The Original.
The Unforgettable.

Setting the standard for over 20 years.

BOOK NOW

Why Guests Return Year After Year

Five large yellow stars in a row on a black background, bordered by a thick yellow rectangle, representing a five-star rating.

"Our family of 3 enjoyed an afternoon cruise w Tiana and Jess today. We typically aren’t inclined to leave a formal review like this but they exceeded our expectations on every level. It was cool to see 2 badass women work the catamaran and navigate the waters like pros. We were probably quite boring for them as we just wanted to swim, noodle around and relax. They totally picked up our vibe from the outset and met our speed. It was a memorable afternoon and that’s saying something as we’ve taken many private luxury boating excursions over the years. This is right up there. We arranged some catering as well. From a pricing standpoint it was all very reasonable. Highly recommend !"

Nicholas - June 2026

Five large yellow stars in a row on a black background, bordered by a thick yellow rectangle, representing a five-star rating.

"We booked the Wyuna for an anniversary trip morning sail. Captain Loki and first mate Jackie were amazing! They made our trip special beyond what we could have imagined. The boat itself is incredibly comfortable and well equipped for all sorts of water activities. Being in the gorgeous water, paddle boarding and swimming was wonderful. We can’t wait to come back and enthusiastically recommend Sail Bermuda as a must when traveling here!"

Alan - May 2026

Five large yellow stars in a row on a black background, bordered by a thick yellow rectangle, representing a five-star rating.

"We were traveling with a large group of friends on a Bermuda cruise and booked a private charter for our group of 15 friends and kids on the Elusive. It was a spectacular experience and highly recommend this boat and the company. From day one Sail Bermuda was very responsive to our inquiries and promptly answered any questions or clarifications we needed. They even noticed that a different pick up location would be a better option and reached out to make that change. Our captain and guides for the day were Tianna, Abby, and Jackie and they saw to it we had an amazing day. On the day of our sailing in Bermuda it was sunny but high winds (25 mph) and we were all worried about the sailing. Our captain Tianna reassured us and after a short sailing found the most spectacular cove. The cove was smooth as glass, despite the wind, and furthermore we were the only boat there. We had ample time to relax, snorkel, paddle board, jump of the boat. It was really an amazing 3 hours and we would sail with them again when we are back in Bermuda."

William - May 2025

The Sail Bermuda Standard

With over 20 years in the charter business, Sail Bermuda brings a level of experience, consistency, and trusted service that few can match. Our longevity reflects the care, professionalism, and passion we’ve poured into creating unforgettable moments on the water. Rooted in a deep love for our island, we take pride in sharing Bermuda’s beauty, hidden gems, and vibrant spirit with every guest who steps aboard.

Pristine, spacious catamarans

Elegantly designed, impeccably maintained, and fully equipped for comfort, luxury, and style.

Exclusively private, fully customized charters

No shared tours or per-head bookings—just your group, your way.

Experienced, attentive crew

Passionate about exceptional service and making your time on the water truly unforgettable.

Premium onboard comfort

Relax and explore with top-tier snorkeling gear, clear kayaks & SUPs, a floating swim platform, plush beanbags, and a fully stocked bar.

Luxury dining, your way

Bespoke catering and gourmet dining options tailored to your preferences.

Beyond the ordinary

Exclusive add-ons and seamless service for a next-level charter experience.

BOOK NOW

Signature Sail Bermuda Experiences

A white catamaran floats on clear turquoise water near a small sandy island, with lush greenery and distant shore under a blue sky with scattered clouds.

Daytime

Lounge on a bean bag with a tropical cocktail, snorkel vibrant reefs, or glide through crystal-clear waters on a clear kayak or paddleboard...(more)

A white catamaran floats on calm blue water near a small, tree-covered island at sunset, with orange and yellow hues in the sky and a shoreline with buildings in the distance.

Sunset

As the sun dips toward the horizon, the sky bursts into a kaleidoscope of colors, setting the stage for an unforgettable evening...(more)

Four people sit around a table on a boat, enjoying a meal with drinks. The table is decorated with a sunflower centerpiece. Clear blue water and tropical greenery are visible in the background. Everyone looks happy and relaxed.

Corporate

Elevate your corporate experience with Sail Bermuda, where the turquoise waters serve as your meeting room and the horizon inspires new ideas...(more)

BOOK NOW

Our Catamarans

A white catamaran with the name Wyuna sails on clear blue water under a bright blue sky with scattered clouds. The coastline is visible in the background.

WYUNA

47 feet • Accomodates up to 35 passengers • Private charters from $550/hr

A white catamaran sailboat glides on clear turquoise water under a bright blue sky with scattered white clouds. The sails are fully up, and the sea appears calm and inviting.

ELUSIVE

44 feet • Accomodates up to 25 passengers • Private charters from $500/hr

BOOK NOW

FREQUENTLY ASKED QUESTIONS