Private Key West Sunset Sail

This sail was fantastic, staff was very knowledgeable and accommodating. We took 25 family members, staying at the Perry Hotel on Stock Island for a wedding and everyone raved about this sail. Sailboat was very cool and history was interesting. Would do it again in a heartbeat!

The experience was truly amazing. Despite it being in harsh weather, the crew managed to make the best of the situation. It was also interactive and we got to set the sails. You got to talk to the crew one on one and really interact with them as a person. There was tons of beverages and even a cheese plate. One the the crew members named Koss was really amazing, she was able to interact while also preforming her job. She was able to keep the mood light despite the weather being not so light. She made us feel involved and engaged.

We had a great sail with Captain Will and First Mate Cameron. Because the day had gusts up to 26 mph we had great sailing on a wonderful boat. Plan to do it again!

We set sail for my brother’s 40th birthday on a sunset cruise, and it could not have been more perfect. The boat itself was absolutely beautiful—clean, comfortable, and clearly well cared for. From the moment we stepped aboard, the captain and first mate made us feel welcome. They were incredibly knowledgeable, genuinely kind, and effortlessly friendly, sharing great insights while keeping the experience relaxed and fun. The sunset was stunning, the ride was smooth, and the entire trip felt both special and seamless. A huge bonus was the convenience—they picked us up directly at Sunset Key and dropped us off in Key West, which made the evening completely stress-free. An unforgettable experience from start to finish. 5/5 stars, and I would absolutely recommend this cruise to anyone looking for a memorable time on the water.

Pretty boat high end services, even an opera singer. This boat has it all. Small and intimate. Had a birthday sail, which didn’t disappoint. Loads of rain , a waterspout, and an amazing sunset.

Absolutely incredible experience aboard Malabar X. The whole process was really great booking was easy, we then had to move the sail and Sunset Sail Key West was so accommodating and made the switch easy. The sail was just fantastic, the crew was knowledgeable and able. Most importantly the beer was cold. Would return every month if I could. If you are going to Key West, you must sail with these folks.

Amazing experience I highly recommend using this company if your looking for a cruise in the keys. The crew was great and very informative about the keys and the price was great.

Had a lovely time out on the water off the historic Key West port, aboard the 33 foot High Tide. Harley and Casey were wonderful hosts, and were very knowledgable about the local waters. We were provided with plenty of ice, water, and soft drinks during our sunset sail, and thoroughly enjoyed our time under sail. The cheese platter was a nice little nosh while taking in the scenery. Thanks again for all your skill and hospitality!

We took our grandmother on a sunset sailing for her 85th Birthday. We were on High Tide with Harley and Casey. They made the trip so wonderful. We all had an amazing time. And that was due to them. They made sure we saw the sunset perfectly. Truly a wonderful experience. We would highly recommend this sailing to anyone!

I wanted a sail that was just that, a sail, not a booze cruise or snorkel or sunset sail. They gave me exactly what I was looking for. We spent 4 hours cruising in 12 to 15 knot winds on a beautiful day. The crew, Logan and Hannah were an absolute delight and allowed me to help work and sail the boat a Glander 33. The website wasn’t very clear about what they provided in terms of snacks and liquids but that wasn’t the fault of the crew. The only recommendation I have is that it is time for a new set of sails.

Before I start this I want to personally thank the Captain and Mate for taking our reservation at last minute and making my wife's birthday memorable! We started our evening out under smooth waters of the Florida Keys and passed Mallory Square, the captain told us lots of stories about the history of the area and pointed out landmarks and we had a great time talking! A short time later we got to see the Navy Seals training from a helicopter on our way out to sea so that was a treat to say the least. We kept going out and was lulled into silence with the stunning sunset over the stunning water. It looked like it was out of a fairy tale. When the sun went down and we turned to go home we were met with another stunning view. The moon had risen was full over the waters overlooking Key West. It was so beautiful it could make you cry. I think this is the first time I was sad that something was over. This is most assuredly something that I would want to do again!

