Sunset Sail Key West

Gorgeous sunset sail on a beautiful sailboat that is meticulously maintained. Fantastic crew! Very relaxing and romantic. No loud music - just you, the wind, and the waves. Highly recommend!

Sunset Sail Key West was recommended by another tour company, Up The Keys, and we couldn’t be happier with the recommendation. Our group of four went out on When & If for a sunset sail. The crew were very friendly and professional and the Captain focused on safety but was relaxed and approachable at the same time. The crew members, Veronica & Yaan, encouraged participation by asking passengers if they'd like to help with raising the sails. They were more than happy to answer our questions. The schooner is beautiful and historic and had plenty of space for everyone. They even allowed us to go down into the crew quarters. We enjoyed the whole experience and would definitely do it again! And the sunset was amazing!

My husband and I enjoyed this trip for our 2nd anniversary and it was a showstopper! The When and If schooner was built for General Patton (as a history buff, I LOVED it). The crew was so kind and happy and it really made the sunset cruise just the best! Highly recommend!

captain tyler, veronica and yann were the most formidable hosts upon this boat! the owners should be very thankful for the service they are providing and keeping this history afloat! the safety brief, the wine, the cruise, the information, just the most hospitable! and did i mention the wine! truly an unforgettable experience! b&h france.

Wow, what a great experience. The crew was very professional and all took some time to sit and talk about the When & If, their stories and hear our stories. Highly recommend.

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.

My wife and I went on a sunset cruise while in town on our baby moon. We had so much fun and the entire trip was so peaceful. Highly recommend!

Absolutely unforgettable private sunset sail aboard the Malabar X! This historic vessel is stunning, and the captain and crew were incredible—friendly, professional, and made the entire experience even more special. We were celebrating a 50th birthday with a group of 8, and it couldn’t have been more perfect. Everyone agreed it was the best sailing experience we’ve ever had. Huge thanks to Seth and the Sunset Sail Key West team for helping us create such amazing memories—and the sunset photos were incredible too! Highly recommended.

Excellent experience all around! We had a beautiful serene sail and such a welcoming and hospitable reception from Capt. Tyler, and mates Chelsea and Josh. Learned a bit about the schooner and its history. Their safety briefing was very helpful. And they came up with perfect weather somehow! Would do this trip again. A nice variety of complimentary beverages. It was a highlight of our stay with two other couples.

If you are traveling to Key West and even thinking about doing a Sunset Cruise 100% you should call Sunset Sail Key West... Seth and his crew are amazing. Forget all the corporate charters in town..... sailing in a 1930s era schooner while watching the sunset is the highlight of all my trips to Key West. Well worth the value and the little extra time to drive the couple miles to Stock Island.

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!

First time ever on a sailboat for my whole family, none of us are drinkers so it was really nice to have the Conch West to ourselves. They offered music but we preferred the stillness of the night sailing. It was a beautiful quiet evening and Joe and Chris were very accommodating. We loved the experience and will certainly recommend them to our friends.

Captain Andy, and crewmen Zach and Dalton were extremely professional, knowledgeable, and kind. We had a beautiful sail and awesome sunset. We will Sali again next time we are in Key West.

Jeff, who I worked with to book this event was great and very accommodating. And the Crew on When and If were awesome. The problem was the weather. There were 30 mph winds on the evening of our trip and because of that fact the water was very rough. Also with the overcast skies there was no sunset. I wish they just told us that it was not a good night and canceled the trip. Because of the rough surf it was not enjoyable.

Guys=5 stars. Boat =2 stars. The guys who took my family out snorkeling to the reef were awesome. Very nice, informative, patient with the kids, etc. A storm was coming so they were willing to wait it out a couple hours so we had a better experience. A couple of us were still nauseous due to the windy conditions. I was disappointed in the quality of the sail boat, however. It was very old and needs updating so for the amount of money paid, I excepted something better.

This is probably my 20th sailing trip with Sunset Sail Key West, and as usual it was a glorious day on the water thanks to the amazing crew and the wonderful historic yacht (When and If). I've also sailed many times on their smaller sailboat (High Tide) when I want a more private experience. Whether it is a day sail, sunset sail or Wrecker's Race, you will always be treated like royalty.

