eat + drink:
- Bagatelle (Key West) – breakfast/lunch/dinner | seafood-focused American eatery set in an 1884 house with wraparound balconies; if you go for brunch, try the Banana Foster French Toast
- Blue Heaven (Key West) – breakfast/lunch/dinner | landmark for Floridian-Caribbean cuisine & key lime pie, with a funky setting
- Cuban Coffee Queen (Key West) – coffee/breakfast/lunch | counter-serve coffee stand offers traditional Cuban eats, sandwiches & smoothies to-go
- Fisherman’s Cafe (Key West) – breakfast/lunch | takeaway window with a beach-shack vibe for sandwiches with local seafood
- Florida Keys Brewing Co (Islamorada) – brewery | a small micro brewery with an artsy island vibe; brews close to 30 styles of beer annually
- Glazed Donuts (Key West) – coffee | everything here is made from scratch, and they do fritter-style and cake doughnuts, including some exotic ones with hibiscus syrup and candied bacon
- Hogfish Bar & Grill (Stock Island) – lunch/dinner | a true “locals” spot; seafood eatery known for its namesake hogfish sandwich & relaxed atmosphere
- Hungry Tarpon (Islamorada) – breakfast/lunch/dinner | seafood restaurant in with a cook-your-catch option & a bayside deck lit by tiki torches
- Kermit’s Key Lime Shoppe (Key West) – bakery | home to all things key lime
- Lola’s Bistro (Key West) – dinner | a daily changing menu offering fresh fish, shellfish, steaks, vegetables, and pastas
- Matt’s Stock Island Kitchen & Bar (Key West) – breakfast/dinner | seafood & elevated comfort cuisine like crab beignets plus cocktails & water views
- Mattheessen’s (Key West) – bakery | homemade cookies, fudge and ice cream
- Papa’s Pilar (Key West) – distillery | historic tobacco warehouse where you can learn the art of making rum, discover how rum makers craft their unique spirit and uncover untold stories of Hemingway
- Sloppy Joe’s (Key West) – bar | open since 1933, this bar offers live music & dancing plus a separate tap room for sports-watching
see + do:
- Audubon House & Tropical Gardens (Key West) – brick-pathed gardens offer a lush 1-acre view of orchids, bromeliads, and other tropical foliage, an herb garden and 1840-style nursery
- Bahia Honda State Park (Big Pine Key) – one of the southernmost state parks; visitors can relax on the beach, launch your boat from the ramp, or take a snorkeling tour out to the reef
- Bud N’ Mary’s Marina (Islamorada) – world famous fishing marina
- Conch Tour Train (Key West) – 75-minute sightseeing tour of Key West
- Dolphins Plus Bayside (Key Largo) – swim with dolphins in this natural lagoon
- Dry Tortugas National Park – comprises 7 islands, plus protected coral reefs; there are bathing beaches and dive sites including reefs, wrecks, and shallow areas perfect for children and beginners; only way to reach this amazing place is by scheduled ferry, private boat, or seaplane
- Expedition Fishing (Islamorada) – offshore fishing; based at Bud N’ Mary’s Marina
- Hemingway Home and Museum (Key West) – the residence of American writer Ernest Hemingway in the 1930s
- John Pennekamp Coral Reef State Park – park covers an enormous area of around 70 nautical square miles, comprising open water, spectacular coral reefs, on-shore mangrove forests, and tropical hammock forests; take a snorkeling/scuba tour to visit the Christ of the Deep statue
- Mallory Square (Key West) – a plaza located on the waterfront in Key West’s historic Old Town
- Robbie’s of Islamorada – marina that offers fishing cruises, kayak & boat rentals and tarpon feeding
- Southernmost Tip of Continental USA – take a photo at this marker
- Sundance Watersports (Islamorada) – located at Robbie’s; coral reef snorkeling, parasailing, SNUBA (registered trademark), and relaxing sunset cruises
shop:
- Drift Boutique (Islamorada) – a collection of environmentally conscious and handcrafted products
- Green Pineapple Boutique, Yoga, and Wellness Cafe (Key West) – shop for boho-chic clothing & accessories, plus a yoga studio & a cafe with plant-based options
- Key West Island Books – an extensive collection of local interest books
- Peppers of Key West – shop with around 1,000 different types of hot sauce arranged by pepper type, level of heat, and even sauce type—jerk, barbecue, etc.
stay:
- Casa Marina (Key West) – nestled along the southern edge of the island on more than 1,100 feet of Key West’s largest private beach
- Marlin Bay Resort & Marina (Marathon) – offers an award winning marina with access to upscale resort amenities
- Pier House Resort & Spa (Key West) – waterfront boutique resort with a private white sand beach, spa, oasis pool, and award-winning fine dining
- Playa Largo Resort & Spa (Key Largo) – situated along 14.5 acres of secluded beachfront property
- Southernmost Beach Resort (Key West) – this seaside, colonial-style hotel is a block from Duval Street’s boutiques and eateries and a 3-minute walk from the southernmost point in the continental U.S
- The Gates Hotel (Key West) – upscale hotel with a modern, minimalist style
- The Marker (Key West) – this tropical getaway is the newest, luxury hotel in Old Town in the last 20 years
- The Moorings Village (Islamorada) – home to a private, spacious beachfront resort
- The Perry Hotel & Marina (Key West) – featuring the largest deep water marina in the Florida Keys, guests have direct access to water activities, two waterfront pools, three dockside restaurants
