🌅 The 7 Best Key West Sunset Dinner Cruises [2023 Reviews]

Key West is one of the most beautiful places not only in the United States, but in the entire world. It makes sense, then, that tons of tourists flock here every year.

The natural beauty and incredible climate that stays consistent pretty much year-round makes it a great place to hang out outdoors. The natural landscape, ocean, and electric sun come together for gorgeous sunsets every night, and there are many great places to watch them.

However, nothing compares to one of the top Key West sunset cruises, which we’re here to bring you today!

Best Sunset Cruises in Key West

Key West Sunset Sail Aboard SchoonerSmall-Group Key West Sunset Sail with WineKey West: Sunset Cruise with Buffet Dinner and Open Bar
editors choice
Key West Sunset Sail Aboard SchoonerSmall-Group Key West Sunset Sail with WineSunset Cruise with Buffet Dinner and Open Bar Key West
Departure Point:202 William St, Key West255 Front St, Key West201 William St, Key West
Departure Time:Varies by time of yearVaries by time of yearVaries by time of year
Duration:2 hours2 hours2 hours
Includes:Complimentary beer, wine, champagne, soda, individually-plated hors d'oeuvresUnlimited beer, wine and soft drinks, wine tasting, light refreshmentsBuffet dinner, open bar, live music, sunset cruise

Tour Information & Booking

Tour Information & Booking

Tour Information & Booking


Quick Answer: The 7 Best Rated Key West Sunset Sails For 2023

  1. Key West Sunset Sail Aboard Schooner
  2. Small-Group Key West Sunset Sail with Wine
  3. Key West: Sunset Cruise with Buffet Dinner and Open Bar
  4. Key West Sunset Sail with Full Bar, Live Music & Hors D’oeuvres
  5. Key West Sunset Cruise with Live Island Music
  6. Sunset Sail Cruise in Key West
  7. Key West Sushi Sunset Cruise

Key West Sunset Cruise Reviews

1. Key West Sunset Sail Aboard Schooner

Key West Sunset Sail Aboard Schooner

Tour Highlights:

  • Duration: 2 hours
  • Departure: 202 William St, Key West
  • Departure Time: Varies by time of year
  • Includes: 2-hour sailing experience aboard America 2.0, complimentary beer, wine, champagne, soda, individually-plated hors d’oeuvres

If you want to feel like you’ve gone back in time almost 200 years, then you have to check out first tour out! The Key West Sunset Sail Aboard Schooner tour will take you over the beautiful ocean on a replica of the 1851 Schooner America.

This smooth ride is luxurious, a load of fun, and one of the best ways to watch the sun go down on the island. Meet up around 4 pm along with the rest of your group to board the ship. You’re immediately greeted by the crew, who are super friendly and make the experience that much better.

Once you take a seat (or stand if you prefer), you’ll be served with complimentary hors d’oeuvres along with a nice selection of alcoholic and non-alcoholic drinks.

This is a great way to meet other tourists or locals, bring the entire family on board, or simply experience it with your significant other.

Set sail, enjoying the sounds of the water underneath the ship as you head towards Mallory Square. There are a ton of people who come to the square to watch the sunset – wave to them from the ship!

Next, you’ll sail by the famous Fort Zachary Historic State Park, which has its own unique history and looks impressive from the water! At this point, the sun will start going down. However, not before you reach the incredible views that Sunset Pier has to offer!

The neon orange reflects wonderfully off the water, and the music and other people nearby just makes it that much more magical.

Tour Information & Booking

100% refund for cancellations within 24 hours of tour experience


2. Small-Group Key West Sunset Sail with Wine

Small-Group Key West Sunset Sail with Wine

Tour Highlights:

  • Duration: 2 hours
  • Departure: 255 Front St, Key West
  • Departure Time: Varies by time of year
  • Includes: Unlimited beer, wine and soft drinks, wine tasting, light refreshments

Are you a lover of wine and/or beautiful sunsets on the water? If you are, then you’re the perfect guest for the Small-Group Key West Sunset Sail with Wine Tour! This is a bit more of an intimate cruise, where the one prior to this was made for the larger crowds of people.

