Key West Luxury Travel Guide
Key West was one of the destinations we talked about visiting when we were dating. We wanted to visit the southernmost point of the continental United States and Cuba, too. Did you know it’s only 93 miles to Havana from Key West? Since our dating days, I’ve become dear friends with someone who lives in Key West, which made our visit even more special. As a result of the US’s cruel oil embargo and other sanctions against Cuba, it wouldn’t have been wise to visit this time. Still, we hope for a kinder, more peaceful future and look forward to visiting our southern neighbors someday. Despite having to cut our journey short, I hope this Key West Luxury Travel Guide helps you plan a wonderful visit to this gorgeous, welcoming part of the tropical world.
How to Reach Key West
We drove from Palm Beach to Miami, then through the Florida Keys, ending in Key West. It was one of the best road trips we’ve ever done! I can’t recommend driving enough. Of course, flying is another direct, simple method if you’re visiting from afar. Unfortunately, there aren’t many reliable, regular methods of public transportation. After all, it is the southernmost part of the continental US!
How to Get Around Key West
Key West is very walkable. It’s also a great place to ride bikes if you prefer to explore that way. Otherwise, driving, ride sharing, or taking the local Lower Keys Shuttle is your best bet. There’s a surprisingly great amount of free parking in the area, although electric vehicle chargers were difficult to find.
Best Time of Year to Visit Key West
Key West is beautiful all year long. It’s busiest in winter, when snowbirds (people from colder states) migrate south to escape the frigid northern weather. Thanks to its stable climate, the weather is almost always fantastic, with the occasional winter cold snap or tropical storm in summer or autumn.
Where to Stay in Key West
5-star H2O Suites was our home away from home during our time in wonderful Key West. Our premier luxury suite had its own private plunge pool, daily food and drinks, a gorgeous rooftop pool with amazing views, and a courtyard that felt like a private slice of tropical paradise.
Read the full review of H2O Suites.
Where to Eat in Key West
Café Marquesa
The eponymous hotel’s (which has two Michelin Keys) in-house restaurant, Café Marquesa, is the perfect place to dine with loved ones. I recommend the baby gem lettuce salad and Atlantic Halibut. Café Marquesa also has exquisite handcrafted drinks.
Dorada at Casa Marina
We had the most romantic sunset dinner on the beach at Dorada. The food was incredible, the live music was perfectly balanced, and the views were unmatched. If you visit Key West, don’t skip Dorada!
Flaming Buoy
We dined here with friends after our ghost tour went two hours over the allotted time, haha. I didn’t take any photos because it was so late and we were all exhausted, but their curry was the best I’ve ever had, and my regular readers know I love a good curry! Ps. The owners are the nicest guys ever!
Little Pearl
This fabulous spot is perfect for a romantic night out, a girls’ get-together, or just because. I recommend the Chef’s Tasting Menu! They won’t lead you astray.
Lolita’s
One of my favorite meals in Key West, Lolita’s is right on the water, has excellent drinks, and some of the freshest fish I’ve ever had. It’s all about balance, right? I recommend the Pink Dragon Lemonade, Prickly Pear Mojito, and Strawberry Cactus Cooler (all of which can be made zero-proof, which is what we did). I had their Chiptole Salmon Salad, and Robin had their fish tacos, as did our friends!
Louie’s Backyard
Located on the water, Louie’s Backyard was our first lunch in Key West, and it set the bar HIGH. Everything was delicious. The waves in the background were lovely and reminded me of being home in Petoskey. I loved their Grilled Salmon Salade Niçoise!
Moondog Café
Moondog Café is the BEST place in Key West to go if you have a gluten allergy or Celiac Disease like me! Everything can be made GF. Plus, they have a massive case of grab-and-go baked goods, nearly all of which are GF. Did I mention everything we had was so delicious that we went back three separate times? I miss Moondog Café already!
I recommend their GF tropical pineapple cake, matcha latté, and seafood omelette.
The Roost
We had drinks here with friends who introduced us to a bunch of their local friends. As you can imagine, we had a wonderful time. The drinks were great, too, and they can make just about anything you can think of. They also make excellent zero-proof mocktails, too!
Tavern ‘n Town
If a restaurant offers grilled tilefish, I’m there. Tavern’ n Town had some of the best tilefish I’ve ever had, and they were very careful with my gluten allergy. I always appreciate people who are kind about that, because it’s not like I have a choice. The vibes, the atmosphere, and their carefully curated menu were all outstanding.
