Top Bermuda Sailing Tours

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.

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.

Take in the key landmarks of Bermuda on a half-day sightseeing tour by coach from King's Wharf. Visit the Royal Naval Dockyard and learn about British colonial rule of the 1600s. Then, see the famous pink-sand beaches at Horseshoe Bay. Pickup and drop-off from the cruise port is included.

There’s no better way to discover Bermuda’s secret coves and hidden beaches than aboard your own private craft. This Catamaran sailboat, good for up to 15 guests, comes equipped with a restroom, snorkeling gear and even stand-up paddleboards (SUP), so you can make the most of the Great Sound’s serene waters. Catering and drinks can be arranged for an additional charge.

Experiencing the best of Bermuda can be difficult with limited time on the island. Make the most of your time on shore on a coach tour of the island’s highlights, including Gibbs Hill Lighthouse, John Smith’s Bay, UNESCO-listed St. George's Town, and Hamilton. Along the way, enjoy free time to shop, stroll, and snap photos, and travel between dispersed locations with ease via air-conditioned coach and ferry.

- 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

Explore the waters of Bermuda on this 3-hour cruise aboard a catamaran. Sail through the island's aquamarine waters to a quiet spot on the Great Sound, then decide how you want to spend your time. Relax on the boat with a complimentary rum cocktail or soft drink, or take to the water on a kayak, a paddleboard, or with snorkeling gear. Pick your own activity to suit your needs.

Discover Bermuda’s natural beauty, capital city, and famous coastline on a half-day tour from King’s Wharf, complete with shopping and a beach experience. Visit the Crystal Caves—home to dramatic limestone formations and underground pools—then enjoy a guided walking tour through Hamilton with time to browse shops and boutiques on Front Street. End your experience with a relaxing swim at Horseshoe Bay, known for its soft pink sand and turquoise waters.

Dedicated foodies and anyone who just likes a good meal will enjoy this three-hour food-focused tour of Hamilton, Bermuda. Go beyond the menus of the typical tourist restaurants and experience local a variety of flavors. Meet in the center of town and walk between several different delicious tasting stops, seeing and learning about Bermudan culture, history, and architecture along the way.

Immerse yourself in Bermuda's underwater world without getting wet during this 1.5-hour glass-bottom boat cruise. Relax in a comfortable vessel, peering through the boat's glass bottom at the marine activity while listening to your crew's informative commentary. See the seagrass beds where turtles find their lunch, the bustling coral reefs, and the shipwreck of the HMS Vixen.

Explore the underwater world off the coast of Bermuda while wearing a Hartley diving helmet. During this 3.5-hour eco-tour, don the specialized helmet and climb down the ladder of the fully-equipped glass bottom boat, then simply walk around on the ocean floor. Delight in this unusual underwater activity, which is easier than snorkeling or scuba diving and more interactive. Spend 30-40 minutes traipsing around the sea's sandy bottom, getting a close look at the vividly colored coral reefs. Use of all equipment, including wet suits, is included. Hotel pickup and drop-off not included.

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.

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.

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.

Get out on the water in Bermuda on a kayaking tour. Paddle along Bermuda’s pristine coastline, getting closer to the tropical plants and cliffs than you could on a large vessel. Paddling in a non-motorized boat also heightens your chance of spotting marine life. Take a break on a secluded beach and have time for a swim before making your way back to the starting point.

Sail around Bermuda's scenic coastline with this catamaran cruise departing from Kings Wharf. Listen to your captain's commentary on the history and culture of Bermuda as you sail toward your destination, a snorkeling spot on the island's reef. Jump in using the provided equipment to explore and spot some of the animals your captain mentioned in his talk. Other flotation devices are available for those who wish to swim and lounge. Wind up with some refreshments on your sail back to Kings Wharf.

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.

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.