2026-06-29T02:50:57.288Z

Truly the best captains out there!! We went out with Aaron and had the most incredible day. He showed us a range of places and catered to whatever we wanted to see. It was such an amazing time! If you have the opportunity to go with Capt Aaron, you won’t be disappointed!

2026-06-24T15:52:03.588Z

Key West Captains was extremely helpful in finding the perfect sailing excursion!

2026-06-23T16:37:28.487Z

Key West Captains have been amazing at facilitating super fun water adventures!! They have several boats and trip itineraries to choose from and they made it super easy to book. I recently went on their Midnight Express boat to the local sandbar with some friends. It was such a good time!!! Captain Brian and Mate Alexandra were super friendly, helpful and set the party mood! That boat was super comfortable with lots of sitting space for all my friends, even with a full boat. Lots of storage space, built in coolers, and even a toilet on board which was quite convenient. The boat ran very smoothly and it felt like we were floating at one point over the glassy, flat calm waters. Epic day of boat riding, sandbar hopping and ended with an amazing sunset by downtown Key West. Looking forward to booking again in the near future 😎

2026-06-22T19:06:37.600Z

This was our second time booking with Key West Captains. The first time, we had Captain Brian for the day. He did an amazing job showing us around the waters and teaching us the ins and outs of the boat. He was professional and knowledgeable.The second time, we chartered a boat from their fleet with Captain Cam and First Mate Alexandra. We had 11 people in our group, and we couldn’t have asked for a better crew. Cam and Alexandra were incredibly accommodating throughout the trip out to Snipe Keys.I definitely recommend Key West Captains and look forward to booking with them again. Great experience!

2026-06-18T13:19:28.584Z

10/10 our group loved Captain Brian and Alexandra. From initial planning to execution, their team made us feel totally supported. Our corporate clients loved the experience. Would certainly book again!

2026-06-14T23:46:27.138Z

Just finished a wonderful 4-day catamaran Charter with Key West Captains. We sailed to Marquesas, Boca Grande, the Tight Tower ... and truly enjoyed the incredible beauty of the Keys and the numerous activities in the water and on the beach. Our captain Patrick and crew Tara are absolutely amazing!! They are so friendly, knowledgeable and supportive. They are great musicians, too! They taught the kids a lot about sailing and the nature. Absolutely unforgettable charter with our great new friends there ... thank you!!

2026-06-07T16:35:46.340Z

We had the best day on the water for our friends 50th birthday 🎉 Captain Brian was a lot of fun & joined in the chats & was completely awesome & professional!!!Would definitely chatter him again!

2026-06-07T15:07:28.734Z

The highlight of our Key West trip. Captain Brian took us to some amazing spots & showed us a great time! We got to see dolphins up close. Highly recommend!

2026-06-07T15:05:15.407Z

Had the BEST experience! Our captain Brian also made the experience 100x better. He made everyone feel comfortable, took us to and island to snorkel, took us out to see a wild pack of dolphins and snorkel at an abandoned ship. Definitely the best day and highlight of our trip!

2026-06-06T21:57:36.231Z

2026-06-06T16:42:33.181Z

2026-06-06T15:58:59.212Z

2026-06-06T15:05:44.132Z

Awesome job - awesome boat - well worth it! Had a blast! Thank you!

2026-06-06T15:03:49.753Z

He was very nice and chill and we saw dolphins which was sick

2026-05-07T20:16:55.879Z

Captain Brian was so attentive, fun and professional! He was very knowledgeable of the area, and even grilled for us while making us feel extremely safe during our girls weekend trip! The 38’ Tiara was clean, gorgeous, and comfortable for a large group. Highly recommend!

2026-03-05T17:25:54.871Z

Captain Brian is awesome. Super nice guy, first class act all the way.

2026-03-04T23:06:33.567Z

Captain Brian the GOAT

2026-03-04T23:06:18.027Z

Captain Brian was amazing, highly recommend!

2026-03-04T23:03:13.054Z

We had a great time

2026-02-24T05:15:55.050Z

First Mate Alexandra and Captain Brian were the absolute best! Captain Brian was an awesome experienced captain who took us all around Key West. First Mate Alexandra was so attentive, helpful, organized and an amazing photographer! I would absolutely use this duo again in the future. Truly the best team and they helped make our afternoon out on the ocean one to remember forever! We felt safe and so well taken care of. During the planning process they were also both so responsive, helpful, knowledgeable with such great communication. Highly recommend!

