Reviews

My husband and I traveled from Chicago to Key West and secured a reservation on this Sunset Cruise. I would highly recommend it! The staff was very knowledgeable and had great senses of humor. We would come back again and again!!!

– beezerdog

Personnel were very enjoyable and professional. They spent time answering questions and talking to the people on the ship. The ship was very nice as well. We would definitely recommend it to our friends.

– TiffanyMcKin

The boat ride was very relaxing, and the staff is courteous and generous with drinks. When it got a little chilly out, they were quick to bring us blankets. The sunset was gorgeous. We had a great time.

– naciotola

My husband and I were driving from Miami to Key West for a long weekend. We found the sunset sail on the chamber of commerce web site and bought tickets for the Saturday evening sail. We absolutely loved this incredible experience!!!!! The captain, crew and support staff were awesome! The sailboat was clean and comfortable and they provided liquid refreshments. This was the highlight of our trip and we will definitely do this again!

– laurarn7

I did three sails with the Adironduck this fall, 2 in NYC (Sunset and Fall Foliage) and 1 Sunset trip in Key West. All the 3 of them were fantastic and I highly recommend them. The schooner is nice, the crew, I went with Andrew and his guys, is great and they provide a relaxed atmosphere far away from all the normal tourist staff! So, go for it, you will never forget these tours! Thank you very much!

– boattrip2008

Captain and her crew in my daughter’s words were “Kick-ass awesome!” Beautiful ship on a beautiful, breezy day created smooth, fast sail.

– widmerc

A group of 10 friends and I had the BEST time on this sail! The Captain and his crew were so nice and funny, and they kept our glasses filled with champagne and beer! The boat is gorgeous and comfy, and we sailed all around Key West. Got to see other islands, lots of other boaters, and had a blast! Key West is the southernmost point of the US, so sailing out into the water was beautiful – endless water and sun!!! We did the early afternoon cruise, but I bet the sunset cruise is amazing!!!

– jsammon99

The America 2.0 is a wonderful boat to sail on. It is fast and easy to sail (or just sit and watch the scenery). The crew was very courteous and made the trip a real joy. The day sail seemed to be better than the evening cruise if you want to enjoy the wind. The wind seemed to drop to minimal speed at night. So if you are in to sailing talk to the crew about which trip is best for you.

– rwalloch

My wife and I had an Awesome sail! The crew was knowledgeable, professional and fun! Thanks Very Much for a Great Time!

– Gary33

Great crew. Were a little hesitant about taking our 2 young children but they were great and had no issues.

– Michaelson5

beautiful boat, great crew, good time

– jonslotoroff

Great fun to be on a big boat with able crew, good wine, dear friends, sitting on a tilted deck with the wind in your faces.

– jbierden

Nothing better on a warm clear Key West night than a full moon sail. The captain and crew were very friendly and the free soft drinks, beer and wine made for a relaxing time.

– at21lin

We had a wonderful experience with a top notch captain and 2 great crew members who were extremely friendly and welcoming. Made for a great trip.

– sbo1961

We had a great time that we went two nights in a row. Excellent staff and captain. Thanks so much.

– DebbiB

We were on our anniversary and this was our last night and it was fabulous, the captian, astronomer, and crew were great, entertaining and made the cruise most enjoyable, we will take it again as soon as we get back to Key West! Ps. Best dollar value in KW!

– bettygulley

Delightful evening with attentive captain and crew. The staff was absolutely focused on their guest’s enjoyment. The whole family learned a lot and was fascinated bu the constallations. FUN!

– Edginny520

Well worth the money. Crew was awesome. This is not a party boat as some of the other sunset cruises are. We had a great night full of stars!

– georgemul

Enjoyable sail, although there wasn’t much wind that night…the moon and stars over Key West were lovely. Our astronomer really gave us a new appriciation for the stars.

– alison13

Not a cloud in the sky… The trip was fantastic. I learned a bit about sailing – it takes a lot of knowledge of how to tack and lots of strength to hoist those huge sails. The captain and crew were very friendly, helpful and just all around fantastic. The lunch and liquid refreshments were also excellent. We, aboard the America 2.0, of course, toasted our wide victory with champagne.

– AMPShearer

This is our 3rd year participating in the Wreckers Race, it’s a fabulous opportunity to sail on one of the fastest schooners. Highly recommend an afternoon on the water on this vessel or a sunset cruise.

– Susanbmoore

We enjoyed the Wrecker’s Race. It’s nice to be on the water and have fun. Lunch was good and the crew was great!

– GallupJH

I didn’t really expect a race, more of a glorified, tourist day sail. I was surprised to find it was pretty much a real race. In between jibes, the crew served beer, wine and champagne, but was never too far away from tending sails. The big boat sailed well and was fast! The crew were well experienced and fun. Personally, I was prepared to be disappointed but instead got to sail in a race in Key West, on a fast boat, and win! Only wish there had been an awards ceremony afterwards. It was a highlight of our Key West trip.

