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The Best Florida Keys Road Trip from Key Largo to Key West

December 3, 2011

It’s not every day you can drive to an island, much less an entire chain. Grab your car, your sunglasses and a road trip buddy, and take a driving tour of the islands of the Florida Keys. Here’s the can’t-miss stops along the way.

Florida Keys Through Instagram Photos | How to Dress (or Undress) for Fantasy Fest

Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Dock
Who says you have to endure TSA lines, checked bags and bad inflight movies to experience an authentic island escape? The Florida Keys offer mainland accessibility with all of the indulgences you crave in a beach vacation – laid-back bars, fresh local seafood, and miles of sand, sea and Florida’s famous sunshine in every direction. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Snorkeling
Kick off your road trip with a stop at the John Pennekamp Coral Reef State Park in Key Largo for a guided snorkeling or diving excursion in the Florida Keys National Marine Sanctuary. Mile marker 102.5. Thinkstock
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Islamorada
For dinner, head to Lazy Days Restaurant on the oceanside of Islamorada for the day’s fresh catch and a cold draft beer. Mile marker 79.9. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Hotel
After dinner, check in at one of Islamorada’s intimate beachfront inns or guesthouses, such as the charming Pines & Palms Resort. Mile marker 80.4. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Twilight
Wherever you stay on Islamorada or throughout the Florida Keys, set the alarm a little early to catch the sunrise over the sea. Many properties offer complimentary use of kayaks for an even better view. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Tarpon
After sunrise, grab breakfast at the nearby Midway Café, then head down the Overseas Highway to Robbie’s Marina, where a few dollars buys you a bucket of baitfish and the chance to feed a school of hungry tarpon by hand. Mile marker 84.5. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Snappers
For lunch, grab a bite at the Hungry Tarpon next door, or head up the road to Snapper’s on Seaside Avenue, for the catch of the day. Mile marker 94.5. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Key Lime Pie
Wherever you dine, don’t forget the house key lime pie. Frequent visitors to the Florida Keys have their favorites, but the only sure way to find the best slice is to try them all. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Moorings
Squeeze in a little beach time on your way south through the Keys. The Moorings Village has a pristine stretch of shoreline perfect for a little sun and a photo op. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Grill
When dusk falls, head to the nearby Morada Bay Café for an elegantly laid-back dinner on the open-air patio. Mile marker 81.6. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Sunset
Thought the morning’s sunrise was spectacular? Just wait for a Florida Keys sunset. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Dolphin
On your way through Marathon, don’t miss the chance to swim and interact with dolphins at the not-for-profit Dolphin Research Center – a world-class educational and marine rehabilitation facility. Mile marker 59. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | No Name Key
In the afternoon, refuel with lunch and a cold beer at the nearby No Name Pub on Big Pine Key. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | SUP
After lunch, grab a kayak or standup paddleboard and hit the water with Big Pine Kayak Adventures on Big Pine Key. Mile marker 30. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Key Deer
While on Big Pine Key, see if you can spot a roaming Key Deer – a protected endangered species indigenous only to this area. Thinkstock
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Overseas Highway
Before evening, jump back on the Overseas Highway and head south. Next stop: Key West! Thinkstock
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Souvenir
Need some retail therapy? Don’t fight it. Souvenir junkies will find an array of roadside shops and stands to peruse all the way down to Key West. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Southernmost Point
When you make it to Key West, swing by the Southernmost Point beacon at mile marker zero for the Keys’ must-do photo op. Late afternoons and early mornings are the best times to avoid lines at this popular spot. Thinkstock
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Marquesa
Though it’s petite, Key West offers plenty of accommodations near bustling Duval Street. We love the Marquesa Hotel, an elegantly restored 1884 property just a block from Duval and only four blocks from Mallory Square. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Waterfront
Once you check in, drop your bags and head to Mallory Square at twilight. Stroll along the waterfront, browse local craft kiosks and catch a street performance, then find a seat at whichever outdoor restaurant strikes your fancy. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Waterfront
The waterfront near Mallory Square draws a crowd of sungazers at dusk. Find your spot along the seawall to spot one of Key West’s famous blazing sunsets. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Duval
The next day, buy a hop-on pass with the Old Town Trolley and spend the day exploring the sights of Key West, such as BO’s Fish Wagon, Kermit’s Key Lime Pie Shoppe, and the Key West Lighthouse. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Butterflies
Families shouldn’t miss a stop at the Key West Butterfly and Nature Conservatory, home to nearly 60 butterfly species and over 20 species of exotic birds. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Raw Bar
In the evening, head to Margaret Street and grab a table at the Half Shell Raw bar in the former shrimp-packing district of Key West. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Harbor
After dinner, stroll along the harbor toward William Street. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Charter
End the evening with a sunset sail aboard the Schooner Western Union for beautiful views of the Key West waterfront at twilight. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Sloppy Joes
Alternatively, landlubbers shouldn’t miss a night of drinking, mingling and live music at Sloppy Joe’s Bar on Duval – one of Key West’s most beloved nightlife venues. Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Hemingway
You don’t have to be a literary fan to enjoy the historic Hemingway Home and Museum – arguably one of Key West’s top attractions, particularly during the annual Hemingway Days festivities (at left: 2011 “Papa” look-alike winner, Matt Gineo). Reagan Johnson
Florida Keys Road Trip | Things to Do in the Keys | Road Trip | Aerial
Stopped at all the sites on this list? The Florida Keys still have so much to offer that you may find yourself repeating this road trip again next year. And the year after. For more on what to do in Key West, pick up a copy of The Key West Bucket List by resident David L. Sloan – then join the conversation on our Facebook page to share your picks for the very best of the Florida Keys. Thinkstock
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