Beyond Old Town: Dining on Private Sunset Key, Stock Island & Deep-Sea Fishing

Once you have explored the streets of Old Town, three easy excursions take you across the harbour channel or one bridge east to experience private island dining, working shrimp-boat marinas and world-celebrated sportfishing.

1. How Non-Guests Can Visit Private Sunset Key (Book a Table at Latitudes)

Looking 500 metres west across the main ship channel from Mallory Square, you see a palm-fringed 27-acre island of pastel beachfront cottages with zero cars: Sunset Key. Because the island is private, you can only board the ferry with a confirmed breakfast, lunch or sunset dinner reservation at its beachfront restaurant, Latitudes.

• The Complimentary 7-Minute Ferry: book a table at Latitudes (if sunset dinner is booked two months ahead, breakfast or lunch is much easier to reserve and just as scenic). Check in 20 minutes early at the Opal Key Resort Marina (245 Front Street, next to Mallory Square) and ride the complimentary 7-minute launch across the harbour to dine at outdoor tables on the sand under coconut palms.

2. Exploring Stock Island (Mile Marker 5, Working Marinas & Tiki Docks)

Cross the Cow Key Channel Bridge onto neighbouring Stock Island, the working maritime heart of the Lower Keys, where commercial Key West Pink Shrimp trawlers and lobster boats unload their catch alongside marina hotels like The Perry Hotel & Marina:

• The Hogfish Bar & Grill (6810 Front Street, Safe Harbor): an open-air, thatch-roofed locals' tiki dock tucked behind boatyards. Order the signature Killer Hogfish Sandwich, made with fresh-speared local white hogfish fried golden and topped with Swiss cheese, mushrooms and onions on Cuban bread.
• Key West Tropical Forest & Botanical Garden (5210 College Road): walk shaded boardwalks through the only frost-free natural hardwood hammock forest in the continental US.

3. World-Record Sportfishing (The Flats vs Deep-Sea Gulf Stream)

With more IGFA saltwater world records than any destination on Earth, book a half-day charter either sight-casting on the shallow turquoise Flats (for tarpon, bonefish and permit) or trolling offshore in the Gulf Stream for mahi-mahi, sailfish, tuna and yellowtail snapper, which Key West seafood restaurants will cook for your dinner via 'Hook & Cook'.