– rshroundo

America 2.0 is a beautiful schooner. The crew is exceptionally experienced, friendly and make you feel very welcome. We would recommend this sail to everyone.

– BerniceB

Before booking, I read some reviews about sail key west. Everything they said was true-the staff were friendly and attentive. The afternoon sail gave us a chance to see the islands from a different perspective. If you are looking for a peaceful afternoon on the water, this is for you.

– traveler42

The crew were very nice,kept things light. Very peaceful, relaxing afternoon on the water.First time on a sailboat -won’t be my last. Next time I would like to try the sunset cruise.

– FEQuick

This was a great excursion. It was a windy and cool day, but the crew handed out blankets to keep us warm. There were lots of other sail boats of all sizes on the water and it was quite a sight. The crew was cordial and very outgoing and were skilled at putting and taking down the sails. All in all, it was a great afternoon activity.

– chaslin

Took the 1:30pm day sail on the America. Capt Ron and crew were great, as was the boat itself. The sails provide plenty of shade on at least half of the boat if you’re concerned about the sun during the afternoon sail. You might even get to drive the beautiful boat!

– kerri88

What a fantastic way to spend a few relaxing hours In Key West! My mom had never been on a sailboat so we decided to take the Mother’s Day mimosa sail. We couldn’t have asked for a more attentive, respectful, cheerful crew and the ship was spotless and comfortable. Between that and the reasonable price, we were so happy we went! Thank you to the crew and the captain for a beautiful morning!

– ktoce1

This sail was outstanding, had a great time the crew was very friendly and worked hard to see that we had the best time.

– LindaRoshong

I am a travel agent and I would recommend this excursion to anyone. Our family had a lovely time.

– thecruisechi

The entire staff was so kind and hospitable and put in so much effort to make the trip worthwhile. Made all of the mama’s feel special! Would definitely go again!

– courtneyrose

The crew was wonderful and America 2.0 is a beautiful boat. We would highly recommend the Mimosa cruise to anyone visiting Key West during Mother’s Day.

– MWasko

Very well done. Ship was very clean and crew very cordial and courteous. Highly recommended.

– kmirrington

I purchased the tickets for the Key West lighted boat parade as a birthday gift for my boyfriend. It made for a very memorable birthday for him and the lighted boats were really fabulous to view from the water. We couldve just watched from the dock but this made it very special. The captain and crew were fun and professional.

– mlepore

We joined the Adirondack III for the Holiday Lighted Boat Parade. It was nice to be part of the boat parade instead of watching from land. They served drinks and conch chowder, which was great.

– ebbienc

Our cruise on America 2.0 exceeded all expectations. Service was sublime with attention to all details of presentation, sanitation, efficiency, comfort, and safety. I can’t wait to cruise again on this spectacular vessel.

– RONALDHECK

We took a vacation over the Holidays to Key West and wanted to experience a Cocoa and Carols Sail. The views were breathtaking, the sailors were extraordinarily helpful and kind. The atmosphere was joyous and fun was had by all. Blankets were provided for those that were chilly and the refreshments were lovely. I would sail again next time I am in Key West!

– valerieclift

I highly recommend the Cocoa and Carols cruise: great and friendly crew, amazing views, new acquaintances on board, and perfect holiday entertainment!

– marianne57

We did this on a whim. While driving down to Key West we decided to take this Cocoa and Carols cruise. The crew was VERY friendly and willing to visit and tell you anything you wanted to know about the ship, Key West, or any other topic. It was chilly in the evening in December so bring a lite jacket or sweatshirt. The crew did have nice blankets to wrap in if desired. We were under “sail” as soon as we were out of the harbor as the winds were perfect for the trip. Lots of other water craft and sail boats out so very fun to see. The holiday music was fun and festive! The sunset was outstanding and memorable, along with the full moon rising over Key West at the same time. This was one of the most memorable experiences for us on this trip.

– BruceEstrem

This is becoming a yearly Christmas Eve tradition for my wife & myself. The crew is always exceptional. The reading of “The Night Before Christmas ” on the way back to the docks was a great touch.

– kirklhicks

My husband and daughter and her husband did the Sunset Sail on Christmas Eve aboard the America II and it was the best sail that I’ve experienced in years. For one thing, it was a true sail — not the typical sunset cruise where they motor most of the time. The price is well worth it as the boat is new and there are no where near as many people on board, making it much more enjoyable. The crew was friendly and knowledgeable. As a local who has lived in Key West going on 10 years I would highly recommend the America II sunset cruise sail as a wonderful Key West experience.

– CindyMorris

This is the third year we’ve been out with these guys on Christmas Eve. We keep coming back because of such an awesome experience. Hope to be back again next year.

