Planning the Ultimate Florida Road Trip: What to See and What to Wear
- adriana
- 4 days ago
- 4 min read
Updated: 2 days ago
Photo Credit: Image by StarZImages from Getty Images Signature
There’s something magical about packing up the car, rolling the windows down, and hitting the open road, especially when your destination is somewhere as iconic and colorful as Florida. It doesn’t matter if you're a local Miamian or a visitor ready to experience all that Florida has to offer, a well-planned road trip can be the perfect adventure.
If you want to truly enjoy the journey, it’s all about smart planning - what to see, where to stop, and yes, what to wear. Florida’s road trip vibes are all about comfort, style, and being ready for anything.
Start in Miami: Where the Sunshine Begins
Kick off your Florida road trip in the vibrant heart of South Florida, Miami. This city is a cultural melting pot packed with energy, flavor, and color. Grab a pastelito and cafecito in Little Havana before cruising down Ocean Drive for that classic beach-glam moment.
What to Wear in Miami
Think light layers and bold colors. A stylish tank, flowy shorts, and sunglasses are your best friends here. If you’re strolling through Wynwood or grabbing drinks in Brickell, don’t be afraid to rock a stunning outfit. It’s Miami, after all.
Photo Credits: Image by Lunamarina
Stop 1: The Florida Keys
From Miami, head south toward the Florida Keys. Take the scenic drive over the Overseas Highway and let the ocean views set the tone. Key Largo, Islamorada, and Key West each have their own charm, from watersports and tiki bars to Hemingway-inspired charm.
Must-See Spots
John Pennekamp Coral Reef State Park: Snorkel among tropical fish.
Islamorada: Perfect for a seafood lunch and a paddleboard session.
Key West: Visit the Southernmost Point and enjoy the island’s famously laid-back vibes.
What to Wear in the Keys
Easy-breezy is the theme here. Lightweight fabrics, breathable swimwear, and sandals will take you from kayak to dinner. Throw a pashmina or wrap in the car for those surprise breezy moments by the water.
Photo Credits: Image by Jorge Tapia2021 from Getty Images
Stop 2: The Everglades
Heading back up, make a detour through Everglades National Park for a totally different vibe. Here, it’s less about beach scenes and more about getting a peek at Florida’s wild side.
Must-See Spots
Shark Valley: Rent a bike or hop on the tram for gator sightings.
Anhinga Trail: A short but scenic hike with serious wildlife payoff.
Airboat Tour: Yes, it’s touristy but also thrilling.
What to Wear in the Everglades
Light, breathable activewear and sturdy sneakers are key. Don’t forget bug spray and a hat to protect you from both the sun and the occasional mosquito party.
Photo Credits: Image by ore by typhoonski from Getty Images
Stop 3: Naples and Sanibel Island
Drive west and you’ll hit the Gulf Coast, starting with Naples, a sophisticated beach town known for its beautiful sunsets and chill atmosphere. From there, head to Sanibel Island, a shell-hunter’s paradise with uncrowded beaches and no high-rises in sight.
Must-See Spots
Naples Pier: Perfect for a sunset photo op.
Sanibel Lighthouse Beach Park: Great for shelling and laid-back vibes.
J.N. “Ding” Darling National Wildlife Refuge: Nature lovers, this one’s for you.
What to Wear on the Gulf Coast
On this stretch, channel relaxed resort vibes. Think oversized linen shirts, comfy sandals, and bikinis underneath for impromptu swims. It’s the perfect spot to show off your personality with fun accessories or a bright bikini piece from Scummy Bears — their festival-inspired clothes are surprisingly versatile for beach days.
Photo Credits: Image by Kasra Keighobady from Getty Images
Stop 4: Tampa to St. Pete
Heading north, stop in Tampa for a mix of urban fun and waterfront charm. Then swing over to St. Petersburg for laid-back beach culture and one of Florida’s coolest art scenes.
Must-See Spots
Ybor City in Tampa: Cuban history, vintage shops, and hand-rolled cigars.
The Dalí Museum in St. Pete: Surrealist art meets waterfront views.
Pass-a-Grille Beach: A quiet, underrated gem for sunset lovers.
What to Wear in Tampa and St. Pete
This stretch of the trip is ideal for flexible looks that can go from museums to beach bars. Bring something that lets you play up your individuality. Something edgy, colorful, or layered.
Stop 5: Orlando and Central Florida
Sure, you know Orlando as theme park central, but the city also has growing culinary and nightlife scenes that locals love. And the road trip vibe doesn’t have to stop once you park.
Must-See Spots
Walt Disney World or Universal Studios: Obvious, but still iconic.
Lake Eola Park: Rent a swan boat or catch a Sunday market.
Winter Park: A charming nearby town with boutiques and galleries.
What to Wear in Central Florida
Orlando weather is notoriously humid, so lightweight clothes are a must. Choose outfits that can handle lots of walking, indoor air conditioning, and outdoor heat. And don’t forget to bring an outfit change in the car if you plan on grabbing dinner somewhere trendy after a long park day.
Final Stop: St. Augustine
Round out your trip by heading northeast to St. Augustine, the oldest city in the U.S. It’s rich with history, cobblestone streets, and Spanish colonial vibes. After all the beachy stops, it’s a great change of pace to wind down.
Must-See Spots
Castillo de San Marcos: Explore centuries-old stone forts.
St. George Street: Pedestrian-only shops, galleries, and cafés.
Vilano Beach: Quieter and a bit rugged — perfect for sunset watching.
What to Wear in St. Augustine
A flowy maxi dress or button-down linen shirt fits the historic-meets-coastal vibe of this city. Comfort is still key, but a touch of old-world charm doesn’t hurt here either.
Final Thoughts
From sun-kissed beaches and historic towns to hidden gems off the beaten path, Florida has a little bit of everything. With the right itinerary and the right outfits, you’ll be ready for spontaneous detours and that unbeatable road trip freedom.
What you wear should reflect both comfort and character. So fuel up, cue your road trip playlist, and let the Sunshine State guide your next great adventure.