“A memorable custom sailing experience for a large family” - Carlton from Austin, Texas

"We booked a full day and went snorkeling and swam with the stingrays when it was less crowded. We also had a great lunch at Kaibo. We had 8 adults and 9 kids" - Kerry, June 2015

"From stingray city to starfish point to snorkling, riding a wave runner, tubing and jumping off the boat and everything in between this day was great. Jon was a great captain" - Frank, New Jersey

"We went sailing, snorkeling, visited the friendly stingrays, and searched for starfish! Best of all, we had a day away from our cruise crowds" - Bill and Clare, Florida

Phone:  +1 345 927 1127

E Mail: bookings@mainstaysailing.com

Whether you require a day sail or a two week Cayman to Cuba explorer, we will do our best to shape an itinerary to suit you. Small groups are our specialty, maintaining guest numbers at around twenty for day sails and up to six for live aboard charters.

Day Charters


Half Day Sail (4 hours)


A great way to explore some of Grand Cayman's North Sound. Enough time for 2 or 3 stops of your choice - Swimming with Stingrays, an offshore sail, a few stops along Grand Cayman's Barrier reef? And still have enough time for a relaxing sail back to the dock!


Full Day Sail (7 hours)


Enough time to do it all! (everything!) Even a pit stop at a restaurant of your choice, or, if you would rather bring a picnic and have lunch onboard while floating around the Caribbean Sea, we can recommend caterers that can take care of that for you! - This is our most popular and well loved trip and, we are very proud to hear our guests repeatedly say that it's 'The best day of their Vacation'


Sunset Sail (2 hours)


We are so lucky in Grand Cayman to have such picture perfect sunsets over the ocean - every day!  A perfect way to wind down while relaxing on the bow nets with a cocktail in hand. If the conditions are right and everyone is willing we could even have a sunset swim.

Offshore sailing and overnight charters

mainstay charter

Cayman Explorer (3 days, 2 nights)


A great way to live aboard a charter boat before you commit to a week long trip.  We can make suggestions as to where you can anchor for the evening and keep you entertained with activities. We can sail around to Seven Mile Beach (deep sea fishing along the way), stopping at The USS Kittiwake and other wrecks for snorkeling and also see the wonderful snorkel sites on the West Side.

The evening meals can be at any waterfront location, we will 'dinghy' you in.  Provisions are excluded.

Offshore to Cuba! (7 Days)


For the trip of a lifetime!  Cayo Largo, Cuba lies due north and about 24 hours away by sail.  The Easterly Tradewinds make this a very comfortable ride, with the chance of catching Mahi Mahi and Tuna along the way.  We would prefer guests to have some previous sailing experience as you will be holding watches through the night.  Your Cap't Jon is an RYA Yachtmaster and Theory Instructor so you may want to polish your navigation skills along the way.  Once we arrive there is an option to take a 25 minute flight (around $90us) to wonderful Havana for an evening or, we can cruise the coastline for the best snorkel/spear fishing/lobster hunting (our onboard bbq gets plenty use on this trip!)

Up to 6 guests.  Provisions, visa's, docking fees and optional flights are NOT included.

Dolphins on the way to Cuba