jewels of the windward islands

By the time February rolls around, we think you’ll be ready to escape the winter weather, and what better way to do that than by joining Huckleberry Travel on a luxury yacht sailing trip to the hidden gems of the Caribbean. We’ll be hosting a sailing on the Wind Surf — a ship with tall sails operated by one of our favorite cruise partners, Windstar Cruises. And if you join us, we’ve got some exclusive amenities to share with you!

This is the Caribbean of days gone by - deep blue waters, quiet coves, and tropical islands dotted with powdery beaches and lush green hillsides. Join Huckleberry Travel on a luxury yacht sailing from Barbados, and you'll experience the rugged natural beauty of St. Lucia, little-known isles that are off the tourist radar, and so much more. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled. This is everything that makes the Caribbean synonymous with Paradise.

With a port of call every day, at small ports where the big ships can't go, this is the perfect opportunity to experience the Caribbean in an authentic, immersive way. What better way to escape the coldest days of winter than sailing on a yacht with tall sails through the Caribbean?

About Windstar

Windstar Cruises offers a vacation experience that is 180 degrees from ordinary. We invite you to step away from the crowds and enjoy a small ship experience where freedom is the order of the day and casual elegance is the style of choice. Each yacht allows guests to sail among only 148-342 guests for a more intimate and personalized travel experience; all while you travel to the world’s most legendary places, best small ports, and hidden harbors. For anyone yearning for a more authentic travel experience, your yacht has arrived.

Windstar Cruises partners with the James Beard Foundation, which nominates and chooses winners of its culinary excellence awards. Cuisine on board is curated by Beard Foundation Award winners, with special culinary excursions available at ports of call on the itinerary.

About the Wind Surf

On any day, Windstar's flagship, Wind Surf, draws admiring glances as she glides majestically into port with her tall sails billowing. Spacious staterooms have lovely ocean views, comfy queen beds, and terrific bathrooms.

When you return to your stateroom, the luxury gets personal. Windstar’s signature bowls of flowers and 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 recently underwent a significant renovation in November 2019 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. A new Officer’s Suite, which might be the only one of its kind, provides you the chance to stay in the heart of the officer quarters tucked right behind the Bridge.

Plus, when you book through Huckleberry Travel, our fares include exclusive Virtuoso Amenities, such as a $250 experience credit, which Huckleberry Travel can use to create an exclusive shore experience for you, and a special welcome reception for our private group.

What do you think? This is a small ship that goes where the big ships can’t, so contact us if you’d like to reserve your preferred stateroom!