We arranged for an outing on When & If on 01/13/24 with our friends and family as a part of our wedding weekend celebration. We had such a positive experience I would highly recommend this ship and crew! Captain Matt was very knowledgeable and friendly and Dalton was SO kind and really made the excursion top notch! We had such a great time and it really made our weekend extra special. We also really enjoyed the wines!

Amazing experience. I had a memorable night and definitely unforgettable. Giving it 4 starts just because the boat was not that safe at night. On the way back we were almost at dark the whole time because it kept going in and out and also it is a very old boat so be aware that there's not motor to help the boat lol

We had an amazing, relaxing sail with Joe and Dan! We would definitely do this again.

Awesome experience. Short notice booking. Open bar and appetizers. Sunset was beautiful as always. Captain was great!

A sunset cruise on the historic "When and If" was amazing! Great crew, great way to relax and enjoy a beautiful sunset. Wine and beer are complimentary and I would chose this same cruise every time I come to Key West!

Extremely happy with this cruise!! Favorite activity in Key West!! Staff was professional and friendly, very willing to answer questions, and patient with some of the more demanding guests! Great experience at only $99 per person, will do again!!

Booked snorkel trip two hours before the boat was scheduled to leave, got family off beach, paid $20 for parking...checked in and they cancelled due to choppy sea. No call saying they were cancelling...would have stayed at beach and saved my time and parking fee!

We loved our Starlight cruise with Seth and Libby (and, of course, Leilani!) Their boat was easy to locate at the marina, and was extremely comfortable. My husband and I cuddled in on the bean bags to enjoy the ride out in the dark. Leilani snuggled up next to us as the best surprise of the trip! They took great precautions for Covid, and we only removed our masks on the private charter once we were out on the water. What we were most grateful for, however, is that about halfway into the trip I started to feel a bit seasick. Libby and Seth were so kind, and happily took us back to shore. I suppose I don't have my sea legs, but we absolutely loved this trip. I'll just remember some dramamine next time!

What an interesting ship! We brought our own beverages and chose from a high variety of nut, fruit, and cheese tray (way better than cheap included alcohol). The cruise and sunset were delightful (of course) yet the craftsmanship and history of the boat made it even more memorable. Go on this one!

We had a fantastic time on our sunset sale. The entire staff was friendly and attentive. 10/10. Thanks zack!

Absolutely an amazing experience. I was just hanging out with some buddies and we saw this classic ship with a sunset tour. We asked if it was accessible "definitely not" but staff was so awesome and accommodating. We loaded me and my big power chair and off we were. The view was stunning and the boat ride was choppy but so much fun. The cheese, wine, beer, and crackers were a nice touch but the view and excitement of being on a sailboat in my wheelchair was the main attraction for me. Highly recommend giving it a try and if your in a wheelchair it's a must try.

Fantastic experience! The crew were super friendly and hard working. The sunset was spectacular

Pleasant way to spend your evening in the Key West. You can go into the sea, have some drinks, snorkel for a while, have some appetizers and most importantly, watch the sun set. I'll definitely recommend trying it out.

Took a parasailing trip with Matt and Miles and it was fantastic. The 2 were very professional and provided us with a great time and experience. Price is very affordable and well worth it. They offered to take photos and they turned out amazing. Will definitely be back!

Best way to see a sunset in Key West. Beautifully restored all wooden sailing vessel, originally owned by Gen. George Patton. The captain and crew were fun and knowledgeable and guests were invited to help raise the sails and steer the boat which was a lot of fun. Very peaceful to be gliding across the ocean under sail, with not a care in the world. Highly recommended!

This was a fun and relaxing experience! This wasn't a party boat but if you are looking for a romantic night on the water for 2 I highly recommend Sunset Sail.

Got a recommendation from a local restaurant that we couldn't ignore...that was to check out a sunset cruise while here in Key West. Booked it just hours before we went on the cruise and it still had room for us. This isn't just another packed full catamaran going out to watch the sunset. This sail on the sailboat was a blast! The crew was very attentive to the passengers when the bar opened up. Once we left the port they opened the sails and before we knew it we were cruising. If you can't handle the lean of the sailboat this might not be for you as it's not a smooth ride. It was an adventure to say the least. The sunset couldn't have been better as we were served plenty of snacks and drinks (to include wine, beer, sodas available). When the sun was setting we were able to get our pictures in during a calmer ride before the speed picked up for our journey back home. Well worth the price for the experience! If you haven't ever been on a sailboat...this is the place to do it and the crew to go out with! Best sunsets on the East Coast and best crew to take care of you and they make it all seem so easy for what they do! Thanks for an amazing ride out on the ocean!