Make sure to check in approximately 30 minutes before the departure time the crew advises you of, ensuring everyone gets on board and comfortable. We found the crew to have incredible attention to detail, and were very friendly, putting safety at the forefront of the operation.

Once you board the 65-foot schooner, you’ll realize that there’s plenty of seating room, and you won’t be squashed in with other passengers.

Once you set sail, you’ll be served a choice of wine, 4 different kinds of beers, along with delicious charcuterie selections such as a wonderful cheese, cracker, meat, and olives plate.

Rest assured the crew will keep the wine flowing with 8 different selections available! We personally enjoyed the summer sausages, brie, and green apples with honey, however, there really is something to suit any taste.

If you’re looking to plan a fantastic date night with your other half, this is really the way to go due to the smaller group sizes and alcoholic beverage selections against a stunning background.

Watch the sun go down over the horizon of endless shimmering water, with the sun reflecting off of it. This creates an orange glow that looks almost unreal at times. Make sure to take out the camera for some excellent photo ops!

Tour Information & Booking

100% refund for cancellations within 24 hours of tour experience


3. Key West: Sunset Cruise with Buffet Dinner and Open Bar

Sunset Cruise with Buffet Dinner and Open Bar Key West

Tour Highlights:

  • Duration: 2 hours
  • Departure: 201 William St, Key West
  • Departure Time: Varies by time of year
  • Includes: Buffet dinner, open bar, live music, sunset cruise

Who doesn’t love endless food and drinks? If you’re enjoying a wonderful vacation in Key West, you shouldn’t have to limit yourself and try everything that catches your eye. On the Key West: Sunset Cruise with Buffet Dinner and Open Bar tour, you don’t have to!

This is yet another 2-hour, intimate cruise with smaller group sizes. With that being said, if you’re going with a significant other, it’s a great date night option. However, just as well, it’s a fun time for the entire family though it tends to lean more towards adults.

Are you looking for a calm, relaxing cruise tour instead of a party cruise? There are plenty of both in Key West, and this one falls into the category of the former, despite the ship being called “The Party Cat”.

The smooth ride on the ship along with the chill music makes for a serene way to enjoy the afternoon.

Once you board, enjoy a buffet comprised of fresh tropical fruit and dishes. You can expect options such as: roast pulled-pork in mojo sauce, deep-fried sweet plantains, black beans and rice, grilled chicken, friend fish, mixed veggies, pasta with mini shrimp, along with Cuban bread and butter.

Drinks are also delicious, with endless margaritas, rum runners, champagne, beer, wine, and spirits. After dinner, head upstairs to the upper deck to groove the night away to some live music!

The local musicians are very talented and entertaining, setting the tone for a fun evening as you watch the sun set with the electric colors spreading across the sky.

Tour Information & Booking

100% refund for cancellations within 24 hours of tour experience


4. Key West Sunset Sail with Full Bar, Live Music & Hors D’oeuvres

Key West Sunset Sail with Full Bar, Live Music & Hors D'oeuvres

Tour Highlights:

  • Duration: 2 hours
  • Departure: 205 Elizabeth St , 205 Elizabeth St, Key West
  • Departure Time: Varies by time of year
  • Includes:Beer, wine, champagne, sangria and soft drinks, chef’s selection of hors d’oeuvres, full liquor bar included, live music from local Key West musicians

If you’re on the hunt for an amazing sunset cruise but are on a budget, put this one at the top of your list! The Key West Sunset Sail with Full Bar, Live Music & Hors D’oeuvres is all that and more.

Oh, but it’s not just a cruise! It’s a 2-hour excursion where you get to try a little bit of southern flavor with peel-and-eat shrimp and an upscale twist with fresh hors d’oeuvres. If you want to escape the crowds that gather on shore to watch the sunsets, we can’t think of a better way to do it!

