Key West Schooner Sunset Sail With Bar & Hors D'oeuvres

Amazing relaxing cruise on a beautiful sailing ship. We are going to do this again. Crew was attentive and professional. I can't say anything that was lacking. Highly recommend!!!

They cancelled the tour same day with no reason given. We were lucky to get on another cruise tour the same day.

Captain Janet and her two crew mates made the experience very fun. The boat was easy to find and the overall experience was great. Janet was very friendly and answered all kinds of questions from people while also steering and guiding the boat masterfully. It’s always a pleasure to see people great at their jobs and enjoying it. The two guys helping out were very sweet and made sure everyone had drinks and the three plates served (veggies with ranch, shrimp cocktail, and cheese and crackers) were all tasty. I don’t think anyone on board had a bad time.

Amazing Sail! Captain Janet and her incredible crew gave us the experience of a lifetime! Never having been on a schooner before we weren't sure what to expect but it was exciting and was also the last sail of the season in Key West!! What a hard working group who were expert in getting to and from, providing snacks and beverages and raising and lowering the sails which is something I will never forget. If you are in Key West or New York, you must experience a sail on America 2.0!! You will not be disappointed in the least. Thank you!!

We went out on a very windy day and what an awesome time it was. Great crew, great service, great fun !!! Awesome sunset !!

Our Captain and tour guides were amazing!

A wonderful experience! The booking process is so easy. So was the boarding process. The captain and crew were amazing – thank you so much to Captain Jana, and her crew, Chelsea and Milo. They made the sail so much fun! The ship is beautiful, the ride was fantastic, the drinks and hors d’oeuvres, were yummy, and the sunset never disappoints. It was our favorite thing to do on this vacation. Will definitely do it again.

Worth it! Pay the extra money for this over the catamaran boats. Food and wine was great but the sailing and crew were even better.

It was an awesome experience. The crew, Ray, Chelsea, and Brad were wonderful. Best experience so far in Key West.

The crew is fantastic. Not just sailors, but great hosts. Our wine glasses were never empty, and the snacks just kept coming.

Best experience ever. The crew was awesome and the vibe was abwesome. It’s pure dialling boat so we loved it

snacks are minimal. boat is lovely. crew friendly and considerate. lovely to be on real sailing ship

It's not a rock concert, it's not a dance club- it's a cruise, quiet and peaceful and serene: the way God intended sailing to be..

It was so beautiful! We had the perfect evening weather wise! But what made it even more amazing was the crew! Captain Janet, Mary & Chelsea were so sweet and so knowledgeable! It was so fun watching them put the sails up and take them down! They were also wonderful hostesses! They made sure we always had a fresh drink in our hand. The hor d’oeuvres were fresh and tasty! I highly recommend doing this sail! We will definitely do it again if we come back! One of the highlights of our trip!

Amazing amazing experience. What a well put together crew and vessel.!! drinks and snacks were on point worth every penny and more!! Book this!!!👏

Amazing fun crew that started the cruise off with making everyone feel comfortable and well informed!

Our experience with the Sunset Sail was amazing. The Captain and Crew were knowledgeable, welcoming and very friendly. We would definitely recommend this experience.

What a wonderful time we had with a great sunset. The crew was super nice and so informative. This was our 2nd trip we brought family to enjoy what we already liked. Thanks Milo and Jade and others for a fun sunset trip.

Staff was extremely kind and made sure everyone was comfortable. Was a beautiful sunset. Would totally revisit this experience.

Dan, Chelsea and Molly did a great job! We had smooth sailing and enjoyed beverages and yummy snacks—veggies, cheese and crackers, shrimp cocktail and brownies!

Unfortunately, we were cancelled due to high winds and choppy seas. But kudos to the staff, who had advised us by 3:30PM by email and phone. Another group wasn't so lucky, as their vendor was waiting until 5PM to make a decision. If you've been to Key West, you know this affects shuttle and dinner plans.

It was absolutely awesome! Great ambiance, great choice of drinks, snacks/cheeses were yummy. The entire crew was super friendly, nice conversations. The sailboat was beautiful, well maintained, clean...perfect! Of course the sunset was a great moment. Very tempted to do it again 😅

Good selection of drinks and snacks. Staff were all very friendly and engaging with all the guests. My wife is now a huge sailing fan.

Truly one of the most memorable vacation experiences my wife and I have had. The captain and crew of America 2.0 were amazing in every way.

Oh my what a beautiful sail we had! The Schooner America 2.0 is a terrific ship. The wind was perfect, the captain and crew (Janet, Brad and Elliott were amazingly skilled, professional and fun! Refreshments were great and the skyline displayed its amazing colors! Highly recommend!!

This was our second trip of the day and was exactly what we needed beautiful sailing ship with a great crew. The evening was relaxing and chilled out. A perfect end to the day would definitely recommend.

We had an amazing sunset sailing experience with Captain Janet and her crew aboard the America 2.0! From start to finish, everything was perfect. The crew was friendly, attentive, and made the whole experience feel fun and relaxing. Watching the Key West sunset from the water was absolutely beautiful, one of those unforgettable moments. Captain Janet made us feel safe and welcomed, and you can tell she truly loves what she does. Highly recommend this experience to anyone visiting Key West, it was definitely a highlight of our trip! 🌅⛵

From the easy booking to the wonderful experience this was a perfect trip. Captain Janet and her crew made this sunset sail our best ever. America 2.0 is an awesome ship and her crew was the same. They tended to our every need and impressed with their professionalism. We will definitely do this again with our boys and theirs families.

