Bermuda isn’t just about pink beaches and pastel-colored cottages; it’s also a prime destination for sailing lovers. The island’s calm, clear waters and abundant marine life make it an ideal spot to explore by boat. Whether you’re looking for a lively day on the water, a romantic sunset cruise, or a private adventure, Bermuda offers a variety of options. We especially love the Restless Native Catamaran Sail and Snorkel Tour for its combination of scenery, storytelling, and water fun, and the Rising Son Catamaran Adventure for its relaxed vibe and water activities. For a truly luxurious experience, the Private Catamaran on Elusive promises personalized service with bespoke options.
If you prefer a shorter but memorable outing, the Restless Native Sunset & Swizzle Cruise captures Bermuda’s magic as the sun dips below the horizon. For those seeking exclusivity, private charters like the Wyuna or Elusive give you the flexibility to craft your perfect day. Below, you’ll find detailed insights into each tour, helping you choose the best sailing experience for your trip.
1. Restless Native Catamaran Sail and Snorkel Tour
At number 1, this 3.5-hour cruise takes you on a pink catamaran around Bermuda’s coast. The highlight is definitely anchoring in a private cove for swimming and snorkeling, with gear included. The captain’s engaging tales about Bermuda’s history, folklore, and trivia add a meaningful layer to the cruise. You can lounge on the deck sipping rum swizzles or enjoy boat-made chocolate chip cookies. Plus, the included stand-up paddleboards and kayaks make it easy to explore at your own pace.
What makes this tour stand out? The combination of relaxed water activities, excellent storytelling, and the friendly crew, which consistently earns 5-star reviews. Travelers rave about the stability of the catamaran and the informative guides. A typical trip offers a perfect blend of sightseeing, fun, and refreshments, making it ideal for families or groups seeking a lively yet laid-back experience.
Bottom line: If you want a balanced mix of exploration and relaxation with positive reviews, this tour is hard to beat—especially for first-timers or cruise travelers.
2. Rising Son Catamaran Adventure in Bermuda
Number 2 on our list highlights a 3-hour adventure aboard the Rising Son II, leaving from Kings Wharf. The boat is sleek, and the waters of Great Sound are perfect for sightseeing. The crew offers snorkeling above reefs and kayaking or paddleboarding at the anchor, giving you the freedom to choose how to spend your time. The complimentary rum cocktail and onboard music add to the relaxed vibe.
Unique features include the opportunity to spot marine life and enjoy a secluded swimming spot. Reviewers love the laid-back atmosphere, calling it “the best snorkeling trip,” with one mentioning the knowledgeable crew making everyone feel comfortable. The trip’s flexibility and water activities make it a great choice for families, couples, or groups who want a personalized experience.
Bottom line: For a smooth, immersive day on Bermuda’s waters, this tour combines fun with ample time to relax and explore.
3. Restless Native Catamaran Sunset & Swizzle Cruise
Number 3 offers a 1.5-hour sunset cruise on a catamaran. As Bermuda’s sky turns to twilight, you’ll sip rum swizzles, munch cookies, and listen to island-style music and commentary. This tour operates until October, making it a perfect evening outing.
What makes it special is the opportunity to experience Bermuda’s coastline at sunset with minimal crowding and a friendly crew. Reviewers describe it as “simply amazing,” praising the gorgeous sunset views and attentive staff. It’s ideal for couples or small groups looking for a romantic or relaxed way to end the day.
Bottom line: If you’re after a romantic, scenic evening with a laid-back vibe, this cruise delivers.
4. Private Catamaran Swim, Sail, Snorkel, Cliff Jumping, SUP
Number 4 is for groups wanting a bespoke adventure. This private 3-hour charter can accommodate up to 15 guests and offers customized exploration of Bermuda’s secret coves, reefs, and beaches. The boat is equipped with restroom, snorkeling gear, and stand-up paddleboards, perfect for making the most of your time on the water.
What makes this tour unique? The flexibility to tailor your day—whether snorkeling, cliff jumping, or just relaxing. Reviewers emphasize the well-planned route and friendly crew, calling it “super relaxing” and “beautiful sites.” It’s ideal for families or groups celebrating special occasions who want exclusivity and control over their day.
Bottom line: For a luxurious, private experience that you craft yourself, this tour offers unmatched flexibility.
5. Bermuda Private Catamaran: Snorkeling, Shipwrecks & Cliff Jumping
At number 5, this personalized 3-hour private charter takes you to Bermuda’s iconic shipwrecks and caves. You can snorkel, paddleboard, or cliff jump, with options for lunch onboard. The boat features comfortable seating, a restroom, and hotel pickup, making logistics easy.
What sets it apart? The ability to customize your route and enjoy a private experience. Reviewers appreciate the seamless communication and the stunning underwater scenery. It’s well-suited for families or groups who want a tailored day on the water in a relaxed setting.
Bottom line: For a personalized, all-inclusive day with options for meals and water activities, this tour hits the mark.
6. Private Catamaran Charter on Elusive
Number 6 offers a luxury private sailing experience aboard the Elusive, perfect for up to 15 guests. Over 20 years of experience means the crew knows Bermuda’s waters well. You decide whether to snorkel offshore reefs, paddle around secluded islands, or cliff jump.
What makes this tour special? Its bespoke nature—every detail is tailored to your wishes, with hand-picked anchorages and a focus on seamless service. Reviewers love the personal attention and luxury feel. It’s best for travelers seeking a private, high-end day with flexibility.
Bottom line: If exclusivity and customization are your priorities, this charter offers a luxury experience with professional guidance.
7. Catamaran Sunset Sail
Number 7 is a 1.5-hour cruise ideal for sunset lovers. Enjoy scenic views of Bermuda’s coastline, with a complimentary rum cocktail and live commentary. It’s a relaxed way to soak in Bermuda’s evening ambiance.
