Bluesail Yachting
Bluesail Yachting
5
Scuba & Snorkelling • Boat Tours • Boat Rentals • Dolphin & Whale Watching • Stand Up Paddleboarding
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9:00 AM - 6:00 PM
Monday
9:00 AM - 6:00 PM
Tuesday
9:00 AM - 6:00 PM
Wednesday
9:00 AM - 6:00 PM
Thursday
9:00 AM - 6:00 PM
Friday
9:00 AM - 6:00 PM
Saturday
9:00 AM - 6:00 PM
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About
Immerse yourself in the tranquil beauty of the Florida Keys and experience a vacation of a lifetime with TripAdvisor's 3-time Traveler's Choice Award Winner, Bluesail Yachting. Established in 2018, Bluesail holds a 5-star rating for all things sailing and has been recognized by Fatherly.com and Maxim as a top charter experience in Key West, Florida.
Explore the hidden gems of Key West with one-of-a-kind charter experiences including 6-10 hour day and sunset sails, plus, multi-day custom charters to unforgettable destinations like the Marquesas Keys and The Dry Tortugas with knowledgeable, experienced, and licensed Captains. For those seeking to expand their sailing expertise, Bluesail Yachting is an accredited sailing academy offering 3, 5, or 7 day education aboard a 38' sailing monohull or 40' sailing catamaran. To complete the cycle of your love for yachting, Bluesail can also assist in selling or buying the yacht of your dreams.
Discover the world of sailing with Bluesail!
Key West, Florida
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Awards
Travelers' Choice
2022
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Detailed Reviews: Reviews order informed by descriptiveness of user-identified themes such as cleanliness, atmosphere, general tips and location information.
Popular mentions
5.0
89 reviews
Excellent
88
Very good
1
Average
0
Poor
0
Terrible
0
Amelia K
1 contribution
Feb 2023
What a magical experience.
My husband stumbled on Bluesail while looking for rental properties for a short stay in Key West. We just went for it, not quite knowing what to expect. Our daughter is six years old, and we weren't sure how she would take to being out on a boat for an extended period of time. Also, I don't necessarily like strangers, let alone being trapped at sea with them! But we decided to roll the dice—and I am so glad we did.
The boat itself is lovely, comfortable, and well-appointed. It’s the Kaimana crew, however, that made this trip a dream. From the moment we stepped onto the boat, Captain Tyler and First Mate Brittany made sure that we were happy and relaxed. Their impeccable hospitality gave us space as a family while remaining thoughtful and attentive. As the trip went on, we discovered that they are also a pleasure to talk to, full of local knowledge and insights about the Keys and the critters who live there.
Brittany prepared delicious, fresh meals (fruit and yogurt parfaits for breakfast, fish tacos with jicama slaw for lunch, a beautiful dinner of steak and lobster one night and a low country boil the next)—and she makes a killer cucumber jalapeno margarita. Our itinerary, meanwhile, was the perfect balance of activity—snorkeling on the reef, checking out a cool sandbar, walking along the shore of an uninhabited island at sunset, swimming in a swimming hole—and spaced-out sun & sea bliss as we cruised around in between.
We saw all kinds of fish, sea turtles, and dolphins!—who obligingly swam along with us for a while. When our daughter got scared snorkeling, Brittany played with her on the boat while my husband and I explored the reef. By the end of the trip, she, Brittany, and Tyler had become great pals. It was so sweet! We spent one night anchored under the stars (so many stars!), and it was cool enough to leave the windows open and sleep with the sea breeze blowing over us, tranquility itself.
I couldn’t recommend Bluesail Yachting more highly—just a perfect vacation in every way.
My husband stumbled on Bluesail while looking for rental properties for a short stay in Key West. We just went for it, not quite knowing what to expect. Our daughter is six years old, and we weren't sure how she would take to being out on a boat for an extended period of time. Also, I don't necessarily like strangers, let alone being trapped at sea with them! But we decided to roll the dice—and I am so glad we did.
The boat itself is lovely, comfortable, and well-appointed. It’s the Kaimana crew, however, that made this trip a dream. From the moment we stepped onto the boat, Captain Tyler and First Mate Brittany made sure that we were happy and relaxed. Their impeccable hospitality gave us space as a family while remaining thoughtful and attentive. As the trip went on, we discovered that they are also a pleasure to talk to, full of local knowledge and insights about the Keys and the critters who live there.
Brittany prepared delicious, fresh meals (fruit and yogurt parfaits for breakfast, fish tacos with jicama slaw for lunch, a beautiful dinner of steak and lobster one night and a low country boil the next)—and she makes a killer cucumber jalapeno margarita. Our itinerary, meanwhile, was the perfect balance of activity—snorkeling on the reef, checking out a cool sandbar, walking along the shore of an uninhabited island at sunset, swimming in a swimming hole—and spaced-out sun & sea bliss as we cruised around in between.