Meet up at the tour office located between Conch Republic and Schooner Wharf 30 minutes before the departure time (around 4 pm). Board the sleek, 60-foot catamaran that sports a whopping 1,500 feet of deck space!

With smaller group sizes, everyone has more than enough room to walk around and mingle, or kick back and relax.

The crew is incredibly friendly, and always attentive and there to make sure everyone has a great time. Once you board, you’ll be able to revel in amazing live entertainment, and all-you-can-eat drinks and snacks.

Yep, you read that correctly! The music does vary, but typically you’ll have some jazz and smooth music to accompany you. Drinks consist of beer, soft drinks, sangria, full liquor bar, wine, champagne, and more.

As the sky starts changing colors, you’ll cruise by important landmarks along the coast, such as Mallory Square, Navy Mole Fort Zachary Taylor Historic State Park, and more. Make sure to take your camera out to take some photos of the blue waters meeting the orange sky!

Tour Information & Booking

100% refund for cancellations within 24 hours of tour experience


5. Key West Sunset Cruise with Live Island Music

Key West Sunset Cruise with Live Island Music

Tour Highlights:

  • Duration: 2 hours
  • Departure: 631 Greene St , 631 Greene St, Key West
  • Departure Time: 4 pm
  • Includes: Appetizers, dishes, alcoholic beverages, soft drinks

Does dancing to some island grooves from local musicians while you eat, drink, and enjoy a beautiful sunset on the water sound like a good time to you? Then give the Key West Sunset Cruise with Live Island Music a good look! This is yet another cruise that’s easy on the wallet and a couple of hours of good vibes.

From the very get-go, it’s an awesome experience thanks to the attentive and friendly staff, and positivity all-around. We should let you know that this is kind of a more upbeat experience than the others, which have a more relaxing setting.

The band plays everything from reggae to rock, and the crowd can get a bit lively! However, it’s a ton of fun! The crew will escort you onto the spacious catamaran, which is clean, and looks to be quite new.

There’s ample seating everywhere, aside from the large dance floor so you can bust a move without worrying about anyone getting in your way!

Enjoy unlimited appetizers, beer, margaritas, wine, sangria, champagne – whatever you feel like having! There are plenty of soft drinks and water available as well, if you don’t want any of the other options.

Enjoy cruising along the calm waters as the sky turns pink, orange, and yellow, reflecting off of the ocean. You’ll get to see Mallory Square, Sunset Key, and Key West Harbor as you sail along.

This is a very welcoming experience, with a lively atmosphere that’s perfect for guests of all ages! However, it may not be ideal for children who do not like loud music as this is a live band. It’s a great way to dance a little, enjoy cruising along, and have some appetizers while being back just in time for dinner!

Tour Information & Booking

100% refund for cancellations within 24 hours of tour experience


6. Sunset Sail Cruise in Key West

Sunset Sail Cruise in Key West

Tour Highlights:

  • Duration: 2 hours
  • Departure: 631 Greene St , 631 Greene St, Key West
  • Departure Time: 4:00 pm
  • Includes: Sunset sail, snacks, coolers of ice with cups and bottled water

Next up, we bring you the Sunset Sail Cruise in Key West, which is a crowd favorite. Have you ever thought that being a pirate may be fun? Well, then this tour should immediately hit the top of your list because you’re about to get as close as possible to that!

We’re sure there’s no other Key West sunset cruise like this one, as you’ll be riding on the island’s most photographed ship? Why does it hold this title?

Because the Schooner Jolly II Rover is the only squared-rigged, topsail schooner in the Historic Seaport! You may have heard of it referred to as the island’s famous “Red Sails in the Sunset” tall ship!

If sailing catches your interest, you’ll love how interactive this cruise is. You’ll be able to help raise the sails, steer the ship, and “shoot the cannons”. However, it’s never obligatory. You can be as involved as you want, no pressure.

The crew is one of the friendliest we’ve encounters, which is really saying something! It’s not uncommon for the ship’s owner to come out and visit with everyone, either. The crew will give an interesting historical account of the ship, the area, and much more.

