Last Updated on November 28, 2022

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Located at the southernmost point in the United States, Key West is a beautiful area, filled with nightlife, sandy beaches, and unforgettable sunsets.

One of the best ways to watch the sun go down is by actually getting out on the water, rather than heading to popular places such as Mallory Square.

Taking a sunset cruise in Key West, Florida allows you to avoid some of those crowds, see the sunset with a new perspective, and enjoy the cool breeze off of the ocean.

Here are 9 of the best options for cruises to watch the sun go down in Key West.

 

Top Choice: Award-Winning Sunset Cruise With Drinks

Sunset Tiki Boat Tour In Key West

 

 

Best Sunset Cruises in Key West

 

Hop on board this custom-built floating tiki bar and experience the famous Key West sunsets in a more personal way.

This tour is rated 5 Stars on Trip Advisor with over 50 reviews!

 

Tour length- Approximately 2 Hours

Hop on board this custom-built floating tiki bar and experience the famous Key West sunsets in a more personal way.

With a maximum of 6 people per boat, you’ll be able to spend time with your family, friends, or partner as you cruise around the harbor, admiring the setting sun.

Bring your own snacks and drinks to enjoy as you cruise around, as cups, ice, and a blender are provided on the boat.

The captain and crew will let you in on some local knowledge of the area as well as tell you where popular landmarks are and watch for wildlife in their natural habitat.

 

What’s Included With This Cruise?

  • USCG certified captain
  • Local knowledge from your captain and crew
  • Cups, ice, and a blender to use for your BYO drinks
  • Bottled water
  • 2-hour uncrowded cruise on a tiki boat

 

 Here’s what a past guest said about this tour:

What a great experience!!  It’s a must do when coming to key west. Captain Morgan was fun and very knowledgeable.  Can’t wait to do it again in the future.

Billy_M

 

 

This tour is rated 4.5 Stars on Trip Advisor with over 35 reviews!

 

Tour length- Approximately 2 hours

 

This beautiful cruise allows you to escape the crowds that are often found on land for a cruise around the waters of Key West.

The fun begins as soon as you’re on board with drinks including soda, bottled water, and alcoholic beverages, as well as sushi platters and other hors d’oeuvres.

While you enjoy your snacks and drinks, watch the sunset beyond the horizon and check out some of the landmarks on shore including the Key West Lighthouse and Mallory Square.

Whether you’re visiting with family or are taking a special someone out on a cruise, this option will surely be enjoyable for anyone.

 

What’s Included With This Cruise?

  • Alcoholic beverages, soda, and water
  • On-board restroom
  • Sushi platters and other various snacks
  • Pass-bys of popular landmarks

Here’s what a past guest said about this tour:

Beautiful sunset, great group of people, outstanding captain and mate!  Plenty of food and drink A must for anyone visiting Key West

Tim_H

 

 

This private 2-hour cruise gives you and your group the chance to experience part of Key West that not many others get to see.<br />

This company is rated 5 Stars on Trip Advisor with over 20 reviews!

 

Tour length- Approximately 2 hours

 

This private 2-hour cruise gives you and your group the chance to experience part of Key West that not many others get to see.

With the chance to escape from the crowds and spend time with just your friends or family as you watch the sunset over the horizon as the colors fill the expansive Florida sky.

Enjoy the provided soda and snacks or take a bit of time to cast a line and see what kind of fish you can catch.

Your captain will sail you over the waters and into a calm area, filled with lush mangroves, where you’ll have many photo opportunities.

 

What’s Included With This Cruise?

  • Private 2-hour guided sunset tour
  • Soda and bottled water
  • Snacks
  • Use of fishing gear
  • Photo opportunities in lush mangrove forests

Here’s what a past guest said about this tour:

Our private sunset tour was amazing and relaxing!  Captain Tim talked about history of the area before taking us to see mangroves.  The kids had an amazing time out in the open ocean before heading back and watching a beautiful sunset!  Highly recommend!

nellyholland  

 

 

This unique tour will be unlike anything you’ve ever done before, and will have those on shore wishing they had booked this sunset cruise in Key West!

This company is rated 5 Stars on Trip Advisor with over 40 reviews!

 

Tour length- Approximately 2 Hours

 

This unique tour will be unlike anything you’ve ever done before, and will have those on shore wishing they had booked this sunset cruise in Key West!

