As a road trip junkie, I design my trips to offer a well-balanced blend of beach, culture and nature.
This 14-day solo road trip, which explored five destinations, started and ended in Miami, providing me with opportunities to experience Florida’s east and west coasts, the Keys, and a central city gem.
Here are my recommendations for things to do, places to eat, and places to stay on this 425-mile journey, including Delray Beach, Islamorada, Lakeland, Tampa, and Miami Beach.
Portions of this trip were hosted and are listed at the end. All opinions expressed are entirely my own.
Route Overview
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Stop 1: Delray Beach
Delray Beach, aka “The Village by the Sea”, offers small-town vibes with amenities found in bigger cities.
You can walk everywhere, but on hot, humid days, the Freebee, an on-demand ride-share service, transports you between the beach and Pineapple Grove Arts district.
What Not To Miss:
- Wakodahatchee Wetlands – Nature lovers and photographers will love the birdwatching, alligator spotting, and serene wetlands. I didn’t spot any alligators, but read the signs and heed the parking instructions or risk the ire of other visitors.
- Delray Municipal Beach – Beach and water lovers find watersports, sunbathing, and this beach relaxing. Be sure to rent a beach chair to secure your personal belongings.
- Pineapple Grove Arts District – Public art, boutique shopping, and galleries draw visitors to this lively spot. Cruise in your convertible to show off.
- Silverball Retro Pub & Arcade – Two floors of loud, lively, and colorful arcade games offer countless pinball machines, Skeeball alleys, Wiffle Ball, and more. Because of the noise level, they even provide earplugs.
Best Place To Stay:
The Ray Hotel Delray Beach, Curio Collection by Hilton, offers luxury lodging near the Pineapple Grove Arts District. I walked to the main drag, Old School Square Park, and many restaurants.
Read my review here for more great places to stay in Delray Beach.
Great Places to Eat:
- Campi at The Ray Hotel – The steak and seafood dinner was amazing – every course, from the bread to the antipasti and salad, was delicious.
- Lulu’s – The charcuterie board and fresh seafood come highly recommended.
Stop 2: Islamorada
Islamorada, nicknamed the “Purple Island” because of the violet-tinged sunsets, sits in the heart of the Florida Keys. Famous for world-class sport fishing, vibrant coral reefs, and a laid-back atmosphere, it draws visitors year-round. It is a perfect place for anglers, divers, and boating enthusiasts who love “island time” as much as I did.
What Not To Miss:
- Rain Barrel Village – An iconic arts and crafts destination. I had to capture a selfie with Betsy the lobster.
- Florida Keys Brewing Co. – Try the sample flights, which showcase the microbrewery’s tropical craft beers in a fun atmosphere.
- Florida Keys Food Tour – Discover local cuisine and history with expert guides. We learned how to blow the conch (pronounced “konk”) shell, enjoyed authentic Key Lime Pie, and boarded the full-scale replica of Ernest Hemingway’s boat, Pilar, at the Worldwide Sportsman store.
- Florida Keys History and Discovery Center – Exhibits featuring piracy, hurricanes, shipwrecks, early settlers, and progress in the Keys in a cool, upscale interior.
Best Place to Stay:
Casa Morada – A boutique hotel with luxurious suites and a private island. Casa Morada, in the heart of Islamorada, offers boat excursions and beach activities for guests seeking adventure or relaxation.
I enjoyed the view of the Gulf from the Starfish Suite and the balcony while sampling the breakfast buffet.
Great Places to Eat:
- Lorelei Restaurant & Bar – Waterfront dining known for its fresh fish dip and conch chowder. I sampled my first conch here. (Pronounced “konk”).
- Pierre’s – Fine dining boasts stunning sunset views. Choose a seat on the oceanfront balcony or settle inside, like I did, to watch the spectacular sunset through the windows.
Stop 3: Lakeland
Lakeland, a city between Tampa and Orlando known for its beautiful lakes, is an excellent destination for outdoor water activities or strolling in the historic downtown area.
What Not To Miss:
- Florida Southern College – Home to the most extensive Frank Lloyd Wright architecture collection, offering in-depth tours of the buildings and grounds. I found the final project of his life absorbing.
- Bonnet Springs Park – This family-friendly park offers outdoor adventures, nature trails, and a tram with scheduled stops around the property.
- Circle B Bar Reserve – Wildlife viewing with alligator sightings and countless birds. The entrance, with its moss-covered trees, impressed me.
