Florida may just be one of the least understood states in the USA. With a mix of cultures, 300-year history, and unique coastal settings, each of the state's cities have a distinct character. From The Florida Keys’ slow-paced paradise to Orlando’s thriving theme parks, we’ve narrowed down a guide to Florida’s must-see destinations for a week-long trip.
Key West is one of the most exotic, warm-weather destinations you'll find the continental U.S., making it the ultimate starting point for a trip through Florida. With a long history as a getaway for writers, like Tenessee Williams and Judy Bloom, as well as presidents Harry Truman and John F. Kennedy, the tiny island at the southern tip of the Florida Keys has fostered an eclectic culture. For a quick history lesson, plan a morning visit to the Ernest Hemingway Home & Museum where you’ll get a glimpse into the renaissance man’s personal life, his writing studio, and encounter one of the six-toed Hemingway cats that still live at the residence.
Grab a bite at Eaton Street Seafood for lunch, where they’ve become famous for their juicy stone crab and crispy conch fritters. Take the afternoon to explore the pastel-hued town by foot or rent a scooter for a breezy joy ride around the island. Obligatory stops along the route include the Fort Zachary Taylor State Park, the Southernmost Point marker, Clinton Square Market’s bevy of boutiques, and the gardens surrounding West Martello Tower.
Sundown in Key West is a local ritual that needs to be experienced to fully understand the essence of the island. Every day the people flock to Mallory Square with a piña colada or a glass of Papa’s Pilar rum in hand to watch as the sun slowly dips into the translucent waters of the Gulf of Mexico.
As darkness creeps over Key West, the city truly comes alive, and not just the bar scene. Take a guided ghost tour by Ghosts & Gravestones to learn about the city’s hauntingly mesmerizing past like the tales behind Robert the Doll and the Key West Cemetery.
The day ends as it began, with another tribute to Hemingway, but this time at his favorite dive bar, Sloppy Joe’s, that continues to serve up ice cold beers since opening in 1933.
Day 2: Day Trip to Upper Keys
A scenic drive north along the 7-mile bridge that divides the Atlantic Ocean with the Gulf will land you in the Upper Keys, composed mainly of Key Largo, Tavernier, Islamorada, and Marathon.
The Upper Keys are best known for their idyllic natural beauty providing the ultimate backdrop for wildlife spotting and watersports. Go deep-sea fishing with Sea Monkey Charters led by Captain Casey Scott, or plunge into the diving capital of the world in Key Largo, which boasts incredible sites teeming with tropical fish like the Christ of the Abyss statue. Families with children can spend the morning at the Dolphins Plus Marine Mammal Responder Center, which offers dolphin encounters in their natural environment and educational programs that teach the values of wildlife conservation.
Once you venture back to dry land, grab lunch and a slice of the world’s most heavenly Key lime pie at Mrs. Mac’s Kitchen. That’s a contentious statement to make in these parts of town, but one bite of the creamy tart will dissuade further debate.
With a full belly, you’re ready to embark on a tour of the craft breweries scattered around the islands for a taste of their inventive local fruit infusions. A must try at Islamorada Brewery & Distillery is the “No Wake Zone,” a key lime coconut ale that complements the breezy beach atmosphere.
End the day with a drive past The Moorings Village, a historic resort where Netflix’s hit series "Bloodline" was filmed. Pull up an Adirondack chair at Morada Bay, the resort’s luxurious waterfront dining destination just across the street. If you’re lucky enough to be visiting during a full moon, you’ll be treated to a moonlit beach bash featuring stilt walkers, fire breathers, and live reggae bands.
Day 3: Travel to Miami Beach
Cruising down the famous Ocean Drive towards your accommodation at the Marriott Stanton South Beach will make you feel like you're on the set of a music video. The Art Deco-inspired hotel exudes a trendy beach club vibe in the heart of the exclusive South of Fifth neighborhood. With rooms offering views of the jewel-toned ocean, it's hard to peel yourself away to explore the lively beaches, world-famous restaurants, and upscale shops that sit just down the street.
Meander along Miami Beach’s main roads for a self-guided architectural tour of the immaculately-preserved 1920s gems found along Ocean Drive, Collins Avenue, and Lincoln Road. You’ll come across the Wolfsonian, an ornate Mediterranean Revival-style museum built in 1927 that displays a massive collection of North American and European art and design pieces. If you’ve worked up an appetite, browse the stalls at Time Out Market, a food hall serving creative pop-up concepts by some of the city’s most celebrated chefs including Antonio Bachour, Norman Van Aken, and Scott Linquist.
After soaking in the South Beach sights, venture over to the mainland for a glimpse of the real Miami. Pay a visit to Coconut Grove—the oldest part of the city—with its stately mansions, peacock-filled parks, and cute cafes like Panther Coffee or Books & Books for an afternoon caffeine kick. If you’re looking to stretch your muscles a bit, rent a kayak, paddleboard, or catamaran from Miami Watersports to explore Biscayne Bay.
Change out of your swimsuit into a more fashion-forward ensemble for dinner and a night out. On your way into the city center, you’ll pass by the illuminated Freedom Tower, a national landmark that welcomed Cuban refugees in the 1950s and is now a museum. Make a reservation at NIU Kitchen for Catalan cuisine in a cozy corner of Downtown, Pubbelly Sushi’s outpost in Brickell City Center, or Versailles on Calle Ocho if you’re craving the hearty Cuban food that locals have grown up on.
As the clock approaches midnight make your way to any of Miami’s pulsating clubs. If your hips sway to the beat of salsa and bachata you can’t miss Ball & Chain in Little Havana, where a live band mounts the iconic pineapple-shaped stage every weekend. If hip hop and house music is more your speed, head to Basement located within the glitzy Miami Beach EDITION Hotel. The club’s DJs spin sets that will keep your feet moving on the dance floor and the underground ice rink. Yes, you read that right.