Absolutely loved the entire experience . They had by far the best hospitality and customer service I have EVER experienced in my entire life. They definitely love their jobs . Alex was hilarious and helped us with everything and made us feel at home . The captain Shawn was so nice and helpful . The whole entire crew just gave us the most amazing experience . The only thing we did not like was the banana boat experience . It was extremely slow and hard to get on . The thing that topped off our entire experience besides the drinks at the bar that were amazing was seeing the dolphins .

We did a private sunrise sail for two. It was beautiful. Captain Cody was fantastic. He told us about the history of the area and how the boat worked. We had a cute doggie sailing buddy who gave cuddles.

Absolutely perfect sail! Couldn't ask for a better experience! Loved the private sail with just my love and the 2 man ship crew aboard. They were experts on the ocean and made us feel safe and welcomed. They took pictures for us. And informed us when we took a fun turn into the wind that kept us on high alert and gave some laughs. The bean bag seats were comfortable and all around amazing breath taking sunset views. We are doing this again when we come and and will do the private sail again! So awesome! Thanks for the experience! Loved it! 10/10 recommend

We booked a sunset cruise on our last night in Key West. It was easily the highlight of our trip. A two hour sailboat tour cost only $100 per person. You can reserve the entire boat for $395. We lucked out as we were the only passengers on the sailboat. They book a maximum of six passengers. Seth (the captain) and Jenny (the first mate) did a fabulous job! They were both extremely friendly and made sure we were enjoying the experience. Seth tells some really great stories! When we got back to the hotel, my friend Alicia exclaimed, "They were so nice...I want to be their friend!" Sorry honey, you can't be their friend...we're going back to Dakota tomorrow. Seth made sure to get us in a great position to watch the sunset. Beautiful. Serene. I've attached pictures but the pictures don't do it justice. Why book a sunset party cruise with 80 other people (at least 50 of whom are douches), a cheesy lounge singer, and a shitty buffet with food straight off the Sysco truck? Spend a few more bucks and have an awesome experience on a sailboat with a max of five other people. You only live once...it is so worth it! I cannot recommend it more highly!

Kris and Kelsey were our captain and first mate. We went for a sunset cruise on 4/4. It was one of the BEST trips ever!!!! They made us feel so comfortable and made it a fantastic experience. There were 6 adults and we all fit very comfortably on the boat. They let us drive the sailboat which was really amazing! We would highly recommend to all!!!! We will be back

I had an amazing experience with sunset. Nice crew, we did all the water sports, the food was available all the time and it was everything very safe. I love it and I would highly recommend it!

This was a sweet cruise and highly recommended! Great wines to sample and buy, delicious cheese and dried fruit, and a few selections of water. The vessel has 80+ years of history, it's stunningly beautiful, and lighting fast. The crew is kind, funny, interested in answering any and all of our questions with a smile, and, very importantly, they're expert sailors who keep you informed and safe. This is the schooner and company everyone should pick when they're in key west!

We can't recommend this Sunset sail enough! The captain and crew were fabulous, the service is on point. And what can I say about sailing on a classic schooner? The boat comes alive and you truly feel a part of the sunset.

AMAZING EXPERIENCE! My Husband and I celebrated our honeymoon in Key West and this sunset sail was our last adventure before heading home. This crew couldn't have been more welcoming, personal and just good people overall. I would highly suggest doing this, heck do it twice! Thank you endlessly for an amazing sailing experience.

Was searching for things to do in key west and found this on groupon. Loved that we would have our own boat and wouldn't have to worry about being crowded or drunken partiers. And I saw some of the bigger, cheaper boats when we were getting ready to go out. Packed like sardines with drunks. Not family friendly. We went on high tide (I think that was name. It was green boat) and our crew was Chris and Kelsey. They were awesome. Had the boat clean and stocked for us and we're very helpful with getting us situated and ready to sail out. As we left the pier they shared info on boats, sailing and wildlife that was interesting and they answered all of our questions. They tried to help us find wildlife. The best part was that after 45 minutes of sailing we asked if we could stop and swim. And they said yes! They quickly and efficiently anchored the boat, got life jackets for the kids, and helped us get into the water. It really enhanced the experience. After the swim we headed back and they continued to give great service, including recommending some favorite restaurants. I would definitely go out again with them, even without a groupon. Next time maybe the gourmet dinner sunset cruise or the longer snorkeling one

