The Perfect Getaway: Get your group together for an amazing week in Key West
There’s plenty to explore in this sun-filled spring break destination, from an Old-Florida-meets-Caribbean culture to a remote national park and idyllic white-sand beaches.
By Jessica Poitevien | December 21, 2023
Key West marches to the beat of its own drum, with an eccentric-yet-relaxed island atmosphere. A prime destination year-round, the area is especially idyllic in springtime before the heat of summer and unpredictability of hurricane season arrive. It’s also the ideal location for adventure, buzzing nightlife and unique history. Here are some highlights for the perfect Key West getaway:
Quirky landmarks: Visit the Southernmost Point in the continental U.S.
Ultimate sundowner: Don’t miss the daily sunset celebration at Mallory Square
National park adventure: Take a ferry or seaplane to explore Dry Tortugas National Park
Monday
Morning
Welcome to Florida! If you’ve flown into Miami for your Key West vacation, grab your rental car and hit the road heading south. When passing through Homestead, take a worthwhile five-minute detour to visit the Robert Is Here Fruit Stand. It’s a quintessential stop on the way to Key West, and the perfect chance to refuel with fresh smoothies — including some made with tropical fruits for an authentic Floridian vibe to hit the ground running.
Photo Credit: Emergent
Afternoon
Half the fun of taking a road trip from Miami to Key West is exploring the roadside attractions along the way. Make a pit stop in Islamorada to visit the History of Diving Museum, with its collection of vintage underwater equipment, and Rain Barrel Village, a tropical garden full of shops with souvenirs and the work of local artists. A stop at Robbie’s of Islamorada is also a must for lunch, as well as a uniquely Florida experience — hand-feeding giant tarpon fish.
Photo credit: VISIT FLORIDA
Evening
Once you’ve reached Key West, the last of the islands that make up the Florida Keys, check into Casa Marina Key West, Curio Collection by Hilton, your home base for the week. After the nearly 4-hour drive, we suggest taking it easy by admiring the hotel’s historic architecture, indulging in a spa treatment or taking a dip in the oceanfront pools. Reserve the Toes in the Sand dining experience to enjoy your first meal in Key West on the hotel’s private beach.
Tuesday
Morning
Start your first full day in Key West with a short walk to visit the buoy marking the Southernmost Point of the continental U.S. This historic landmark is undoubtedly one of the most iconic photo-ops on the island, marking the spot that’s 90 miles (145 kilometers) away from Cuba. After snapping a few pics, walk up bustling Duval Street and grab breakfast at Banana Cafe, a popular French-style bistro, specializing in sweet and savory crêpes.
Photo credit: Jessica Hirsch
Afternoon
Spanning just 4 miles (6.4 kilometers) long and 2 miles (3.2 kilometers) wide, Key West is easy to explore on foot, bike or on an informative trolley tour. Stop by some of area's main attractions, like the Key West Lighthouse and Mile Marker 0, which signals the beginning of U.S.1, an interstate running from Key West to Maine. Literature lovers shouldn’t miss the Ernest Hemingway House & Museum, then grab lunch at Sloppy Joe’s, one of the notorious writer’s favorite spots.
Photo credit: Scott Barnette
Evening
Key West is known for its vibrant sunsets, so much so that there’s a daily sunset celebration. Each evening visitors and locals alike gather at Mallory Square to watch the fiery spectacle as the sun dips into the Gulf of Mexico and the plaza fills with local artists, food carts and street performers. Take in the show, then walk over to Pepe’s Cafe & Steakhouse, the oldest eatery in Key West, for some of the best surf and turf in town.
Wednesday
Morning
Get an early start to the day with a quick breakfast at Cuban Coffee Queen. The sandwiches are filling, the coffee is strong and the stand even has a photo-worthy “Greetings from Key West” mural. From here, it’s a short walk to board the Yankee Freedom III ferry, which will take you to Dry Tortugas National Park. For an added dose of adventure, take a seaplane flight to the park. No matter your mode of transportation, be sure to book well in advance as both options regularly sell out.