Great private sunset cruise on High Tide sailboat. They kept us out of the rain and it was fun to see where the rain was falling all around us while we stayed dry. We ordered the cheese tray and brought wine. I was impressed with the cheese tray, expensive cheeses plus prosciutto and salami. They supplied water, sodas and seltzer. We would have paid a similar price for our family to do the large party public sunset sail -50 plus people on the boat. This was much nicer for us. Joe and Mark were our captains. Great guides!

When we found out we had an all woman crew we were excited. Jade (Captain) & Tabitha (mate) made our memorial cruise, peaceful and fun for our family. We couldn't have asked for a better send off for our friend. Thanks Eric and Michael

What an experience! Logan was a wonderful captain! Tabitha made sure we were having a great time. The boat was beautiful and held our group of 10 comfortably. The conversation was wonderful. There is no better way to see the beautiful Key West sunset. Highly recommend this private sail!

I recently proposed to my girlfriend on the sunset sail and it couldn’t have been a better experience. The Captain Dan and his mate Tabitha took really good care of us and made the moment truly special. There is no better way in Key West to watch the sunset and I would definitely recommend the trip.

Captain Dan and First Mate Puck (too many Jeff’s in Key West, so he christened himself Puck) were friendly, fun, and first rate sailors. Spectacular sunset sail. Definitely a five star experience. Six stars, if the scale allowed! Steve and Nancy H

I got a private sunset sail for my hubbys birthday. The boat was beautiful and the crew were friendly and fun. I highly recommend using this company.

Chartered a private sail for a proposal and it was a great experience. The captain and mate were wonderful people and made the experience comfortable and fun. I would recommend the sailing with this company anytime. I will definitely use them next time I go back to do just a regular sail and or snorkel trip.

Captain and crew were courteous and professional. The boat was cleanend and well maintained. It was a relaxing and pleasant experience.

A relaxing and enjoyable evening on the "High Tide". A gentle ride back and forth in the bay while admiring the sunset.

We booked the sunset sail for my daughter's spring break for college. It was absolutely the highlight of our visit to Key West. We brought our own bottle of wine (and elected not to bring any food as we had dinner reservations right after the sail) and had a wonderful sail on a nice windy evening. The crew was very personable and we had a great time interacting with them. Watching all the other crowded boats going out I am so happy we booked the private sail. Some of the other boats looked like one big spring break party. The sunset was beautiful and we got plenty of great pictures. We will definitely book this trip the next time we get to Key West. I highly recommend the sunset sail.

We had the privilege of sitting in the cockpit with the captain of the When and If and had an amazing time. I asked her if we would see any dolphins so she asked to a spot where there was a potential to see them and we were fortunate enough to see three come close to the boat! I highly recommend sailing with Captain Kelsey and her crew on this beautiful sail boat. The company and views were exceptional.

My husband booked this private sunset sail for my birthday and we had the time of our lives! The crew, Captain Finbar and Sean, were very sweet and knowledgeable. I can't forget the 4-legged crew member, Lailani, or better known as Security, who was the best behaved and lovable dog I have ever met. The sail took about an hour to get out far enough to see the sun set over the water. There was barely a puff of breeze so sailing was rather difficult to do, but that didn't dampen our spirits. You can't change the weather. We did still have a blast watching the crew work the sails. We ended up having a beautiful sunset to watch all the way down to the horizon line, and then about an hour ride back to the marina. My husband also ordered the optional cheese plate. It was bought from a local wine bar (due to COVID) and was perfect for a light snack. Water and soft drinks were also provided and Sean was happy to supply us with some whenever we needed. Sean was also a great conversationalist. He was easy to talk to and gave us a good local perspective of Key West. He also gave us a little history about our Captain Finbar, the Admiral of the Conch Republic Navy and local legend. We cannot wait to book another private sunset sail in the future. It's well worth the cost for a unique and special experience you can only get in the Florida Keys.

