Romantic Sailing Trips

ST. CROIX

Start your evening with a serene sail on the Caribbean Sea during the enchanting sunset hours. The Wave Dancer Private Sunset Cruise with Caribbean Sea Adventures is a private charter that can accommodate groups. The beautiful Wave Dancer, a vessel designed for comfort and style, accommodates up to 16 guests. Sit back and soak in the sounds of the sea as you sip on complimentary St. Croix-style rum punch. And be on the lookout for sea turtles or dolphins bobbing along in your sailboat’s waves!

Do you dream of dancing under the stars with your love, surrounded by the sea? Lyric Sails Sunset and Full Moon Sails are epically romantic, featuring live music so you can dance on deck under the spectacular Caribbean sunset or by the enchanting glow of the full moon. The boat, a 63-foot custom catamaran named Jolly Mon, sails along the picturesque Frederiksted coastline of St. Croix. Cruises typically last about two hours, with complimentary rum punch fueling the fun.

ST. JOHN

Expect an evening of fine dining, relaxation and romance aboard Cruz Bay Watersports’ Dinner Sail to Lovango. This 4.5-hour luxurious evening cruise aboard a deluxe catamaran whisks you to the private island of Lovango Cay. The journey begins at the The Westin St. John Resort Villas, where guests are treated to hors d’oeuvres and a full open bar. Upon arrival at the Lovango Resort & Beach Club, you’ll enjoy a coastal Caribbean dinner prepared by an award-winning culinary team, paired with spectacular sea views and live music. After dinner, enjoy access to the luxury beach club, join in entertaining games, take in the views while sipping craft cocktails, or shop the eclectic retail village before boarding the return moonlit cruise.

Midnight Sun Boat Charters offers a breathtaking Sunset Dinner Cruise. You’ll ply the Caribbean Sea as the sun sets over the islands, then get dropped off for dinner in Cruz Bay. You and your partner can take your pick from fine dining restaurants, including Morgan’s Mango and Extra Virgin Bistro. The sailboat will wait and take you back to your departure point after dinner. If you’re looking for a more exclusive sailing experience, Midnight Sun also offers private charters.

ST. THOMAS

Celebrate your love island style! If you’re looking for a deluxe sailboat trip, book a half- or full-day private luxury catamaran charter with Seas the Day Charters and design your very own romantic sailing excursion. Opt to sail from St. Thomas to St. John or Water Island and customize your trip with stops for snorkeling or swimming. Pricing is all-inclusive and includes captain and first mate fees, free-flowing rum punch and snorkeling gear.  

Raise your glass to the natural beauty of St. Thomas at sunset aboard the Someday Charters Champagne Sunset Cruise. You’ll set off from Yacht Haven Grande Marina just as the sun begins to set, and circumnavigate Water and Hassel islands along the southern coast of St. Thomas. Enjoy premium drinks from the on board open bar paired with hors d’oeuvres and charcuterie, plus a grand champagne toast. Though certified for up to 26 guests, the cruise is limited to 12 people to ensure ample space and exceptional personal service. For a more personalized, ultra-romantic experience, opt for a Private Champagne Sunset Cruise, which offers flexible pick-up points and the same luxurious amenities for you and your love, with champagne flowing on board all evening long.

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