Sunset Sail In Key West With Beverages Included

If you want a relaxing, less crowded sunset sail, this is your pick! The 2 person crew was great and was an enjoyable evening!

Excellent time. Would go again. Not a party boat which we did not want but plenty of alcohol included!! Captain and first mate were fantastic. Trainee too. Very relaxing with a beautiful sunset.

We had an absolutely incredible sunset sail with Steve, Michael, and Colin! From start to finish, the entire experience exceeded our expectations. The crew was exceptionally friendly, welcoming, and knowledgeable about Key West, sharing fun facts about the area while making everyone feel completely comfortable and safe on the water. The sailing route was beautiful, the drinks were fantastic, the prices were incredibly reasonable, and the music was perfect for the atmosphere. Everything about the experience felt relaxed, fun, and authentic to the Key West spirit. You could tell the crew genuinely loves what they do, and their enthusiasm made the evening that much more special. We’ve visited Key West many times, and this was easily one of our favorite experiences! We truly cannot recommend this sunset sail enough and will absolutely be making it a tradition every time we return to the island. Thank you, Steve, Michael, and Colin, for such a memorable evening!

Captain Steve and Ransom made this excursion a relaxing experience. Great views of the sunset. And a killer song track.

It was a very enjoyable experience. The 2 crew members were wonderful. Drink was served as soon as we left the dock. Kudos on the music selection. The sunset was spectacular!

Everything was great...the staff, the weather, the crew... but the directions to the boat were extremely misleading and even tought we arrived in the area 30 minutes early, we almost ended up missing the cruise. At the end of Front St., there is a sign indicating the company was directly ahead, but it was not. We came to find out later that the sign was directing people to the company's admin offices.

We travel to Key West every Oct or Nov with the Central Florid Corvette Club CFCA . We have booked with Floridays for a Sunset Sail to watch the sunset and have alwasy had a great time. Captain Steve and First Mate Mathew made the Oct 2026 trip very enjoyable for the CFCA group of 13. Obie & Ramona Young.

Steve and Emily did a great job. We enjoyed our tour very much.!!

Such a fun sunset sail We had a great time. The crew was fantastic, the weather was perfect, and the views from the boat were beautiful. It was a fun evening from start to finish and one of the highlights of our time in Key West. Highly recommend!

This was our favorite thing we did in Key West. The sunset sail was so relaxing, we had a very small group of 5 total on the boat and it was perfect. I am so glad we booked this over a party cruise. The guides were so friendly and made it an all around great experience!

Excellent experience. Friendly staff. We had a beautiful evening on the water watching the sunset and enjoying Key West harbor.

We did the sunset sail in Key West and it was perfect. Great value for the price and an awesome crew (of 2). The captain was great and even positioned the boat perfectly to get the best photo opportunities. Drinks included, so a great time was had by all.

Really expensive for a boring harbor cruise. We didn't sail very far and sat in the same spot for about 20 mins at sunset. No commentary about what little we did see. The sunset view was basically the same as it would have been from the shore. The sailboat was cramped for the number of passengers and we spent a lot of the trip crammed up against the rail so people could get by to use the bathroom. Crew was generous with drinks which was good and bad as it prompted a lot of sing alongs with the too loud music. Not the relaxing romantic evening we were hoping for.

It was a great experience! Even with poor weather, the crew made it a great time and we still got to enjoy the ocean views.

Absolutely fabulous, highly recommend. Liz and Courtney were awesome. Weather was great. The wife and I had a wonderful time.

Great exerience, highly recommend if you prefer a less crowded trip. Liz and Jared were great, we were under sail and had a great sunset experience. Great value and great trip.

Peaceful and friendly trip. We had 16 people on the boat plus 2 crew. If you don’t want a “party boat” this is for you!

Our original trip was canceled but Fish Monster rebooked us with no issues. Our sunset cruise was amazing, thanks to Doug and Ransom! The sunset was beautiful, the boat was nice, the staff was accommodating and the drinks were cold. Thank you!

Courtney and the captain were great! The captain was incredibly cool, and Courtney was attentive and shot some great photos of my family. We had a great experience and would recommend this to anyone looking to do a sunset cruise in Key West. The best part about our boat was how limited they were. There were 6 other guests on board excluding the captain, deckhand, and my party of 4.

We had a really nice time on the sailboat and enjoyed every minute. We were welcomed really friendly and were well looked after throughout the whole trip. I‘m glad we chose this trip over the other providers .

The crew was amazing. The sunset was amazing. The drinks were good, and it was an all-around really good experience. It's not a crowded tour where there are a ton of people and you can't have an enjoyable time. I'm glad we got to actually sail.

it was apparently canceled several days before excursion but trip advisor still charged us and kept telling us of upcoming event the supplier said they tried to tell us but voicemail was not received the email looked like a scam that did not follow the advice of trip advisor our last thing to do on or later in life honeymoon was s bust since we arrived on time the day of and found out that it was canceled apparently you have to ask for refund several hours after trip was to happen we continued to get reminders from trip advisor with ticket attached

Great experience! The hosts were wonderful, accommodating, and knowledgeable. Nice beverage options. The views were absolutely beautiful.

