Most Popular
From $750 · whole boat
Sunset Cruise
Cayman’s phenomenal sunsets from the North Sound or Seven Mile Beach, drink in hand. Watch for the Green Flash.
Check AvailabilityPrivate Charters · Grand Cayman
Grand Cayman Boat Charters Designed Around You
Your boat, your day, your itinerary
Instant confirmation · Family owned & Caymanian crewed
Private Boat Charters
Discover Grand Cayman by Private Boat Charter
Surfside Charters is a family-owned, Caymanian-crewed private charter company departing Camana Bay, Grand Cayman. Choose Bamboozled, a 56ft sailing catamaran for up to 30 guests, or Mojito Majic, a 38ft power yacht for up to 10. Trips include Stingray City, snorkeling, Starfish Point, sunset cruises and fishing, from US$750 for the whole boat.
Grand Cayman is truly best experienced from the water. The North Sound serves as a breathtaking natural playground, where calm seas, shallow sandbars, and protected coral gardens create the perfect backdrop for everything from vibrant reef snorkeling and wildlife encounters to casual cruising and fishing.
When you book a private charter with Surfside Charters, the day belongs entirely to you. Free from the rigid itineraries and crowded decks of public tours, your group has the freedom to choose your destinations and activities and set your own pace.
We pair luxury and local expertise with a deeply personal, guest-led approach. Whether you are accommodating different ages, interests, or comfort levels, we specialize in crafting seamless experiences tailored uniquely to you.
Avoid Crowded Tours and Explore at Your Own Pace
Private charters let your group enjoy Grand Cayman without the limitations of large group tours. Spend longer snorkeling, move to a quieter destination or relax onboard while others swim.
- A yacht reserved for your group
- Flexible stops and departure times
- Personal attention from a knowledgeable crew
- Activities suited to your interests
- Space to relax in comfort and privacy
Create a Custom Itinerary With Local Cayman Knowledge
Tell us what your group wants to experience, and our local captains will help create a practical route based on weather, water conditions and timing. Your customizable Grand Cayman itinerary may include Stingray City, Coral Gardens, Starfish Point, Rum Point, Kaibo Beach, fishing, mangrove channels or Bio Bay.
Secure Your Private YachtChoose Your Experience
Choose Your Grand Cayman Charter Experience
Surfside offers private charters for different schedules, group types and vacation plans. Whether you want to see the best-known North Sound destinations or spend an unhurried day aboard a luxury yacht, your experience can be adapted around you. Prices are for the whole boat — not per person.
Most Popular
From $1,250 · whole boat
Half Day
Stingray City and the Sandbar, snorkelling at Coral Gardens or the Barrier Reef, and Starfish Point — at your own pace.
Check Availability
Best Value
From $1,850 · whole boat
Full Day
Everything in the half day, plus lunch on board or ashore at Kaibo, and a sail through the Mangrove Channel.
Check Availability
From $1,250 · whole boat
Fishing Charter
Reef or deep sea, with the drop-off just a quarter mile from shore. All tackle, bait, captain and mate included.
Check AvailabilityCharter Experiences
Explore Each Charter in Detail
Every itinerary is built around you. Here’s what each of our most-requested Grand Cayman charter experiences looks like.
Half-Day Grand Cayman Boat Charters
A four-hour charter is ideal for guests who want to experience selected North Sound highlights without committing the whole day.
A half-day private charter might combine Stingray City with Coral Gardens or Starfish Point. Your captain will help select a realistic route so the trip feels relaxed rather than rushed. Morning and afternoon departure options may be available.
Full-Day Private Boat Charters
A seven-hour full-day private charter gives your group more time for destinations, activities and relaxation.
You may combine Stingray City, reef snorkeling, Starfish Point and lunch near Rum Point or Kaibo. Full-day trips also provide more flexibility for fishing, paddle boarding, using our state-of-the-art sea bobs, or simply enjoying the yacht between stops. The additional time creates a more complete Cayman boating experience.
Grand Cayman Sunset Cruises
A private sunset cruise offers a peaceful way to enjoy Grand Cayman’s coastline and evening sky.
