Best Sunset Sail in Key West

The Key West sunset is world famous, well at least I think it is.  The sunset celebrations are what first attracted me to visit Key West.  Any place that celebrates sunset, every night, sounds like my kind of place.  Imagine, spending all day in Paradise, and then, drink in hand, you head out to celebrate the end of an amazing day and the start to a fabulous evening.  Yep, my kind of town.  And, I think it’s safe to say it’s your kind of town as well.  Want to see a Key West sunset from a new perspective?  Then you have to check out a Key West sunset sail… but, which one is the best sunset sail?  

Yeah, I know, I hear it a lot when I talk to visitors, you mean I have options??  Yep, many.  But, let’s break them down into easy bite size pieces.  First, what kind of boat do you want to go out on and then what kind of experience?

There are sailboats, catamarans, floating tiki bars among some other choices.  Then, do you want a private charter or part of a group?  Party atmosphere or more laid back.  See… simply choices right?  Nope, I didn’t think so either.

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My first experience on the waters around Key West was aboard Danger Charters.  We did the Wind and Wine sunset sail, and let me say, it set the standard for all others going forward.  Not sure if was due to the fact it was the first one or that it was just an amazing time.  Almost all of the sunset sails in Key West are about 2 hours in length.  Just enough time to board the vessel, head out on the water, see the sunset and then head back to the dock.  On the Wind and Wine excursion, you will be aboard one of their 65 foot schooners.  You will enjoy tasting up to 8 different types of wine and 5 different beers.  They serve light appetizers as well.  So, if you are hungry, don’t think of this as dinner.  These will be your appetizer and should tide you over until your dinner.

They do a great job to make sure each person on board feels like they are part of the group.  The crew is attentive and answered all of my questions about what we were seeing.  Because it is a larger boat, you can feel a bit overwhelmed and kinda stuck in your seat.  There isn’t a lot of room to walk around and get a different perspective.  But, the crew does make sure the boat is turned so each side gets a good view of the sunset.  This is more of an intimate sailing as they limit the number of passengers.  

sunset sail key west

Another option is the America 2.0.  She offers a premium sailing experience.  This is a 105 foot sailboat modeled after the Schooner America which was the winner of the first “America’s Cup” in 1851.  The 2.0 reflects her eco-friendly nature.  She doesn’t have a diesel engine, rather a large battery bank.  What does this mean to me?  She a beautiful boat and she simply glides on the water.  We went out on a sail, the wind was blowing.  I started to freak a bit but was assured by Kevin, that it would be a great adventure.  Side note, I get seasick easily, so I was pretty concerned that I would not enjoy the sailing.  But, to my surprise, it was one of the smoothest sails I have ever been on.  So, don’t be fearful to go out in a bit of wind aboard the America 2.0.  Downside?  She’s only in town during the winter months.  Come Spring, she heads north to New York.  So, plan accordingly.  Like Danger, they serve beer, wine, and light appetizers.   There is usually a larger on this sailing.

sunset sail key west

One of my biggest surprises was sailing the Floridays.  This is a 54 foot sailing yacht that limits passengers and lets you enjoy the sunset while avoiding the crowds.  Not being a sailor, and not sure what the technical term is, but there is a low center section, unlike Danger and the America 2.0.  So, no matter what side of the boat you are on, you can very easily see the sunset while still sitting.  Due to the smaller size of the crowd, I find it much easier to move around.  Each time I have been out with the Floridays it has been exceptional.  They serve beer, wine, champagne, and margaritas, soda, water, but no appetizers. 

Sunset Dinner Cruise

Want to have live music, dinner, and drinks?  Then choose this sunset dinner cruise.  This sunset sail is aboard a 65 foot Gold Coast Yacht and offers an air conditioned main cabin.  Enjoy the sunset and water views from the upper deck which enjoying the music from the live band.

Sunset Water Sports

Party Boat Options

I get it, while in Key West, you want to continue the party out on the water.  If that is what you are looking for, then you really need to check out these options.  First, Fury offers either the Commotion on the Ocean or a seasonally offered Champagne Sunset Cruise.  Commotion on the Ocean is aboard a 65 foot catamaran with a live band.  They offer beer, wine, margaritas, hot and cold appetizers, which are all ok.  Honestly, the appetizers are really nothing to write home about, but if you haven’t had dinner, or need something to tide you over, they will work.  What I liked about this option, is the ability to walk around and explore the different views from the boat.  

The Champagne Sunset Cruise is offered seasonally and aboard a 45 foot catamaran.  No appetizers served, but this cruise offers a smaller group and tranquil setting to enjoy the waters around Key West and the sunset.

things to do in key west

Second, check out the newest booze and party boat option in Key West, the Key West Party Boat.  If you have seen those trolleys in other cities that you peddle, this is like that, just on the water.  You and your friends, will sit around a center section and peddle the boat while on the water.  This is a BYOB boat, so, the best part?  You can bring exactly what you want to drink.  Don’t feel like peddling?  No problem, they have an engine that will let you sit back and still enjoy the ride.

Key West Party Boat

Cruisin’ Tiki

This is a really fun way to see a Key West sunset.  It’s actually a floating tiki bar.  You will sit on bar stools and a captain will power and drive the boat from behind the circular bar.  The captains on these boats have what is called a “six pack” license.  This means they are limited to only 6 passengers.  Each of the Tikis carries six plus the captain.  A great thing about these tours is they are also a BYOB tour… you can bring whatever you want to drink on the boat.  They offer a cooler to keep your drinks cold as well. My favorite part about this option?  The looks, waves, and horn toots you get while out on the water.  It’s really a lot of fun and a unique experience.

cruisin tiki key west

Private Charter

Now, I thought I had seen and done Key West until I went out with Captain Howie with Make it So Charters.  He offered a different perspective to not only Key West, but a Key West sunset.  Like the other captains in the area, the boat is limited to 6 passengers, and the captain.  For sunset, he offers two options.  The Classic trip, which is around the historic seaport and Sunset Key areas.  Or, the Sandbar Sunset.  This is by far one of the most popular options.  You head out to a sandbar where you get out of the boat and explore the area around the sandbar, and with your feet in the water and toes in the sand, you watch the sunset into the water.

With each option, Captain Howies serves you his world famous cheeseboard and a complimentary bottle of wine or champagne.  Trust me the cheeseboard with the baked brie is to die for!  I had never been out to a sandbar until I went out with Captain Howie and it is by far one of the most amazing experiences of my life.  Trust me, this one is the creme de la creme of all the options.

Of course, there are many many more options, but these are my favorites.  Each of these options offers a different perspective to the same world famous Key West sunset.  The only question, in the end, is what kind of experience do you want? Private…. Group… sailboat…live band… you get the idea.

What’s your favorite way to see a Key West sunset? 




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