Where to Stay
- Southernmost Hotel On The Beach: 1319 Duval St, Key West For a luxurious getaway located within walking distance of Key West’s coolest tourist attractions, look no further than the Southernmost! This Key West resort collection anchors the end of Duval Street, making it a great ending and beginning to the infamous strip you’ll be spending a lot of time on during your vacation. Large, well-appointed rooms, a vibrant pool and bar scene, and quiet sandy strips where you can recline and reflect all make this an ideal place to stay. Ask for a room with a private balcony when you book, and enjoy the view of the lapping waves when you wake up every morning.
- Ambrosia: 622 Fleming St Key West If you’re looking for more of a classic, quirky Florida Keys bed and breakfast situation, Ambrosia is an excellent choice. It’s just far enough away from the hustle and bustle of Duval Street, that you’ll have an idea of what it’s like to be a Key West resident tucked away in the Old Town historic district. You can get a suite, a townhouse, or a stand alone cottage. Some rooms are themed, so if you’re seeking a romantic island getaway, consider the Honeymoon Room or the Jungle Room. Rawr!
- Big Pine Key Fishing Lodge: 33000 Overseas Hwy, Big Pine Key For a more rustic and rural experience, consider staying in the mid to lower Keys. The Big Pine Key Fishing Lodge offers comfortable cabins or campgrounds for those who enjoy vacationing in a tent or with an RV. Accommodations at this family owned, family friendly site are clean, well maintained, and you can expect to interact with the island’s resident endangered species – Key Deer that are about the size of a large dog. So cute!
Where to Eat:
- Sarabeth’s Kitchen: 530 Simonton St, Key West This outpost of the celebrated New York chain is nothing like its city counterparts. Colorful and outdoorsy, the Sarabeth’s in Key West is the ideal spot for breakfast or brunch. With muffins and fresh squeezed juices to die for, you’ll want to go back for more before your vacation’s over.
- Louie’s Backyard: 700 Waddell Ave, Key West Reservations in advance are strongly recommended for what might be Key West’s most popular restaurant. Over the past 25 years, Louie’s Backyard has earned a reputation as being one of the world’s most romantic restaurants. Having dinner at sunset here, is like dining in paradise. Do yourself a favor and order the best lobster bisque you’re likely to have for a while. Savor every bite of a meal you’re not going to forget anytime soon.
- Blue Heaven: 729 Thomas St Key West Minimal parking. A location off the beaten path. A wait for as long as two hours, just for breakfast. What’s the big deal with Blue Heaven? Quite simply, there’s nowhere else like it. You’ll encounter kitty cats and chickens and dyed in the wool drunks at the bar, nursing a hangover with one of Blue Heaven’s infamous egg benedicts. Stuff yourself with a slice of their key lime pie before you go.
- El Siboney Restaurant: 900 Catherine St Key West This unassuming restaurant tucked away deep in the residential part of Key West may not look like much from the outside, but it’s earned its reputation as the best Cuban food in the island. The line will stretch around the corner for dinner, so be smart and head there for lunch. Es muy delicioso.
- Square Grouper: 22658 Overseas Hwy. Cudjoe Key There is so much amazing food to be found in Key West. In the Middle and Lower Keys, it can be harder to find a gourmet culinary experience worth writing home about, with the sole exception of Square Grouper. It’s worth leaving the choices of Key West, just to experience the inventive, amazing cuisine of this marijuana-themed, only-in-the-Keys restaurant.
Where to Drink:
- The Green Parrot: 601 Whitehead Street, Key West There are no shortage of bars in the Keys, but of all the bars in Key West, The Green Parrot is the most culturally significant. It’s divey, grimy, and not a tourist trap. Belly up to the bar and be prepared to meet some of the Conch Republic’s more quirky characters.
- Kelly’s Caribbean Bar and Grill: 301 Whitehead St, Key West The home of one of Key West’s best happy hours happens to be the birthplace of PanAm airlines. And it happens to be owned by former Top Gun leading lady, Kelly McGillis. This lovely, outdoorsy bar and restaurant is a great place for dinner, but with a great happy hour every day from 4 to 7, complete with discounted appetizers and killer wings – Kelly’s is a must-do for any happy hour aficionado.
