Grand Cayman is a sailor’s paradise. The calm, clear waters around the island make for some of the simplest and most scenic sailing in the Caribbean. Whether you want to snorkel with stingrays at Stingray City, relax on a luxury yacht, or enjoy a sunset cruise, there’s a perfect option for every type of traveler. The tours on this list stand out because they combine authentic experiences with excellent service and a good sense of value. For example, the Private Luxury Catamaran Tour combines a personalized itinerary with top-notch comfort, while the Yacht charter offers a custom adventure tailored specifically to your group.
If you’re trying to decide what kind of sailing experience suits you best, this guide will help. From intimate private charters to family-friendly day trips, we’ve included options that cater to different budgets, interests, and activity levels.
Quick Overview
This list covers a variety of sailing experiences in Grand Cayman: private luxury and yacht tours, private catamaran journeys, and scenic sunset cruises. Each offers a unique way to see the island’s highlights—like Stingray City, Starfish Point, and Rum Point—from the water. Follow the links for details on each tour’s itinerary, reviews, and pricing, and find the perfect match for your Cayman vacation.
1. Private Luxury Catamaran Tour to Stingray City and Snorkel
At number 1, the Private Luxury Catamaran Tour stands out for its blend of comfort, knowledge, and value. This 4-hour trip takes you exploring the North Sound on a beautifully appointed vessel, with a maximum of 15 guests to ensure an intimate experience. The tour includes snorkeling at the barrier reef — home to the highest coral density in Cayman — and a visit to Stingray City, where friendly southern stingrays glide through shallow waters. The captain also takes you to Starfish Point, a peaceful beach where you can see the iconic red cushion sea star up close.
What makes this tour special is the focus on both education and leisure. The crew shares insights about the marine life, making it educational without feeling like a lecture. Reviews highlight the friendly staff and the authentic stingray encounter, with one guest remarking, “Stingray City was a blast and even better than online photos.” The price per group is $2,250, which includes all activities and allows for a relaxed, exclusive experience.
Bottom line: This is a fantastic option for small groups seeking a high-end, private adventure with plenty of snorkeling and freshwater interaction with marine animals.
2. Private Yacht 48 ft Sting Ray City, Snorkel & Starfish Beach
Number 2 on our list is the 48-ft private yacht that offers a full-day adventure. This yacht comfortably fits up to 16 guests and provides full customization, including options for snorkeling spots, visiting Stingray City, or relaxing at Starfish Beach. The yacht features modern amenities, a clean and upscale marina departure point, and the option to add jet-ski rides for extra excitement — a rare perk that appeals to thrill-seekers.
Guests rave about the personal touch — “Erick and Nate made the experience so fun and memorable,” one reviewer says. The crew’s flexibility and attention to detail make this yacht perfect for families or groups wanting a tailored day on the water. The tour lasts about 4 hours and 5 minutes, offering time to snorkel, hold the stingrays, and relax at Starfish Point or Rum Point afterward.
Since this is a private yacht, it’s suited for those who want a more exclusive experience with the option to add extra activities. The $2,150 price ensures a plush, personalized trip that is both fun and memorable.
Bottom line: For groups wanting a flexible, private experience with the option to include jet-skis or additional snorkel stops, this yacht is a fantastic choice.
3. Private 4 hour Catamaran Tour
Third on our list is the Private 4-hour Catamaran Tour, perfect for travelers who prefer a tailored experience in a smaller, more relaxed setting. Aboard the Buccaneer, a stunning vessel, you can choose between snorkeling, visiting Stingray City, or Starfish Point — or any combination of these. The flexibility is the key here: you set the pace and the focus.
This trip is ideal for small groups (up to 15 people), with reviews praising the boat’s comfort and the guides’ professionalism. One quote describes the trip as “super fun,” and many appreciate the staff’s effort to make the day special, even with weather challenges. The tour costs $1,499 per group, making it a good value considering the personalized approach and the inclusion of activities like snorkeling and stingray encounters.
This option is best suited for those who want a private experience but don’t need all-day activities. It’s perfect for families, couples, or small groups who want to avoid crowds and have a say in their itinerary.
Bottom line: If you want a private, flexible tour with options for snorkeling and stingray interaction, this is a smart pick.
4. Grand Cayman Catamaran Tour to Stingray City and Rum Point
The fourth position features a 5.5-hour sunset cruise on a luxurious 65-foot catamaran. This tour is designed for those who want to combine the iconic Stingray City experience with a relaxing afternoon at Rum Point. Starting at just $123.50 per person, it is one of the most affordable options to enjoy a multi-activity day on the water.
The itinerary includes swimming or snorkeling with stingrays at the sandbar, then a two-and-a-half-hour stop at Rum Point — known for its white sands and waterfront bar. The reviews highlight the smooth ride, friendly crew, and the opportunity to get up close with stingrays — “swim and snorkel with them in the shallow water, and they come up for kisses,” one guest notes.
This tour is especially good for families or couples who want a laid-back, scenic experience with plenty of time to relax on the beach afterward. The highlight is the combination of marine interaction and leisure, all on a spacious yacht.
Bottom line: For those seeking a relaxed, budget-friendly trip with a mix of snorkeling and beach time, this sunset cruise fits the bill.
5. Stingray City Catamaran Sunset Tour
Finally, the Sunset Tour offers a shorter, more romantic experience. For about two hours and $59 per person, you’ll sail on a Buccaneer Catamaran to Stingray City during the magical hours of sunset. This is perfect if you want a memorable, photo-worthy experience without a full-day commitment.
The tour includes holding, feeding, and kissing stingrays, with the chance to enjoy the vibrant Caribbean sunset from the deck. Reviewers mention the helpful crew and the peaceful atmosphere, with one stating, “What an unforgettable adventure, especially with the sunset views.” The tour is suitable for all ages, and you can choose to stay dry or get in the water.
This cruise is ideal for travelers short on time or looking for a romantic outing. It’s also a budget-friendly way to experience the charm of Grand Cayman’s marine life.
Bottom line: If a short, scenic cruise with the thrill of stingray interaction and sunset views appeals to you, this tour makes for a memorable evening.
How to Choose the Best Sailing Experience in Grand Cayman
When selecting the right tour, consider your budget, time availability, and interests. For a private, all-inclusive experience with luxury touches, the Private Luxury Catamaran or the Yacht might be your best options. If you prefer flexibility and a more intimate setting, the Private 4-hour Catamaran offers excellent value.
For a fun, family-friendly outing that combines multiple stops at a reasonable price, the Grand Cayman Catamaran to Stingray City and Rum Point is hard to beat. If you’re short on time or want a romantic sunset experience, the Sunset Cruise is perfect.
Booking early is recommended, especially during peak seasons, since these tours tend to fill quickly. Consider your group size and activities — snorkeling, relaxing, or adding special features like jet-skis — to pick the best fit.
Grand Cayman offers diverse sailing options tailored to different tastes and budgets. Whether you seek a private luxury charter or a scenic sunset cruise, you’ll find a memorable way to enjoy the island’s stunning waters. For most travelers, a combination of these experiences—like a day trip to Stingray City with a sunset finish—provides a well-rounded, authentic Caribbean adventure. So go ahead: book early, pick your style, and prepare for some truly unforgettable moments on the water.