Florida Keys

The All-American Road Trip

Bucket list alert! Looking for an unforgettable road trip experience?

Then plan a trip down the Overseas Highway, known as the All- American Road Trip. The most ideal situation is to start in Miami or Fort Lauderdale, rent a convertible, and then fly home from Key West.

Arrive on a late-morning flight to either Miami or Fort Lauderdale, and pick up your car rental at the airport. Put the top down, set the first destination in your nav, and hit the open road! You’ll be out of the city with the ocean in view within the hour. First up: check in to your accommodation in Key Largo. Once you’re settled, it’s time to grab some dinner at Snook’s just in time to watch the sunset. Enjoy the evening listening to live music and getting into the full island state of mind.
After a restful night’s sleep, it’s time to hit the road! We suggest heading to Mrs. Mac’s Kitchen for the best breakfast in The Keys. After breakfast, head across the island to John Pennekamp State Park. Spend a few hours kayaking, walking the nature trails, or even taking a snorkeling trip out to the reef to see Christ of the Deep or the Spiegel Grove shipwreck. After a day in and on the water, get cleaned up for a nice evening meal at Alabamas Jacks.
DAY 3 Check out of your Key Largo accommodations, it’s time for a new island! Islamorada, here we come! Also known as the “Village of Islands,” Islamorada is perhaps the quietest of the chain. If fishing is your thing, we’d recommend an all-day fishing charter; this is the sport fishing capital of the world after all! If not, then today is about slowing down and taking it all in. Check into your hotel, browse a few local shops, check out the History of Diving Museum, and then spend the afternoon at Robbie’s for a unique Keys experience.

Florida Keys sample itinerary
Check out of your Islamorada accommodations in the morning because Marathon awaits! Also known as the “Family Key,” Marathon hosts a plethora of activities. We suggest touring the Turtle Hospital first, then spending the afternoon at the Dolphin Research Center. Swim with the dolphins and learn all about their conservation efforts. You can’t go wrong choosing a restaurant for dinner, there are so many great choices!
Day five is going to slow things down in Marathon. Start the day by taking a stroll along the new-old Seven Mile Bridge, recently converted to a pedestrian path. Stop by the Pigeon Key Museum and learn all about the history of Henry Flagler and his railroad expedition in the 1800s! In the afternoon, grab a picnic lunch and head to Sombrero Beach. Finish off the day with dinner at Sunset Grille and watch the sunset over the Seven Mile Bridge.
The moment you’ve been waiting for has come! After breakfast and checking out of your Marathon accommodations, set your sights south and begin your day by driving over the Seven Mile Bridge. Turquoise waters stretch as far as the eye can see, spotted with fishing boats and sails. Make sure to wave at Fred the Tree! Next, we suggest stopping at Bahia Honda State Park in the Natural Keys to spend the afternoon basking in the sun and enjoying the best beach in the Florida Keys. Not wanting to get dressed up for dinner? Stop at Hogfish Bar & Grill for a rustic dining experience with some of the best food in The Keys.
DAY 7 – 10

Florida Keys sample itinerary
You’ve made it to the end of the road! Wake up on day seven in Key West. If time permits, we recommend a minimum of three days in Key West before flying home. Turn in your car rental, and opt for either bikes or a golf cart, the preferred ways to get about the island. Can’t miss sites include: the beach at Fort Zach, strolling down Duval, Sunset Pier, and grabbing a selfie at the Southernmost Point. Whether you choose a sunset sail, Cruisin’ Tiki Tour, night kayaking in the mangroves, or all of the above, getting out on the water is a must. You are sure to eat well, too! Visit Kaya, Blue Heaven, Hot Tin Roof and Sunset Pier. Part of the appeal of Key West is being able to come and go as you please! So many incredible experiences await.

Though you may never be able to pick a favorite Key, exploring the Florida Keys and the Overseas Highway is a must-do vacation. With so much to explore, and the ability to go at your own pace, The Keys are waiting for you!