Contemplating and relaxing sailing event for sheer enjoyment! Capt.Doug and 1st mate Ransom treated us as honored guests and showed us a beautiful sunset sail! Don't miss this one unless you're a wild party animal! Barbara Moore, FL June 28, 2026

Great charter! Very chill and relaxing. The crew were great!! Great to be out on the ocean. Not a loud party cruise, the vibe is much better on this charter!

Sun set in Key West wss fantastic The crew was great. Very accommodating for me and my cane. Cold beer, good drinks and a fantastic sunset Cant ask for more

After some initial confusing directions for the meeting point, the company came up trumps and we had a wonderful sunset cruise with skipper Liz and first mate Emily. Both were very friendly and professional and the sunset was pretty spectacular.

Great way to see the sunset in key west. We received several reminders before our booking about the meeting place and departure time. The meeting place was easy to find and we left on time. The crew were very professional and nice. They checked on each and every passenger during the cruise. I highly recommend if you want a calm and relaxing sunset cruise.

Love the fact that this Sunset cruise was only allowing a small amount of people to be on the boat. My boyfriend gets claustrophobic and with the limited amount of people allowed him to relax and enjoy this ride. Plus, the music on board was not loud so we can meet others on our boat and converse with normal conversation instead of shouting. Thank you again for a wonderful and beautiful cruise and highly recommend this one. :)

This was so amazing! They were so kind and it was an absolutely beautiful experience! Don and Ransom are amazing.

Great experience. Captain Doug was extremely understanding when we messed up the time. Had an excellent cruise and would absolutely do it again

Magical experience for everyone. Our son’s girlfriend said she had ‘never seen a more beautiful sunset’ (and she is very well travelled)! To top it off, everything was heightened by two great captains, Eric and Ransom, who were kind, attentive, and professional. It was a truly lovely evening, which we will not forget any time soon. Thank you for a fantastic time!

Beautiful sail with beautiful sunset captain and 1st mate were very nice and always asking if we needed another drink!

Crew is great, beautiful sunset sail. Highly recommend. Smaller group makes for a much more relaxed and enjoyable experience.

If you want to view the sunset in the most relaxing way, this excursion is for you. Very peaceful and calming.

Really great time. Our family agreed this was our best excursion this trip. Sailed out and around Sunset Key. Watched the sunset. Note, accessing the boat is through the hotel, in the back.

A 90-minute schooner sailing experience to view the sunset from Key West with wine, beer and nonalcoholic beverages included. Casual small-group sailing a highlight of our trip. Definitely recommend!

It was a nice experience from someone who's definitely a land girl, this was a nice and relaxing experience. We originally booked a tiki cruise, so glad we changed to a more low-key, relaxing excursion.

This is my second time sailing with these folks. 10/10 solo experience. It’s not a party boat with loud music and drunks, just a nice and peaceful sail with a friendly crew and always nice customers. Pick this one if you want some sunset sips on a smaller scale.

Perfect for the wife and I. The crew were great. We’ll do it again each time we come back for vacation.

We booked this sunset cruise as it appeared to be smaller and less crowded than others and the reviews were great. Well it did not disappoint! Only 8 guests aboard so it felt like a private charter! Liz and the crew were awesome and very attentive. The sunset itself was spectacular-no surprise for Key West. It was also my wife’s birthday which made it extra special. She had a blast! I would highly recommend this cruise for anyone not looking for the party boat experience. Quiet, low key and just awesome!

This is the sunset sail if you want a quiet small group. Nice timing for the sunset. Everyone has a seat. Quiet music playing. The cruise to take if you don’t want the loud party crowd. Drinks included

Friendly staff! Great boat. Limitless drinks and the weather was perfect. Not even hot out in the water

Beautiful sunset! Our crew was awesome and very friendly ! Highly recommend this tour to get those great sunset pics!

Great experience, the crew was so welcoming and friendly. I loved that they moved often to get the best views and the Rose on board was nice and strong. Will book again !

Captain and first mate were super friendly and gave us great views of the sunset. The boat was roomy and not crowded at all like other sunset cruises. Drinks were nice and cold.

Great atmosphere, very attentive and friendly.2ns time on this cruise. Not crowded, very relaxing. Thank you for a great time!

We did a sunset sail cruise with our friends and it was a fabulous trip! The captain and first mate were so attentive and took wonderful care of us! We had beautiful views of the gulf and the sunset along with celebratory drinks . They answered any and all questions we asked and were so knowledgeable of the area. It was the best night of our trip and we highly recommend you try any of their trips!

We were able to see a beautiful sunset in a relaxing and romantic environment. The staff was great and very friendly.