Top Bermuda Sailing Tours

Finding a quiet place to swim and snorkel around Bermuda can be difficult without a boat. This catamaran cruise takes you sailing around the island before anchoring in a private cove where you can enjoy the water without the crowds. Along the way, your captain shares stories of Bermuda’s history and local legends to keep you entertained.

Enjoy both comfort and style as you take in scenic views of Bermuda's coastline on this sunset cruise. Watch the sunset over the water—from a vantage point many travelers miss out on—and relax with a complimentary rum cocktail. As you cruise the pristine waters, listen to entertaining, discussion-style commentary and island music. Feel the warmth of true Bermudian hospitality throughout.

Exploring Bermuda's coastline can be tricky without a boat of your own, but this evening cruise keeps things simple. Head out onto the water to enjoy the sunset from a unique vantage point aboard a 50-foot (15-meter) catamaran, then return to land with plenty of time to enjoy the rest of your evening. While onboard, sip on classic Bermudian rum cocktails and enjoy the sounds of island music—a truly relaxing experience in paradise.

- Private 1.5-hour sunset cruise aboard Kona, a sleek catamaran - Scenic sail along Bermuda’s coastline with golden hour views - Ideal for couples, small groups, and special occasions - Enjoy the onboard bar or bring your own beverages and snacks - Licensed local captain ensures a smooth, safe, and relaxed experience

This is not your average boat charter—Sail Bermuda offers a luxury private sailing experience that’s entirely your own. Whether you want to snorkel offshore reefs and shipwrecks, paddle around a secluded island, or jump from cliffs into turquoise waters, we’ll shape the day around you. With over 20 years of experience, we’ve been perfecting the art of bespoke charters—knowing when and where to go, how to avoid the crowds, and how to make every moment seamless. From hand-picked anchorages to onboard catering served with care, every detail is handled so you can relax. You won’t find rigid itineraries or crowded decks here—just space, comfort, and the freedom to explore Bermuda at your own pace, with a knowledgeable local crew by your side. Please note that you may bring up to 15 passengers in total, including yourself. All of our charters are private, so it will be just you and your group on board.

Take to Bermuda’s tropical waters on this boat trip. Go swimming, snorkelling, or paddle boarding, or soak up the sun on the boat deck. Don’t worry about hiring any water equipment separately; simply pick up one of the onboard snorkels and boards. Perfect for larger groups and families where some want to relax and others want to have fun playing in the sea.

This is not your average boat charter—Sail Bermuda offers a luxury private sailing experience that’s entirely your own. Whether you want to snorkel offshore reefs and shipwrecks, paddle around a secluded island, or jump from cliffs into turquoise waters, we’ll shape the day around you. With over 20 years of experience, we’ve been perfecting the art of bespoke charters—knowing when and where to go, how to avoid the crowds, and how to make every moment seamless. From hand-picked anchorages to onboard catering served with care, every detail is handled so you can relax. You won’t find rigid itineraries or crowded decks here—just space, comfort, and the freedom to explore Bermuda at your own pace, with a knowledgeable local crew by your side. Please note that you may bring up to 15 passengers in total, including yourself. All of our charters are private, so it will be just you and your group on board.

Departing from either Dockyard or Hamilton, step aboard Redemption, our spacious sailing catamaran, for a fun and relaxing half-day on Bermuda’s crystal-clear waters. Guided by our friendly crew, we’ll chart a scenic course—weather permitting—towards a secluded beach or a vibrant snorkeling reef, based on your preference. Once anchored, dive in to explore the underwater world with complimentary snorkel gear, or glide across the water on an inflatable paddleboard. Whether you’re soaking up the sun on deck or splashing in the shallows, this experience is the perfect escape from the crowds. Ideal for couples, families, or small corporate groups, Redemption offers a tranquil and intimate way to experience the best of Bermuda’s coastline.

Step aboard a three-hour luxury catamaran experience designed for adventure and relaxation. Your journey begins with a warm welcome from our lively crew, who are not only entertaining but also deeply knowledgeable about the islands’ rich history and secret spots. Glide across sparkling turquoise waters as the catamaran’s spacious deck and elegant lounge suite offer the perfect setting to soak in the sea breeze. We’ll anchor at a secluded bay where you can dive in for a refreshing swim, try your hand at paddle boarding, or simply float and unwind in the calm waters. Between activities, enjoy a comfortable hangout in the shaded lounge or sunbathe on the deck while sipping a chilled drink. Throughout the tour, the crew shares captivating stories of the islands—tales of seafarers, hidden coves, and cultural heritage—bringing the scenery to life. This luxury catamaran tour blends adventure, leisure, and local insight, delivering an unforgettable afternoon on the water.

At Sail Bermuda, a sunset charter isn’t just a sail—it’s your own private escape, curated with care. You’ll glide across calm waters aboard the luxury catamaran Elusive, with no crowds and no preset script. Sip wine, enjoy a hand-selected meal, and take in the shifting sky from the best seat in Bermuda. As night falls, your captain can point out constellations overhead—adding a quiet magic that few ever experience. This is sunset, the Sail Bermuda way: personal, peaceful, unforgettable. Please note that you may bring up to 15 passengers in total, including yourself. All of our charters are private, so it will be just you and your group on board.

At Sail Bermuda, a sunset charter isn’t just a sail—it’s your own private escape, curated with care. You’ll glide across calm waters aboard the luxury catamaran Wyuna, with no crowds and no preset script. Sip wine, enjoy a hand-selected meal, and take in the shifting sky from the best seat in Bermuda. As night falls, your captain can point out constellations overhead—adding a quiet magic that few ever experience. This is sunset, the Sail Bermuda way: personal, peaceful, unforgettable. Please note that you may bring up to 15 passengers in total, including yourself. All of our charters are private, so it will be just you and your group on board.