As you sail, make sure to take advantage of the unlimited snacks and ice-cold water onboard. On here, you won’t be hearing any music or rowdy environments. This tour is designed to be peaceful and allow you to take in the experience of sailing while enjoying the natural beauty around you.

You’ll cruise into Man O’ War Harbor, see Christmas Tree Island, mansions on Sunset Key, Mallory Square, Navy Mole, and Fort Zachary Taylor!

Tour Information & Booking

100% refund for cancellations within 24 hours of tour experience


7. Key West Sushi Sunset Cruise

Key West Sushi Sunset Cruise

Tour Highlights:

  • Duration: 2 hours
  • Departure: Barefoot Billy’s Boat Cruises – Garrison Bight Marina , 719 Palm Ave, Key West
  • Departure Time: Varies by time of year
  • Includes: Alcoholic beverages, bottled water, soda, snacks, restroom on board

You’re probably already aware of the fact that Key West has some of the best seafood in the United States. This means that there’s a ton of good sushi offered on the island as well. If you want to enjoy some delicious sushi rolls while watching the pink sunset electrify the water and sky, check out the Key West Sushi Sunset Cruise!

This boat is one of the smallest ones of any sunset cruise we’ve seen in Key West, however, this offers a more intimate experience that’s great for sharing with your loved one(s). The captain and crew do a great job of keeping you entertained while making sure everyone is tended to properly.

Once on board, you’ll be served platters of sushi so make sure you save some room! This is a great way to get to try different types of rolls that you haven’t had before. There are plenty of other snacks and many beverages available as well, just in case someone in your group isn’t a sushi fan.

Even if you are bringing the entire family, there’s enough fresh food for everyone with everything cooked to perfection!

While the captain tours you around, they’ll share many stories, personal anecdotes, and historical accounts that will have you at the seat of your chair!

Cruise by Mallory Square, Fort Zachary Taylor Historic State Park, Key West Lighthouse and Keeper’s Quarters Museum (seemed to be most peoples’ favorite), and the incredible Southernmost Point.

This is the lowest latitude land in the contiguous North American States so make sure to get a photo or two!

Tour Information & Booking

100% refund for cancellations within 24 hours of tour experience


Why You Should Take a Dinner Cruise in Key West

key west dinner cruise

Taking a Key West dinner cruise, especially at sunset is a great way to experience the beauty and charm of this unique island in Florida.

  1. Scenic Views: Key West dinner cruises have awesome views of the sunset, the coastline and of course the ocean. You can enjoy the stunning natural beauty of the area while enjoying a meal.
  2. Unique Experience: A dinner cruise in Key West is a unique and memorable experience, especially if you are celebrating a special occasion like an anniversary or birthday. It is a romantic way to spend an evening with a loved one or a fun way to enjoy time with friends and family.
  3. Delicious Food: Most Key West dinner cruises offer a variety of delicious food options. It will range from fresh seafood to traditional American cuisine. Most cruises include live music or entertainment during and after dinner.
  4. Convenience: A Key West dinner cruise is a very convenient way to enjoy an evening out on the water without the hassle of navigating the island or finding parking. Some cruise operators even include transportation to and from the boat.
  5. Historical and Cultural Value: Key West has a rich history and culture. Some dinner cruises offer educational and informative commentary from the boat captain about the area’s history and landmarks. This is a great way to learn more about the island while enjoying dinner.
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The Key West Sunset Sail Aboard a Schooner is our Editors Choice for the best Key West sunset cruise

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Robert Baker

Robert is a content writer and editor at World Guides to Travel where he shares his love for the great outdoors. He also writes in-depth travel blogs for other websites around the world. Robert is passionate about the environment and uses his writing to educate people about the advantages and importance of sustainable living. Robert enjoys creative writing. In 2009, his children’s novel Sally Hemings & the Good Associates won the Children’s Fiction section of the You Write On Book of the Year Award.
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