With fewer than 300 inhabitants and miles of secluded beaches, it's easy to feel as if you're on your own private island. Saline Bay is a delightful anchorage that separates the Caribbean from the Atlantic - and a perfect place to play with some of the toys from the Watersports Platform.

Les Saintes

This is the Caribbean as you’ve always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.

Basseterre

With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean’s small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.

Gustavia

Affectionately known as St. Barts, the Caribbean’s most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island’s signature ti punch as kite surfers fly by.

Itinerary Map

Why Windstar?

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

Wind Surf, the world’s largest sailing ship, 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.

Itinerary Overview

Philipsburg, Charlestown, Roseau, Mayreau, Les Saintes, Basseterre, Gustavia, Philipsburg

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Terms & Conditions

* Conditions apply. Offer is limited, subject to availability and change without notice. Promotion is correct and valid at the time of publication. Booking and full supplier terms and conditions apply. Valid for new bookings only and not combinable with any other offer (unless stated). Pricing is inclusive of RCI Exchange Fee of SGD 164.

All fares are displayed in SGD, 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.