Cruising the Windward Islands: A 7-Day Yachting Escape

by | Yachting

The Windward Islands, nestled in the southern Caribbean, offer some of the most diverse landscapes and thrilling experiences for yacht enthusiasts. Following in the wake of our previous voyages through the U.S. Virgin Islands and the Leeward Islands, this itinerary blends relaxation with adventure, taking you through the best of the Windwards.

Day 1: Barbados – A Grand Welcome

Start your journey in Barbados, where you can dock in the Port of Bridgetown. Spend the day exploring historic Bridgetown, a UNESCO World Heritage Site, or anchor off Payne’s Bay for some beach relaxation. For dining, consider The Cliff, known for its breathtaking views and world-class cuisine. The island also offers excellent snorkeling and diving opportunities around Folkestone Marine Park, just a short journey from the capital.

Exclusive Yachts - Bridgetown, Barbados
Exclusive Yachts - Beautiful scenery of Saint Lucias Twin Pitons with flowers

Day 2: Saint Lucia – The Pitons Await

Depart from Barbados and journey to Saint Lucia, where the famous Pitons—two volcanic spires—greet you as you approach the island. Anchor at Soufrière Bay for an up-close view of the Pitons. Marigot Bay is another great spot to dock, offering a calm and scenic anchorage with lush surroundings. This bay is often described as one of the Caribbean’s most beautiful harbors.

Day 3: Discover Saint Lucia’s Beauty

Take in the beauty of Saint Lucia as you cruise along its stunning western coast. Stop at Anse Chastanet, a tranquil beach ideal for snorkeling and swimming, or head to the nearby secluded Anse Mamin, accessible directly by yacht. For an unforgettable adventure, visit Sulphur Springs, home to the world’s only drive-in volcano, where you can not only take a guided tour but also enjoy a rejuvenating mud bath or relax in the therapeutic hot springs.

Exclusive Yachts - Anse Mamin is a bay on the coast with a small black sand beach in the district of Soufrière, Saint Lucia. It is located near Anse Chastanet and the two beaches are linked by a rocky path under the cliffs
Exclusive Yachts - Wallilabou Bay, Saint Vincent and the Grenadines - December 19, 2018: View from the shore out to sea and coconut palm at Wallilabou Anchorage - Pirates of the Caribbean's Port Royale - Saint Vincent.

Day 4: St. Vincent – Unwind in the Grenadines

Head toward St. Vincent, a volcanic island with a raw, unspoiled beauty. Drop anchor at Wallilabou Bay, known for its role in the “Pirates of the Caribbean” films. The bay offers good anchorage and an opportunity to explore the nearby waterfalls or simply relax in the peaceful surroundings. Alternatively, navigate to Admiralty Bay in Bequia for a more vibrant scene, with local eateries and beach bars.

Day 5: Grenadines Adventure – The Tobago Cays

Cruise into the stunning Tobago Cays, a protected marine park that is a favorite among yacht enthusiasts. The shallow, crystal-clear waters are ideal for anchoring close to shore. Spend the day snorkeling with turtles, exploring the coral reefs, or simply lounging on the pristine beaches of Petit Tabac or Baradal Island. These secluded cays offer the ultimate in remote, natural beauty.

Exclusive Yachts - Aerial drone view of tropical islands and turquoise Caribbean sea of Tobago cays in St Vincent and Grenadines
Exclusive Yachts - Grand Anse Beach St George Grenada The Caribbean

Day 6: Cruise to Grenada – Spice Island

Head south to Grenada, the “Spice Island” of the Caribbean. Anchor in Prickly Bay or the Carenage, both offering calm waters and access to the island’s vibrant culture. Spend the afternoon cruising along Grenada’s scenic coastline, with a stop at Grand Anse Beach, a two-mile stretch of white sand that’s easily accessible by yacht. For dining, The Beach House offers a beautiful beachfront location with a menu inspired by local spices and seafood.

Day 7: Grenada – Relax and Reflect

On your final day, take time to enjoy Grenada’s secluded beaches and bays. Morne Rouge Bay, also known as BBC Beach, offers a peaceful anchorage with calm, shallow waters—perfect for a relaxing final swim. For those seeking a bit of adventure, journey around the island’s southern tip to visit Hog Island, a remote spot that’s popular with the yachting community.

Exclusive Yachts - Palm tree lined Morne Rouge beach, Grenada

A yachting trip through the Windward Islands offers a perfect balance of adventure and tranquility. From the vibrant culture of Barbados to the serene waters of the Tobago Cays, each day promises new experiences and breathtaking views. Whether you’re seeking relaxation, exploration, or a mix of both, this itinerary is your gateway to the Caribbean’s southern treasures.

Ready to embark on this unforgettable journey? Discover how our Yachting Membership can make this dream a reality.