Choosing a private boat charter in Grand Cayman can feel simple until you start comparing boats, group sizes, inclusions, routes, and pricing. The right option depends on the kind of day you want on the water, not just the name on the hull.
In this guide, we compare several leading charter companies, highlight where each stands out, and help you narrow down which one may suit your plans best overall.
Quick Answer: Which Private Boat Charter to Book
Surfside Charters is the best private boat charter in Grand Cayman for most groups. It runs the only two-vessel pairing here that covers both ends of a charter day: a 56ft sailing catamaran carrying up to 30 guests (14 recommended), and a 38ft Intrepid 377 that fishes the drop-off and reaches Rum Point fast. Both half-day and full-day rates are published in full.
Four operators below each excel on something unique. Under twelve guests with young children, skip to Crazy Crab. Want the widest choice of hull, consider Cayman Yacht Charters.
- Surfside Charters: Best overall
- Cayman Yacht Charters: Best fleet range
- Crazy Crab Private Boat Charters: Best for families and first-time snorkelers
- Sail Cayman: Best established track record
- Cayman Luxury Charters: Best for weddings and celebrations
How We Ranked These Grand Cayman Boat Charters
We set the ten criteria before scoring anyone, based on what people ask when they call a charter company: how many guests fit, what the day costs, what arrives on the boat with them.
The Criteria We Scored
Fleet, maximum guests, departure point, durations, included food, water toys and booking terms are published facts, so we checked them directly on each operator’s website on 12 October 2026. We scored crew on years operating and local knowledge, where captains who know these waters beat a fleet count. Licensed and insured status are the final contributing factors.
Our comparison focuses on the practical details that can genuinely shape your charter experience
The Top 5 Best Private Boat Charters in Grand Cayman
1. Surfside Charters: best private boat charter overall
Surfside Charters is an owner-operated company running two very different boats out of Camana Bay. Bamboozled, a 56ft Lagoon sailing catamaran, accommodates up to 30 guests. Mojito Majic, a 38ft Intrepid 377, takes up to 10, 8 recommended, and runs the reef and deep sea fishing charters at competitive rates.
Surfside holds a license for Kittiwake and the Department of Environment’s Wildlife Interaction Zone permit for Stingray City. The food is the quiet differentiator here: charters can include fruit platter, chips, water and soda, guests can bring their own drinks, and a private chef can come aboard on 72 hours notice.
Pros
- Takes up to 30 guests on Bamboozled, perfect for larger groups and corporate outings
- Fresh fruit platter, chips, water and soda on every charter, plus cheese and charcuterie on request and partner catering on 48 hours’ notice
- Seabobs aboard Bamboozled, plus paddleboards, wakeboard, kayak and tubing for additional fun
- Holds the licence for the Kittiwake wreck, with itineraries customized on the day to conditions
- Instant online booking
#### Cons
- Corporate charters carry an automatic 17% gratuity; on all other charters, gratuity is at the guest’s discretion
- Bioluminescence trips run on request only, aboard the smaller boat
Best for: Groups of eight to thirty who want a relaxed day built around them, with snacks aboard and an experienced and attentive crew.
2. Cayman Yacht Charters: Best Fleet Range and Vessel Choice
Cayman Yacht Charters operates the deepest fleet on the island, and that is the reason to call them. Catch the Cat is a 47ft Lagoon sailing catamaran. Alongside it sit a Leopard 43 power catamaran, a Leopard 39 sailing catamaran, and Sea Ray 42, 44 and 48 motor yachts. The fleet also includes a Cranchi 64HT, a Pearl 80, a Cobalt 25, and three fishing boats: an Everglades 435, a Sea Hunter 37 and a Twin Vee 31.
A private catamaran charter here is bookable online with rates published by duration, extra hours at $600 and a full-day BBQ at $70 per head. Nothing is cheap, but nothing is hidden either.
Pros
- Around a dozen vessels covering sailing and power catamarans, motor yachts, center consoles and dedicated fishing boats
- A Jet Ski included on catamaran charters
- Catamaran takes up to 35 guests, with guests above 12 at $100 per head
Cons
- Additional guests cost $100 per head, double the $50 surcharge on a comparable charter at Surfside
- Extra hours run $600 on the catamaran, and a Kaibo pickup is a further $250, full days only
- A large fleet means the crew you get varies more than at an owner-operated company
Best for: Groups who care which hull they are standing on, and anglers who want a purpose-built fishing boat.
3. Crazy Crab Private Boat Charters: Best for Families and First-Time Snorkelers
Crazy Crab Private Boat Charters runs two World Cat power catamarans: Lil Blue at 25 feet for six adults, Red Shank at 29 feet for ten. Every Crazy Crab charter comes with a captain and a guide, and the guide leads the snorkeling. For a family with mixed swimming confidence, that changes the day: non-swimmers get a hand rather than a wave from the transom.