- Bok Tower Gardens—This National Historic Landmark with beautiful gardens boasts a world-famous carillon, which filled the air with magical sounds that followed me throughout the property.
- Downtown Lakeland & Munn Park – I loved strolling this historic district along charming brick-lined streets, exploring shops and restaurants.
- Living Water Boat Cruises, Winter Haven – Chain of Lakes boat tours navigate 24 interconnected lakes, including historic Cypress Gardens, now Legoland.
Best Place to Stay:
Home2Suites by Hilton – Conveniently located near major attractions, this budget lodging works well for families and solo female travelers. I appreciated the laundry facilities for guests.
Best Places to Eat:
- Grillsmith – This popular eatery is close to Home2Suites and offers delicious signature steaks and craft cocktails.
- Nineteen61 – The upscale service and ambiance blended well with the friendly patrons. They specialize in Latin American cuisine.
- Harborside – Our boat cruise began and ended at the dock, where we enjoyed lakeside seafood dining with sunset views and traditional seafood dishes.
Stop 4: Tampa
Tampa, on Florida’s Gulf Coast, has many waterfront attractions. In the early 1800s, it was a U.S. Army fort and then a Confederate stronghold. The 1880s railroad boosted its economy and cigar production.
What Not To Miss:
- Tampa Riverwalk – 2.6-mile scenic path with dining, entertainment, and attractions. Take a Smartphone Audio Walking Tour.
- Ybor City – Ybor City, once the “Cigar Capital of the World,” is a lively historic district with Cuban cuisine and nightlife. I spent a delightful hour entertained by the professional tour guide cum manager of a cigar store.
- Florida Aquarium – One of the best aquariums in the U.S.
- Amalie Arena – Hosts the Tampa Bay Lightning, concerts, and other events. It is within walking distance of the Tampa Downtown
Hilton . - TECO Line Streetcar – I explored Tampa on the free trolley, from downtown through the Channel District to Ybor City.
Best Place to Stay:
Hilton Tampa Downtown – Central location with modern amenities and great dining in the hotel.
Best Place to Eat:
The
211 Restaurant at
Stop 5: Miami Beach
Miami Beach, a barrier island east of Miami, is known for its luxurious waterfront mansions, historic hotels, and stunning views of Biscayne Bay and the Atlantic Ocean.
What Not To Miss:
- Miami Beachwalk – The 9-mile Miami Beachwalk is a pedestrian and biking path along the Atlantic coast, connecting South Pointe Park to North Beach.
- South Beach – Art Deco buildings, palm-lined streets, and Muscle Beach were fascinating.
Best Place to Stay:
Hilton Cabana Miami Beach Resort – Hotel on Millionaire’s Row in Miami Beach with a private beach, two pools, and complimentary bike rentals.
Best Places to Eat:
Why go anywhere else when you can get the freshest, most interesting, and 3-dimensional meal?
- Allison Restaurant & Bar at
Hilton Cabana Miami Beach Resort – Great Cuban food and drinks. I love three-dimensional meals, and this did not disappoint. - Coffee House at
Hilton Cabana Miami Beach Resort – I enjoyed a delicious bagel and lox breakfast with freshly brewed coffee at the Coffee House.
Safety Tips for Solo Female Travelers
I followed these safety tips on my solo road trip from Miami to Tampa:
- Drive only during daylight hours – I make this a habit whether visiting a new destination or driving around my hometown.
- Book hotels with 24-hour front desks, ensuring a safe and easy check-in.
- Pack a small cooler – I always carry water and snacks in case of emergency, especially in hot climates like Florida during the summer.
- Use valet parking when available. It adds security, especially in large cities like Miami and Tampa.
- Stick to the main highways (I-95, I-75, and US-1) and avoid unfamiliar back roads, especially at night.
- Plan your fuel stops. Find busy, well-lit areas. Few gas stations serve the Overseas Highway.
- Avoid walking on beaches alone at night. Stick to well-lit and populated areas.
Best Time of Year to Take A Road Trip from Miami to Tampa
Late fall through early spring offers the ideal window for a Florida road trip. Unseasonably cold and windy weather surprised me and the locals during my winter visit. Skip hurricane season, which runs from June through September.
Comped
Hilton Hotels, Casa Morada, Visit Central Florida, Circle B Bar Reserve, Bok Tower Gardens, Living Water Boat Cruises, Florida Southern College, Grillsmith, Nineteen61, Harborside
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