7-Day Leeward Islands Crewed Motor Yacht Itinerary
Discover St. Martin, Anguilla, St. Barths, Saba, and St. Kitts on a 7-Day Leeward Islands Crewed Motor Yacht Itinerary
Day 1: Grand Case | Day 2: Anguilla | Day 3: Saba Island | Day 4: St. Kitts and Nevis | Day 5: Gustavia, St. Barths | Day 6: Colombiers, St. Barths | Day 7: St. Martin | Day 8: St. Martin
A Leeward Islands crewed motor yacht charter promises moments of pure bliss defined by secluded beaches, turquoise waters, and a kaleidoscope of untouched flora and fauna. With ample space and seamless service, this is the perfect family-friendly escape. Step on board a Benetti, Sanlorenzo, or Azimut motor yacht, and watch your journey unfold in an array of peaceful floats in crystaline waters, the Leeward Islands' finest dining experiences, and vibrant evenings that feel like a dream.
For over 20 years, the charter experts at Boatbookings have curated custom itineraries that our clients love and continue to come back to. We are thrilled to work with you to create your next dream vacation through the Leeward Islands. Take a look at this sample itinerary that perfectly blends chic island capitals, pristine anchorages, and immersive water sports, all delivered with the effortless grace of a world-class crew and exceptional onboard gastronomy.
Map of the Leeward Islands Charter Itinerary
Day 1: Grand Case
Embark on your luxury crewed motor yacht at 2:00 pm in St. Martin, where two worlds meet and mingle beneath the Caribbean sun. Your embarkation point, Marigot, is a charming town on the edge of the Caribbean Sea. Settle into your private yacht with a perfectly chilled Caribbean Spritz as you cruise along the coast of St. Martin to Grand Case. Ahead is an afternoon full of relaxed swims as you take your first dive into the turquoise waters of the Leeward Islands, straight from your swim platform. With your yacht's private arsenal of water toys at your disposal, you can immediately take advantage of the calm bays and explore the shore with a paddleboard or Seabob. As the sun sets, savour a welcome dinner under the stars, featuring grilled Caribbean spiny lobster with lime butter. After floating in dream-like waters and testing the most popular new water toys, your first day will set the tone for a week of powdery beaches and secret coves where every day feels like a passport to somewhere new.
Day 2: Anguilla
Today, you will cruise for about an hour and a half to Anguilla, where a dreamy coastline and white sandy beaches make for an indulgent morning of swimming and snorkeling in the cerulean shallows. With a private tender, you can take an easy ride to a nearby reef to encounter Caribbean marine life with a SeaBob. For lunch, venture ashore to Savi Beach Club and try their grilled mahi-mahi with mango salsa. Their entire menu consists of mouthwatering dishes, all infused with Caribbean flavors and local ingredients. You'll spend the afternoon at anchor, where you can enjoy the freedom of a sunny day and calm waters. Grab a lifejacket and a jet ski and speed across the water in a friendly competition. Or, if you are looking for a more relaxed experience, head to the beach and stretch out on the sun-warmed sands. Just before dinner, head back to your yacht for cocktails on the foredeck with stunning views of the sunset, then dig into a gourmet dinner while the stars begin to make their appearance.
Day 3: Saba Island
Wake up and sail to a true hidden gem, Saba Island, also known as the "Unspoiled Queen." Rising sharply from the sea with mist-shrouded peaks and emerald rainforests, Saba Island is known for its dramatic volcanic terrain, lush landscape, and scenic hikes. Saba's charms are subtle and sublime with rare access to winding hiking trails and breathtaking views. Back on board, lunch will feature slow-roasted jerk chicken with coconut rice. Your professionally trained chef will create meals akin to fine dining experiences, all from the comfort of your luxury motor yacht. Take advantage of the calm waters and go for an afternoon swim or try your yacht's E-Foil. Saba is also known for vibrant coral gardens and a kaleidoscope of marine life. For an intimate look at this unerwater paradise, grab a tank and BCD for an unforgettable dive. Tonight, you will step off the yacht and head to either Brigadoon or Tropics Cafe for a taste of the local Caribbean cuisine!
Day 4: Saint Kitts and Nevis
After a four hour sail, you will arrive in St. Kitts, the island of contrasts, where lush volcanic peaks rise dramtically from turquoise waters and history whispers from every cobblestone. Enjoy a leisurely morning with paddleboard yoga and snorkeling. Then, indulge in an onboard lunch featuring blackened snapper with citrus butter before making the 35 minute sail to Nevis. Quiet elegance awaits at Nevis, where time slows down and you are encouraged to lie beneath the shade of coconut palms until sunset. Emerald hills encourage gentle hikes while golden beaches provide a serene escape from the world. Spend a relaxing afternoon on Pinney's Beach where the sound of the sea and cool breeze will lull you into a sunsoaked nap. As evening falls, head to Sunshine's Beach Bar or The Gin Tap for a lively evening with island-style dining, upbeat music, and great views.
Day 5: Gustavia, St. Barths
Today you will cruise to Gustavia, St. Barths, where golden sands and designer boutiques welcome you to a day where the only schedule that exists is the one you create. This is an island that distills the French Riviera into a sun-drenched Caribbean jewel. Spend the day at Shellona or Nikki Beach and enjoy the beachside glamour that only a SeaBob or Jet Ski can provide. If you are feeling the need for an adventure, a trip to Moke Rental Cars is a must for a self-guided tour around St. Barths. This allows you the freedom to explore on your own and hop between the best beach bars on the island without a second thought for the time. For a fun, vibrant evening with a Caribbean-fusion cuisine, go to Le Ti St. Barth for dinner. Nestled in the heart of St. Barths, this staple has one of the best nightlife scenes on the island. Enjoy the glamorous atmosphere, craft cocktails, and electric music all night long.
Day 6: Colombiers, St. Barths
Today you will explore Colombier, St. Barths' most elusive spot, where there are no roads, no bars, and little to no tourists. Anchor off the rugged coastline of the enchanting Colombier Nature Reserve where a cresent of power-white sand is framed by rolling green hills and impossibly clear water, perfect for a day of snorkeling, swimming, and thrilling tender rides. For adventurous guests, the lookout point beckons with panoramic views of the island. You can also stretch out on board your yacht for a peaceful day of sunbathing, where you can watch sea turtles glide gracefully by, or get in the water with an E-Foil and explore the shores yourself. Lunch will feature grilled tuna tataki with sesame and citrus. Dine ashore this evening at Le Tamarin, in a lush garden setting where you will feel as if you were placed in the middle of a rainforest setting.
Day 7: St. Martin
Cruise back toward St. Martin, stopping for a swim and an onboard lunch featuring herb-roasted beef tenderloin with chimichurri. Take advantage of this last afternoon and calm waters to use the yacht's water toys for Jet Ski or SeaBob sessions. Dinner will be a celebration of the week you spent exploring the Leeward Islands. Dress in your finest evening wear and toast the journey with a sunset Caribbean 75 cocktail, then enjoy a delicious dinner under the stars.
Day 8: Disembark in St. Martin
Enjoy one last breakfast on board before disembarking and traveling onward to your next destination. After a week in paradise, you will leave with sun-kissed skin, unforgettable memories, and an immediate desire to return. If you enjoyed your crew, be sure to exchange information, so when you come back, you can sail with the team you know and love.
Leeward Islands Charter Guide | St. Martin | St. Barths | Anguilla | Antigua and Barbuda | Windward Islands
Caribbean Charter Guide | British Virgin Islands | US Virgin Islands | Caribbean