Hop aboard this famous pirate-ship-like sailboat that has become one of the most photographed ships in the Key West area.

The boat has been nicknamed ‘Red Sails in the Sunset,’ and guests may even have the opportunity to help shoot the cannons on board or raise the sails.

You’ll sail around the ocean, looking in on some of the most popular landmarks on shore, including the historic seaport, Mallory Square, and Zachary Taylor State Park.

You’ll also be provided with some snacks to munch on as you cruise, as well as bottled water. 

 

What’s Included With This Cruise?

  • Sunset sail on a pirate-ship-like boat
  • Snacks
  • Bottled water, cups, and ice
  • A unique experience

Here’s what a past guest said about this tour:

We had the best time in our sunset cruise!  The boat was amazing and the staff was so friendly!!!  I wish we could go again!!

Karmella_F

 

 

 

If you’re looking for a great way to spend some time with your family or significant other when on a vacation to Florida, this private sunset boat tour will be perfect for you.

This tour is rated 5 Stars!

 

Tour length- Approximately 2 Hours

 

If you’re looking for a great way to spend some time with your family or significant other when on a vacation to Florida, this private sunset boat tour will be perfect for you.

This personalized experience gives you the opportunity to enjoy watching the sunset on the ocean without the crowds you’ll find on the shore.

Your captain will bring you on a tour of the Key West Harbor and Sunset Key while they teach you about the history of the area.

Because it’s a private cruise, you’ll have the opportunity to see the best views of the shore and a beautiful sunset, which Key West is well known for.

 

What’s Included With This Cruise?

  • Water and ice
  • Sunscreen
  • Private, personalized sunset cruise
  • Information about the area from your guide

Here is what a past guest said about this tour:

Captain Rick very friendly Super clean boat My wife and I enjoyed every minutes of the cruise Provide well explained description of surroundings Highly recommended

Jacques_P

 

 

Enjoy this 2-hour cruise on a luxury catamaran as you glide over the clear, emerald waters of the Gulf of Mexico

This tour is rated 4.5 Stars with over 420 reviews! 

 

Tour length- Approximately 1 Hour and 30 Minutes

 

Enjoy this 2-hour cruise on a luxury catamaran as you glide over the clear, emerald waters of the Gulf of Mexico.

As you sail around the ocean, grab yourself a glass of complimentary champagne, beer, or a cocktail from the cash bar that’s available on board.

The knowledgeable captain will give you some local guidance on where the best places to watch the sunset are and take you away from where the crowds gather.

Although there will be many other groups on the cruise, there will be plenty of room to wander around and enjoy yourself.

 

What’s Included With This Cruise?

  • 2-hour sunset cruise on a large catamaran
  • Variety of wines, champagne, sangria, and beers
  • Soda and water
  • Cash bar with cocktails available
  • Knowledgable captain leading you to the best views

Here’s what a past guest said about this tour:

Very nice crew. Everything was very nice.  A must see while your at Key West.  The champagne was good.  Also had Landshark and Shock Top on tap.  Thanks to all!!

Alethia_C

 

 

Photo Credit- Floridays/Fish Monster

Hop aboard this beautiful sailboat and sail along the coast to experience a spectacular Key West sunset, on this award-winning cruise.

This tour is rated 5 Stars with over 420 reviews! 

 

Tour length- Approximately 1 Hour and 30 Minutes

 

Hop aboard this beautiful sailboat and sail along the coast to experience a spectacular Key West sunset, on this award-winning cruise.

You’ll have the opportunity to watch the Mallory Square Sunset Celebration from the water, without having to deal with the crowds.

Enjoy a few drinks, including soft drinks, water, or alcoholic beverages as the crew brings you to some of the best places in the area to view the sunset.

You’ll get to experience one of the best sunset sail experiences in Key West with great vantage points and plenty of room for all aboard.

 

What’s Included With This Cruise?

  • Alcoholic beverages
  • Soda and bottled water
  • Tour passing by famous landmarks
  • Uncrowded tour with attentive crew members

Here’s what a past guest had to say about this tour:

This was a beautiful sunset tour!  The staff was very attentive, she made sure to refill our drinks the entire time.  The weather was amazing.  And the scenery / views were gorgeous.  Was a relaxing ride.  Prefer a sail boat over the catamaran, because it doesn’t have the fumes and the loud noise from the motor.  Loved the vibes !

