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Address: Cayman Yacht Club, West Bay, Grand Cayman
Phone Number: +1 345 927 1127
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Grand Cayman's finest private sailing charter.A beautiful 45' catamaran...

Grand Cayman's finest private sailing charter.A beautiful 45' catamaran with plenty of space for up to 20 guests. The yacht offers 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.

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TripAdvisor Reviewer Highlights

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Great Times!

We had the most amazing day out on the water with Jon and Oscar! So many fantastic qualities, I could go on and on. We were three generations, and they were just fabulous and... read more

5 of 5 starsReviewed yesterday
Princeton Junction, New Jersey
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28 Reviews from our TripAdvisor Community

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Princeton Junction, New Jersey
1 review
5 of 5 stars Reviewed yesterday NEW

We had the most amazing day out on the water with Jon and Oscar! So many fantastic qualities, I could go on and on. We were three generations, and they were just fabulous and attentive to all of us. Definitely the highlight of our trip to Grand Cayman!

Thank lissyl437
Saint Louis, Missouri
1 review
5 of 5 stars Reviewed 2 days ago NEW

Capt John, Oscar, and Wes all did a great job our excursion! Our whole group had an great day! I would absolutely recommend Mainstay Sailing to all my friends We will absolutely be back to the Cayman Island And we will absolutely be back to visit Capt John!

Thank Julie G
Springfield, Missouri
Level Contributor
9 reviews
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed 4 days ago NEW via mobile

John and his mates Wes and Oscar were great! Just great friendly people. We swam with the stingrays, snorkeling on the reef and went to starfish beach. Coolers available for drinks or a frig for sandwiches as well as they had fresh fruit for us. Pineapple, watermelon, and honeydew, etc. We had 13 people with plenty of room. Highly recommend... More 

Thank KelliCrane
2 reviews
5 of 5 stars Reviewed 6 days ago NEW

what a wonderful day we had with john and oscar! beautiful boat, amazing crew! the day could not have been better. jon was a great captain, guide, teacher. oscar too! learned a lot and had so much fun. a memorable day!!! highly recommend to anyone! best day ever!!!!

Thank stephencU7400PW
Level Contributor
5 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 6 helpful votes
5 of 5 stars Reviewed November 13, 2015

We booked a full day trip with Jon aboard the Enchantress, a beautiful, top notch catamaran for our last full day in Grand Cayman. Jon was very helpful and accommodating, even going as far as picking us up at Kaibo since we were staying on the East End. He was willing to tailor the day to what we wanted to... More 

1 Thank Magnolia22Ca
Austin, TX
Level Contributor
68 reviews
13 attraction reviews
common_n_attraction_reviews_1bd8 34 helpful votes
5 of 5 stars Reviewed June 19, 2015

Our family of 8 adults and 8 grandchildren chartered this catamaran, The Enchantress, for a 7-hour sail to celebrate a major wedding anniversary. Captain John and mate Oscar kept us all busy and entertained throughout. From 3 places to snorkel, a private stingray city side-trip (away from tourists), including reef-snorkeling, we had plenty of variety. They also gave us options,... More 

2 Thank Carlton E
1 review
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed April 13, 2015

We booked mainstay based on the trip advisor reviews and we were not disappointed. Jon and Oscar were so welcoming and showed us a great day. 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. There... More 

1 Thank kerry c
Fairfax, Virginia
2 reviews
common_n_attraction_reviews_1bd8 3 helpful votes
5 of 5 stars Reviewed January 26, 2015

This was our family's second trip with Captain Jon and his crew. We booked a 1/2 day of fun the week of Christmas 2014. It was the BEST day of our Christmas vacation. The Enchantress is a beautifully maintained catamaran. Captain Jon and his crew took great care in making our trip comfortable and extremely memorable. We enjoyed chatting with... More 

2 Thank Jen D
Grand Cayman
1 review
5 of 5 stars Reviewed January 15, 2015

We chartered Mainstay on the 31st December 2014. I live in the Cayman Islands and had family visiting for Christmas and New Years so I really wanted to impress. Jon and his first mate Oscar did not let me down. Prompt to respond to all my questions, easy to book, great value, amazing client service. Champers was served promptly at... More 

Thank Jennifer E
Freehold, New Jersey
1 review
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed August 7, 2014

From the moment we contacted Jon everything went really well. Jon, Oscar and David made our whole day excursion extremely fun and entertaining. 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 and made sure that our entire... More 

1 Thank Frank C

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Questions & Answers

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Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
  • How should I dress for this tour?