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Best Key West Sunset Spots in Florida (and Everything Else to do on the Islands Too!)

By June 18, 2019 June 22nd, 2019 10 Comments

Key West! It’s as far south as you can get on American mainland soil. People pilgrimage here in droves for the sunshine, party scene and laid-back vibe special to this string of islands. If you’ve done a bit of everything in Florida like me, why not give the keys a try on your next visit?

best key west sunset spot by sail boat florida

A Breakdown of a Key West Itinerary

How to Get to The Florida Keys


First of all, ‘Key West’ is just the last land mass on the string of the Florida Keys. Also, a ‘key’ is simply an island without a fresh water source. Know that if you drive to Key West, all the way to the end, it’ll add an hour or two to your journey than you think. Key West is the most southern part of the U.S.

adoronidak chairs at isla bella resort marathon key florida

There are a few airports in the Florida Keys, including on Key West. Most flights are routed through Atlanta or another Florida city if you’re coming from the east coast of the U.S. If booked in advance, flights are roughly the rate rates as any other Florida destination, including Miami and Orlando. Check airlines like Delta and JetBlue for the best rates, or search via Skyscanner to compare.

We opted to fly into Miami and drive to the Florida Keys. This is perfectly feasible and allows for multiple destinations at once. It’s also good to have a car in the keys if you wish to see a few different islands/keys. Anyways, it’s about three and a half hours from Miami to downtown Key West. If you get stuck behind a crawling RV, there’s plenty of restaurants and shops to poke around in on the way down. Going over the seven mile bridge and seeing the mangroves below is gorgeous and would be missed if you fly directly into Key West.

Best Key West Sunset Spots


Sailboat siluette at sunset in key west florida with classic harbor line

With all this said, you might wonder the ultimate question: Where can I watch the sunset in Key West? Luckily, now your Key West trip is now perfectly planned. Once you arrive, you’ll want to take all this knowledge and fun to scope out ideal Key West sunset locations every evening to really see the show.

A Key West sunset is something special. You’ll most likely experience a spectacular ball of fire floating gently toward the horizon. People swear by specific spots, whether it’s from a catamaran out on the water or a swinging pier with happy hour drinks. Here’s a few we discovered that are our favorites.

Mallory Square: For decades, this strip has been the place to enjoy sunsets in Key West. It’s not one particular spot, but stretches through various restaurants, markets and shops. This is an official/unofficial gathering and celebration that often includes street performers, music and special food to indulge as the sun goes down. It’s easy to find in downtown Key West, just follow the tunes.

Pier B: A little ways from Mallory’s chaos is this pier for something a bit quieter. You can catch the sunset in key West from either side of the pier. There’s not much here – you won’t find food or live music. But if you’ve done the party and want a tranquil finale, this is a great spot to savor.

Via charter boat or cruise: I think this was the best sunset we experienced the whole time in Key West aboard the sleek and chic tour. You get an unobstructed view from the water this way. The sailing cruise (if there’s wind) lasts about 90 minutes with a small group, and includes some passed hors d’oeuvres and beer/wine. We loved it as a group of couples, and the baby did well on his first big ship too. It’s a beautiful boat that goes up to New York City for the summer too.

Sunset Pier: Over the water at the tip of Key West is a wonderful spot for drinks and food. It’s part of the Ocean Key Resort & Spa – you might need reservations during peak season for a great spot on the pier. It’s at the end of Mallory Square and there’s tons of seats with umbrellas near the live music.

Key West Hotels on Beach


When you get to the Florida Keys in the south, you’ll realize quickly this isn’t the spot for beaches. Which is fine! The scenery is just as beautiful, and you’ll always be close to the water.

Isla Bella Resort in marathon Key Florida

One gorgeous option for Key West hotels on beach property is The Isla Bella Beach Resort. It’s brand new, opened just this month. The light and airy spaces for check-in, pool-side lounging and large rooms are upping the game when it comes to luxury Key West hotels on beach front property. Now, they had to BUILD a beach to claim this though! It’s also technically on Marathon key, about an hour from Key West. So you can spend a couple nights here on the beach before partying on Duval Street later in the trip.