Review highlights include “beautiful boat with open bar,” and “friendly, knowledgeable crew,” making it suitable for couples and small groups. The trip’s timing at twilight is perfect for capturing great photos.
Bottom line: For a short, scenic escape into Bermuda’s sunset, this cruise combines comfort with memorable views.
8. Good Vibration Catamaran Sail, Swim & Snorkel
Number 8 features a 3-hour trip on the Good Vibration. The boat caters to larger groups and families, offering opportunities to swim, snorkel, or paddleboard. Onboard rum swizzle cocktails and social atmosphere make it fun without fuss.
Distinctive details include the easy check-in and the well-maintained boat. Reviewers mention the professional crew and the quality of the snorkeling spot. It’s perfect for travelers who want active fun and socializing.
Bottom line: If you need a family-friendly, activity-packed day on Bermuda’s water, this tour fits the bill.
9. Private Catamaran on Wyuna
Number 9 offers a luxury private sailing tailored to your wishes, similar to the Elusive experience. Up to 15 guests can indulge in snorkelling, paddleboarding, or just relaxing. With over 20 years’ experience, the crew ensures a seamless and personalized day.
What makes this optional stand out is the flexibility and attention to detail. Reviewers note the professional service and beautiful waters. Best suited for special occasions or intimate gatherings.
Bottom line: For an exclusive, customizable luxury cruise, Wyuna delivers a personalized experience second to none.
10. Bermuda By Sunset “Private Catamaran”
Number 10 is a 1.5-hour private sunset cruise. It’s perfect for small groups or couples seeking a personalized experience. You can bring your own drinks or enjoy the onboard bar, with golden hour views and relaxing music.
Reviewers appreciate the intimate atmosphere and stunning sunset. It’s ideal for celebrating special occasions or just enjoying Bermuda’s coastline in peace.
Bottom line: For a private, romantic sunset experience, this cruise offers a relaxed and beautiful setting.
11. Private Sunset Charter on Elusive Catamaran
This luxury private sunset sail mirrors the Wyuna’s offerings but focuses on a personalized experience aboard the Elusive. You’ll glide across calm waters, enjoy fine wine, and take in Bermuda’s nighttime sky with optional star-spotting.
Best suited for couples or small groups seeking peaceful luxury. Reviewers mention the quiet magic of this sail, making it a top choice for special celebrations.
Bottom line: For a romantic, exclusive evening, this private sunset cruise delivers a serene and memorable experience.
12. Kings Warf Catamaran Cruise, Snorkel & Refreshments
Number 12 is a 3.5-hour cruise departing from Kings Wharf, offering a more traditional Bermuda sailing experience. It includes snorkeling on the local reef, refreshments, and captain commentary on Bermuda’s culture.
What makes this tour notable? The convenient location and duration make it appealing for cruise passengers. Reviewers mention good snorkeling gear and the interesting commentary. It’s best for those wanting a balanced mix of sightseeing and water fun close to port.
Bottom line: For cruise ship travelers, this tour provides easy access and a solid water experience.
$148.26 per person
13. Private Sunset Charter on Wyuna Catamaran
This private 3-hour sunset cruise offers the same personalized luxury as its sister tours, perfect for small groups wanting a quiet evening on Bermuda’s waters. Sip wine and enjoy spectacular views as the sky shifts colors.
Ideal for intimate celebrations or a peaceful end to your day. The customizable experience earns glowing reviews.
Bottom line: For a private, elegant sunset outing, this tailored cruise is an excellent choice.
$2,150.00 per group (up to 15)
14. Redemption Catamaran Private Day Sail
Number 14 provides a half-day private sail on the Redemption. Departing from Dockyard or Hamilton, you choose your water activities, from snorkeling to paddleboarding or relaxing on deck.
What sets it apart? Its flexibility and personalized approach make it perfect for families or couples celebrating a special day. Reviewers praise the seamless experience and friendly crew.
Bottom line: For a customizable private day on Bermuda’s waters, this tour offers a relaxed and flexible setup.
$1,133.00 per group (up to 14)
15. Redemption Catamaran Private Sunset Sail with Captain
The final entry is a 3-hour private sunset sail ideal for romantic evenings or small groups. Glide along Bermuda’s coast, enjoy calming music, and watch the sunset in privacy.
Perfect for celebrating love, anniversaries, or just unwinding with friends. The peaceful setting and personalized service make it a memorable choice.
Bottom line: For an intimate, peaceful sunset experience, this private sail stands out.
$1,133.00 per group (up to 14)
How to Choose Your Perfect Bermuda Sailing Experience
When selecting among these options, think about your budget, group size, and what kind of experience you want. For a lively day with water activities and storytelling, the Restless Native Tour offers great value. If you’re seeking luxury and privacy, the Wyuna or Elusive private charters are hard to beat. Budget travelers will appreciate the sunset cruises or the Kings Warf tour, which provides a solid experience close to the port.
Booking early is advisable, especially for private options, to secure your preferred date and time. Consider the season—the Sunset & Swizzle cruises operate until October, making late summer ideal for sunset watching. Always check the weather forecast before booking, as calm seas make for the best sailing days.
Bermuda’s sailing options are as diverse as the island itself. For a fun-filled day with plenty of water activities, the Restless Native Catamaran Tour is hard to beat. If you’re craving intimate luxury, private charters like Wyuna or Elusive will give you a bespoke experience you’ll never forget. And for a simple, scenic evening, the Sunset & Swizzle Cruise is perfect. No matter your style or budget, Bermuda’s waters beckon—so book early and set sail for your own unforgettable adventure.