What to Do In & Around Key West
Attend a Festival
There’s always something to do in Key West! We were there during their Art Festival and the Florida Keys Seafood Festival, both of which had plenty of live music, awesome artisans, and delicious seafood.
Beach Day
Part of Key West’s charm is its gorgeous white sand beaches. Smather’s Beach, Fort Zachary Taylor State Park, and Clarence S. Higgs Memorial Beach were our favorites. If you have a four-legged friend of the canine variety, bring them to Dog Beach, right next door to the restaurant Louie’s Backyard. It’s Key West’s only dog-friendly beach!
Explore Fort West Martello & Key West’s Garden Club
Located inside a historic Civil War fort, Key West’s Garden Club nurtures this tropical paradise, located right on the water. See massive birds of paradise, an enormous orchid collection, and bountiful botanicals, many of which are native to Southern Florida. Admission is free!
Get Spooked on a Ghost Tour
We were invited on a ghost tour with US Ghost Adventures, and because we are interested in history, we decided to try it. What was supposed to be an hour tour ended up being nearly three, so if you’re in a hurry, be sure to let your guides know. Otherwise, it was a fun and spooky way to learn about Key West’s wild local history.
Above: Curry Mansion Inn*, the meeting spot for ghost tours
(*Supposedly haunted!)
Go Shopping
Key West had more unique, small businesses than most US cities we’ve visited. Check out Key West Pottery, Island Contemporary by painter & artist Kaitlin Spain, and Besamé Mucho, Key West’s most charming boutique. Don’t forget to bring an extra suitcase (or three!)
Above: Island Contemporary
Above: Key West Pottery
Above: Besamé Mucho
Hemingway’s House
I don’t like Ernest Hemingway. He cheated on every woman he was ever with, including all four of his wives. He neglected his son, swindled friends and acquaintances alike, and enjoyed hunting large game for sport in Africa (his first visit resulted in 103 large game murdered by him alone), further evidence of his unabashed cruelty. He was also a notoriously violent drunk. But history loves to celebrate mediocre white men, so I can’t mention Key West without mentioning his beautiful house, which is arguably one of the area’s most popular attractions.
Redeemably, Hemingway House is famously the home of a colony of around 60 polydactyl cats, which is to say they have six toes! If you love cats, stop in, because the ticket price helps care for them. They’re so cute!
Key West Museum of Art & History
Explore the history of art and culture in Key West inside this iconic, red museum in Mallory Square.
Learn About Local Flora at Key West Tropical Forest & Botanical Garden
I love learning about new plants when I travel. For my fellow botany & horticulture fans, this is a great spot to slow down and learn about the region’s rich, tropical plant heritage. The specimens growing here are gorgeous.
Rooster Spotting
Key West is home to hundreds of wild roosters. Without natural predators, their populations have exploded. You’ll see them wandering outdoor patios, into open-air shops, and even crossing the streets!
Southermost Buoy
Visit the southernmost point in the continental US and take a photo with the Southernmost Buoy. You can’t say you visited Key West without getting a photo here. Lines are much shorter earlier in the day and just after sunset, though the lighting is still great.
Sunset Sail
Charter a sunset sail and sip around Key West while enjoying the magnificent colors of the tropical waters around the island.
Stroll Truman Annex
One of Key West’s most pleasant neighborhoods, Truman Annex was formerly the winter home of President Truman. Visitors can enjoy a museum and a tour of the grounds inside.
Visit Dry Tortugas National Park
Charter a sailboat or take a seaplane to Dry Tortugas, one of the United States’ most remote national parks. Plan a full day for this, and book at least three months in advance, if not sooner. Charters sell out very quickly, as do seaplanes.
Visit The Key West Butterfly and Nature Conservatory
Walk amongst hundreds of free-flying butterflies amidst exotic plants and birds in this spectacular conservation zone, unlike anywhere else in Florida. It’s truly magical!
Visit Mile Marker 0
Self-explanatory! It’s the end of the road– literally!
Safety
The only real dangers in Key West are having too much fun, getting a sunburn, and maybe encountering something unfriendly in the water (unlikely). Keep an eye on your belongings, as with anywhere, lock your hotel room doors, and stay in the well-lit parts of town at night. Key West is very safe; You’re going to have an amazing time!
Special thanks to our incredible friends Emmy & Ian for showing us around. Lifelong Key West residents, they were the best tour guides we could’ve asked for!
Explore my adventures in the Florida Keys, Florida, and the United States.