– kirklhicks

We loved this. Had never done it before and so glad we did. Definitely recommended. Will go again.

– Rikkirocket

We made our way to the boat about 30 minutes before setting sail and enjoyed the surroundings. Once aboard, the crew was fantastic and catered to everyone! The cruise was absolutely incredible and made a perfect Christmas memory for us. We will definitely be returning!

– kwente70

My husband and I went for a sunset sail on America 2 on the Christmas holiday. There was no sunset, but the winds were strong, and we just FLEW over the water! The schooner is SO smooth on the water. My husband is a sailor, and he was is heaven! The captain and two crew were friendly, efficient, and made us all have fun. This is no booze cruise – it’s an experience you won’t forget!

– CarrieODell

This sailing excursion was the highlight of my trip! My friend and I did the NYE Sunset Champagne Sail. I loved everything about our holiday trip! We all, on the boat, got to know each other very quickly. The crew were TOP NOTCH. Very personable and so polite. They were the perfect hosts making sure I had everything I needed. I also enjoyed the opportunity to help the crew set the sail. I took amazing photos of the gorgeous sunset and our beautiful sailboat. I only wish I took a Sunset Sailing trip the first night I arrived. If I did, I would have signed up to sail every night of my 7 day vacation! No kidding! Thank you for such a wonderful experience! I hope to see you again soon! -Sue from Lake Tahoe, CA

– swaters99

First time my wife and I were on a schooner for NYE. The sail was very relaxing and the sunset was incredible. The relaxing mood of the fellow passengers made for wonderful conversations and I feel that a great time was had by all.

– ranchero

The boat, the crew, the experience was beyond my expectations. First class! Not the ordinary sunset boat ride. Perfect for NYE. Sailing is the only way to go. Good food and an intimate setting. You even arranged for the sun to peek below the clouds at sunset. Especially enjoyed the Schooner Dance that Captain Chris performed!

– melapp

The management team and crew of America 2.0 made our NYE sunset cruise a top choice for a Key West experience. There were even yummy snacks! This lovely wooden vessel convinces me that a sail every week, not just when guests come, could satisfy my salty soul when Old Town feels a tad closed in.

– MarnyHeinen

WE BOARDED THE BEAUTIFUL SCHOONER AND WERE GREETED BY THE FRIENDLY CREW. FREE BEER AND WINE WERE COMPLIMENTARY ALONG WITH CHEESE TRAYS AND SHRIMP. THE BOAT IS ABSOLUTELY BEAUTIFUL AND I HAD A GREAT TIME ON MY BIRTHDAY (NEW YEARS EVE). THIS IS THE SECOND TIME WE HAVE CELEBRATED ON THIS BOAT AND IT SURE BEATS GETTING SQUISHED BY THE CROWDS ON THE DOCK!

– JOYCENYDAM

It was a great combination of being at a popular event without having to deal with the crowds. The wooden sailing ship was in beautiful condition. The staff was courteous and responsive to our needs. The provisions were delicious chicken wings, hot and meaty; and the champagne just kept flowing. We were located right across from where the Schooner Wharf Wench was lowered at midnight. And the other passengers were diverse and interesting. Lovely time and we would do it again !

– djoveges

The boat provides a private view of the Dropping of the Pirate Wench from the mast. As Europeans used to massive firework displays at New Year, the event was fun. There was free flowing champagne and some crudites and dips to wet our tastebuds, and the crew worked hard to integrate everyone who wanted to be integrated without being intrusive. As relative oldies we were happy to pay the relatively high price to be able to sit and be served in comfort rather than fight our way among the crowds on shore. It suited what we wanted perfectly.

– DougMoffitt1

Food was good, service was great, drinks were limited in variety, but plentiful. Great view of the pirate wench drop. Nice people as fellow passengers. Glad I experienced it, beautiful vessel.

– thekfeltons

We enjoyed a delightful evening on the Schooner America 2.0. The boat was tied up at the epicenter of Schooners’ Wharf’s New Years celebration. While a large crowd attended their event, we sat, listened to music, enjoyed appetizers and pleasant conversation. The crew was very hospitable. It was a great evening. Don’t go; there were very limited tickets and I need room to bring all of my friends next year.

– johnwalshlfd

My wife and I decided on a whim to go sailing and asked our bartender at Sunset Pier of a good experience and he suggested Classic Harbor Line. We were lucky enough to purchase two tickets for the New Year’s Day sunset champagne cruise aboard America 2.0. It was a great experience from start to finish with a totally professional crew very keen to making your sunset voyage a memorable one. I have nothing but good thing to say about the boat, skipper, and crew. VERY recommended.

