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The 6 Best Florida Road Trip Destinations And Itineraries

1. Amelia Island

Getting there

Take Interstate 95 to Interstate 295 and cross the Dames Point Bridge in Jacksonville, which travels over the St. Johns River and connects to Heckscher Drive, delivering drivers to the island by way of two state parks.

Ritz-Carlton, Amelia Island
Ritz-Carlton, Amelia Island

Where to Stay 

Travel to Amelia Island and you’ve almost made it to Georgia. Many of those who work on the island even reside in the northern state. The Ritz-Carlton, Amelia Island is a quiet beachfront resort guarded by sand dunes that are uncommon on most Florida beaches. The Ritz offers the brand’s notoriously luxurious accommodations in 446 guest rooms. Visitors can enjoy three pools, a golf course, kid’s activities and four restaurant options ranging from a casual pub to collared-shirts-only dining.

Amelia Island

Where to Explore

10 a.m.

Saddle up for a therapeutic jaunt down the beach—on horseback. Kelly Seahorse Ranch offers guided, one-hour rides through canopy trees in Amelia Island State Park to a private beach that extends to the southernmost point on the island.

Things to do in Amelia Island


Head to Fernandina Beach to grab lunch at The Salty Pelican. The quaint town has an old-Florida charm similar to Key West, and the restaurant is at the tip of Centre Street with a harbor view of Amelia River. The Seared Tuna Nachos with seaweed salad, goat cheese and wasabi sesame seeds can’t be missed. After indulging in copious amounts of seafood, wash it all down with a drink at The Palace Saloon, Florida’s oldest bar, which dates back more than a century.

3 p.m.

Book a custom facial at the spa at The Ritz-Carlton, Amelia Island, and ask for Patty as your therapist—she’s been working at the hotel for 26 years. Arrive early enough to visit the steam room and sauna before the service, which includes a brush cleanse, skin analysis, exfoliation, mask and scalp massage.

Amelia Island visiting

8 p.m.

Make reservations at The Ritz’s fine-dining concept, Salt, inspired by the ocean, which is visible through floor-to-ceiling windows. To match the restaurant’s moniker are a variety of infused salts—like citrus lime and Parmesan truffle—that rotate and are placed on each table for guests to sprinkle on bread and butter. Adventurous eaters can even add dashes to their entrées if desired. And a gift shop offers servings of the salts for purchase.

Kelly Seahorse Ranch
Horseback riding along the Atlantic shore with Kelly Seahorse Ranch

2. Miami

Getting There

Driving A1A might take a bit longer than jumping on the highway, but a view of the ocean to your left the whole way down is well worth it—as is a stop at Biella Ristorante in Sunny Isles Beach. Fuel up for the second half of the drive by ordering the Ravioli di Pera e Gorgonzola, a tasty spin on ravioli that includes pear and ricotta served with Gorgonzola cream sauce and topped with balsamic vinegar and truffle oil.

things to do in Miami
The Betsy - South Beach from Ocean Drive

Where to Stay

Literature lovers find The Betsy - South Beach feels like home—each room in the Forbes Four Star and AAA Four Diamond rated boutique hotel has a bookshelf decorated with hardbacks. There’s even a writer’s residency program on site, which has sponsored more than 500 creatives. It’s somewhat of an ode to owner Jonathan Plutzik’s father, three-time Pulitzer Prize finalist Hyam Plutzik, who wrote the book Letter from a Young Poet. The title is showcased in each of The Betsy’s 130 guest rooms, as are novels like The Betsy by Harold Robbins.

where to stay in Miami
Faena Theater

Where to Explore

10 a.m.

Stick to the Italian food theme and start the day off with a pasta brunch at The Alley. In the breezeway connecting Ocean Drive and Collins Avenue next to The Betsy—where the trash used to be taken—is now a casual pizzeria led by chef Laurent Tourondel. Order breakfast items with Italian twists, like the Rigatoni Carbonara or the Panetone French Toast. But also be sure to ask the chef for the Cacio e Pepe, which comes just as you would find it in Rome.

where to eat in Miami
Cacio e Pepe served at The Alley

1 p.m.

