Updated: January 06, 2025
If you are craving a few days of island life filled with ocean views, a slower pace, scrumptious seafood and stunning sunsets, head to the Florida Keys. One of the most scenic and unusual drives in America is driving 113 miles from mainland Florida to Key West on U.S. Highway 1. Here are some tips on where to stay and what to do on a three-night road trip island hopping in the Florida Keys.
Plan to spend your first night in one of the northern keys. Key Largo is bigger and livelier than the more serene key of Islamorada. About an hour and a half from Miami International Airport, Islamorada is filled with boutique hotels and vacation rentals. Discovered by the Spanish in 1513, the name means “purple island.” With 24 miles of canals, Islamorada is known as the Sport Fishing Capitol of the World because backcountry sport fishing and saltwater fly fishing were pioneered here. The Gulf Stream is only 10 to 20 miles offshore from here.
Islamorada is made up of six islands. If you want to sound like a local, it’s pronounced “Eye-la-more-ah-dah.” When my friend Carroll and I arrived at Casa Morada in the late afternoon, the feeling of the world slowing down washed over us.
The waterfront resort is a small oasis with sixteen suites and two guesthouses. A couple of the resort cats sauntered by as we checked in. I did pet two of them but didn’t check to see if any have six toes like the Hemingway cats in Key West. We stayed in the garden jacuzzi suite with a king bedroom and day bed in a separate living room.
After watching the start of a stunning sunset from Casa Morada, we did a short walk to Lorelei Restaurant for dinner at the restaurant along the bayside. The sunset cocktail and mahi tacos made a perfect pairing as I swayed to live music and the sun slipped away on the horizon.
After a leisurely morning at Casa Morada, we hit the road southbound for the two-hour drive from Islamorada to Key West. Driving through the Keys isn’t to be rushed. Be on island time and enjoy the ride because each key is unique and worthy of stops. Keep an eye out for Key deer, listed as an endangered species in 1967, but thriving today. They can be seen throughout the Keys, but you’ll most likely spot at least one as you drive across Deer Key and on Big Pine Key where the National Key Deer Refuge is located.
Seven Mile Bridge is a great spot to stretch your legs on the drive. The Old Seven Mile Bridge was a rail-to-road conversion when the state of Florida purchased an abandoned Florida East Coast Railway right of way for $640,000 in 1936. When the bridge was completed in 1938, it gave people the ability to drive from Miami to Key West without having to take a ferry. The modern Seven Mile Bridge was completed in 1982 and is the longest bridge in Florida. Driving over the open water is beautiful but make a stop for a stroll or bike ride to savor the bridge view a little longer.
Key West is filled with a variety of accommodations from bed and breakfasts to swanky hotels. One of the swankiest is Ocean Key Resort and Spa drenched in colorful island vibe décor. The luxurious resort has the prestigious address of Zero Duval Street and has a great view of the sunset pier and the Gulf of Mexico. We checked into a two-bedroom suite and felt miles always from the intoxicating revelry of Old Town Key West. We didn’t venture too far for dinner and retreated to the waterfront dining of Hot Tin Roof. The restaurant’s ambiance was inspired by Tennessee Williams’ play Cat on a Hot Tin Roof. The cuisine is a unique blend of Florida and Caribbean flavors dubbed conch-fusion or “Floribbean.” Order a Hot Tin Tini made with chilled pineapple-infused vodka for a tropical cocktail or sip one of the Tennessee Williams-inspired craft cocktails. Start your dinner with their arugula and goat cheese salad and end it with a slice of key lime pie.
The next morning, I set out early for a walk before Key West woke up. From Ocean Key, it’s 1.2 miles to the Southernmost post buoy. It was early enough that the Key West chickens outnumbered the people on the streets in the historic Old Town. The free-roaming chickens are descendants of a jungle fowl believed to have been brought by settlers from Cuba and other Caribbean islands.
The six-toed cats living at the Hemingway House are a must-see too! When I got to the Spanish colonial home at 907 Whitehead Street that Ernest Hemingway bought in 1931 and lived in for eight years, there was a cat curled up on the pathway in the tropical garden of the front yard. It was too early for the house to be open but if you have time on a Key West trip, tour the home that was built in 1851. Look for the polydactyl cats that are descendants of Hemingway’s first cat, Snow White, given to him by a ship’s captain. Hemingway finished A Farewell to Arms, penned Death in the Afternoon and To Have and Have Not along with other works while living in Key West in the 1930s.