Nice schooner with a pretty cool story. Superb, young and knowledgeable crew. I arranged for a private charter due to having a party of greater than 6 people and covid concerns. However, I think you would get the same experience without a private charter for about ¼ of the money. Pictures showed snacks such as fruit platter and cheese and crackers but apparently due to covid that wasn’t available. Yet they did still handle our beverages prior to serving them?! That’s fine and I get it, but it would have been nice to be told that as we didn’t eat before hand and didn’t bring any snacks aboard. Overall it was a great sail but nothing special and not worth the money. In my humble opinion bother with the private charter. There are plenty of sailing vessels doing sunset cruises to choose from.

Our sunset cruise on the High Tide was exceptional. Captain and mate were very nice and sunset was beautiful. We would definitely recommend!

This was the highlight of our trip to Key West! IN the midst of the pandemic, it was amazing to have the opportunity to see the sunset from the Ocean view!! Our crew composed of Kelsey and Alia were over-the-top amazing and took this experience to the next level! We would quickly do this all over again the next time we visit the Keys!!

Amazing experience, one of our best nights in the Keys! Definitely recommend for a COVID safe activity.

Highly highly recommend. What an insane great time. The entire thing was a blast. The sunset is stunning , the staff is absolutely incredible. The entire thing beginning to end was just over the top awesome. They take pics and post on their Facebook page which is really cool. A++++++. Thanks again guys! We’ll be back.

It was Fantastic!!!! Our crew was just excellent and we did have an enjoyable, happy and relaxing evening. Erick and Harley are the best!!

Thanks to Captain Joanne and crew Elijah our small group of friends had a spectacular time on the water. The weather was perfect which made for a tranquil and relaxing sail. Even spotted a dolphin! The sloop High Tide is the perfect size to get close to the beautiful waters off Key West and experience an intimate sunset sail. Couldn't have asked for a better time. Thanks guys!

We had an awesome time with Dan & Remy. We booked this charter for a group of 5 including my parents and everyone thoroughly enjoyed it. Big thanks to both of those guys for an awesome cruise.

An excellent sunset cruise. What was supposed to be a small group of people ended with my wife and I having a sunset cruise to ourselves. Because the original ship was still having work done on it and would not be ready for our trip he offered a cruise for just the two of its or we could go out on another excision with a group of six. W jumped at the chance of having the ship to ourselves. Brendan was our captain and Jeremy was his first mate. When we got there they upgraded or vessel to a bigger schooner( conch west). The crew was friendly and courteous the whole time.. It was relaxing and very romantic. Even got to see a dolphin swim by our boat and the most beautiful sunset we've ever seen. On to of that the crew had nothing but great things to say about the owners and how Well they were treated. Says a lot about this company. We'll be back the next time we're here.

Always wanted to try a sail boat this was perfect . We went as a family trip with friends ( couples) brought some alcohol and had a great time. Friendly staff and very informative about the island and what’s around it. They took our pictures and the sunset was great to see . Definitely better then a party boat for sure and worth the money

Four of us on the High Tide. The crew was great and the ride was smooth. Not a lot of wind that day but the views were spectacular. Such a better experience than a booze cruise on a big boat.

Captain Dan and Brennan were so friendly and knowledgeable! Couldn’t have imagined a better pair to navigate the boat. The ride was so enjoyable - both smooth, yet exciting. The views were breathtaking! They were very accommodating and helpful with the food and drinks we brought on board. And they were willing to take any photos we wanted. I could have sailed on this boat all day and night. It is an excursion well worth every penny!!! Seriously, you won’t regret it.

Very punctual and on time with everything. Captain and first mates were super professional and helpful. Would definitely go again!

We booked a private sunset cruise with this company after having another cruise with someone else the day before not show up. This second experience was no better - we took a ride share to Stock Island where the boat was located only to show up and someone tell us the boat was not working. Why they didn’t let us know in advance is beyond us. The only thing we really wanted to do this trip was take a sunset cruise for our anniversary and it was ruined. Extremely disappointing and would not recommend.

What a great sunset sail aboard the “When and If, a schooner commissioned by General Patton for his personal use. The boat is in excellent shape and the crew was amazing and knowledgeable, interacting graciously with all on board, even encouraging the guests to participate in raising the sails! The wine and cheese was a nice, elegant touch and very good. What a wonderful way to end our Key West vacation!