We recommend Sunset Sail for a great low key tour while in Key West. We had a not so good experience the year before that once we made the owner aware he told us if ever back to give them a call. We came back this year and received another trip and it was great. Capt. Joe was friendly and Aleah is very sweet and knowledgeable about the island. The way the company handled the situation and made it up to us this year was very professional and reassuring that they do care about your vacation.

My family sailed on the When and If sailboat over the weekend and we had an amazing experience! The crew was accommodating and very knowledgable. They provided everyone with a beautiful trip! Highly recommend!

Fantastic adventure on the open water! We went out on The High Tide and our lovely crew were a delight. The ship was just right for six passengers and we all had a marvelous time riding the waves. Captain Laura even permited my mother to take the wheel. As the sun sank to the horizon hors d'oeuvres appeared and we snacked as we returned to port at dusk. The highlight of our vacation, I cannot praise them enough! Yes the larger ships are grand but for true adventure give the High Tide a try.

It was a beautiful day for sailing and we were lucky enough to call and book a 2-hr day sail with Captain Seth and his crew of Jenny and Joe. The boat ("When and If") is a an exquisite wooden boat that was built for General George Patton. The crew took great care of us, let us help with the sails, and were super friendly. I highly recommend this great crew for your sailing desires -- day cruise, sunset, or otherwise.

Magical. Not the "party cat" thank god. A wonderful way to end your day. They have beer, wine and non alcoholic drinks. But fun just to sail, watch the sun go down and the skilled crew.

Rough water and winds made this unbearable. I was sick most of the time and puking. Couldnt enjoy the wine or cheese and the little gal sharing it had a tough time because we were on such an angle everyone had to hang on or get tossed over. Not the best experience but the crew were amazingly nice.

We had such a great time sailing around with Captain Dave and First Mate Morgan on the High Tide. She is an older boat but clean and she cuts through the water very nicely. There is plenty of room for a couple of friends to join you for a daytime or sunset sail. If you are looking for a nice peaceful experience, this is it! Captain Dave and Morgan spoke very highly of the owner and gave a list and description of the other boats in the fleet. Next time we are down in Key West we are going to book a sail on the When and If. Just an FYI - I commend both on their docking skills! You must experience how they get the High Tide in and out of such a tight area! Thanks for such a great experience! I would highly recommend this company!

We (group of 8) were fortunate to book a last minute, two hour sail on board the beautiful wooden sailboat When And If. Captain Seth and his crew were delightful and the winds were perfect for sailing the length of Key West. If you want to get on the water and enjoy the peace of a small group on a beautiful boat, this is it!

Victor and Kayla were excellent people and we had a blast. The boat was clean and comfortable. We went on the 90 minute tour and it was a perfect way to spend an afternoon. Victor gave suggestions on local places to try. His burger suggestion was spot on!

This is the second time myself and my wife have been on the cruse. It was wonderful and the crew were more than accommodating ! I would highly recommend this and it is a must when coming to "The Keys " !!

Very nice cruise. The captain and first made were nice and friendly. It is a relaxing time , good for a group of friends. The cheese plate was very tasty. I would go again.

We went out on "When and If 1939" on New Years Eve for the sunset sail. The seas were a little choppy, but you wouldn't have known it with Captain Seth at the helm. He and his crew; Tristin and Jonathan did a terrific job and were delightful hosts. Once we were underway, they served water, wine and hors devours. The selection of cheeses were particularly good. The sail was a perfect amount of time and lined up well to experience the beautiful sunset. We definitely plan to go out again as more friends arrive to visit. It is now on our 'must do' list.

A definite must do. Captain Ashley & Gary ensured we had a great time. They are not only knowledgeable and professional but also funny and gave our sunset sail a personal touch. I am glad we booked this activity and I would do it again without hesitation. Let's not forget to mention the beyond words amazing sunset!

We came down to the Keys for a weekend with a group of 5 ladies and wanted to do a morning sail before we left. The captains were very friendly and welcoming! We had an awesome time on the sea. Thank you for a great experience!