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Sail With Friends Cayman
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Sail With Friends Cayman

See all things to do
See all things to do
Sail With Friends Cayman
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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
Awards
Travelers' Choice
2024
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Sail With Friends Cayman
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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 wait time, length of visit, general tips, and location information.

Popular mentions
5.0
5.0 of 5 bubbles1,090 reviews
Excellent
1,088
Very good
1
Average
1
Poor
0
Terrible
0
Diane B.
2 contributions
5.0 of 5 bubbles
Best water excursion EV-ER!
Jan 2020
My family of 10, 8 adults and 2 granddaughters ages 4 and 7, chose to vacation for the first time on Grand Cayman this year. One of the things we enjoy doing is taking a local boat trip. Our son did the research this time and found “Sailing With Friends”. He thought, they must be doing something right when over 1,000 reviews are at a 5! Well it proved to be an amazing experience for all. The crew of Patrick, Alice and Oz couldn’t have been nicer or more accommodating when it came to making us feel welcome and comfortable. Not only were they very informative and caring for our safety, they went above and beyond our expectations to ensure that we had the best experience. They provided fruit and snacks and a delicious conch ceviche fresh from the ocean. Oz and Alice joined us in the water when snorkeling and swimming with the stingrays. Their expertise and easy manner, especially with our little ones, was reassuring and made for a positive fun filled adventure. A bonus was Alice took pictures of everyone in the ocean up close and personal with the stingrays and immediately sent them to us. They will certainly be our recommendation to others visiting the island and looking for a great way to enjoy all Cayman has to offer!
Written January 30, 2020
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.
Jaclyn W
1 contribution
5.0 of 5 bubbles
Half day charter to stingray city
Feb 2020 • Family
Sail with friends was the perfect half day charter to sting ray city. We had 9 adults and 2 children under the age of 2. We left at 8am and got to sting ray city before the cruise ship crowds (I recommend the morning charter) from there we went to a lovely snorkel spot and then onto starfish point. We even stopped for mudslides on the way back! Alice, Patrick and Oz were so nice, they made sure we had a great time and everyone felt safe. They even had a little Fischer price boat for our toddlers to play with aboard. It really was the perfect day and wouldn’t have been possible without them!
Written February 6, 2020
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.
Scott B
Minneapolis, MN1 contribution
5.0 of 5 bubbles
Great day on the water!
Feb 2020
My family and myself had a wonderful 1/2 Day on the water with Alice, Patrick and Oz! The crew was fantastic and the accommodations were great. We had a great time snorkeling, going to Stingray City, and Starfish Point.Oz made sure everyone had a great experience in the water, from holding the stingrays to tracking down starfish. The little one in our group especially like the hot pizza in the ocean. They have a great operation from start to finish and I would highly recommend to anyone looking to book a charter.
Written February 19, 2020
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.
susan19692016
The Woodlands, TX4 contributions
5.0 of 5 bubbles
AMAZING!!!!! Best thing to do while in Grand Cayman.
Jan 2020
Friends recommended Sail With Friends. We worked with Alice to book our trip. From the moment we spoke to her, we knew this is was the "right" team for our family. We have 3 daughters, and one was extremely nervous about our trip. Alice picked up us from our resort and drove us to the boat launch. We were met at the boat by Captain Patrick and Oz. The waves were a little rougher than normal, but Captain Patrick reassured us and our daughters had so much fun. Once we arrived at Sting Ray City, Oz jumped in and introduced us to his favorite sting rays. Alice was right there with us, encouraging my middle daughter. She took amazing pictures for us. Once back on the catamaran we had a yummy fruit platter that the we gobbled up. We then went to a coral reef and swam with more sting rays and saw hundreds of fish. We headed to Star Fish Point and docked, and saw beautiful starfish. Once we arrived, Alice surprised us with pizza! We then stopped and had a drink and then headed back to the boat launch.
Alice took us back to our resort. We have traveled to GCM 9 times and this is the VERY BEST tour we have ever done. I wish we would have taken advice from our friends sooner! We are home now and my daughters are still talking about it. I highly recommend Sail With Friends. You will not be disappointed!
Written January 7, 2020
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.
WoodFamVA
Annandale, VA2 contributions
5.0 of 5 bubbles
So worth it!
Apr 2022
