Explore The Florida Keys with The Travel Mom
Follow along with The Travel Mom, Emily Kaufman and lifestyle journalist Tommy DiDario as they journey through The Florida Keys & Key West, discovering memorable ways to relax, explore, dine and connect with the island chain’s colorful culture and natural world.
From wellness escapes and fascinating history to only-in-the-Keys wildlife encounters, fresh seafood and luxurious hideaways, their travels offer plenty of inspiration for creating your own Florida Keys itinerary.
Wellness, Keys Style
In the Florida Keys, wellness can mean a morning yoga session, a rejuvenating spa treatment or simply getting outside and letting the water, sunshine and island surroundings work their magic.
Start at Bungalows Key Largo, a luxurious yet laid-back adults-only, all-inclusive oasis well suited for a wellness-focused getaway. Its Zen Garden Spa sets a tranquil tone with treatment rooms, steam and other therapies, while outdoor waterfront cabanas let tropical breezes become part of the spa experience.
Prefer wellness with a little more movement? Explore the resort by cruiser bike, take a yoga class or get out on the water by kayak or standup paddleboard. Bungalows' all-inclusive offerings include nonmotorized watersports and wellness activities.
Beyond the resort, the Keys turn exercise into adventure. Paddle through quiet mangrove estuaries to explore the backcountry around places such Geiger Key Marina, RV Park and Fish Camp, or take to the clear subtropical waters on a standup paddleboard. For a higher-altitude perspective, parasailing combines an adrenaline boost with unforgettable views.
Just offshore from Key West, Sunset Key Cottages offers another way to find your balance. The private 27-acre island is only about 500 yards from Key West yet feels a world away.
The takeaway? In the Keys, wellness doesn't have to follow a schedule. Ride, paddle, stretch, swim, or simply find a quiet spot beneath a palm tree and do absolutely nothing.
Explore the Stories Behind the Islands
Crossing the Seven Mile Bridge is one of those unmistakable Florida Keys moments: blue water seems to stretch forever on either side as the Overseas Highway carries you from the Middle Keys toward the Lower Keys and Key West.
It's also a reminder that the journey itself is part of the experience here.
Throughout the island chain, museums, historic homes, galleries, open-air markets and music venues reveal the people and events that shaped the Keys.
In Key West, begin at the Key West Museum of Art & History at the Custom House. The landmark red-brick building introduces visitors to the island's history and creative spirit through exhibits and collections.
Then head to the Ernest Hemingway Home & Museum, where the Nobel Prize-winning author's second story writing studio offers a glimpse into one of the most productive periods of his career. And don't forget the home's other celebrities: the famous polydactyl (six-toed) cats.
Nearby, the Key West Lighthouse & Keeper's Quarters rewards those willing to climb its 88 steps with sweeping island views. Back on the ground, exhibits share stories of the lighthouse keepers and their families.
But Keys culture isn't confined to museums.
Browse open-air markets and meet local artists at Robbie's of Islamorada or explore shops and galleries around Key West's Historic Seaport. Music is just as deeply woven into island life, from performers playing at waterfront venues to the legacy of Jimmy Buffett, whose Shrimp Boat Sound recording studio became part of Key West music history.
Anyone curious about how the Keys came to be can spend time at the Florida Keys History & Discovery Center in Islamorada. Nearby, the History of Diving Museum chronicles humankind's quest to explore beneath the sea through artifacts, equipment and exhibits devoted to diving history.
Whether you're drawn to literature, architecture, art, music or maritime history, leave room in your itinerary for discovery. Some of the best Keys stories are found between the big attractions.
Taste Your Way Through the Keys
Come hungry.
Florida Keys dining ranges from fish-camp casual to toes-in-the-sand elegance, but seafood is naturally one of the stars.
In Marathon, Keys Fisheries is a laid-back waterfront favorite where the famous lobster Reuben piles lobster, sauerkraut and Swiss cheese onto grilled bread. Depending on the season, stone crab claws offer another quintessential taste of the Keys. Add conch chowder and a slice of Key lime pie and you've assembled something close to a Florida Keys culinary greatest-hits list.