Pick up a book from your room, and find a quiet reading nook. Hiding places meant for guests to disconnect are incorporated throughout The Betsy’s terraces and hallways. Two years ago the hotel took over the historic Carlton Hotel and expanded into the art deco building to incorporate a rooftop pool, library and an atrium for events. Guests in the new wing may luck out and see a wedding take place in the courtyard below their balconies at night.

staycation in Miami
Bookshelves complete each room in the hotel

7 p.m.

Make reservations at LT Steak & Seafood, located across from The Betsy’s Lobby Saloon. Sit inside and enjoy sounds from a live jazz band on Saturday nights, or take terrace seating and people watch along Ocean Drive. The waiter will advise not eating too much of the warm bread brought to the table, which is hard to do after breaking off a piece that’s crisp on the outside and light on the inside. If the basket is left empty, just make sure there’s room for the Short Rib Bao Bun and Soy-Wasabi Ahi Tuna Tartare.

9 p.m.

Call a 5-minute ride north to the Faena Hotel, and enter the property’s all-red, intimate theater for the show Sensatia, which has extended its runtime through August. On a Thursday, Friday or Saturday night, watch performances by acrobats to pyro-belly dancers and sip The Muse cocktail, prepared with vodka, house-made grapefruit, rosemary, lemon and activated charcoal.

3. Key West

Getting There

There’s only one way to drive to the Keys: via two lanes of sometimes unmoving traffic. Break up the long drive to the southernmost point of the United States with a stop at Playa Largo Resort & Spa in Key Largo, and maybe even extend the trip a few days with a night stay there. The resort boasts secluded beachfront views, private cabanas, a spa, water sport programs and more.

Things to do Key West
Ocean Key Resort & Spa’s signature restaurant

Where To Stay

Once you get to Key West, drive down Duval Street toward the Gulf of Mexico until you hit the water. That’s where you’ll find Ocean Key Resort & Spa, a seaside resort that is both vibrant with modern design and sophisticated with classic elements. Find hanging gardens over walkways, three eateries on site, an Eastern wellness spa and more. Every room has a view, either looking out on the Gulf, the Key West Harbor, Mallory Square or Duval Street.

staycation in Key West
The hotel pool

Where To Dine

Hot Tin Roof at Ocean Key Resort & Spa is a notorious waterfront dining spot. Set reservations about an hour before dusk in order to settle in at the table before watching one of Key West’s famous sunsets sink over the harbor. Order the Lobster Mac and Cheese and Key West Pink Shrimp, and sip on The Rose Tattoo, made with Ciroc red berry, raspberry, lemon, sugar and prosecco. It wouldn’t be a trip to Key West without Key lime pie. Grab a slice during brunch at Blue Heaven, which is famous for the wild chickens that roam freely throughout the outdoor dining area.

where to dine in Key West
Bath ritual at the hotel spa

Where to Explore

10 a.m.
Step back in time at the Ernest Hemingway Home and Museum, the residence of the distinguished author who lived in Key West for more than 10 years. At this U.S. National Historic Landmark you can find Hemingway’s typewriters, fun facts about his infamous romances, insights into his novels and six-toed cats purring around the grounds.

where to explore Key West
One of the property’s deluxe suites

1 p.m.

Clearly Unique Charters isn’t named without reason. The boat rental company offers kayak tours of the Great White Heron National Wildlife Refuge in clear kayaks, allowing passengers to see marine life below and around them. The tours also include snorkeling at coral reefs, sponge gardens or shipwrecks.

Great White Heron National Wildlife Refuge
Ocean Key offers the perfect sunset view

7 p.m.

A nightly arts festival takes place at Mallory Square, and the sunset celebration attracts hundreds of visitors each evening at dusk. Enjoy live music, magic tricks, street performances and, of course, a view of the disappearing sun.

arts festival at Mallory Square
Hot Tin Tini cocktail

9 p.m. 

After a long day of adventure, unwind with a beer or two. The Porch is a local hotspot on Duval Street that isn’t overrun by rowdy tourists. Set in an old house converted into a craft beer and wine bar is a quaint hangout with comfy porch seating and multiple rooms to choose from. 