Relax aboard one of our exquisite boats while your captain selects a scenic route through the North Sound or near Seven Mile Beach. Sunset cruises are well suited to couples, families, celebrations and guests who want a shorter, slower experience on the water.
Stingray City, Starfish Point and North Sound Adventures
Stingray City is one of the Cayman Islands’ most famous experiences. Its shallow sandbar allows visitors to enter the water near wild southern stingrays.
A Stingray City private charter can also often include Starfish Point, Rum Point, Kaibo or nearby snorkeling locations. Your crew can adjust the order of stops based on water conditions, timing and crowds.
Coral Gardens, Barrier Reef and Seven Mile Beach Snorkeling
Grand Cayman offers excellent snorkeling in crystal-clear water filled with tropical fish, coral reefs and diverse marine life.
Our professional crew provide snorkel equipment, recommend appropriate locations and support less-experienced swimmers. Reef snorkeling at Coral Gardens or the Barrier Reef can be combined with Stingray City, Starfish Point, Seven Mile Beach or relaxed cruising.
Grand Cayman Reef and Deep-Sea Fishing Charters
Grand Cayman’s deep drop-offs and productive coastal waters make it an ideal destination for both action-packed reef fishing and offshore big-game excursions.
Whether you are interested in bottom fishing for snapper and grouper or trolling offshore for mahi-mahi, wahoo and tuna, your crew will provide everything needed for a memorable trip. Fishing activities can be tailored to seasoned anglers or combined with snorkeling and sightseeing stops for a well-rounded day on the water.
Customize Your Private Charter Experience
Choose the activities, destinations and pace that feel right for your group, then let Surfside turn them into one seamless experience.
Explore Charter OptionsBuild Your Day
What You Can Add
Mix and match as many as the clock allows. You set the schedule, and you spend as long at each stop as you like.
Stingray City & Sandbar
Around 90 wild Southern Stingrays roam the North Sound. Stand in 2–4 feet of water at the Sandbar, or snorkel Stingray City in 12 feet of crystal-clear water.
Snorkelling
Coral Gardens, the Barrier Reef, the Kittiwake wreck, Cemetery Beach and Eden Rock. Gear is provided for every guest.
Starfish Point
A protected beach speckled with Red Cushion Sea Stars in knee-deep water — one of the most photographed spots on the island.
Bioluminescent Bay
Thousands of bright sparkles in the water after dark. Runs year-round, but only about two weeks each month due to the moon cycle.
Simple to Book
How It Works
Pick your date
Check live availability online and choose the trip length that suits you. Instant confirmation by email.
Tell us your wishlist
Stingray City, snorkelling, Starfish Point, fishing, sunset, catering — we build the itinerary around it.
Step aboard
Meet your crew at Camana Bay 10 minutes before departure — or arrange a pickup from anywhere our boats can reach. We handle everything else.
Included With Every Charter
Nothing Extra to Buy
- Snorkel gear for every guest
- Life jackets & snorkel vests
- Fresh towels
- WiFi & Bluetooth music
- Fresh fruit platter
- Chips & light snacks
- Bottled water & soda
- Food for the stingrays
- Noodles & sun floats
- All tackle & bait on fishing trips
Want more? We can add breakfast, lunch or dinner on board, or bring a private chef with 72 hours’ notice.
See Catering OptionsQuality & Elegance
Sail by Luxury Catamaran or Cruise by Power Yacht
The right yacht shapes the feel of your charter. Surfside offers two premium vessels with different strengths, allowing you to choose between spacious sailing comfort and fast power-yacht flexibility.
Up to 30 guests
From $2,300 · whole boat
Bamboozled
A luxurious 56-foot Lagoon sailing catamaran offering generous indoor and outdoor spaces, shaded seating and a stable platform for enjoying the Caribbean. Ideal for families, celebrations, corporate outings and private groups of up to 30 guests.
Up to 10 guests
From $750 · whole boat
Mojito Majic
A sleek 38-foot Intrepid power yacht built for fast, comfortable cruising. Her wide cockpit, dive platforms and boarding ladder make her suitable for snorkeling, fishing and water sports. Ideal for guests who want to visit several destinations efficiently.
Reviews
Rated 5.0 by Our Guests
5.0
TripAdvisor · Google · FishingBooker
Guests consistently single out the same three things: a crew that goes out of its way, boats that are immaculate, and a willingness to reshape the day around whatever you feel like doing.
