Bluesail Yachting
Bluesail Yachting
Scuba & Snorkelling • Boat Tours • Boat Rentals • Dolphin & Whale Watching • Stand Up Paddleboarding
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9:00 AM - 6:00 PM
9:00 AM - 6:00 PM
9:00 AM - 6:00 PM
9:00 AM - 6:00 PM
9:00 AM - 6:00 PM
9:00 AM - 6:00 PM
9:00 AM - 6:00 PM
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 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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Detailed Reviews: Reviews order informed by descriptiveness of user-identified themes such as cleanliness, atmosphere, general tips and location information.
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89 reviews
Very good

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.
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.

Christina R
11 contributions
Nov 2020 • Family
Spoiled, we were absolutely spoiled by our experience on SV Rogue Angel. From the moment we began communication with Captain Rick, I knew we were in for a real treat. He did an excellent job feeling us out for our plans for the trip and then instantly began customizing our experience. Our family has been toying with the idea of purchasing a catamaran to live on for a period, so this was a perfect next step.

Prior to setting foot on the boat, we were sent links to NauticEd courses to begin to learn the art and edicate of sailing. Once onboard, Captain Rick had us actively involved in the process at a level that we were completely comfortable. He referenced many of the topics from the NauticEd classes and helped us move the course learning to the real world. Rick was very elegant in his ability to read our levels of understanding, re-explaining as needed, and never speaking over our heads. Getting to be an active partner in the sailing experience was a huge highlight for our family.

SV Rogue Angel is impeccably clean, well stocked with exactly what you need but with enough open space for us to store our personal belongings. With the family on board, all our scuba gear, and provisionings we never felt cramped.

Rick also knew about our family's passion for diving. His experience in the area allowed us to find the best dive sites given the currents and swell and because of his vast experience, he was able to pick mooring balls at each site that provided the passengers on the boat maximum comfort while getting the divers close to the best diving. The lobster spot he took us to was excellent! Lobster on the grill at sunset was an excellent way to celebrate the harvest.

"What else can I do to make this experience perfect for you?" was asked several times during our trip. With the sailing, swimming, diving, lobstering, fishing, rope swinging, and a little relaxing, the only complaint we have is that we need longer days to fit it all in.

Hands down, Bluesail and SV Rogue Angel provide a top notch experience and we recommend them without hesitation. We will be back; this experience can't be beat!
Written November 20, 2020
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 not only sharing your experience/review, but also for sharing such incredible images and video on our Facebook page! Captain Rick is one of our favorites, and knows that boat like the back of his hand. I love that Rick’s passion for sailing and the guest experience shined when you came to visit us earlier this month! We’re very much looking forward to hosting you and your family again in Key West down the road...thanks again!
Written December 7, 2020
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

William O
Eastern Pa14 contributions
Sep 2021
We chartered Rouge Angel for 3 days, Sept 2021. I cannot begin to tell you how great Bluesail is to deal with! From start to finish they provided one of the best experiences we have ever had. Scott, Brittany, Jen & Kaitlynn were so accommodating and accessible. They literally bent over backwards to insure that we

Be sure to request Captain Jack for your skipper. He is everything you could ask for in a skipper & then some! Incredibly knowledgeable in all things sailing, boat operations, maintenance, all of the areas to go to around key west. He was patient with our group of newbies but even better he was willing to explain everything and shared some great stories of his adventures!
Written November 6, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Wow what an awesome review!!! On behalf of myself and the entire Bluesail Team, thank you so much for sharing your feedback. Brittany, Jen, Jack, myself and the entire team here truly enjoyed working with you on this one, and really hope we see you again soon here in Key West. Until then, have a terrific holiday season and remainder to your 2021. ~ Scott & The Bluesail Team
Written November 15, 2021
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.

