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Mainstay Sailing
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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
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Reviews (80)
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All reviews captain john sailing catamaran starfish point stingray city sail home big fun splash pool snorkeling stops day trip rum point grand cayman an absolute blast highlight of our trip took great care private charter great pictures lion fish
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11 - 20 of 80 reviews
Reviewed January 25, 2018

Capt Jon and is mate Andrew were first rate. We had a wonderful 4 hour charter from the Cayman Yacht Club to Rum Point, the mudslides don't disappoint, Stingray City where we swam with and fed the stingrays, then on to a snorkeling reef and...More

Date of experience: January 2018
1  Thank Mark11746
Reviewed January 23, 2018 via mobile

My husband and I value the precious family time with have with our 2 daughters, 18 and away at college and 14 and in high school. This year we choose the Caymans for our family holiday. Day one was our sail day. I could not...More

Date of experience: December 2017
Thank Ketchkelly
Reviewed January 5, 2018

Can't praise Tilly and JB enough for making this day so VERY special for all of us. It was by far the best day we had on our visit to Grand Cayman and we look forward to coming back not only because we loved GC...More

Date of experience: December 2017
Thank Usa_ohioSbk
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded January 25, 2018

Great response! Your best day is ours too. Thank you. Cheers, Jon.

Reviewed January 3, 2018

We have done many day sailing trips throughout the Caribbean and Pacific. This was by far the best! Tille and JB did so much to make the trip meet our needs. They went above and beyond. We will treasure our memories of this trip. Starfish...More

Date of experience: December 2017
Thank denverburkes
Reviewed December 31, 2017

We have been coming to Grand Cayman for many years during the Christmas holidays and recently had our 4th outing with Captain Jon which speaks to the quality of the experience that you will have. We have found it worth every penny to spend the...More

Date of experience: December 2017
Thank WVEDTrvlr
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded January 25, 2018

Hi WVEDTrvlr It doesn’t make it easy for me to figure out who you are with that Trippy name ! I’m guessing it’s Will-I-am ....not to blow your cover :) Anyway, cool review, thank you ....and may we have many more years of entertaining you...More

Reviewed December 29, 2017 via mobile

We can’t say enough great things about our half day charter. We were three families and everyone had an incredible experience. The snorkeling was amazing. Kids had a blast. Could not have been a better experience. We look forward to chartering with them again!

Date of experience: December 2017
Thank douglikestotravel
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded January 25, 2018

Cheers Doug 🍻 If the kids are happy....Mum and Dad are very happy ! This seems to be our recipe for smooth sailing with my family as well :) Hope to see y’all next year. Jon

Reviewed November 30, 2017

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

Date of experience: November 2017
Thank debbbiescreen
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded January 25, 2018

Hi Debbie A wonderful review that we all appreciate so much. See you next visit.....nature willing. Cheers, Jon

Reviewed November 8, 2017

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

Date of experience: November 2017
Thank Kell5y
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded December 12, 2017

Hello Kelly Thanks for taking the time to post a great review. I was as nervous as you hiding the ring in a conch shell !! Great day, great result...congratulations! See ya next year. Jon

Reviewed November 1, 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

Date of experience: October 2017
Thank VictoriaMarieD
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded November 5, 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 October 4, 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

Date of experience: October 2017
Thank PamD8897
jonnoGrandCayman, Owner at Mainstay Sailing, responded to this reviewResponded October 29, 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

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