Elevated experience💕 Lovely evening with a great crew! Drinks came quickly and we were able to actually sail with a nice breeze. Brought 84 year old mother and had no issues boarding. Appreciate the assigned seating, eliminates the crazy rush to board like most other sunset cruises. Highly recommend!

Brilliant sunset sail! Great crew, amazing boat, a wonderful time!!

The experience on the open water exceeded our expectations. The windy conditions added to the speed and adventure. The crew of Ray, Dan and Jayde were attentive and very knowledgeable

The best way to see the sunset in Key West on this cruise. The staff was unbelievable- so worth the money for this beautiful experience!

Absolutely loved it! Captain and crew were professional, attentive and overall awesome! Dolphin sighting a bonus!

Make sure you go to the green awning on the left when you arrive. We got caught up in the wrong line to the right and almost missed the cruise. Aside from the arrival confusion all else was truly exceptional. Great crew, beautiful, clean, and comfortable ship, a truly relaxing and enjoyable excursion.

A great sunset sailing tour with a quiet vibe and great crew (Rae, Brad and Jade). Our ship wasn’t crowded so good opportunities to move around and see the views from different angles. Would highly recommend.

Beautiful boat and wonderful captain and crew. They all worked very hard to make the cruise fun and it was!! Highly recommend the sunset cruise!

Amazing! Captain crew were professional well skilled and provided an amazing sailing experience!

Wow! What a fabulous sunset sail on the America 2.0 schooner. Our group of 6 had such a relaxing and fun time. We were so fortunate to have such beautiful weather too. Captain Rae, along with Chelsea, Brian and Brad, were THE BEST! We look forward to returning to Key West and sailing again. This vessel and crew will be in New York Harbor in July 2026-I would highly recommend booking an excursion with them!

Ray, Jade & Brad were awesome! We had such a great time on our sailboat cruise. The crew was incredible and attentive and had so much wonderful energy to share! Highly recommend!

Green Flash, amazing. We had such a delightful pleasant sunset cruise on America 2.0 with Capt Heather and crew Dan and Ray. The weather was perfect and the boat is beautiful. The crew was very attentive and the snacks were great. Huge selection of beverages. Highly recommend and will go with Classic Harbor lines on our next KW trip

A thoroughly enjoyable cruise! Captain and crew were awesome, weather great and the sunset was magnificent.

We took a sunset cruise on the America 2.0. It was a beautiful evening with a nice wind made the sale so enjoyable. The rustling of the wind with no motor was a quiet invigorating experience. The crew of Jan, Mary, Dan and Milo were terrific attending to their sailing duties while waiting on patrons. They delivered to your assigned seat your choice of beer, wine or champagne. Veggie platters, cheese crackers, shrimp cocktails and a brownie to top it off were also provided. We saw a beautiful sunset as well. A great, relaxing experience, rounding off our week in Key West. Look forward to a return trip.

We loved it, felt safe but it was an exhilarating way to sèe the sunset. Definitely the best we have done and we have done a few sunset cruises

This sunset sail was the perfect way to watch the sunset. The crew took excellent care of us. Our drinks were never empty and the apps were perfectly light and filling. We sailed the whole trip except for in and out of the marina which was awesome. Saw dolphins who were jumping in our wake which was a highlight. The sunsets in key west are killer and this is a great relaxing and sweet way to watch it. It was between this sunset sail and a party boat for my husband and I on an anniversary trip and this was definitely the right move.

My wife and I and three other couples enjoyed and spectacularly beautiful evening on a Key West Schooner Sunset Sail (by Classic Harbor Line). The very capable young adult crew did an outstanding job of handling the ship and cheerfully provided 4 different simple but delicious Hors d'oeuvres plus a selection of liquid refreshments including adult beverages. The crew members were friendly, informative and sociable. The ship was well maintained and in excellent condition. The view of the sunset was amazing. In all respects this was a very memorable experience. I highly recommend this experience for your next trip to Key West.

This was a fantastic sail. Staff was great. Capt Janet was great too. Food was nice too. We had ranch and veggies, cheese and crackers, boiled shrimp and a brownie for dessert. The drinks were free flowing also. I would do this again on the next visit. The only problem is finding the ticket booth. We went to three different ones before we found the correct one. It could be market for easier access.

Our outing was wonderful - smaller group of people, attentive and knowledgeable crew - Rae, Chelsea, and Brad - great night overall.

Awesome time on the America 2.0, and the crew - Rae, Chelsea, and Brad - was fantastic. Great experience to see the hoisting of the sails once we were out on the open water. The food was good, nothing flashy, but tasty. The sunset was beautiful and we even had a bonus dolphin sighting along the way. We enjoyed this trip from start to finish!

It was a great sailing day. Good wind. Crew was excellent and very professional. The drinks and hors dourves were good. The crew was very organized in their service of the snacks. The captain and crew were enthusiastic and informative.