As mentioned, there’s not a lot of sandy beaches in Key West (or any of the keys). But the Isla Bella has cleverly curated a small sand beach just next to their large pool. You can also enjoy lounging in sun pods or a dip in any one of the other four pools on site.

Inside suite isla Bella Resort Marathon key Florida

Isla Bella is ideal for groups, as they specialize in suites. We shared a two-bedroom suite as four adults and a baby, with a gorgeous wrap-around porch overlooking the mangroves. There are some food options on property as well, but as they were working out the kinks with a new hotel (and per a tip of  a fellow guest), we opted to eat at places nearby instead.

As for actual Key West hotels who can claim they’re on the beach? The Hyatt Residence Club is an option. They have a very small sandy beach near their pool, as does the Marriott next door. The Hyatt is made for more long-term stays, so it does not have the amenities other hotel have, but suites are spacious and equipped with full kitchens.

Hyatt Residence key west florida

Sunset Key Cottages is an upscale option, wonderful for groups who like suite. They have a beach on the other side of the key that also sports pools and dining options.

Active Things to Do in Key West


Key West is best experience on the water. While beaches aren’t sandy and accessible like other Florida destinations, there’s a thriving boat culture and a whole mess of water sports to check out. Below, Christian reviews the kayaking and jet skiing on the keys.

Kayaking Tour of the Mangroves – Key West Eco Tours

Starting off from beautiful Sombrero Beach on the Atlantic side of the keys, we put our kayaks into Sister Creek.  While the water is clear and warm – there is much to see.  As we kayaked up the creek, our guide showed us the radio towers from Radio Marti – which used to broadcast anti-communist propaganda into a Cuba!  We then turned off Sister Creek into narrow mangrove “trails” just wide enough for our kayaks to get through.  Avoiding tree limbs, we paddled through the shady mangroves, seeing heron in the trees and mullets in the water (it’s Florida, but no pun intended!).

Kayak eco tour marathon key florida

Winding our way through the trails, we would occasionally come out into lakes or ponds.  These lakes on Boot Key are generally shrinking because of the mangrove growth – although there might be some delay to this constant creeping because of Hurricane Michael in 2018.  In the clear waters of the lake, we could see Cassiopeia – a species of jellyfish that lays upside down on the bottom of the lake.  Our guide, who apparently is immune to jellyfish stings, picked one up to show us!  These little guys are upside down because they have algae in their tentacles that use the sunlight and create energy for the jellyfish!  Their mucus can sting – but it’s only a mild sting.

As we followed a last trail back out to Sister Creek, we came out of the peace and shade of the mangroves.  The tide was coming in, making our paddle back to Sombrero Beach a bit of a workout. However, it gave us a chance to make a breeze and watch the Pelicans fishing.  It was an incredible couple of hours with Key West Eco Tours.

Jet Ski Tour of Key West

Barefoot Billy’s Watersports operates out of The Reach – a Waldorf Astoria resort on the Atlantic side of Key West.  Calling ahead, I booked a 10AM tour – trying to hide from the mid-day sun as much as possible.  Upon reaching the kiosk, I was given a PFD (life jacket) and was shown a screen to watch a mandatory safety video.  This certainly had me feeling a little uneasy!

However, our guide, Charlie, was awesome.  Instructions and video complete, we waded out through the seaweed (it’s only there temporarily!) to get onto our machines.  Most of the wave runners they operate are made for two people – so there is plenty of power to go around.  Our route would be a complete circumnavigation of Key West – heading west past the southern most point in the US.

I was nervous at first, but our group of seven skis headed out in a line – and I was trying to keep up!  Opening up the throttle, you can really feel the breeze and water beneath you.  It was a little rough further out, but I never felt unsafe.  We stopped at various locations – such as Mallory Square and Sunset Key for Charlie to give us the run down of the significance of each place.  Turns out, just after the glitz and glamour of Sunset Key – there’s Wisteria Key – an island famous for people being naked and having a few too many cocktails!