Photo credit: Scott Barnett
Afternoon
After the two-hour ferry ride or 40-minute seaplane flight to Dry Tortugas, you’ll arrive at one of the most remote national parks. Spend the afternoon snorkeling through the coral reefs; touring Fort Jefferson, the nation’s largest 19th century fort; relaxing on the beach and keeping your eyes peeled for local wildlife, including nearly 300 species of birds. A boxed lunch will be provided to ferry travelers, but seaplane visitors will need to pack their own food.
Photo credit: VISIT FLORIDA
Evening
After a long day at the national park, you’ll probably want to freshen up and rest before dinner. Key West is known for its laid-back vibe, but you can venture to Little Pearl in Old Town for a refined dining experience focused on local seafood. This restaurant offers three dinner seatings (5 p.m., 7 p.m. and 9 p.m.) where a carefully curated four-course menu is served. Expect creative dishes like crispy lobster with spicy peanut sauce and miso tres leches for dessert.
Thursday
Morning
Dedicate time this morning to all the local activities you might have missed on your first day of exploring. Start with a convenient breakfast and coffee at Morrison’s Market in Casa Marina before walking to the Key West Butterfly and Nature Conservatory to immerse yourself amid hundreds of free-flying butterflies and exotic birds. History buffs shouldn’t miss the Mel Fisher Maritime Museum where you can learn about a 1622 Spanish shipwreck and the infamous Key West treasure hunter who found it — ornate jewelry, canons, gold and silver coins included.
Photo credit: SPARK
Afternoon
You won’t want to leave the Keys without enjoying a proper beach day, so make your way back to Casa Marina, home of the largest private beach in Key West. Relax in the sand and sea, paddle around in a kayak or boost your adrenaline by renting Jet Skis. For the ideal experience, reserve a beachfront daybed. When it’s time for lunch, the attentive hotel staff can bring food and drinks straight to you.
Evening
Embark on a sunset cruise departing from your hotel for an unforgettable sundowner, soaking up your final views of Key West at dusk. For dinner, Azur is sure to leave an impression with its seafood risotto or rack of lamb with rosemary jus. The perfect nightcap — or party-starter, depending on your mood — is just a few blocks away on Duval Street. As the epicenter of Key West nightlife, Duval stretches from the Gulf to the Atlantic with 43 bars along the way.
Friday
Morning
It’s time to pack your bags and drive back to Miami. Before leaving Key West, indulge at a local hot spot, Glazed Donuts, for breakfast. This place is so popular, it’s usually sold out by noon. And this is not your run-of-the-mill donut shop — everything here is made from scratch and you’ll find inventive flavors like mango habanero, brown butter hazelnut and the Florida Keys-inspired Key lime pie donut. Freshly roasted coffee is also on the menu to help wash it all down.
Afternoon
Continue your journey north with a pit stop at the city of Marathon’s Turtle Hospital, where you can tour a facility that rescues and rehabilitates sea turtles. Marathon is also a gateway to the recently restored section of the Old Seven Mile Bridge. Once open to vehicular traffic, then closed for several years, it’s now a park for jogging, fishing and unbeatable photo-ops. Your last stop on the road back to Miami should be in Key Largo for award-winning conch chowder and homemade Key lime pie at Mrs. Mac’s Kitchen.
Photo credit: VISIT FLORIDA
Until next time!
Whether you’re traveling solo, with friends, family or your special someone, spending time exploring the natural beauty and history of Key West is always a good idea. You’ll leave sun-kissed, refreshed and relaxed thanks to the soothing white-sand beaches, fresh seafood and plenty of good vibes to go around. Oh, and be sure to check out Key West’s robust calendar of festivals and events for your next visit!
Photo credit: Patrick Farrell and Peter W. Cross
Hero image credit: SPARK
Jessica Poitevien is an international storyteller with more than a decade of experience in writing and editing. Born in New York, she caught the travel bug throughout multiple moves that brought her to California, Spain, Colombia and her current home base in South Florida. She has visited over 40 countries (and counting!), including several solo trips, and also considers herself an expert in destination weddings and unique honeymoons — her own was two months long. When she's not traveling, she enjoys making social media content, trying new food and acting as a travel agent for friends and family.
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