Snorkelling stops, Stingray City, Starfish Point, sunset sails and bioluminescent bay trips — including more than one engagement at sea.
Check Availability Read Reviews on TripAdvisor Google Reviews
This charter was spectacular!
“The crew was professional and flexible. They went above and beyond to make our day so special from the hospitality to showing us an incredible time at stingray city. The boat was very luxurious! Such an outstanding company, and we look forward to more outings!”
Great Cruise on the Bamboozled!
“My wife and I with two other couples took the beautiful Bamboozled out for a 3 hour cruise and even stopped at stingray city. Was an amazing time, amazing ship and amazing crew. Will definitely always be first call when we come back. Crew was so fun and respectful of anything we wanted to do and such a great guide at the stingray city part. Even let me take my drone for a spin and plenty of pictures! Thanks captain Glen, Stephanie and all the crew!”
Life Memory
“What an amazing charter! We had a great day, great crew and great memories! It’s like I tell my family, we will have a lot of memories in our lives but only a few life memories. Those are the ones I’m after and that’s what we got with Surfside Charters! Thanks guys and can’t wait to do it again!”
Why Surfside
Why Choose Surfside for a Private Cayman Boat Charter?
Surfside Charters is an owner-operated Cayman charter company built around personal hospitality, local experience, and lasting memories. Guests choose Surfside because they want more than just transportation between attractions — they are looking for a fully private charter, premium vessels, and a professional team that possesses an intimate understanding of these local waters.
Professional Crew & Local Captains
Our captains and crew bring professional training and practical experience to every charter. Team credentials include captain qualifications, first aid, CPR, marine radio, safety training and PADI certifications. Local knowledge helps the crew select suitable destinations and make weather-based itinerary adjustments.
Comfort, Catering & Activities
Surfside can coordinate equipment, food, drinks and activities so your group can focus on enjoying the day. Available options include onboard catering, optional private-chef service, snorkeling equipment, paddle boards, sea bobs and personalized pickup arrangements.
Private Charters for Everyone
A private charter makes it easier to plan one experience for guests with different interests. Children can enjoy calm-water stops while adults snorkel. Couples can create a quieter day. Surfside also welcomes corporate groups, family gatherings, birthdays, anniversaries and other special occasions.
Before You Book
Frequently Asked Questions About Grand Cayman Boat Charters
Your charter generally includes the yacht, captain, professional crew and equipment for the activities selected. Food, drinks, catering, fishing tackle and special arrangements depend on the vessel and itinerary. Surfside will confirm all inclusions before departure so your group knows what is provided and what to bring.
Choose a four-hour charter for selected North Sound highlights or a seven-hour charter for additional destinations, lunch and relaxation. A two-hour sunset cruise suits guests looking for a shorter evening experience.
Choose Bamboozled for spacious sailing, group comfort and onboard hospitality. Choose Mojito Majic for faster cruising, fishing, water sports and visiting multiple destinations efficiently. Bamboozled takes up to 30 guests (we suggest 14 for ultimate comfort). Mojito Majic takes up to 10 guests (we suggest 8).
Yes. Private charters are particularly suitable for families because the pace and activities can be adjusted around the group. Our crew can recommend calm-water stops, suitable snorkeling locations and a balanced itinerary for different ages. Parents can also coordinate food, drinks, equipment and special requests before departure.
Camana Bay is our home berth, and most charters depart from there. We are also happy to arrange pick-ups from anywhere we can get the boat into — just ask when you book. Please arrive 10 minutes before departure.
CaymanKind
A Piece of Cayman for Everyone
Whoever you are and wherever you come from, there is a piece of Cayman that will speak to you. It could be our melting pot of cultures that causes the best traditions to rise to the top. It could be the finer things in life that only seem to get better here. It could be the works of Mother Nature or the skills of our artisans. Odds are, what resonates with you will be all of the above and more.
Meet the CrewBook Your Charter
Book Your Private Grand Cayman Boat Charter
Your vacation time is valuable. Spend it aboard a private yacht with a flexible itinerary, a knowledgeable crew and uninterrupted time with the people you came to be with.