Continue south to Stock Island, just outside Key West, where Hogfish Bar & Grill serves its signature hogfish sandwich with Swiss cheese, mushrooms and onions on Cuban bread. It's the sort of casual, waterfront spot that captures the come-as-you-are spirit of the Keys.
Heading north? Robbie's in Islamorada pairs food with an experience. Grab fish tacos and other casual fare, browse the open-air market and then wander down to the docks for one of the Upper Keys' most famous attractions, the resident tarpon. Visitors can purchase fish to feed the giant “silver kings” that will leap at the first sight of someone dangling bait over the water.
For an entirely different dining experience, take the ferry from Key West to Latitudes on Sunset Key. Here, beautifully presented cuisine, seafood and expansive Gulf views create an elegant island finale, especially around sunset. The restaurant is open to non-resort guests, but reservations are required to access the boat launch. For special occasions be sure to reserve far in advance to make sure you’re able to secure your preferred reservation date and time.
And wherever you eat, check the day's specials. Some of the most memorable Keys meals begin with a simple question: What's fresh today?
Meet the Wild Side of the Keys
The natural environment isn't merely the backdrop to a Florida Keys vacation. It's one of the destination's greatest attractions — and protecting it is a responsibility shared by residents and visitors.
In Marathon, take an educational tour of The Turtle Hospital, the world's first state-licensed veterinary hospital dedicated to sea turtles. Visitors learn how injured turtles are rescued, treated and rehabilitated, with the goal of returning them to the wild whenever possible.
A short drive away on Grassy Key, Dolphin Research Center combines marine mammal education and research with opportunities to observe dolphins and California sea lions. Interactive programs offer an even closer look at the animals, many of them rescues, and the work being done to understand and care for them.
To discover what lies beneath the surface without getting wet, board a glass-bottom boat from Robbie’s of Islamorada or John Pennekamp Coral Reef State Park for a look at the Keys' coral reef ecosystem. Snorkeling and scuba excursions offer an even closer view.
On Big Pine Key and surrounding islands, slow down and keep watch for diminutive Key deer. The National Key Deer Refuge protects habitat for the endangered species as well as other native wildlife. Visitors can also explore places such as the Blue Hole, where an observation platform and walking trail provide opportunities for wildlife watching.
Experiences like these are reminders that traveling responsibly matters here. Observe wildlife from appropriate distances, never touch coral, choose reef-friendly activities and follow local guidance for protecting the places you've come to enjoy.
Add a Little Luxury
The Florida Keys may be famous for a laid-back attitude, but laid-back and luxurious aren't mutually exclusive.
In Key Largo, Bungalows Key Largo pairs its adults-only, all-inclusive concept with private garden and waterfront bungalows, tropical landscaping, pools, dining, watersports and spa experiences. Each bungalow has its own veranda, soaking tub and outdoor shower.
Farther south, Little Palm Island Resort & Spa takes the private-island idea to another level. Located about three miles offshore from Little Torch Key and accessible by boat, the secluded adults-only retreat offers an upscale take on barefoot island living.
Then there's Sunset Key Cottages, a quick ferry ride from Key West. The resort's private-island setting feels secluded, while the attractions, nightlife and historic streets of Key West remain just minutes away. One- to four-bedroom cottages also make Sunset Key an option for couples, families and groups seeking more space.
And you don't necessarily need to book a luxury resort to add an indulgent moment to your vacation. Reserve dinner overlooking the water, schedule a spa treatment, charter a boat or simply give yourself an unscheduled afternoon beside the sea.
Make the Journey Your Own
Emily and Tommy's travels show there isn't one right way to experience The Florida Keys & Key West.
Spend one morning stretching beside the water and the next climbing a lighthouse. Paddle through mangroves, meet a rescued sea turtle, browse the work of a local artist or linger over fresh seafood at a waterfront table. Splurge on a private-island dinner — then spend the next afternoon happily wearing flip-flops at a fish shack.
Most importantly, don't try to rush it all.
The Florida Keys stretch more than 100 miles from Key Largo to Key West, and each region has its own character, attractions and reasons to linger. Build some breathing room into your itinerary, take the Overseas Highway at an island pace and leave space for the places you didn't know you wanted to stop.
After all, sometimes the best part of a Florida Keys itinerary is what happens between the plans.