4. Sarasota

Feel for the Town

Pegged as “Florida’s cultural coast,” Sarasota delivers with its vibrant arts community spanning the historic downtown and surrounding neighborhoods. Find entertainment on any street, with places like The Florida Studio Theatre and the Sarasota Opera House. Or, travel to one of the keys or Lido Beach for a day of surf and sand.

things to do in Sarasota
Art Ovation’s rooftop pool and bar

Where to Stay

At the center of downtown is Sarasota’s new playground and artistic hub: Art Ovation. This urban property offers a sophisticated stay with a connection to creativity on every level. Gallery wall spaces are filled with artwork from Florida artists as well as students, alumni and faculty from the famed Ringling College of Art and Design. Guests can take part in ukulele and art and yoga classes on the rooftop deck, or relax in a cabana at the pool overlooking the city. Plus, the property is within walking distance to local restaurants and more than 20 art galleries and attractions.

where to stay in Sarasota
Marie Selby Botanical Gardens

Where to Dine

A staple in the heart of the Theatre and Arts District, Bijou Cafe is the go-to spot before—or after—a trip to the opera. Or, Boca Kitchen Bar Market is just south of Main Street on Lemon Avenue and gives off a South Florida vibe with unlimited bubbly and creative takes on brunch classics.

where to dine in Sarasota
Aerial view of Ca’ d’Zan

Where to Explore

10 a.m.

If fluffy pancakes piled high sounds heavenly, place an order at Station 400. This quaint breakfast and lunch spot is housed in a restored train depot that dates back to 1852. Sip on a blood orange and hibiscus specialty mimosas before diving into lemon curd and fresh blackberry flapjacks.

where to explore in Sarasota
Rooms in Art Ovation feature artistic touches

Find yourself in the middle of “The Greatest Show on Earth” with a trip to The Ringling. Spend the afternoon viewing stunning artwork inside The John and Mable Ringling Museum of Art with entry into the Circus Museum. Plus, tour the grounds of John and Mable’s 36,000-square-foot palace, the Ca’ d’Zan. The waterfront mansion features a Venetian Gothic-inspired exterior and interior.

The Greatest Show on Earth
The waterfront mansion Ca’ d’Zan

4 p.m.
Nature lovers, and even those who don’t have a green thumb, will be amazed at the Marie Selby Botanical Gardens, home to a living collection of rare tropical plants. The oasis offers exhibits year-round. During July, tour the “In Dialogue with Nature: Glass in the Gardens” display.

7 p.m.

Perched over Sarasota Bay, St. Armands Circle offers four quadrants of lovely shops, dining options and more. For fresh seafood dishes and cocktails, stop by Shore St. Armands and sit outdoors while toasting to the evening.

5. St. Augustine

Feel for the Town

Three words: Canons, cobblestones and carriages. America’s oldest city—claimed by Spanish explorer Juan Ponce de León—continues to amaze visitors daily and give insight into Florida’s long past.

things to do in St Augustine
AAA Four Diamond premier property, Casa Monica

Where to stay

Live like a royal at the oh-so-historic Casa Monica Resort & Spa, located downtown and just steps from Flagler College. This AAA Four Diamond premiere property was built in 1888 and was the county courthouse in the 1960s. It has since received a luxurious face-lift with Spanish-Moroccan inspired design elements applied throughout guest rooms and spacious, multi-floor suites.

where to stay in St Augustine
St. Augustine Lighthouse and Maritime Museum

Where to dine 

One of the town’s most raved about restaurants is The Floridian, an idyllic spot to grab lunch. Find southern favorites like fried green tomatoes, shrimp po boy and a spin on the Cubano. Don’t leave town without a trip to Columbia for a taste of classic Spain with plenty of sangria to go around. For a nightcap, head to the Ice Plant, which is set in a restored factory building that dates back to 1927.

where to dine in St Augustine
Castillo de San Marcos

Where to Explore

11 a.m.