Jack H
2 contributions
Dec 2020
While no strangers to boating, this was our first bareboat catamaran charter. We planned this family get away months in advance. Scott was very responsive to various inquiry emails, from my daughter and myself. Upon arrival at the dock, Scott advised us that one of the heads was currently under repair and that our boarding would be delayed by an hour or so. He was very apologetic and did everything he could to limit this minor inconvenience ( great customer service!!).
While on location Scott and Jen were very attentive and readily available to answer questions. Scott even loaned us his Yeti cooler for our voyage. The 40' Kaimana was as advertised. 6 of us stayed on the boat for a total of 6 nights with 3 days/2 nights of it, at sea. While the boat was totally fine for 3 couples, if you can foot the extra cost, we toured the larger Rogue Angel, which was more spacious offering a larger kitchen and with all staterooms having dedicated showers. Either way, we would be happy to book either boat in the future. We hired Captain Tyler and he was on point! Professional, friendly, accommodating and most important, very competent piloting the boat. It was like having a 7th family member on board. We will definitely be back with Bluesail and Capt Tyler. A week sail to Cuba and back is on the bucket list. Hopefully sooner than later, when visiting Cuba opens back up. Side note, Stock Island Marina also a great dockage location, bathroom & showers very clean. Being on property of the Perry Hotel with bar and dining options also a plus.
Written December 30, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Jack - Thank you so much for the review and feedback!! It was an absolute pleasure to work with you and your family throughout the process! While we generally get along well with all our guests, you and your family were next level guests in so many ways! Beyond taking care of the boat and being incredibly understanding about some of the unexpected maintenance that took place, you made me and the entire Bluesail team feel like a member of your family. I honestly could not have asked for a more incredible family to work with, and I know Captain Tyler felt the exact same way when you all took the boat out on charter. Working with your family was a truly memorable experience, and we can't wait to have you back to Key West when Bluesail starts sailing to Cuba again (hopefully this year, fingers crossed!!). From the entire Bluesail family here in Key West, thank you so much for everything and we wish you and your family a very happy and healthy 2021! Cheers, Scott
Written January 17, 2021
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Washington DC, DC13 contributions
Dec 2021 • Couples
The perfect getaway. Every year I try and detach and get a reset and this was that and far more. Four of us went out for five days. We went to dry tortugas, marquesas keys and hopping between small islands and hidden lagoons. Having the motorized catamaran in the fleet allowed us to cover a lot more water and see more.

A special thanks is needed to Scott and the bluesail crew. Another booking service messed up our charter and at last minute we were linked up with Scott for a sailing. He not only went above and beyond to make sure our charter with bluesail was amazing, but went far beyond what could be expected to make up for the issues caused by the other charter company. There are no lengths Scott won’t go to to ensure the trip was incredible. For example, one morning we decided to go stand up paddle boarding. The captain realized there was only one paddle for the two boards. Wasn’t a big deal to us, SUP wasn’t something we absolutely needed to do to have a good day. No shortage of adventure or relaxing activities out there. A few hours later, through the choppy open sea came a little dinghy. Scott had taken a dinghy for an hour and a half just to drop another paddle! I never asked, nor would have ever expected such a gesture, but he insisted they would always do what they needed to make a wrong right. He proved it time and time again over the trip even when the wrong wasn’t related to blue sail.

If you decide to sail with bluesail, I would be remiss not to recommend captain Jack. Scott booked captain Jack for us and he was incredible! Experienced, knowledgeable, personable and will ensure you hit the best spots. If you sail with him, make sure you bring rum! He’ll refuse to drink any, but will give you a good story of why you always have it onboard. Incredible captain and just a good person all around. Was a pleasure having him onboard. Made the trip incredibly relaxing and an enjoyable experience!
Written January 14, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

Fishers, IN6 contributions
Dec 2020
We found Bluesail through an airbnb site, but because we wanted to do a few extra things like charter the boat itself out one day we ended up booking directly with Scott and the Bluesail team.
We stayed on the "Rogue Angel" late December of 2020 for an intimate NYE with our closest friends. The boat was pristine and housed 5 of us nicely. It was great having 3 separate bathrooms The kitchen was perfect to make ourselves a few breakfasts and warm up some leftovers. We had access to the hotel (Perry) pool as well as the marina's additional showers, which came in handy as hot water for 5 people daily plus doing dishes could be a bit much. The hotel also has a shuttle every hour on the hour that can take you into downtown Key West!
Scott was extremely responsive and personable when we were doing our booking. We even had a conference call with him to iron out additional details as well as get suggestions from him on local restaurants and a place to provision food for our chartered day out (Provisions of Key West - Chef Callie).
A member of the Bluesail team, Jen got us all checked in and answered any questions we had. She made us aware of the intricacies of the catamaran and where many things were located.
We had an exceptional trip and everyone we worked with at Bluesail and those he recommended we work with (Chef Callie & Captain Tom) made our trip memorable. We will be choosing Bluesail again upon our return to the Keys.
Written January 5, 2021
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 posting such an incredible review!!! You and your group were truly a pleasure to work with from the very start, and are so thrilled you enjoyed the trip down. I know Captain Tom had an absolute blast as well, so from our entire team here in Key West, thanks so much!!! We're looking forward to seeing you all again soon here in the Keys. Fair winds!
Written February 9, 2021
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

Jon W
15 contributions
Feb 2020
This really describes the essence of what I have personally experienced with the folks at Bluesail Vacation Yachts & Sailing Academy of Key West Florida. This group is not one of your typical sailing workhorse charter companies or sailing schools. They are personable, friendly, passionate experts who made me feel at home no matter what the weather. Everything is so clean and ‘shipshape’!

