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.

Cayman Islands Sailing Charters

Features Animals
George Town KY1-1010, Grand Cayman
+1 345-525-1222
Website
Share
Save
Review Highlights
Great day out on the water with friends!

My friends and I had a GREAT time out on the water with Captain Ben this past weekend. We went to... read more

Reviewed 29 January 2018
Jessica H
Rum punch and mimosas and nature

Captain Ben and Catherine were great leaders for our day long trip. We enjoyed a visit to Starfish... read more

Reviewed 26 January 2018
Nancy H
,
Sevierville, Tennessee
via mobile
Read all 54 reviews
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Overview
More
Sail around the beautiful Cayman waters with Cayman Islands Sailing Charters. Offering luxury sailing trips aboard our 36' trimaran. Visit Rum Point, Starfish Point, Stingray City or wherever you desire around Cayman. As our guest, enjoy your very own Captain taking you to wherever you choose.There is so much to take pleasure in and relax on your private sailing boat. Our boat is your boat.
  • Excellent91%
  • Very good5%
  • Average0%
  • Poor1%
  • Terrible3%
Travellers talk about
“captain ben” (30 reviews)
“cayman islands” (11 reviews)
Closed Now
Hours
Hours Today: 07:00 - 20:00
LOCATION
George Town KY1-1010, Grand Cayman
CONTACT
Website
+1 345-525-1222
Write a ReviewReviews (54)
Traveller rating
Traveller type
Time of year
Language
All reviews
"captain ben"
in 30 reviews
"cayman islands"
in 11 reviews
"starfish point"
in 7 reviews
"stingray city"
in 21 reviews
"personal attention"
in 3 reviews
"private charter"
in 4 reviews
"camana bay"
in 3 reviews
"great snorkeling"
in 2 reviews
"sea life"
in 3 reviews
"catherine"
in 4 reviews
"sails"
in 4 reviews
"seas"
in 5 reviews
"kaibo"
in 6 reviews
"mangroves"
in 5 reviews
"blast"
in 6 reviews
"reef"
in 12 reviews
"company"
in 6 reviews
Filter

1 - 10 of 53 reviews

Reviewed 29 January 2018

My friends and I had a GREAT time out on the water with Captain Ben this past weekend. We went to all the great spots, (starfish, kaibo,stingray) and he was very informative, engaged, and inviting. He also had a paddle board on the boat that...More

Thank Jessica H
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 26 January 2018 via mobile

Captain Ben and Catherine were great leaders for our day long trip. We enjoyed a visit to Starfish Point, Stingray City and Kaibo Beach Bar. We were served mimosas, Rum punch and waters to enjoy. The boat was roomy enough for 7 girls to be...More

Thank Nancy H
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 17 January 2018

Had a private charter with some friends on the 'Be Happy' with Captain Ben. Just a great time overall. Ben was very accommodating and tailored the trip to what we wanted to do. We hit up Stingray City, stopped to do some snorkeling by the...More

Thank Adnan M
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
See more reviews
Reviewed 6 January 2018

I took my wife, 5 teenage children, two grandmas (72 and 85),and my sister and brother in law out to sea with Captain Ben and his first mate Paul during a cruise stopover after Christmas. We did a 4 hour sail. I could not have...More

Thank James D
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 2 January 2018 via mobile

Went out with Captain Ben with a group of girlfriends and had a blast! Starfish Point, Sting Ray City, sun and surf! It was the perfect day! The “Be Happy” is the perfect size for a fun day out and Ben took great care of...More

Thank Rachael I
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 30 December 2017

It was AWESOME! We had so much FUN!! You could touch the STINGRAYS!!! The STARFISH TOO!!!! Then sailing while drinking my favorite beers and enjoying the WAVES!!!!! It is amazing to go SCUBA DIVING TOO!!!! We dove off the north Walls and saw some amazing...More

Thank Colt I
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 24 November 2017

We called several other charters, we were looking for a last minute trip for our friends who had two kids 5 and 3. Captain Ben was so great accommodating us, he didn't try to charge us extra because we were making a last minute reservation...More

Thank Sil K
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 10 July 2017

We chartered the "Be Happy" for a day of sailing and snorkeling on Grand Cayman. My family (my parents, my kids, me and my husband) had the best day with Captain Ben and Darrell! It was pouring rain when we met Ben near our cruise...More

Thank Amy D
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Ben W, Owner at Cayman Islands Sailing Charters, responded to this reviewResponded 17 July 2017

Hey Guys! Captain Ben here thanks for the great review! I will pass on your regards to Daryl. Im so happy your Parents and your whole family enjoyed the time on board " Be Happy". Next time you come to Grand Cayman i hope we...More

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Reviewed 27 June 2017 via mobile

Capt Ben and 1st mate Richy are Awesome! Couldn't ask for more personal sight seeing than what they provided. Took us to the best spots to see reefs without the crowds. These guys are top notch, highly recommend if you are wanting that personal attention.More

Thank aappss66
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Ben W, Owner at Cayman Islands Sailing Charters, responded to this reviewResponded 17 July 2017

Hey, Captain Ben Here! Thank you for taking the time to write this review. Its always a highlight to our work week when these come in and ill make sure to pass on your regards to Richi. I hope everything is going great for you...More

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Reviewed 10 June 2017 via mobile

We were looking for something special to end our week at Grand Cayman and this certainly hit the mark. We did a special twilight private sail with Captain Ben and the entire family had a great time. We toured the mangroves then set off to...More

1  Thank Garmans
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Ben W, Owner at Cayman Islands Sailing Charters, responded to this reviewResponded 17 July 2017

Hey Guys!!! Captain Ben here, thanks for writting this review. It was so cool to be out sailing through the sunset into the night and watch the full moon rise! At Cayman Islands Sailing Charters we love running custom trips such as this as it...More

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC
Nearby
Nearby HotelsSee all 18 hotels in Grand Cayman
Britannia Villas Grand Cayman
13 reviews
.29 miles away
Grand Cayman Marriott Beach Resort
5,831 reviews
.44 miles away
Comfort Suites Seven Mile Beach
1,501 reviews
.49 miles away
7 Mile Beach Resort and Club
213 reviews
.52 miles away
Nearby Restaurants
Gelato & Co. Cremeria Italiana
404 reviews
.08 miles away
Jessie's Juice Bar
129 reviews
.06 miles away
Mizu Asian Bistro + Bar
301 reviews
.07 miles away
The Brooklyn Pizza + Pasta
265 reviews
.05 miles away
Nearby Attractions
Adventura Cayman
38 reviews
.19 miles away
West Indies Wine Company
61 reviews
.01 miles away
Barker's National Park
113 reviews
.25 miles away
Royal Palms Beach Club
630 reviews
.27 miles away
Questions & Answers
Get quick answers from Cayman Islands Sailing Charters staff and past visitors.
Note: your question will be posted publicly on the Questions & Answers page.
Posting guidelines
Submit
Membership_Slide_Up_Placement_on_Attraction_Review
Get 10% off your next tour or activity booking.
Valid for new TripAdvisor sign-ups only.
Join TripAdvisor