Once we got well on to the shallow gulf side of Key West – our guide stopped for 20 minutes to let us really push the boats to their limits.  This side of the island had smooth water, and because of it’s shallowness, there weren’t any boats for us to run into.  I was able to push the jet ski above 45 miles per hour!

We then headed further around the island – to Boca Chica Key.  This little key had submarine berths carved out of the rock beneath it.  The US navy used these back in the 1960’s when they thought about expanding their air station.

From there, we headed through the narrow Boca Chica Channel and stopped off Boca Chica beach for a brief swim in the warm shallows.  We had to keep tabs on the boats as they slowly drifted inland towards the beach!

Afterwards, we put full throttle on and headed back to the resort.  All in all, the tour lasted about 90 minutes once we got on the jet skis and it was awesome experience.

Don’t forget to fully embrace the feel of this beautiful place by sporting your Florida attire! My husband looked trendy and fun in his Baja Llama shirt, which is an awesome brand that donate proceeds to help projects like ocean plastic clean-up. It worked great for the jet ski to avoid burns and lounging for happy hour too.

Baja LLama blue and flower shirt in Marathon Key Florida

Laid-Back Things to Do in Key West


Action adventure is a thrill, but let’s slow things down a bit. The Florida Keys have wonderful attractions, many steeped in rich history or celebrate local natural wonders. Most listed below are almost within walking distance, but you could easily do it all in a day or two.

Classic Harbor Line

I mentioned this above for Key West sunsets, but this was an easy breezy activity anyone would love to try in Key West. The staff are wonderful and buying tickets/boarding is super simple too. Jet skis and kayaking are more active, but you can let other sails this time and simply enjoy the gentle ride.

Go to Hemingway’s Old Homestead

bathroom with cat hmeingway house key west florida

So you should be mildly interested in Hemingway – or dig cats – to make an afternoon there special. Famed author Hemingway, who wrote titles like The Sun Also Sets, took residence in Key West for several years. He bunked up with one of his four wives; I’m not sure which one! But the passionate tour guides will certainly regale you with stories of his colorful personal life while touring the home. You can take home special copies of his books sporting stickers commemorating your visit. We bought our copy of Hemingway’s Havana by Robert Wheeler to feel inspired – and hope that will be our next destination to visit!

Hemingway's havana by Robert wheeler at Hemingway House Key West FloridaVisit the Southernmost Tip

There’s a big old buoy at the end of Key West marking the southernmost tip of the continental US. It’s also the lowest land, at 18 feet above sea level. On most days you’ll have to queue up to snap a photo with the landmark, but you can probably sneak one on its own in between smiling tourists posing.

striped southernmost point buoy in key west florida

See Butterflies and Flamingos

My mother actually said this was a highlight of her trip last year, so we popped in after seeing the southernmost buoy landmark nearby. It’s a beautiful greenhouse full of gorgeous, exotic butterflies you can walk around and observe. The big finale is a pair of mating flamingos that live in the center of the sanctuary, so close to us you could almost pet them. The baby gleefully squealed through the greenhouse and we adults had a blast too.

Flamingo at bufferfly conservatory key west florida

Where to Eat in Key West (Best Restaurants)


Time to eat! I hope you like seafood, because the catch of the day is often the best thing on the menu in Key West restaurants. However, other meat eaters can rejoice too, as there’s strong BBQ and Cuban cuisine influences too running through the place.

Pepe's Cafe front door key west FloridaPepe’s Café

The easiest spot for a quite meal on a Sunday. There’s no frills and it almost feels like an old fisherman’s cabin. But the food at Pepe’s Cafe is exceptional, homemade and hearty for our group. We tried their pan-fried grouper, ribs and chicken, everything was great. We might have even had out BEST slice of key lime pie there, which is saying a lot! There’s no pretty presentation but the taste makes up for it.

