We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Mainstay Sailing
Booking unavailable on TripAdvisor

Want other options you can book now?
All photos (75)
Full view
Certificate of Excellence
Traveller Overview
  • Excellent100%
  • Very good0%
  • Average0%
  • Poor0%
  • Terrible0%
Travellers talk about
Grand Cayman's finest private sailing charter. Beautiful 45' Sailing catamaran and a 47’ power cat with plenty of space. The yachts offer 4 cabins all with en-suite, large sociable cockpit and deck space.Daysails are our specialty, snorkel the reef...more
Cayman Yacht Club | Yacht Drive , Grand Cayman ., West Bay, Grand Cayman
+1 345-927-1127
Improve This Listing
Reviews (82)
Filter reviews
82 results
Traveller rating
Traveller type
Time of year
Show reviews that mention
All reviews captain john sailing catamaran starfish point stingray city sail home big fun splash pool grand cayman day trip rum point highlight of our trip an absolute blast hour tour feed the stingrays took great care great pictures private charter
Updating list...
1 - 10 of 82 reviews
Reviewed 2 days ago

This is our third time to book a trip with Mainstay Sailing and once again, Jon exceeded our expectations! We took the power cat out with three families, including children ranging from ages 4 to 13 from 11am to 6pm. Jon and Oscar entertained all...More

Date of experience: March 2019
Thank abswiltex
Reviewed 25 January 2019 via mobile

There were four of us on the catamaran for a four hour tour. All I can say was it was amazing!!! Al and Oscar were our “guides” for the day. We started our tour by diving for Conch. Oscar cleaned the Conch and saved the...More

Date of experience: January 2019
Thank dianep510
Reviewed 16 January 2019

Booked a last minute tour and WOW!. We certainly made the right choice. The catamaran boat was awesome. Captain John and his mate were fabulous. Very friendly and made sure we had a great time. Two adventurers were towed behind the boat and had a...More

Date of experience: January 2019
1  Thank 1GiantsMS
Reviewed 8 January 2019

We just returned from 10 great days in Grand Cayman and our day with Captain John and his crew was the highlight of our trip. They are great people who know how to host and have fun. We were a family of 21 from ages...More

Date of experience: December 2018
Thank DayTrip43062
Reviewed 24 July 2018 via mobile

Captain John and Oscar were so fantastic! We had the best day! From snorkeling at a reef, going to Sting Ray City as well as checking out the Starfish area! The music was fun! They had drinks and fruit! Oscar was interactive and in the...More

Date of experience: July 2018
Thank allisony904
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded 29 July 2018

Cheers Allison. A British way of saying ‘thanks’ . We are not leaving anytime soon -back to the British weather ! ...so, come see us again. 👍 Jon and The Chocolate Smoothie.....(Oscar). :)

Reviewed 12 July 2018

This was our second charter with Mainstay and John, the first being 3 years ago, and it was just as amazing as the first time we chartered the trip Captain and crew are extremely kind, helpful and fun. Can't wait for our next trip!

Date of experience: July 2018
Thank jasb-tx
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded 29 July 2018

Thank you kindly for your review. Texans rule ! So does that Tito’s ....in moderation :)

Reviewed 10 July 2018

Our group of 11 spent a grad day with Captain John on his 47' cat. Stop where you wish, snorkel where you wish, enjoy the day. We called ahead and had the boat stocked with refreshments and snacks. What a way to spend the day!!!

Date of experience: June 2018
Thank MikeStefHalJoJ
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded 29 July 2018

Thanks for the shining stars Mike. Imagine doing that every day 😎 ! Love it...... We will hopefully see you again soon. Nature willing. 🙏

Reviewed 9 July 2018

Al and Oscar were awesome and took great care of our group of 7. They let us decide what to do and offered suggestions when we asked. They even flew a Texas Flag for us! Nice touch guys! We highly recommend their services. Be sure...More

Date of experience: July 2018
Thank Robb E
Alastair M, Manager at Mainstay Sailing, responded to this reviewResponded 10 July 2018

Thanks so much for taking the time to post a review. Oscar and I had a great time too. It was a pleasure meeting y'all and hope you come back to visit soon. Or at least for the next birthday. Thanks again, Al

Reviewed 8 July 2018

We had a family of 25 with four generations with ages from 2 to 82. Everyone had a great time with Captain John and Oscar. They are super friendly and knowledgeable. We went snorkeling at two great spots, swam with stingrays, played with starfish, paddle...More

Date of experience: June 2018
Thank 222carries
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded 9 July 2018

Thanks so much Carrie. Your comments mean everything to us ....it’s our reward to see smiles on the day and pleasant reviews. I seem to remember that you dealt with the 2 year old and we dealt with the rest. ‘The best day of your...More

Reviewed 12 June 2018

We were 2 families with 4 teenage girls and 4 adults. Al was our Captain and Oscar our guide and they made a great team. Our 1st stop was Stingray City. Words cannot describe the experience, 50 or more Stingrays swimming all around us. Oscar...More

Date of experience: June 2018
1  Thank Patricia T
Alastair M, Manager at Mainstay Sailing, responded to this reviewResponded 10 July 2018

Thanks Patricia. Good of you to take the time the time to post a review. That was a fun day on the water. Hope you guys come back and do it all again soon. Thanks again. Al.

View more reviews
Nearby HotelsSee all 20 nearby hotels
Kimpton Seafire Resort + Spa
942 reviews
.78 km away
Locale Grand Cayman
1 review
1.91 km away
The Westin Grand Cayman Seven Mile Beach Resort & Spa
899 reviews
1.92 km away
Grand Caymanian Resort
107 reviews
1.97 km away
Nearby RestaurantsSee all 349 nearby restaurants
229 reviews
.21 km away
Coccoloba Bar & Grill
287 reviews
.88 km away
The Fish Pot
7 reviews
.89 km away
Morgans Seafood Restaurant
512 reviews
.18 km away
Nearby AttractionsSee all 497 nearby attractions
Sail Cayman Ltd.
388 reviews
.09 km away
Island Splash Watersports
54 reviews
.10 km away
Six Senses Cayman Adventures
1,161 reviews
.12 km away
Acquarius Sea Tours
3,296 reviews
.13 km away
Questions & Answers
Get quick answers from Mainstay Sailing staff and past visitors.
Note: your question will be posted publicly on the Questions & Answers page.
Posting guidelines