We saw all kinds of fish, sea turtles, and dolphins!—who obligingly swam along with us for a while. When our daughter got scared snorkeling, Brittany played with her on the boat while my husband and I explored the reef. By the end of the trip, she, Brittany, and Tyler had become great pals. It was so sweet! We spent one night anchored under the stars (so many stars!), and it was cool enough to leave the windows open and sleep with the sea breeze blowing over us, tranquility itself.
I couldn’t recommend Bluesail Yachting more highly—just a perfect vacation in every way.
Written March 14, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Amelia - Thank you so much for this incredible review!! I just took a screenshot of this and sent it to Tyler and Brittany, and they're both in awe and really appreciate the kudos! They had a blast as well and asked me to thank you for the opportunity to work with you and your family. Honestly it's guests like you that keep us going everyday - our mission is to work with families and friends to help them unplug and recharge the batteries, making memorable and unique Florida Keys memories, and do so on some exceptionally maintained sailing yachts. Seeing reviews like this, and working with amazing folks like you, really help to remind us why we do what we do. Thank you all so much for being such exceptional guests, and we hope to see you all again soon!
Written March 20, 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Das M
1 contribution
Mar 2023
Just amazing! great experience. Tropical islands and lots of learning. The Bluesail team is top notch. Would highly recommend them!
Written March 13, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Thanks for your review! It was really great working with you and your group last week, and we hope to see you back in Key West again for some additional training! Cheers 🍻
Written March 14, 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Craig M
Bethesda, MD2 contributions
Dec 2022 • Family
Just an incredible experience from start to finish. Recommend without any reservations. Great day sailing, snorkeling and paddling - all in 6 hours!
Written December 31, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Craig - Thank you so much for the 5-star review! We really enjoyed working with you as well, and hope the rest of your vacation down here in the Keys was enjoyable. Hope to see you all again down the road. Until then though, have a very Happy New Year! Cheers! 🥂
Written January 1, 2023
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Stuart
5 contributions
Jul 2022
It's been 5 months since our vacation with Bluesail and we are still telling our friends and family how much of an amazing experience our week sailing was. We got to see and experience things that we would not have had the opportunity to otherwise. The sunsets were awesome. We got to see all kinds of sea creatures while snorkeling: sharks, octopus, crab, lobster, conch and a ton of fish!
We took our 2 kids (ages 9, 7) and they had a blast. They loved feeding the fish, snorkeling and getting out on the sand bar at Woman Key.
If you're looking for a customized adventure away from large crowds, then this is it.
We took our 2 kids (ages 9, 7) and they had a blast. They loved feeding the fish, snorkeling and getting out on the sand bar at Woman Key.
If you're looking for a customized adventure away from large crowds, then this is it.
Written December 28, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Stuart - I can't believe it's already been 5 months...seems like just yesterday we were checking you all in. Thank you so much for sharing your experience here in TripAdvisor - completely humbled by what you wrote and looking forward to sharing this with Jack and the rest of the team. I hope you and your family have an incredible holiday season, a very happy new year, and we hope to see you all again soon!
Written December 30, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Keisha A
Key West, FL1 contribution
Oct 2022
There are Big Ships and Small Ships, but the Best Ships are Friend SHIPs! Blue sails is not just a company they are people who care about others. Scott is the best arranged everything for me, my daughter, granddaughter and a couple of girlfriends. We went on the Kaimana, an 8-hour private excursion and sunset sail. Captain Tom was a real pro, he even handled the grill and cook our steaks so we could enjoy and relax. I cant wait to go on another adventure with Blue sail. I cannot thank you enough!
Written December 20, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Keisha - Thank you so much for sharing your feedback!! Hosting you and your family was an absolute delight....after hearing from Captain Tom I think he might have had just as much fun as you and your family, ha! Looking forward to hosting you all again soon. Thanks again for all your support!
Written December 21, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Brandon
Marco Island, FL2 contributions
Jul 2022
We done two private catamaran trips with them and they are absolutely awesome hands down! Would have used them a third time but unfortunately booked up. Thanks again guys for everything!!!
Written December 19, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Thank you so much for sharing your feedback on your charters (x2!) with us. So bummed we didn't have availability for your most recent trip down, but hopeful we'll get a chance to see you for your next trip down. Hope you're all doing well, and thanks again 🙏 for all your support!