 

 

 

This boat will surely give you a unique experience, as you’ll get to set sail on a replica of the 1851 Schooner America.

This tour is rated 5 Stars with over 365 reviews! 

 

Tour length- Approximately 2 Hours

 

This boat will surely give you a unique experience, as you’ll get to set sail on a replica of the 1851 Schooner America.

Sit back in the comfortable seating and view some of the city’s top sights including the Sand Key Lighthouse, Mallory Square, and more, from the water.

Grab some of the complimentary drinks including beer and wine, while you cruise along the turquoise waters of this unique Key West sightseeing trip.

Watch for wildlife in their natural habitat or coral reefs as you watch the sun set beyond the horizon.

Whether it’s for a special occasion or just for fun, this cruise along the Atlantic Ocean will be an amazing experience.

 

What’s Included With This Cruise?

  • Alcoholic beverages including beer, wine, and champagne
  • Non-alcoholic drinks
  • Complimentary hors d’oeuvres
  • Cruise on a replica of the historic Schooner America

Here’s what a past guest had to say about this tour:

We’ve been coming to Key West for 35+ years.  We’ve sailed on many sunset cruises.  The Schooner is by far the best.  The crew is fantastic, very attentive and enjoyable experience.  A must do when you’re in Key West!

Richard_L

 

 

 

Different from all of the other sunset cruises in Key West on this list, this kayaking tour will provide you with a whole new experience.

This tour is rated 5 Stars! 

 

Tour length- Approximately 2 Hours

 

Different from all of the other sunset cruises in Key West on this list, this kayaking tour will provide you with a whole new experience.

Whether you’re brand new to kayaking or have done it your whole life, this guided tour will be perfect for you.

Hop aboard the provided kayaks and leisurely ride off into the ocean and watch the sun go down.

Since this is a private tour, you’ll have personalized attention from your guide, who will help you capture some great photos to remember this experience.

 

What’s Included With This Cruise?

  • Bottled water
  • Kayak equipment including life jackets and paddles
  • Private tour with an attentive guide
  • Personalized experience with just your group

Here’s what a past guest had to say about this tour:

The sunset was amazing, and sitting in a kayak surrounding by nature beats standing in a crowd to watch it any day!

Sherri_I

 

 

 

Key West is the perfect place for tours including sunset cruises

What Should I Wear On A Sunset Cruise?

Typically, there isn’t a specific dress code for a sunset cruise, but you can always call the specific tour company to be sure.

If there is no dress code, you could dress up, or you could go with something as simple as what you wear on a daily basis.

It’s also recommended to bring a light sweatshirt in case it gets cold after the sun goes down, as well as sunscreen for when the sun is still up.

What Should I Bring On A Key West Sunset Tour?

All of the tours on this list will provide almost everything you need, but there are a few additional things to pack.

But avoid overpacking, as this might negatively impact your experience as you won’t be able to see through the kayak as well!

As mentioned, always remember your sunscreen to help protect your skin from the hot Florida sun.

On top of the sunscreen, you’ll also want sunglasses and a sun hat to keep the sun out of your face.  Lastly, bring a water bottle to keep yourself hydrated throughout the tour.

Here are more essentials for your trip!

 

Never hit the water without your sunscreen.  You’ll want at least SPF 30 to protect from the Florida sun.

 

 

Sun Bum Sun Screen 

 

 

If you’re planning a boat cruise, quick drying beach towels are an essential item to pack.  Unlike regular towels, quick drying beach towels are made from materials that dry quickly, meaning you won’t have to worry about them getting wet and heavy as the day goes on.

 Quick Drying Beach Towel

 

 

Bring back memories from your underwater adventure with this waterproof camera!

Waterproof Camera

Keep your phone dry and take beautiful pictures under water with a waterproof phone case. 

Waterproof Phone Case 

Final Thoughts: Key West Sunset Cruises

While there are many places on land to watch the sun go down, one of the best ways it to get out on the water.

This gives you an opportunity to sit back and relax as you watch the colors fill the sky without crowds.

All of these Key West sunset cruises are the perfect way to end the day during a Florida vacation.

Travel Resources

 

Book Your Next Trip!  For Accommodations and short-term rentals, I recommend Booking.com as they are the best in the business when it comes to rates and places to stay.

To Book Activities- For activities, I suggest booking with Viator, they have thousands of 5-star activities to choose from!

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