Climb the St. Augustine Lighthouse and Maritime Museum to witness breathtaking views of the city and receive a behind-the-scenes tour. 

1 p.m. 

Discover all of St. Augustine’s offerings by way of the Old Town Trolley Tours. Learn the town’s history while hopping on and off to attractions including the Castillo de San Marcos, Mission Nombre de Dios, the tallest standing wooden “Great Cross,” the Our Lady of Guadalupe Shrine and more.

St Augustine Great Cross
The Chapel of Our Lady of La Leche on the mission grounds

5 p.m. 

Walk along St. George Street, which shows off St. Augustine’s Spanish and British colonial architecture. Explore boutiques, galleries and restaurants while enjoying live band performances. 

8 p.m. 

By nightfall you’ll have heard the talk around town—ghost tours are definitely a thing. With Ghost Tours of St. Augustine, as seen on the Travel Channel and Discovery Channel, the tour departs at 8 p.m. Learn about the spirits who just might still be lingering around town.

Ghost Tours of St. Augustine

Extend Your Stay

Before heading home, book a stay at Hammock Beach Resort on the Palm Coast. Relax along miles of cinnamon-sand beaches (surf lessons are available), at the 91,000-square-foot fantasy pool complex or with a calming spa service. The property features 320 suites with kitchens and one- to three-bedroom villas. Plus, check out Nicklaus- and Watson-designed championship golf courses and a complimentary putt-putt course.

6. Tampa

Getting There

Feel like you’re riding into the clouds on Interstate 275 as you go over the Sunshine Skyway Bridge, which crosses the Tampa Bay and leads to St. Petersburg. It offers four miles of pure water views.

things to do in Tampa
Oxford Exchange’s coffee bar

Where To Stay 

Stay in the heart of the action at Tampa Marriott Waterside. The downtown hotel sits right on the edge of the Tampa Bay, giving water views and easy access to everything located along the riverwalk. Take a refreshing dip in the rooftop pool, grab a drink at one of its multiple restaurants or enjoy live music in the lobby on the weekends.

where to stay in Tampa
Nikita, a lioness at Big Cat Rescue

Where To Dine

Eat like a native—a Native American, that is. Ulele (pronounced you-lay-lee) celebrates local ingredients once used by Florida’s Native Americans, like princess Ulele who lived in the 1500s. Expect dishes prepared on a large barbacoa grill at the restaurant that’s only a water taxi ride away from the hotel. Or, if you want to take in the sunset while eating some of the best seafood in town, head to Oystercatchers for an upscale yet casual evening that will fulfill your reason for vacationing.

where to dine in Tampa
Tampa Marriott Waterside

Where to Explore

10 a.m.

Fit in a morning workout while trying something new with Tampa Bay Water Bike Co. The bikes, designed to float and pedal on water, aren’t as easy to ride as they look. Pedal past the University of Tampa, take in a view of the downtown neighborhood and watch out for a dolphin or two gliding toward the Gulf.

where to explore in Tampa
Ulele’s barbacoa grill


Lovers of books, brunch and aesthetics have to put Oxford Exchange on their lists. The space boasts a restaurant, bookstore, gift shop, 
coffee bar and co-working offices. 

3 p.m. 

We’ve heard of cat cafés in Asia, but how about hanging with lions, tigers and jaguars for the afternoon? Big Cat Rescue, an animal sanctuary and non-profit devoted to rescuing and housing exotic felines, offers day tours showcasing the home of about 70 animals saved from abuse and abandonment. It’s an educational experience that offers up-close-and-personal looks into the wild.

Big Cat Rescue tampa
Ulele’s exterior, set along Tampa’s Riverwalk

8 p.m. 

Is it just us or do drinks taste better when they’re sipped on a rooftop? EDGE Social Drinkery and Luna Lounge at Bulla Gastrobar offer cocktails, wine and beer with sweeping views of the city.

Hit the Beach

If you can’t vacation without the beach, then extend your stay at The Don CeSar located in St. Pete Beach. The iconic “pink palace” is a seaside oasis with six dining options, beach house suites and a spa. This year the property celebrates its 90th anniversary.