It’s just a few blocks from the Hemingway House to the Southernmost Point Buoy. Go early if you want the iconic landmark of the southernmost point in the continental United States without crowds. Around 7:30 a.m., it was just me and a couple of other early risers snapping quick selfies and photos. I got back just in time to join my friend Carroll for breakfast at Hot Tin Roof. Sticking with an island vibe, I went for the toasted coconut key lime breakfast bread topped with key lime curd and whipped vanilla bean mascarpone. We needed a hearty breakfast for our big adventure for the day involving a seaplane and a historic fort.
One of the most difficult national parks to visit in the United States is Dry Tortugas. The 100-square-mile park is 70 miles offshore of Key West and is made up of seven small islands surrounded by blue water, coral reefs and a vast array of marine life and birds. It is home to Fort Jefferson, one of the largest 19th century forts in America. You can only get there by boat or seaplane. We opted to take to a seaplane and booked a half-day excursion with Key West Seaplane Adventures several months before the trip.
Both the seaplanes and ferries book out weeks and even months in advance. As our pilot Kevin navigated the plane towards Dry Tortugas for our 35-minute flight, everyone had a window seat and headset listening to history and tidbits about what we were flying over. When Ponce de León discovered the islands in 1513, he named them “Las Tortugas” after the abundance of sea turtles there.
We got a birds-eye view of Key West before flying over a shallow area only three to five feet deep known as the "Flats." Flying at 500-700 feet above the water we passed Ballast Key, the coral atoll of the Marquesas Islands and an area called “Quicksands,” where we spotted a bunch of sea turtles in what Kevin called “Turtle Alley.” We also saw two shipwrecks of the World War II Destroyer Escort “Patricia” and the 70-foot work vessel “Arbutus.”
With 98% of Dry Tortugas National Park underwater, Fort Jefferson is impressive on Garden Key, the second largest island in the Dry Tortugas. Kevin did a flyby before landing on the water and taxing up to the formidable structure. On a half-day seaplane excursion, you get two and a half hours at Fort Jefferson. If you want more time, the full-day excursion gives you 6.5 hours there. If you’d rather take the ferry, the Yankee Freedom is a high-speed catamaran that leaves Key West at 8:00 a.m. for a 2.5-hour ride to Fort Jefferson (you can also book directly through AAA for the ferry!) The ferry leaves at 3:00 p.m. for the return to Key West. Built of over 16 million bricks, Fort Jefferson is the largest brick structure in the Western Hemisphere. It was built between 1846 and 1875 to protect America’s lucrative shipping channel from New Orleans where the Mississippi River flows into the Gulf of Mexico and through the Florida Straits connecting the Gulf to the Atlantic Ocean.
We decided to do a self-guided tour of the fort first then go snorkeling. We took in the view at ground level then headed to the second floor where we walked through some of the fort’s 2,000 arches and enjoyed the coolness of the shade. We took the stairs to the top level for panoramic views of the picturesque water filled with marine life. We spent the majority of our time in the fort and only had time for a quick snorkel through a plethora of fish before enjoying the view from above again on our seaplane ride back to Key West.
Tired from a fun day we decided to enjoy happy hour at Bagatelle and splurge on cool treats at Gladiators Ice Cream. I couldn’t decide on just one flavor so I ordered two small cups to sample four flavors of the homemade ice cream. One cup was pineapple and key lime pie flavors and the other was peanut butter and snickers flavors. My favorite was the pineapple and no, I didn’t eat all of the ice cream. It was the perfect sweet ending to a wonderful day.
The next morning, we stopped at Baby’s Coffee, the southernmost coffee roasters in America, for an iced coffee for the start of our drive north. We allotted four hours to get to Miami International Airport in case there was an accident or traffic, which we hit in the last 30 minutes of the drive. We made a couple of stops including a few minutes to stretch our legs back on Seven Mile Bridge and a quick lunch at Tacos Jalisco food truck next to Keys Chocolates and Ice Cream on Key Largo, where a scoop of key lime pie ice cream was the perfect parting treat on a road trip in the Florida Keys.
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Jennifer Broome has stood on the equator, crossed the Arctic Circle, skydived with the U.S. Army Golden Knights, flown with the U.S. Air Force Thunderbirds, and trekked to Everest Base Camp. She is a freelance multimedia travel and environmental journalist for broadcast, digital, and print outlets. She’s also a freelance television meteorologist, content creator, and speaker. Her specialties are adventure travel, solo travel, U.S. National Parks, road trips, and sustainable tourism. She's been to all 50 U.S. states, over 60 countries, and 6 continents. She is on a quest to visit all of the National Park Service sites, and so far has visited over 265 including 49 of the 63 national parks.
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