Day 4: Take the Brightline to West Palm Beach
Hop aboard the Brightline—South Florida’s passenger train connecting Miami, Fort Lauderdale, and West Palm Beach—for an easy and comfortable ride up the coast. Use the coffee and snack-filled ride to caffeinate after the previous night’s outing.
Upon arrival at the station, you’ll land in the middle of Downtown West Palm Beach, a tree-lined neighborhood full of shops, outdoor artwork, and restaurants. Make your way down the street to Restoration Hardware, a massive mansion-like showroom with stunning interiors and a hieroglyphic inspired mural by LA-based artist, RETNA. This isn’t just an opulent furniture store though; head up to the fourth floor for a spectacular brunch at RH Rooftop Restaurant where there's chandeliers dangling overhead, skyline views, and a melt-in-your-mouth lobster roll paired with chilled rosé.
Rent a bike to cycle down the mile-long path to the beaches of Palm Beach Island for a day on the sand. Alternatively, pedal over to Antique Row in search of vintage treasures that once graced the ritzy Old Florida homes of the nearby Billionaires Row.
Wind down for the evening back at The Ben, an Autograph Collection hotel that just opened along West Palm Beach’s waterfront, featuring an exotic mix of alligator motifs, lush greenery and sumptuous furnishings. Sit down for cocktails and a Mediteranean tapas-style dinner at Spruzzo, the rooftop restaurant and bar serving stunning views of the Intercoastal waterway.
Day 5: Drive to Orlando
A visit to Orlando can be adrenaline-filled with visits to the city’s plethora of theme parks, or a laid-back respite brimming with Central Florida charm. If you’re traveling with younger children, odds are you won’t be able to appease them without a trip to Walt Disney World or Universal Studios. However, if you prefer to explore the calmer side of Orlando, plan an early morning hot air balloon ride over the city. Aerostat Adventures and Painted Horizons offer guided tours through the sky for a bird's eye view of the city below, it’s theme parks, and the shimmering lakes that dot Central Florida.
Take a break from the excitement for lunch at Dandelion Community Cafe, a quaint bungalow-style restaurant with a vegetarian-forward menu, and a laundry list of loose-leaf teas and vegan pastries to end on a sweet note.
Spend the remainder of the afternoon browsing Orlando’s plentiful shopping destinations. Whether you’re looking for some indulgent retail therapy at the high-fashion shops like Hermès and Bulgari inside The Mall at Millenia or prefer to hunt for a bargain at the Orlando International Premium Outlets right next door, the city offers a variety of boutiques for every budget.
Kick up your feet back at The Alfond Inn, a stylish boutique hotel in the oak-lined Winter Park neighborhood. Unwind with a glass of wine via Plum's automatic dispenser from the comfort of your suite as you spruce up for dinner. Located within walking distance of the hotel, the new Vinia Wine & Kitchen has earned rave reviews for its sophisticated European fare; from the Ravioli Fatti a Mano with deep Italian roots to the Romeu & Julieta made with a traditional Portuguese pão de queijo recipe.
Day 6: Tampa
Only an hour away from Orlando on Florida’s Gulf Coast, Tampa offers a great day trip option for a change of pace. Take the morning easy with brunch at Oxford Exchange, a bookstore turned gift shop turned restaurant. Sink into a tufted leather booth and order the French toast which includes cinnamon swirl sourdough, fresh berries, and maple syrup with a cappuccino to start the day.
Families can spend the afternoon at The Florida Aquarium for insight on the aquatic and terrestrial animals found around the state, or explore the colorful sights, sounds, and flavors of Ybor City. Tampa’s retro neighborhood is home to a proud Latin population, with Cuban bakeries selling pastelitos and Indie bands playing at The Orpheum. This slice of the city showcases a vibrant mix of cultures that merit a visit.
Before returning to Orlando, gather for dinner over dry-aged steaks at Bern’s Steakhouse. The family-owned eatery has been serving premium cuts since 1956 and is an oenophile's dream with a wine cellar racking up about half a million bottles.
Day 7: St. Augustine
It’s only fitting that your trip through Florida should conclude where the state was first settled. Saint Augustine, along the Treasure Coast, is the oldest continuously inhabited city in the United States. Settled by Spanish conquistador Pedro Menéndez de Avilés in 1565, it changed hands between the British, Native Americans, and Union Troops throughout its history. You can learn all about the port city’s founders and unique backstory with a visit to the Castillo de San Marcos, a military fort and museum on the Northern edge of the Historic District, and at the Lightner Museum, built by Florida pioneer Henry Flagler in 1888.
After learning about the city’s long past, make your way through the winding colonial streets that don’t appear to have changed much since the 16th century. Along the pedestrian-only St. George Street in the Historic District you’ll find small storefronts selling everything from straw-woven sun hats at Earthbound Trading Co. to handmade glass jewelry at House of Z to rustic home trinkets at Red Pineapple. As the aroma of roasted cacao wafts down the street, pop into Kilwin’s Chocolates for a scoop of their toasted coconut ice cream to cool down.
If you’re tired from walking, take a ride on the Old Town Trolley which is a great way to see the city with the “hop-on, hop-off” tour. The trolley makes stops at the city's most important sites including the original city gates, Villa Zorayda Museum, the mythical Fountain of Youth, and San Sebastian Winery that has been producing American wines since 1562.
Finally, celebrate the evening with a toast to your trip over dinner at Columbia, a 110-year-old restaurant presenting Spanish-Cuban cuisine on a porcelain plate. The stunning dining room, decked out in arched windows and vibrant Andalusian tiles, harkens back to the city’s European roots.