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

Cayman Yacht Club, West Bay, Grand Cayman
+1 345-927-1127
Call
Website
Save
Review Highlights
Perfect private excursion

Went with Captain Tilly, JB with 13 family members during a Disney cruise stop in Grand Cayman and... read more

Reviewed 1 week ago
debbbiescreen
,
Silver Spring, Maryland
DAY trip with Mainstsay Sailing adn Capt. JON

Second trip with Capt. JON. This time he helped me plan the perfect proposal for my now Fiancé... read more

Reviewed 5 weeks ago
Kell5y
,
San Angelo, Texas
Read all 64 reviews
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Overview
More
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, swim with the rays, fishing, tubing, exhausting the kids! While you relax.Our rating speaks for itself.See you in The Cayman Islands.
  • Excellent100%
  • Very good0%
  • Average0%
  • Poor0%
  • Terrible0%
Travellers talk about
“captain jon” (10 reviews)
“day sail” (3 reviews)
LOCATION
Cayman Yacht Club, West Bay, Grand Cayman
CONTACT
Website
+1 345-927-1127
Write a ReviewReviews (64)
Traveller rating
Traveller type
Time of year
Language

1 - 10 of 64 reviews

Reviewed 1 week ago

Went with Captain Tilly, JB with 13 family members during a Disney cruise stop in Grand Cayman and it was THE BEST DAY! The boat is spotless. The crew was delightful and so knowledgeable about the sites and marine life (sting rays and starfish, sea...More

1  Thank debbbiescreen
Reviewed 5 weeks ago

Second trip with Capt. JON. This time he helped me plan the perfect proposal for my now Fiancé . Both trip have been spectacular, private, and fun, we fished, snorkeled, swam, visited Starfish point, the Stingrays. and just sailed around cruising the beautiful Caribbean. Felt...More

1  Thank Kell5y
Reviewed 2 November 2017

There was a group of 8 of us celebrating my birthday in Grand Cayman in late October. We had a fantastic day aboard the Enchantress, from the moment we stepped on the boat we couldn’t stop smiling. The initial euphoria has faded a bit, but...More

1  Thank VictoriaMarieD
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded 6 November 2017

Royal Victoria! (I remember the multiple emails). A wonderful review, many thanks for your time to post. I will let the lads know of your satisfaction. It’s our satisfaction too. See you for the next birthday ! Salut. Jon

Reviewed 4 October 2017

Hiring Captain Tilley, JB and the Enchantress were a wonderful way to spend our afternoon. Our group of 8 adults enjoyed every minute, even during the rain. The cat was big enough that we be in our out, depending on our preference. Tilley took us...More

Thank Pam D
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded 30 October 2017

Dear Pam. Thank you for weathering the showers and being bold enough to head out on that challenging day. I love your title, ‘the rain can’t spoil this fun’. You can scurry away .........or dance in the rain. It’s an attitude. We love your attitude...More

Reviewed 7 August 2017

We chose the sailing catamaran for a 7 hour tour - Easily the highlight of our trip. 6 adults and 6 kids from 10 to 24 years old (you get the picture). We had a couple kids say 7 hours on a boat would be...More

Thank coecpa
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded 8 August 2017

Charles. Big thanks for singing our praises with style. This keeps us afloat and rewards us immensely when we receive feedback like this. We hope to see you again, with some new ideas to ensure everyone is entertained....that's our job.... ...and we love it. Cheers...More

Reviewed 28 July 2017 via mobile

I can't say enough great things about our trip with Captain Jon. The day was amazing and our kids had a blast. The mates were incredible and so helpful and actually super protective of the little ones keeping them safe. Our girls continue to ask...More

1  Thank chicagojacobs
Reviewed 28 July 2017

We had a group of 18 people. 4 children, 14 adults and the afternoon could not have gone any better. Cayman is amazing and Jon and his crew made it even better. If your trying to charter a large boat, look no further, Captain Jon...More

1  Thank TICKETBROKERMAN
Reviewed 24 July 2017

I found this company on Trip Advisor when looking for a new company to replace the company we had been using for years.(they recently sold their boat) Tilley and JB gave us the best boat trip we have had......just liked they promised. We did the...More

1  Thank kls20
Reviewed 11 July 2017

This trip was just what we were hoping for! I echo the praises for Tilley and JB. Our group loved them and we all had a great day sailing and snorkeling. The sub wing was a lot of fun for the kids as was jumping...More

Thank FlyingK6517
Reviewed 1 July 2017

When you take six teenagers on a cruise, you need a special type of Captain and crew as well as a special kind of boat (shade for those who have passed sun baking age and lots of deck space for laying out for the teens...More

Thank Rocky M
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded 21 July 2017

Hi Rocky. What an amazing review. Are you an author/writer ? You managed to paint the scene with detail, humour and imagery so accurately. In fact, so well that people may think you were paid for it ! If you guys are smiling, we love...More

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
Submit