Sail With Friends Cayman
Sail With Friends Cayman
5
About
Sail with Friends offers full and half day sailing charters in the protected waters of North sound.Our professional and experienced crew will do evrything to ensure your day on the water is perfect.We have now added a powerboat option .More speed more options same highest possible level of service.We have just added a 38 ft sailing catamaran that can acess the shallow spots that are so popular like the sandbar and starfish point .
George Town, Cayman Islands
Meets animal welfare guidelines

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(165 reviews)
(183 reviews)
(22 reviews)

Most Recent: Reviews ordered by most recent publish date in descending order.

Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as waiting time, length of visit, general tips, and location information.

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5.0
1,070 reviews
Excellent
1,068
Very good
1
Average
1
Poor
0
Terrible
0

Centre for Clin... U
1 contribution
Feb 2024 • Family
Alice and Patrick definitely make you feel like you are sailing with friends. We have sailed with them twice and would highly recommend booking a trip with them. They have decades of experience and their fondness for the ocean is evident as they jump into waters with their guests to show them stingray city and various snorkelling sites around Cayman. Sailing was smooth and safe, food was delicious, and we look forward to booking with them again!
Written 20 February 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Maureenm
2 contributions
Feb 2024 • Family
WOW, if I could give 10 stars, I would! We had the pleasure of doing a 1/2 day tour with Alice, Pat and Oz to sting ray city and to starfish beach. It was incredible, Pat and Alice are just lovely to be around, so knowledge and kind. All were great with our kids, making them laugh and learning lots! The fresh fruit and pizza was such a special treat.

We did another 1/2 day tour today with Alice, Pat and Jeb. Again, 10 stars! We went out to an incredible snorkel area. We were the only ones there and swam with sting rays, so the most beautiful fish and a little ship wreckage with captivated my kids. Again, delicious fresh fruit and a conch ceviche prepared by pat.. we watched Alice bring the conch up from the sea! Then we did some fishing and relaxing. Highly recommend sailing with the wonderful friends
Written 18 February 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Alex C
1 contribution
Feb 2024 • Family
This was my family’s 2nd year in a row chartering the boat with Capt. Pat. This year we were joined by Alice and Jeb. All three of them were fantastic from start to finish! They were super flexible with us helping to move the charter day and timing around after an unprecedented storm arrived on the day we were meant to sail. Their first priority was making sure my kiddos (3 and 5 months) had a great experience. The whole crew was very hands on with the kids and made sure they had an incredible time exploring the water. They even caught a conch and made fresh conch ceviche for us right on the boat. The afternoon was a highlight for sure and we will absolutely be back! - Alex, Jeff, Jamison, Bastian, Tim, Jenny, and Bridget
Written 10 February 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Heidi R
Salt Lake City, UT2 contributions
Jan 2024 • Family
This is a wonderful way to spend a day. Captain Patrick was amazing. He took great care to make sure that everyone, including the children, felt relaxed and had an amazing time exploring the areas around Grand Cayman. Both Oz and Jeb are excellent additions to the days adventures offering up local tips and tricks. We started off the day with visiting the string rays and making sure we knew the best ways to interact with them. Then off for some snorkeling where we saw turtles and many different fish. We then took a leisurely sail to starfish point where we enjoyed pizza, jumping off the boat and checking out all of the starfish. This is such a great way to spend the day with a small group of your favorite people. Can't wait to be back on the water with them again!
Written 5 February 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

ericcox007
10 contributions
Jan 2024 • Couples
Alice and Patrick were once again fantastic sailing hosts. This was our second trip with them, the last being 5 years ago. We chartered their 38 foot catamaran for a 1/2 day sailing trip in Grand Cayman for the 4 of us and we had a fantastic time, again! They were all very gracious (Alice, Patrick and their first mate) and the day was great. In addition to great sailing and fantastic snorkeling at an old ship wreck, they made us ocean fresh conch ceviche fresh from our snorkeling trip, as well as fresh garlic butter sautéed lobster, yes from our snorkeling trip as well! In addition to that are their wonderful life adventure stories. Overall a wonderfully fantastic day sailing in the Caymans. Will absolutely sail with them again! Thank you Alice and Patrick!
Written 1 February 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Gerrydrew
Kanata, Canada2 contributions
Jan 2024 • Friends
This was our second sailing with Pat and Alice, and the new member of the crew Jebb. Fun, helpful, knowledgeable. Even coordinated a slightly earlier start time to avoid the cruise ship rush. We did a half day tour that included Stingray City, Starfish Point and snorkelling. Always a good time and relaxing.
Written 27 January 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Carey G
Ottawa, Canada9 contributions
Jan 2024 • Couples
We had a wonderful experience yesterday with Alice, Patrick and Jeb. Everything was wonderfully organized and they took good care of us. We visited Stingray City, snorkeled at the Aquarium (snorkeling spot), and visited Starfish Point. They organized the trip to try to avoid the crowds which made everything so much more enjoyable. They are such lovely people who make you feel welcome. We have gone out with them every time we come down to Cayman with friends. We highly recommend them. A perfect way to spend time in Paradise.
Written 27 January 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

apg113
New York, NY13 contributions
Jan 2024 • Couples
What a wonderful day aboard "Sail with Friends". After reviewing all the great reviews on Tripadvisor, I decided to charter the boat for my wife and I to celebrate her special birthday. Alice, Patrick and Jeb joined us for the journey and they made it an incredible day taking great care of us. The entire crew are wonderful, kind and lovely people. Alice taught us a ton about the island and has some incredible swimming skills going extremely deep in 8-10k feet of water. It was beautiful to watch. Jeb has the magic touch with the Sting Rays and was able to get my wife and I extremely close to these beautiful creatures. To top it off, Jeb took us snorkeling in at the most unbelievable reef and we saw hundreds of different types of fish. Just an overall amazing experience and I highly recommend them. We even walked away with some amazing photos that Alice took in the water of us!
Written 15 January 2024
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Polly Serpell
12 contributions
Dec 2023 • Friends
What a fun day out! We made a stop at Stingray City, and then went for a snorkel at the reef!
We were lucky enough to be here in lobster season and experienced some fresh lobster cooked on board! Pat and crew are more than welcoming and completely align with the name - sail with friends.
Written 8 December 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Kimberly D
1 contribution
Nov 2023 • Couples
We got married on their catamaran and everything was perfect. The whole crew was so attentive, kind and knowledgeable. They even accommodated a FaceTime of the boat because it’s so hard to plan a wedding from another country! For the ceremony, the captain took care to anchor where the water was the most beautiful aqua color for the most gorgeous photos possible! The crew made us fresh conch ceviche and later provided a champagne toast. We chartered for 6 hours so our special day was not rushed. They customized the time so we could catch the sunset. We could not be happier with the day and whole experience with them and hope to do it again in the future.
Written 25 November 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

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Sail With Friends Cayman (George Town) - All You Need to Know BEFORE You Go (with Photos) - Tripadvisor