The Beach: Pack up your Lilly Coastal Tote and spend a day snorkeling and sunning on the beach. Visit The Dry Tortugas or rent a bike and ride to Fort Zachary State Park.
Tour Hemingway House: Visit author Ernest Hemingway’s noteworthy house across from the Key West lighthouse. Be on the lookout for the six or seven-toed cats …
Lazy Dog Paddleboard Yoga: Too many mojitos at Louie’s last night? Partake in the ultimate balancing act while getting a fun workout in.
El Meson de Pepe: Enjoy salsa dancing and a mojito (or three…the limes are fresh) as the sun sets at our favorite Cuban restaurant.
Mallory Square: “See you at sunset!” This phrase is embedded into the spirit of Key West. Dine and drink with friends as the sun dips below the horizon. Make sure to try key lime pie on a stick before calling it a night.
Key West Handprint Fabrics: Key West holds a special place in our heritage. Here you can drive by the site where Lilly’s fabrics were originally produced.
Buy Me Lilly: Lilly Pulitzer Key West is on the corner of Front and Simonton. Lilly Fact: It’s currently our oldest store.
Blue Heaven: Our favorite days start off with brunch! We swear they have the best eggs benedict on the island. The chickens and cats roaming the property are almost as famous as the food.
5 Brothers: Not up to start the day with a full brunch? Stop by Key West locals’ fave coffee shop for a café con leche.
Paseo: A true local secret with unreal sandwiches. The hidden gem on Grinnell and Eaton is a must-visit with authentic, delicious Caribbean food.
Louie’s After Deck Bar: View the sunset from a different side of the island with a cocktail in hand. Did we mention the mojitos are to. die. for.
The Porch: The happiest of happy hours! Sit outside – on the porch (shocker) and enjoy their amazing wine/beer selection. It’s off the beaten path but well worth the journey.
Latitudes: Private island dining- yes, please! Located on Sunset Key, the ambience and sunset view makes for the perfect getaway. Make your reservation through the Westin Hotel and then take the complimentary ten minute ferry ride over to Sunset Key. Make sure to pack your Bryn Cardigan for the breezy boat ride back.
Square Grouper: An unforgettable fresh local seafood spot that’s ocean side on Cudjoe Key but well worth the drive. Be prepared to wait unless you arrive early though as it gets packed with locals. Again, trust us… it’s worth it.
Nine One Five: Our go-to spot after hours. Located in a historic wooden house…enjoy the atmosphere and people watching of Duval Street while sipping glass after glass of champagne on the patio of this iconic bar. We recommend ALL of the appetizers as well.
Casa Marina Waldorf Astoria: Nestled in its own corner of the island, the legendary resort is where old Key West ambience meets contemporary luxury. Relax by one of two oceanfront pools or bask in the Caribbean sunshine on the largest private beach on the island.
Island City House Hotel: A romantic hotel with LUSH gardens. Insider Tip: Room 24 has the best balcony.
Ocean Key Resort and Spa: A lively but laid-back Key West destination, the resort is nestled between Key West Harbor and Mallory Square where historic Duval Street begins the old town experience. Relax on the resort’s Sunset Pier and watch the sun sink into the Gulf of Mexico with a tropical drink in hand.
Key West knows how to throw a party! Pack your suitcase with our Resort Collection full of tropical prints with hidden flamingos, giant hibiscus and sun soaked bougainvillea. You’ll be set to explore the island in our Callahan Shorts, Resort Top Collection and McKim Sandals in every color and print!