Charters For Custom Multi Day Adventures

Explore multiple islands from the comfort and luxury of our fully staffed sailing yacht The Bailey Grace.

The region's abundant natural wonders, warm tropical climate, and vibrant culture make it a sailor's paradise.

Imagine cruising through crystal-clear turquoise waters, feeling the gentle sea breeze on your face as you explore a vast expanse of idyllic islands.


Sailing the Caribbean also offers the freedom to anchor in secluded coves, untouched by crowds, and enjoy peaceful sunsets, stargazing, and tranquility.

Explore charming coastal towns during multi day adventures, visit historic sites, and savor mouthwatering Caribbean cuisine, blending African, European, and indigenous influences.

With a myriad of sailing routes and destinations to choose from, you can embark on a unique journey tailored to your preferences.

Whether you seek multi day adventures, relaxation, or a vibrant cultural experience.

Sailing around the Caribbean is an amazing opportunity for multi day adventures to
disconnect from the stresses of daily life,
reconnect with nature,
and embrace the laid-back island lifestyle
that permeates this enchanting region.



Welcome to Barbuda, a captivating Caribbean gem! Sail towards this paradise and be enchanted by pristine beaches, vibrant culture, and attractions. Nature lovers adore its unspoiled landscapes and tranquility. Barbuda's world-renowned beaches are a main attraction. Sink your toes into 17-Mile Beach's soft, pink sand or explore secluded coves. Visit the mesmerizing Frigate Bird Sanctuary with over 170 bird species, including frigatebirds. Dining in Barbuda offers exceptional options. Nobu, an exquisite restaurant, fuses Japanese and Caribbean flavors, tantalizing taste buds. For a laid-back experience, Shack a Kai is a must-visit, offering mouthwatering seafood and local delicacies on the charming beachfront. Anchor your boat, step onto Barbuda's shores, and discover natural beauty, warm hospitality, and culinary delights. Unforgettable memories await in this slice of paradise.


Embark on a sailing adventure from Antigua to Montserrat, the Emerald Isle. Depart Falmouth Harbour for a 5-6 hour sail, marveling at the approaching Soufriere Volcano. Upon arrival at Little Bay, enjoy a guided tour of the island. Visit Plymouth, the exclusion zone, Hilltop Coffee House, Runaway Ghaut, black sand beaches, and more unique spots. Experience the excellence of Montserrat's people, molded by nature and nurtured by God. Savor freshly prepared meals aboard the sailing yacht, surrounded by Little Bay's dynamic coastline. Extend your stay for rainforest hikes, snorkeling, fishing trips, or relaxing on quiet beaches. Wake up to refreshing swims or paddleboarding before sailing around the island. Witness the ever-active Soufriere Volcano's view from the sea, a unique experience exclusive to us. Optimal duration: 1-3 nights, but we can customize longer-term adventures, including neighboring islands.


Ste. Marie, Guadeloupe is a sailor's paradise, offering a perfect blend of natural wonders, cultural heritage, and unforgettable experiences.

Start your adventure by exploring the remarkable Pointe des Chateaux, where dramatic cliffs meet the turquoise waters, offering breathtaking views and tranquil hiking trails.

Next, anchor your boat at Anse à la Gourde, a pristine beach with powdery white sand and crystal-clear waters, perfect for swimming, snorkeling, and basking in the sun.

Don't miss out on the unforgettable experience of diving in the Jacques Cousteau Underwater Reserve, renowned for its vibrant coral reefs and marine life. End your day at La Datcha, a lively marina with vibrant waterfront restaurants and bars, offering delicious local cuisine and refreshing drinks.


Dominic, one of the most breathtaking island in the Caribbean Sea! As you sail towards this tropical paradise, prepare to be enchanted by its natural beauty and diverse attractions. One of the must-visit spots is Champagne Reef, a captivating underwater world teeming with vibrant marine life. Dive into crystal-clear waters filled with bubbles, created by volcanic activity, and swim alongside colorful fish and coral formations. After your aquatic adventure, head to Bubble Beach Bar, a unique beachfront haven. Sip on refreshing cocktails while soaking in warm volcanic bubbles that naturally rise from the sea floor, offering a relaxing and rejuvenating experience. Dominica truly is a sailor's paradise!


The stunning islands of St. Kitts and Nevis, a Caribbean paradise awaiting your arrival! As you sail towards these breathtaking twin islands, get ready to immerse yourself in natural beauty and rich history. St. Kitts, with its lush rainforests and majestic volcanic peaks, offers outdoor enthusiasts a haven for hiking and exploring. Don't miss the UNESCO World Heritage site, Brimstone Hill Fortress, which offers panoramic views of the island. Nevis, on the other hand, captivates with its pristine beaches and charming plantation houses. Dive into crystal-clear waters teeming with vibrant marine life or indulge in a rejuvenating spa experience. Whether you seek adventure or relaxation, St. Kitts and Nevis will steal your heart with their unparalleled charm.


The magnificent island of St. Martin, a true gem of the Caribbean. As you approach its shores by boat, you'll be greeted by the breathtaking beauty of this dual-nation paradise. St. Martin is divided between the French and Dutch, each contributing to its vibrant culture. The island boasts pristine beaches, azure waters, and a plethora of thrilling water sports. To tantalize your taste buds, I recommend two exquisite coastline restaurants. Indulge in the delightful fusion of French and Caribbean flavors at Le Temps des Cerises in Grand Case, or savor the fresh seafood and mesmerizing sunset views at Rainbow Café in Simpson Bay. Bon voyage and enjoy the island's enchanting charms!

One must-visit spot is Maho Beach, renowned for its unique charm. Located right next to the airport, it provides an unforgettable experience as planes soar just a few meters overhead before landing.


The beautiful island of St. Barths! Nestled in the sparkling Caribbean Sea, this charming destination offers an unforgettable sailing experience. As you approach the island's picturesque shores, you'll be greeted by stunning white-sand beaches, turquoise waters, and lush green hills. The main attractions here are the beautiful beaches, such as Shell Beach and St. Jean Beach, where you can soak up the sun or indulge in water sports like snorkeling and paddle boarding. Explore the vibrant capital of Gustavia, with its quaint streets, designer boutiques, and delightful restaurants serving exquisite French and Creole cuisine. Don't miss the chance to visit the historic Fort Gustave for panoramic views and immerse yourself in the island's rich maritime history. St. Barths is a true sailor's paradise, offering an enchanting blend of natural beauty, vibrant culture, and luxury.

+1 (760) 529-1733

+1 (760) 529-1733