- Southernmost Beach Café: 1405 Duval St, Key West For fabulous frozen and blended cocktails served within eyeshot of the ocean, head to Southernmost for happy hour. The vibe is fun and vibrant, the drink specials and appetizer specials are phenomenal. Get the hibachi appetizer. You won’t be disappointed.
Where to Shop:
- Naples Soap Company: 128 Duval St, Key West If you’re on the hunt for unique beauty buys in the Florida Keys, you should check out Naples Soap Company. Overflowing with fabulously scented soaps, bath bombs, body scrubs and more, you’ll find amazing gifts for others (and for yourself).
- The Green Pineapple: 1130 Duval Street, Key West This quirky boutique specializes in bric a brac, unique jewelry and accessories. While you shop you can take a break at their in-house/adjoining wine and organic chocolate bar. This is a great place to get yourself a high end souvenir, like some funky earrings or a cool purse made from recycled materials.
- Cottages: 526 Southard Street, Key West Even though it’s located mere blocks away from bustling Duval Street, this quiet, beautifully curated home store feels worlds away. You’ll find useful gadgets for your kitchen, decorative pieces for your living room, and adorable presents to take back home, all carefully chosen by the boutique home store’s world-traveling owner.
- Purely Paradise Natural Bath Products: 1108 Duval Street, Key West This newly opened bath and body care boutique is run by a local mother and daughter team. Their homemade, hand-milled soaps and body butters are decadently rich and wonderfully scented. A great place to stop by if you’ve managed to get a sunburn during your visit!
What to Do:
- Mallory Square: 400 Wall St Key West Two hours before the sun sets in Key West, everyone gathers at Mallory Square for the world’s weirdest sunset celebration. Street performers try to attract crowds and financial support by juggling, doing backflips, or having cats walk the trapeze (seriously). Come for the beautiful sunset, stay for the endlessly entertaining freak show and handmade souvenirs for sale.
- Duval Street in Key West is a mecca for the inebriated, the curious and the quirky. Bars are overflowing with revelry, restaurants are bustling with al fresco dining, and everywhere you look there are attention grabbing teeshirts with crude slogans and wacky weirdness unfolding around you as you explore this thriving thoroughfare. Embark on the Duval crawl and meet some of the island’s friendliest and most fabulous drag queens at 801 Bar at 801 Duval St. Sit and enjoy amazing people watching with delicious homemade goodness at Flamingo Crossing Ice Cream (1105 Duval St Key West). It’s a must for your visit.
- Bahia Honda State Park: MM37, Bahia Honda Key The best beach in the Keys isn’t on Key West. It’s this incredible state park in the middle Keys. The award winning beach and historic bridge has become a landmark location. White sand beaches and aquamarine water, and a lovely little café for your lunchtime needs. Bring a picnic basket, an umbrella, a blanket and lots of sunscreen and settle in for a day in paradise.
- Ernest Hemingway Home & Museum: 907 Whitehead St, Key West Ernest Hemingway’s home from 1931 to 1939 is now a popular tourist destination. Although some of the stories surrounding the house have been said to be of dubious origins, guests can see where and how Hemingway lived, and encounter one of the polydactyl cats he is said to have adored.
- Key West Butterfly & Nature Conservatory: One of the most beautiful and special memories you’ll make on your visit, will be coming to the butterfly conservatory. Open the second set of double doors to this sanctuary and you’ll find yourself transported into a lush garden that is swarming with brilliantly colored butterflies. They’re everywhere you look, so step carefully. If you’re averse to having butterflies land on you, make sure you wear a dark color. Rocking something bright here will get you mistaken for a flower by the endlessly hungry, stunningly gorgeous residents.
Contributing Editor, Patrice Grell Yursik is the creator of Afrobella.com, one of the first blogs to celebrate the beauty of natural hair and ladies of all skin tones and sizes. Affectionately called the Godmother of Brown Beauty Blogging, Patrice takes her readers inside unique beauty, fashion and cultural experiences.