Pros
- A captain and a guide on every charter, with guided snorkeling
- Capacities stated separately for children up to 13, so families can plan honestly
- No cancellation fee more than 72 hours out; between 24 and 72 hours, a 50% charge or a 100% lifetime booking credit
Cons
- Twelve guests is the ceiling, so larger parties need a second boat
- Fishing is not a stated offering
- Compact boats: Lil Blue seats four on the sun deck and five under shade
Best for: Families with young children, nervous swimmers, and anyone who wants to book and pay online tonight.
4. Sail Cayman: Longest Track Record on the Water
Sail Cayman was established in 1996 by Captain Neil and has run private charters ever since, now from the Cayman Islands Yacht Club. It runs four boats. Hull Yes is a 51ft Leopard power catamaran taking up to 27 guests. Zarp and Serenity are coast guard certified 41ft Leopard power catamarans. LazyDaz is a 34ft Ocean Master center console for fishing.
Pros
- One of the longest-established charter companies on the island
- Coast guard certified vessels, including both 41ft catamarans
- Rates published for every vessel, priced by the hour and scaled to group size
Cons
- Food is offered only as a lunch option on full-day charters
- Water toys stop at snorkel gear and pool noodles, with fishing gear aboard
Best for: Travelers who weight a long track record and certified vessels above amenities
5. Cayman Luxury Charters: Best Boat Charter for Weddings and Celebrations
Cayman Luxury Charters runs La Vida, a 2017 51ft Leopard power catamaran, the Sea Star, a 40ft Sea Ray Sundancer, and the Escape, a 36ft Aquila sport catamaran. It cruises 1 to 32 guests around wedding enhancements, anniversary celebrations and birthdays.
Pros
- Snorkel gear and snorkel vests included, with reef fishing bait and tackle on request
- A Jet Ski included in La Vida’s charter rate
- Event specialism covering weddings, anniversaries and birthdays
- Bottled water, soft drinks and ice included on La Vida charters
Cons
- Food isn’t included as standard; lunch is arranged through a restaurant
- La Vida takes up to 28 guests, so groups above that split across boats
Best for: Celebration groups who want an operator used to running events afloat
How to Choose a Private Boat Charter in Grand Cayman
Choosing the right private boat charter in Grand Cayman comes down to more than price. Group size, vessel type, departure point, inclusions and itinerary all shape the experience, so compare the practical details before booking.
- Count your group honestly, including children. Anything over twelve rules out Crazy Crab and pushes you toward other impressive charter options that can handle big groups.
- Decide sail or power. A sailing catamaran gives shade and deck space; a power yacht gives range and reaches the fishing grounds.
- Check the water you want to be in. Stingray City, Coral Gardens and Starfish Point sit in the North Sound, so a North Sound departure such as Camana Bay or the Yacht Club saves an hour.
- Ask what is included before comparing rates. Food, gear and toys move the real cost by hundreds of dollars.
Top 3 Factors to Consider When Choosing a Boat Tour
Match the Boat to Your Group Size and How Many Guests You Actually Have
Group size should be one of the first things you check when comparing private boat charters. Maximum capacity varies between vessels, but comfort matters too. A boat may legally carry twelve guests, yet a smaller group can mean more shade, seating, storage space and room to move comfortably throughout the day.
Sailing Catamaran or Power Yacht: Which Suits Your Day
A sailing catamaran suits a long, social day. Bamboozled, the 56ft Lagoon catamaran, gives flat decks, shade and room for thirty guests, and it sails rather than motors between stops.
A power yacht suits range and speed. Mojito Majic, the 38ft Intrepid, reaches the offshore drop-off in minutes and doubles as the fishing platform. Same company, opposite days.
Check What is Included Before You Compare Rates
A $4,200 charter with platters, Seabobs and snorkel gear aboard is not the same purchase as a $4,200 charter with bottled water. Surfside publishes a full rate card covering both vessels, fishing trips, surcharges above the first 14 guests, and cancellation at 50% from 30 days to 72 hours, and 100% inside 72 hours (full terms). Ask any operator what food comes aboard, what the water toys cost, and what happens if weather cancels the day.
Book a Private Boat Charter with Surfside Charters
Book a private boat charter with Surfside Charters and shape the day around your group, interests and preferred pace. Choose between a spacious sailing catamaran or a fast power yacht, with options for snorkeling, fishing, sightseeing and time on the water.
Published rates make planning easier, while included platters, water toys and experienced local crew add value throughout the trip. Share your dates and group size, and Surfside can help build a private Grand Cayman charter around you.
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