Dream Trip: Boat From Key West to Key Largo

See America's glorious Southeast coastline the best way possible: by boat.

All year, we're collaborating with Waterway Guide Media to bring you the best segments of the 1,243-mile-long Intracoastal Waterway on a journey from Key West, Florida, to Norfolk, Virginia, at the end of the (watery) trail. This issue: a sun-drenched passage from Key West to Key Largo.

Mile 1243: Key West: Sunset Kickoff
Start the journey with a sunset at Mallory Square surrounded by the nightly pageant of tightrope-walking cats and acrobats. (Watch for the green flash.) TIE UP: Dockage rates at the Margaritaville Resort and Marina are $4 per foot.

Mile 1209: Big Pine: Dive-Bar Must
No Name Pub may look like an old wooden cottage on the outside, but venture inside and you will see that the walls and ceilings are covered with thousands of fluttering dollar bills, many with personal messages. Locals know the pizza is the best around.

Mile 1194: Boot Key: Snorkeling Adventure
Join tropical fish, stingrays, and the occasional barracuda at the magnificent coral reef adjacent to Sombrero Key Light. Grab Instagram snapshots at the natural coral limestone arch. TIE UP: Dockage rates at Faro Blanco Resort & Yacht Club on Marathon Key start at $3.50 per foot.

Mile 1160: Islamorada: Fishing Pilgrimage
Of course the Worldwide Sportsman/Bass Pro Shop sells a huge selection of fishing gear and apparel, but it's the saltwater aquarium and the full-size 1933 inspiration for Hemingway's yacht, the Pilar, that make this angler's bazaar worth a port stop.

Mile 1140: Key Largo: Paddle the Mangroves
At John Pennekamp Coral Reef State Park, you can explore 50 miles of natural mangrove trails via kayak, paddleboard, or canoe, or take a guided diving or snorkeling tour. TIE UP: If you have a shallow-draft boat, overnight at a mooring in Largo Sound, which you will share with the resident pelicans.

READY TO SET SAIL? Order guidebooks and begin planning your boating adventures at waterwayguide.com.

NO BOAT (YET)? It's easy to rent or charter any type or size with or without a captain in the Keys. Get hooked up with the right vessel from family-owned Vacation Boat Rentals or Boatsetter.

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