2026-02-24T03:00:25.834Z

Key West Captains made our honeymoon to the Dry Tortugas something truly special. They listened to us and what we wanted and helped to create a once-in-a-lifetime experience for Valentine's Day. My partner set this up prior and surprised me with everything.They went above and beyond in accommodation of our needs and in the level of care they provided. And I believe a great time was had by all.We arrived at the marina and they greeted us and let us know the boat hadn't arrived yet, which gave us time for a relaxed breakfast. The boat arrived and they had brought food and supplies for us.It was perfect conditions for the ride out. They served us a charcuterie and drinks. We snuggled on the couch outside and enjoyed the seaspray, listened to music, and chatted with our hosts.On the way out we stopped at a shipwreck to go snorkeling and chased fish to arrive at our destination a short while later.We unloaded and set up camp. Our hosts cooked us dinner and left us to our own devices to watch the sun set, spend the night exploring the island, listening to the sooty terns, the stars, and each other. This is truly the stuff dreams are made of. I haven't been able to stop thinking about it all since returning.I got up at dawn and saw one of the most beautiful sunrises - there were colors I hadn't seen in the natural world before.I returned to the tent and got up later and found our hosts had laid out rose petals, chocolate, a card, and a stuffed bear along with breakfast. All silently. I was absolutely flooded to tears.We ate and packed up later, went to Loggerhead lighthouse on the boat, did a bit more snorkeling with the barracudas! and then headed back to Key West.On the way back we ran into fog and we stopped to enjoy the quiet ambiance. It was a bit like moving through a portal into our new lives together.We had an amazing sandwich lunch on the boat and snarfed the Mediterranean salad when we arrived back at the marina.All in all it was a ten out of ten life experience thanks to Key West Captains and my partner.Looking forward to more adventures with Brian and Alex!

2026-02-24T01:59:24.603Z

We had an amazing experience with Key West Captains, highly recommend working with them for your vacation. Super fun people, we made new friends!

2026-01-19T16:02:53.003Z

We have done two charters with Capt. Brian and Capt. Patrick. While the Tortugas, Marquesas, and countless other small islands are stunning and absolutely worth the trip, the Captains themselves are absolute professionals whose commitment to providing a good time is the star of the show.Do not hesitate to book a charter with these guys! Can’t speak highly enough about them.

2026-01-04T19:57:34.688Z

Had the best day on the water with Captian Patrick. Super friendly and extremely safe. Would give 10⭐️ if I could.

2026-01-04T14:17:44.743Z

Unforgettable Experience with Key West Captains!Our recent catamaran sailing trip with Key West Captains was nothing short of extraordinary. We spent four days and three nights sailing around the Keys, snorkeling, exploring, and enjoying incredible meals—and every moment exceeded our expectations.Brian, our captain, was the perfect mix of professionalism, safety-first leadership, and quirky fun. He ran the boat with confidence and care, always making sure we felt safe while also inviting us to learn and help if we were curious. Even when weather or boat challenges came up, he went above and beyond to accommodate our requests and ensure we still had the best possible experience.Alexandra is truly one of a kind. She somehow managed to be our chef, bartender, cleaner, host, party starter, tour guide, photographer, videographer, and emotional and physical support system—all while feeling like a genuine friend. We were constantly amazed by her hospitality and energy. We truly never had to lift a finger.From sailing and snorkeling to dinner at Lolita’s and an unforgettable brunch at Little Palm Island (at the crew’s recommendation), every detail was thoughtfully planned and flawlessly executed.This trip was relaxing, adventurous, fun, and deeply memorable. If you’re considering a sailing trip in the Keys, Key West Captains—and especially Brian and Alexandra—are simply the best. We couldn’t recommend them more highly and can’t wait to sail with them again!

2026-01-01T14:09:09.699Z

Key West Captains provided a phenomenal service for our birthday celebration charter over Christmas. From the planning to the execution on board with meals, sailing itinerary, and stopping to enjoy the dolphins... Everything went well. I'd highly recommend them to anyone.

2025-12-29T23:35:25.461Z

Captain Brian and Alexandra spoiled myself and my friends for my 50th birthday! It was a trip of a lifetime!

2025-12-29T18:13:26.413Z

Brian and Alex were epic hosts guides and people! They made the trip better in every way. Thank you both for everything!

2025-12-29T18:04:36.270Z

Freaking amazing trip with B-Rain and Alexandra! Sadly I was sea sick on day one but Alexandra took the best care of me. I sat up top next to the captain and learned a lot from him about the area and sailing in general. After that I felt much better and the rest of the trip was EPIC! Thanks guys for making my friend’s birthday out of this world and leaving us with stories and memories to share for years to come! Highly recommend! You won’t regret it!!!

2025-12-29T18:04:06.750Z

Brian and Alexandra were amazing and couldn't ask for a better crew and experience. They were always willing to change up locatikns when necessary (ie challenging wearher) and make sure the whole experience was something to remember. Highly recommend!