Key West, Florida, makes for the perfect easy long weekend getaway, especially for those hoping to escape the coming winter somewhere equal parts tropical and low-key. While the Florida Keys are all incredibly relaxing, Key West offers up the same easy-going vacation atmosphere, but with plenty of cultural offerings and dining experiences that are truly unforgettable.
As someone who visits Key West yearly, I’ve amassed a whole slew of favorite dining destinations and tourist excursions. Read on to discover some of the best places to stay for waterfront views, the most elegant locales to enjoy local seafood and the best sightseeing options to experience the bold, colorful town just like a local.
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Where to stay
Opal Key Resort & Marina
245 Front St, Key West, FL 33040
There’s not a better location in all of Key West than this luxurious hotel right by Mallory Square and Duval Street. It’s easy to walk to any tourist destination you want (make sure to visit the adorable local aquarium) and it’s even easier to hop on one of the boats docked nearby for a sunset sail. The hotel features 178 extremely spacious guest rooms and suites, with plenty of room to spread out on vacation. The waterfront views of the sparkling marina are unbeatable, and the location will make you feel like you can experience everything Key West has to offer in one weekend.
Opal Key offers up satisfying waterfront views from the cozy balconies–there’s nothing more relaxing than topping off a day of sightseeing by getting a little extra tanning in or sipping on a cocktail from the comfortable terrace seating. Spending time at the pool surrounded by palm trees and coral umbrellas (it feels like an oasis right in the heart of Key West) is an absolute must. Guests don’t have to venture far from their lounge chairs, as there’s staff on hand to deliver everything from towels to sunscreen (and a bar and restaurant right nearby). The colorful Sunset Key Cottages are right across the water from Opal Key and are fully secluded on a private island, making for an ideal romantic getaway.
The Capitana
2401 N Roosevelt Blvd, Key West, FL 33040
The Capitana is Key West’s newest boutique hotel and it’s absolutely deserving of a long weekend stay. Make sure to book one of the villas, which are configured as luxurious, brand-new apartments perfect for a whole family (or two). The incredibly spacious accommodations include a full kitchen, a lounge-ready living room and furnished porches overlooking a canal (you might just spot a manatee) as well as a small hot tub nearby. The bedroom decor is equally elevated, with brand new tiled showers and coastal decor.
One of the standouts at the Capitana is the man-made private beach; Key West isn’t exactly known for its sugar sand beaches, but this isolated area provides the perfect place to spend the day. Guests can experience peak relaxation by renting out a cabana by the shady, mangrove beach or venturing to the lively swimming pool.
Where to dine
Nine One Five
915 Duval St #5, Key West, FL 33040
Nine One Five might be right on bustling Duval Street, but it’s far from touristy. This elegant restaurant is famous for its perfectly cooked filet (although there are plenty of vegetarian options, like the brown butter gnocchi) and ice cold specialty martinis (try the key lime pie version). Sit out front in the garden and people watch or slide up to the trendy bar to get ready for a night out.
Azur
425 Grinnell St, Key West, FL 33040
Azur is a fine dining Mediterranean-inspired destination a few blocks from Duval Street, and it’s well worth a visit for a romantic dinner. Sit outside and prepare to dine like a local while indulging in salads that are truly decadent (the goat cheese paired with rosemary-infused honey is out of this world). Share a bottle of wine from the extensive list and make sure to try the toasted truffle gnocchi.
Moondog Cafe and Bakery
823 Whitehead St, Key West, FL 33040
This hip cafe and bakery tucked away in a sweet cottage is a must-visit for lunch. Venture to the cheerful backyard outfitted with colorful decor for fresh, flavorful and vegetarian-friendly food. Start with the grilled vegetable charcuterie for a unique take on the menu item, and split a grilled pizza with your dining companion. Make sure to save room for dessert, because the cafe keeps a full case of creations they bake fresh daily, from the classic key lime pie to edible glitter eclairs. Venture just down the street after lunch to visit the Hemingway House and museum, where descendants of the famed writer’s six-toed cat Snow White roam free. And if Moondog hits the spot, grab dinner at its sister restaurant, The Cafe, which boasts a similar, vegetable-forward menu alongside fresh seafood offerings.
Blue Heaven
729 Thomas St, Key West, FL
There’s a reason this funky landmark is an all-time favorite with locals and tourists alike. The fresh seafood, served up on the cheerful back porch with live music and truly unbeatable key lime pie, makes for the ultimate vacation dining experience. This wildly popular Key West mainstay also offers plenty of vegetarian options, including the black bean soup and loaded bowl. Another major selling point is that diners can expect to see a rooster or two strolling through the backyard.
Where to play tourist
Danger Charters
255 Front St, Key West, FL 33040
Book a sunset cruise on this sailboat to guarantee a good time. It’s a major bonus if you’re staying at Opal Key Marina, as the boat docks right outside your room. Danger Charters provides everything you need for the ultimate sunset sail, including a wine tasting experience, loads of passed hors d’oeuvres (there’s no need to make a dinner reservation for the same night) and a friendly crew that will make you feel right at home on the high seas.
Guild Hall Gallery
614 Duval St, Key West, FL 33040
Key West is famous for its art scene, including plenty of galleries boasting colorful paintings to bring the vacation vibes home with visitors. Guild Hall Gallery offers the best of everything. This airy, light-filled gallery space features some of the most famous local artists, and you can tote home anything from tiny animal figurines to large florals perfect for your entryway. If you don’t have the patience to pop into every gallery on Duval Street (although you might want to for the air conditioning if you go during the warmer months) this standout space is the absolute best option; there’s art for everyone.
Books and Books
533 Eaton St, Key West, FL 33040
Book lovers flock to this indie bookstore, which has another location in Miami (and a previous iteration in Westhampton) not only for its perfectly curated collection, but for the chance to spot Judy Blume, who works there (she co-founded the shop) and gives recommendations. Look closely at the staff recs, because Blume writes out notes about her favorite reads (a recent one was Gabrielle Zevin’s Tomorrow and Tomorrow and Tomorrow, which Blume calls “such a treasure”). The bookstore showcases a banned books section and has plenty of signed offerings from local authors, including Blume and Meg Cabot. Grab your next beach read and start lounging.