Banana Café

Banana Cafe shrimp salad key west florida

We stumbled in here unexpectedly after the Hemingway House and were wonderfully satisfied. There’s a large menu of fresh salads, entrees and local specialties with a French flair. Definitely don’t miss the key lime crepe to finish. You can sit al fresco at Banana Cafe or get cosy by the bar upstairs.

Blue Heaven

Another famous Hemingway haunt, complete with resident roosters, as goes the legends. The vibe was the draw to Blue Heaven, with a nice live band and most seating outside under strung fairy lights. Honestly, my fish was nothing to really write home about, but we had an amazing server and great cocktails, so it was worth the experience.

Juan Loves Lucy

Juna Loves Lucy in Key west Florida

Yelp says this place is closed! I have no idea why, because we were there a few weeks ago for some of the best Cuban food and cocktails around. It’s hidden around a corner away from the main bustle of Duval Street. They only have a handful of seats and a tiny bar. But, order a round of mojitos with some empanadas, plaintains, arepas and tacos. Alright so the menu items are a little hodge-podge when it comes to ‘Cuban’, but you can always order the Cuban sandwich too.

I hope this leaves you prepared for seeing the best sunsets in Key West, where to stay and what to do in this gorgeous destination. If you need any personal recommendations, get in touch anytime!

two women on a couch on uval street key west florida

Are you big on Florida for vacations? What’s your favorite place in Florida to visit?

sailboat with sunset orange reflection and text saysing Best Key West Sunset Spots

Eileen Cotter Wright

Author Eileen Cotter Wright

Eileen Cotter is a freelance travel journalist and owner of Pure Wander. She's our resident expat extraordinaire and falls down a lot in yoga class. Follow her on Twitter @Crooked_Flight

More posts by Eileen Cotter Wright

Join the discussion 10 Comments

  • I am a big fan of driving to the Keys instead of flying directly in. It’s great to have the car and I still think you can save money routing through Miami or Lauderdale. It seems like you had a lot of fun in Key West. We (actually more me than Jenn) love the jet ski tour from Barefoot Billy’s. I also loved the Hemingway House too.

  • Beautiful pictures! I love Key West. My cousin and uncle live there and any time they invite me down, I jump at the chance. I love the Hemingway House and Blue Heaven. I’d never heard of Juan Loves Lucy, but would love to check that out. I hope they’re still open!
    I’m glad you mentioned the lack of beaches. I don’t think many people know that Key West is usually not a beach vacation. When I’m there, I go fishing with my cousin. Then we do the Duvall Crawl. I’m always in search of good conch soup and key lime pie. 🙂

  • Andi says:

    I spent 2 weeks just a tad outside of Key West with our RV and oh man are those some beautiful sunsets, I also LOVE the color of the water there. I could definitely live there if it wasn’t for those darn hurricanes. But I do love to visit!

  • Janiel Green says:

    I haven’t been to the Florida Keys yet, but am looking into it as they say the Diving there is really quite amazing. Thanks for the tip on going to a different spot to eat other than the hotel, I have a very fickle stomach so that is super important. I had no idea that cuba was only 90miles away either….learn something new everyday.

  • I can’t believe I’ve been all over Florida and never to the Keys. I really want to go now that I’m scuba certified though and go to the national park there. Going to use these sunset spots when I go too!

  • Sarah says:

    Aww I loved reading this – it had me reminiscing on when I was in Key West a few years ago. Actually more like 5 years ago now. I did a cruise with some college friends to celebrate graduation and we had a stop in Key West. We ate on Duval street, went to the southernmost point (my friend was Cuban so this was special), and explored Hemingway House (also special as we were all English majors, lol). Since then I have really wanted to return to Key West. I go to Florida quite often to visit family but I haven’t yet made it down to Key West again – partially because it’s difficult to find an affordable accommodation that looks cute, haha. Going to check out your recommendations!

  • I just love sunsets and this article is just amazing. Very well written article thanks for sharing such information.

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