I am so grateful for the incredible day Patrick, Alice and Oz gave our family! We booked a full day catamaran tour with them for our family of six (three children between 5 and 9 and our au pair). They were able to pick us up from Kaibo at Rum Point since we were staying in North Side (hugely convenient to avoid rush hour traffic to Georgetown - it is real!!). They were so incredibly kind and hospitable, patient and engaging with our children and gave us memories that we will cherish forever. On top of the incredible places they showed us (stingray city, starfish point, coral gardens) we were able to dive for fresh conch and Patrick made a wonderful conch ceviche and then somehow Alice also managed to make a pizza on board! They truly went above and beyond and we felt as though we were among friends we’d known for ages. You will not regret booking your next adventure with them and I really hope we have the chance to sail with them again!! Thank you Patrick, Alice and Oz!!!
Written April 11, 2022
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.
BonVivantVa
Falls Church, VA72 contributions
5.0 of 5 bubbles
Highlight of a great trip. Perfect day with the extended family!
Feb 2020
I cannot recommend Sail With Friends enough. We went to stingray city, snorkeled, and enjoyed starfish point with a group of 8, including a 2 and 5 year old. Everyone agreed it was the highlight of a really great trip. Alice picked us up at the Ritz, and we were at the marina in no time. After meeting Oz and a quick safety briefing by Captain Pat, we were off to Stingray City. Oz did a great job of making sure we all got a plenty of time and a perfect picture with a Stringray. It gets crowded out there, especially if you go with a big group. With only 8 of us, we really got a lot of time to enjoy the rays. Just a few minutes away you can see the reef and we started snorkeling. From the second I put my head in the water, I saw hundreds of colorful fish and two rays just cruising together right under me. At Starfish Point, the kids enjoyed finding and learning about starfish while the adults were enjoying some food and beverages. My favorite part was connecting my phone to the boat's speakers and leisurely sailing back after a great day. The private boat experience was well worth it, but honestly the hospitality of the crew was the best part. Oz made drinks, handled the rays, and was incredible with the kids. He found a playset on board for my son and taught my daughter about the sea life. Pat was great and made sure we had a safe and uneventful trip. Alice was helpful and always there to make sure we were having a great time. The second I opened a bottle of champagne, she was there with glasses for serving. When Alice dropped us off, my daughter told her to tell Pat and Oz that she loved her new friends and had the best day ever. When Alice emailed me some pictures she took, she told me they got misty eyed. We really were treated like friends, and I hope we get to see the crew of Sail With Friends again soon!
Written February 26, 2020
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.
Kendra G
1 contribution
5.0 of 5 bubbles
Absolutely wonderful adventure
Jan 2020 • Business
We had a large group of about 28 people. All of which were adults and many of us unsure and skeptical of stingrays and snorkeling. ALL 28 of us left the boat that afternoon in absolute awe of Alice, Patrick and Oz. They were so friendly and so encouraging to all of us who were afraid. We started the day off at Stingray Bay where we all got a change to hold, feed and even kiss the stingrays! We also went snorkeling which was personally my favorite part. When ventures to starfish point and then they took us to a little beach bar for lunch which was delicious! Alice was beyond helpful in helping me plan the trip for all of us, as well as answer all of my questions. I would recommend Sail With Friends to anybody traveling to the Caymans. It was a day none of us will forget!
Written January 26, 2020
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.
Jessica H
1 contribution
5.0 of 5 bubbles
Highlight of our trip!
Feb 2020 • Family
We had an amazing experience with our family of four. Alice, Patrick and Oz were extremely knowledgeable and kind and went to great lengths to make our experience unforgettable. We had a great time in stingray city, loved snorkeling in coral gardens, and had a great visit to starfish Key. So much fun docking for lunch and felt extremely safe the entire 6 hour trip. Would highly recommend and will use again!
Written February 17, 2020
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.
Sheri
Ottawa, Canada1 contribution
5.0 of 5 bubbles
Half day cruise on a catamaran with Alice, Patrick and Oz
Jan 2020
I was one of seven book club ladies who had the most amazing catamaran experience with Alice, Patrick and Oz. From the convenient pickup at the condo, to Patrick’s interesting tales and knowledge to Oz’s easy banter, the whole excursion was exceptional. Coral Gardens, Stingray City and Barker’s Reef were all excellent snorkelling spots. What a treat to have Alice tour us around Barker’s Reef. It was a truly brilliant morning and the memories will last forever.
Written January 26, 2020
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.
Ron W
Eagle, ID13 contributions
5.0 of 5 bubbles
Catamaran at it best.
Jan 2020 • Friends
We go to the islands at least once a year. We love to go on catamaran trips. Sail with friends was one of the top trips. Patrick, Alice and Oz were great. With the smaller boat the trip was very personal. We had a group of 12 and we all had a great time. They took us to several places and also made a stop for the famous Cayman mud slide at a beautiful beach side restaurant. If you are in Grand Cayman with a group of friends, this is a great day trip.
Written January 23, 2020
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 - All You Need to Know BEFORE You Go (2024)

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