– Ryan_Carmody

Our first time sailing and it was amazing, we would highly recommend booking any of the Sunset Sails. America 2.0 was perfect! The crew was all female by the way and they were great, serving our refreshments all the while keeping a close check on us all to make sure that we were doing fine. When we return to the Keys we would love to sail again with you. Kudos for providing a wonderful time!

– DebPressley

The New Year’s Day champagne sunset cruise is among the best money anyone can spend in Key West… The crew ensures everyone has a good time while making sure safety is prioritized up front – from then on it’s 3 hours of the best views you may ever see in your life… along with unlimited alcohol which is an added bonus. The captain and crew were very pleasant and welcoming, and it was an adventure not to be missed. There are other sailboats in Key West, but this one has class, charm, and a crew to beat the band. A wonderful way to begin a New year!

– Chelsearomer

Away from all the hustle and bustle of the New Years crowds on Duvall Street, we found a little piece of heaven on this beautiful and finely crewed 105′ schooner. We do a fair amount of sailing on our own in Colorado, so we were a little apprehensive of “lowering ourselves” to do the tourist routine on somebody elses boat in Key West. However, within 10 minutes of leaving the harbor, we were moved by the grace, the warm wind, gentle seas, full sails and the splendid views as the sun began to set over the western horizon. Once we were well out to sea, the crew invited us to man the helm which was an uplifting experience in itself. Of course, the engaging crew keeping our wine glasses full helped make the experience more enjoyable! The type of vacationers that are attracted to this kind of activity also contributed to make the experience a great one. This is, without question, the most beautiful sailing boat available in Key West. Highly recommended!

– tedterroux

As a solo traveler, I’m always looking for unique experiences, and this cruise was perfect! The staff was friendly, and the reenactment made me feel like I was back in history. The open deck offered the best views, and the delicious lunch and complimentary drink were a great bonus. Highly recommend this to anyone visiting Key West.

– happy passenger

I brought my two teenagers along, and they had a blast on this Civil War battle cruise! They loved the cannon fire and the excitement of the reenactment, and I appreciated the chance to relax with a drink and a delicious lunch. It’s hard to find activities that appeal to all ages, but this was a big win for our family

– happy passenger

We’re visiting Key West in our retirement, and this cruise was the highlight of our trip! The schooner was stunning, and watching the Civil War battle unfold was so unique. We enjoyed the sandwich and dessert and had a refreshing glass of wine while soaking up the views. It’s a great way to experience a piece of history with a twist

– happy passenger

This cruise was a dream come true for any history enthusiast! Watching the Civil War reenactment on the water was thrilling, and the crew made the experience even more authentic with fun facts and stories. The cannon fire was a great touch! The sandwich from Old Town Bakery was delicious too, making this an all-around memorable afternoon. Will definitely be coming back for the next one.

– happy passenger

My partner and I had so much fun on the Civil War Sea Battle cruise! It was exciting to be part of a reenactment, especially on the beautiful Schooner America 2.0. We enjoyed our complimentary drinks while cheering for the ‘Union’ and dodging the ‘cannon fire.’ The perfect mix of history and adventure in Key West

– happy passenger

Wine, champagne, beer, roses, decorations, and h’orderves all special for Valentine’s day. Funny and friendly crew. Very clean bathrooms.

– csmicfool

very personable Crew that worked hard to make sure we had a good time

– DonnaVoxland

Well worth the money do not hesitate great crew with awesome personality and excellent customer service.

– Juangon1977

The crew was great – friendly, professional, and very polite.

– MarkP1957

Our extended family wanted a special experience, and this cruise was perfect! We had grandparents down to little ones, and everyone enjoyed the Blue Angels show from the perfect vantage point. With a great mix of drinks, lunch, and the spectacular setting on the schooner, it was a celebration to remember.

– happy passenger

I couldn’t have asked for a better way to experience the Blue Angels! The America 2.0 was beautiful, the gourmet lunch was top-notch, and everyone was friendly. Being on the open water with a front-row view of the air show was an unforgettable experience. Highly recommend this cruise for anyone who wants a special way to watch the show

– happy passenger

What an amazing family day on the water! Our kids were thrilled with the Blue Angels show and loved being on the open deck of the schooner. The lunch was a hit, and the staff made sure everyone had a great time, from kids to adults. This is a must-do event for families—it only happens every two years, so don’t miss it!

– happy passenger

Our friend group booked this cruise to catch the Blue Angels show, and it was the best decision! We had plenty of space to relax, catch up, and enjoy a few drinks while watching the show. The vibe on deck was so fun and lively, and the views were unbeatable. Already looking forward to the next one in two years!

– happy passenger

We had an absolutely romantic day out on the Schooner America 2.0 for the Blue Angels show! Between the premium drinks and gourmet lunch, we were spoiled, and the airshow was like nothing we’d ever seen. Watching those planes perform against the open sky, with no one blocking the view, was pure magic. If you’re looking for a memorable date, this is it!

– happy passenger