Written December 20, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Lance J
38 contributions
Jul 2022
What an absolutely amazing adventure onboard SV Rogue Angel! We went out for a week (50 miles west of Key West) with our 8, 10 and 14 year old and did two dives a day on some of the most untouched random reef we could find.
Armed with only our pole spears, we had some awesome underwater encounters. We even had a fight with a goliath grouper over a hogfish. This battle really got the boys excited as it tried to eat our fish up close and personal while we were trying to push it away. I think the boys are quickly finding a love for spearfishing.
After a lot of pole spear practice in the sand over a few days, the boys were able to land their first lionfish with a pole spear! There were sharks, eels, rays, and even a dolphin underwater encounter. We could not have asked for a better trip.
Thank you again Captain Tyler and Scott at Bluesail Vacation Yachts & Sailing Academy for helping to arrange this trip with their beautiful Fountaine Pajot sailing catamaran.
Armed with only our pole spears, we had some awesome underwater encounters. We even had a fight with a goliath grouper over a hogfish. This battle really got the boys excited as it tried to eat our fish up close and personal while we were trying to push it away. I think the boys are quickly finding a love for spearfishing.
After a lot of pole spear practice in the sand over a few days, the boys were able to land their first lionfish with a pole spear! There were sharks, eels, rays, and even a dolphin underwater encounter. We could not have asked for a better trip.
Thank you again Captain Tyler and Scott at Bluesail Vacation Yachts & Sailing Academy for helping to arrange this trip with their beautiful Fountaine Pajot sailing catamaran.
Written July 24, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
brittreejones
Denver, CO62 contributions
Jul 2022 • Solo
I came to Bluesail as someone that knew how to sail, but needed more time on the water.
Scott was very helpful getting me set up for exactly what I needed. He set up my sailing day with Captain Tyler, who was awesome.
Tyler makes you feel comfortable right away and has a great ease about him when teaching. I learned a lot and gained tons of confidence.
I even brought my husband back with me for more lessons!
It’s obvious that Bluesail cares about their business and clients.
10 out of 10!
Scott was very helpful getting me set up for exactly what I needed. He set up my sailing day with Captain Tyler, who was awesome.
Tyler makes you feel comfortable right away and has a great ease about him when teaching. I learned a lot and gained tons of confidence.
I even brought my husband back with me for more lessons!
It’s obvious that Bluesail cares about their business and clients.
10 out of 10!
Written July 4, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Brittany - Thank you so much for sharing your feedback. You were such a delight to work with when you first came to us, and it's been incredible working with and getting to know you and your family since that first visit. Reading reviews like this remind us of why we started this business back in 2018. Thank you so much for being an awesome student and friend to the entire Bluesail team, and we wish you all the best as you make your way toward that Captain license!
Written July 5, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Chip B
4 contributions
Jun 2022
Amazing vacation with Bluesail!! Scott, Tyler, Brittany and the entire Bluesail team were so helpful throughout the planning stage and answering our questions. We had a fantastic week on Kaimana with Captain Tyler! Tyler knows the keys well and took us to great beaches, sandbars, swimming holes and reefs for snorkeling. He is an excellent captain, tour guide, adventurer and overall awesome guy! Our catamaran, Kaimana, was in great condition and was very spacious for our family of five and included all the amenities you need for a multi-day trip. We are thankful for Bluesail and the wonderful family memories we made throughout our sailing trip! We're looking forward to booking another trip with Bluesail and spreading the word to friends as well!
Written June 20, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Chip - Thank you so much for sharing your feedback here on TripAdvisor. The feeling is definitely mutual...we had an absolute blast getting to know you and your family, and I know Tyler felt like part of the family once you all set sail. My only regret was not personally being able to join you out there on the water! Thank you all again for booking with us, and we hope to see you again soon down the road! Until then, fair winds....
Written July 5, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Jourdan K
Glenview, IL5 contributions
Mar 2022
Amazing getaway with my wife. We stayed on Dreams Come True for 5 days and had Captain Jack take us out for a phenomenal day on the water. We were able to see locations around Key West only the locals know about. Scott and his team at Blue Sail were professional, knowledgeable, communicative and so hospitable. Highly suggest renting and staying on one of the numerous boats available. The amenities you have available to you during your stay through the Perry Hotel and Stock Island Marina are beyond wonderful. We cannot wait to go back!
Written March 5, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Jourdan - Thank you so much for the review and for booking with us here in Key West! It was an absolute pleasure hosting you and your wife on M/Y Dreams Come True, and we hope you come back down to see us again for your next trip to Key West. I hope your trip back north went well and that it wasn't too cold when you stepped off the airplane :-)
Written March 5, 2022
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
No questions have been asked about this experience