Their NauticEd classes are the best in the industry and the hands-on sail training trips are very exciting.

Bluesail's list of local referral bareboat captains are some of the most experienced skippers who truly know the waters for places to dive, snorkel, fish, as well as finding the best places to anchor for the evening. They are also excellent cooks so you will find that your meals are prepared nicely. How many people do you know can captain a boat with one hand and cook a good meal with the other?

During a brief squall in the Dry Tortugas on the monohull sailboat Kelsey Marie, the crew and I said 'Let's go for it!' and had one of the most exciting sailing adventures of a lifetime! Close hauled and beating into the wind, vigorously working the sails to optimize our speed, soaked from salt water flying over the bow as we dipped into the waves and everyone smiling almost to the point of laughter.

If you love the open sea or exploring hidden coves, spotting turtles and dolphins, enjoy fishing or just floating around in the water, Bluesail will help you plan it and deliver you to paradise. Whether on a solo trip, with your significant other, or with your family and friends, you will walk away with a lifetime of memories and colorful photos.

During our down times at anchor in the Dry Tortugas or the uninhabited Marquesas Keys, myself, my daughter Kelsey Marie and friends have enjoyed exploring Fort Jefferson and snorkeling the waters around them seeing colorful fish and coral. When docked at the Stock Island Marina Village, we spent time visiting most all the sites on Key West such as the Hemingway Home and the Butterfly Conservatory. We rented scooters for buzzing around town and walked the beaches during a Full moon. Local and fine dining offers everything from Cuban sandwiches to some of the most exquisite seafood.

You could easily enjoy paradise on shore in the marina at the Perry Hotel or just lay back floating on a beautiful yacht.

I will be booking with them again in the future to take a couple sailing courses!
Written October 23, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
Wow...we are speechless, where to begin! We are so humbled by everything you wrote; thank you so much for taking the time to share your Bluesail experience. First and foremost thank you so much for the opportunity to work with you. Shortly after we were introduced you quickly became not just a friend, but a close member of the Bluesail family. Beyond being a fun guy to go out for a sail with, you’ve always been supportive of our program and our team, but more importantly you’re just simply a great guy with a good heart. While we all had a blast sailing with you, some of my fondest memories are enjoying a beer on the back deck or heading over to Salty Oyster at Happy Hour and catching up on life. With each review we receive from our guests, students, and clients, it reminds me of why we started this business. Sailing, to the Bluesail team, is not simply a business and we certainly don’t do this because it’s a big money-maker. We do what we do because of our passion for sailing, and our drive to introduce and explore the sport and hobby with as many good people as possible. You have been a huge part of fulfilling that mission for us Jon, and on behalf of the entire Bluesail team I cannot thank you enough for that. We look forward to sailing with you again soon! Until then, fair winds and following seas my friend…
Written October 24, 2020
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.
Written July 24, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.

vanessa m
Coconut Creek, FL3 contributions
Nov 2020 • Friends
From booking to day of departure- everything was smooth and easy. When talking to Scott, not only did he meet our expectations but exceeded them, always making sure we had what we needed. From day 1, although we arrived a little later than expected, Jen was very welcoming and made sure we knew how to operate everything on board. The yacht was clean, had all the amenities listed and ready for us to have our adventure. Although the weather didn’t behave like we had hoped, Scott made arrangements to go out sooner than later so we may enjoy the beautiful water that the Keys has to offer. Our Captain Tyler was more than knowledgeable, he made us feel very safe at sea and made sure if we wanted to - that the snorkeling and paddle boards we ready to go for us. We will definitely book again through Blue Sail and exclusively as for Captain Tyler. Thanks for an amazing time and wonderful memories.
Written November 9, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
It was so great to wake up this morning to your review...thank you so much for sharing! While it's rare to have a charter impacted by weather in Key West, you and the ladies rolled with the punches like champs! We're really happy we were able to get you out on the water with Captain Tyler as well. Tyler is one of the most well-respected and safe sailors/captains we know so I'm thrilled he was available! Hopefully you were able to enjoy some of the marina and hotel amenities at The Perry as well during some of the bad weather days. We can't wait to host the next ladies trip, looking forward to Round II!
Written November 14, 2020
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

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Bluesail Yachting (Key West) - All You Need to Know BEFORE You Go