My husband and I booked a private sunset cruise on the Free Spirit, with the expectation of a quiet, romantic cruise. When we arrived we happen to walk past the When and If and noted the crews professional look with matching polo shirts. We arrived at the Free Spirit to be greeted by Captain Kevin and Mate Sean who were significantly more casual, more like they had come from a fishing charter. The boat was a bit tired looking. The website says a cooler with water and soft drinks are provided. Sean told us if we wanted some water we could go down into the cabin and get it ourselves. Captain Kevin told stories about his life and life in Key West, non stop for at least the first half hour to 45 minutes. We were able to relocate to the bow to have a bit of quiet and enjoy the sail and sunset. When we boarded and the Captain started the engine, a loud grinding started, which he explained was just the engine. Not to worry, we could sail without it. Mate Sean had to keep giving Captain Kevin tips on piloting the boat, including not to go out too far as he was concerned with how the engine sounded. Captain Kevin and Mate Sean were very nice, just not what we expected. All in all, the weather and sunset was beautiful but we were disappointed in the level of service and quality given the amount of money we had spent.

I booked my husband and I a private sunset cruise on the High Tide. It was perfect. The crew was friendly and accommodating and we saw the most perfect sunset. Highly recommend this sailboat, company and crew.

Was excited about the sunset sail but rain caused it to be canceled. Rescheduled for the next morning -11 to 1 which was not the same as a sunset sail. Called company to try to cancel due to wind and cold weather. Told me they had already turned down others - no fool would have requested a sail on this particular day! They would not refund money $395 so no other choice but you lose money or to try. Captain and first mate were excellent but could tell they were not convinced worth a sail day. I survived about an hour- shivering and green with a friend so told them to go back to dock. Got back to hotel and threw up and slept alll day due to chills and feeling nauseous. A sail that should have been fun, calm, and 2 hours turned into a nightmare. It was a waste of time and money - the company should have honored my request to cancel when I called that morning. Would not recommend through this venue. They should have agreed for me to cancel.

We did a private sunset sail on the High Tide to celebrate an anniversary last week. I unfortunately didn't catch our captain's name, but both he and Kelly were awesome. We lucked out and had great weather and a great sunset, but either way I think we still would have had a blast. I would highly recommend!

It was our first time in Key West. We had a family of 4 with two young kids. The captain and crew were awesome! Not only were they great to have a conversation with, but they went the extra mile to make sure we had a good time. The captain got in the water with the kids to look for starfish and crabs. We also enjoyed the fruits and snacks on board. The best part is when my daughter got to sail! Captain Mark was so patient and she still talks about it to this day.

Captain Mel and her first mate Kelly were awesome! Such professional sailors and wonderful people. We felt like they had invited us into their home. One of the highlights of our vacation to Key West. I'd do it again!

This sail was absolutely perfect. Captain Mark and his Deckhand were so professional and accommodating.. All 6 of my guests were super happy with the sail! The boat is super comfortable! We really did enjoy the sail and look forward to sailing with this crew again in the near future. Highly recommend it!

A group of my friends and myself went on a sail for my birthday, Capt Mark and Kelly made it awesome, they laughed as hard as we did. I highly recommend a sail with High Tide and definitely ask for Mark and Kelly. And a shout out to Jeff for making this possible for us. Thank you all for a memorable night.

Captain Mel and Sean were the best. This was the best of any sunset cruises we’ve ever done. The sail was beautiful. There were no other boats around, and the sunset was more spectacular than usual.

Thank you Mel and Shawn for an incredible evening. It was such a pleasure getting to know the crew as well as experiencing a peaceful wonderful sunset. My wife and I could not have asked for a better experience. If you want to get away from the crowded party boats and enjoy an experience to remember book the Free Spirit and ask for Mel and Shawn. You won’t be disappointed!!

No better way to see the sunset in Key West than with a private sail on the "High Tide"! Forget the crowds and commercialism of Mallory Square and book a trip on the High Tide. You'll sail (yes - sail, not motor around), for two hours and enjoy the sun setting into the ocean. It's also beautiful to see all the other boats that are out at that time.The crew was great, and we'd definitely do this again if back in Key West.