Living in Southwest Florida means you’re perfectly positioned for incredible day trips in every direction. Within just a few hours, you can snorkel in the Florida Keys, explore rooftop bars in Miami, wander artsy beach towns, or cruise through the Everglades spotting wildlife.
Whether you’re looking for a beach day, a foodie adventure, or a true Old Florida escape, these easy getaways make the perfect excuse to hit the road.
Here are some of our favorite unique day trips from the Naples, Bonita Springs, and Fort Myers area.
Snorkel Islamorada & Spend the Day in the Florida Keys
If you leave Southwest Florida early enough, you can be snorkeling in crystal-clear turquoise water by late morning.
Islamorada is one of the best Florida Keys destinations for a day trip because it gives you that tropical Keys atmosphere without the long drive to Key West. The water is stunning, the boating scene is unmatched, and there’s no shortage of waterfront restaurants to stop at after your excursion.
Book a snorkeling or sandbar trip and spend the day out on the water exploring reefs, spotting tropical fish, and soaking up the sun.
Afterward, grab lunch or dinner at one of Islamorada’s iconic waterfront restaurants like Lazy Days or Lorelei Restaurant & Cabana Bar. Fresh seafood, frozen drinks, and sunset views make the perfect ending to a Keys day trip.
Suggested itinerary:
- Leave Bonita/Naples around 6 a.m.
- Arrive in Islamorada late morning
- Snorkeling or boat excursion
- Waterfront lunch or dinner
- Key lime pie stop before heading home
Spend a Chic Day Exploring Brickell & Downtown Miami
Need a break from beach-town life? Head east for a completely different Florida experience.
Brickell feels modern, energetic, and upscale, with rooftop restaurants, luxury shopping, waterfront views, and endless dining options. It’s the perfect day trip when you want city energy without hopping on a plane.
Start your day at Brickell City Centre before grabbing brunch or lunch nearby. Spend the afternoon walking along the Miami River, stopping at rooftop bars, or venturing into nearby neighborhoods like Wynwood or the Design District.
This trip is especially perfect for:
- Girls’ days
- Date days
- Food-focused adventures
- Shopping trips
The best part? You can experience an entirely different side of Florida and still make it home the same night.
St. Pete: Murals, Rooftops & Waterfront Views
St. Petersburg has quietly become one of Florida’s coolest cities.
It’s artsy, walkable, vibrant, and full of personality. Between colorful murals, waterfront parks, rooftop bars, and museums, there’s enough to fill an entire day without ever feeling rushed.
Start with coffee downtown before exploring the city’s famous mural scene. Visit The Dalí Museum, stroll the St. Pete Pier, or spend the afternoon relaxing at nearby beaches like Pass-a-Grille or St. Pete Beach.
Before heading home, grab sunset cocktails overlooking the water at Pier Teaki or another rooftop downtown.
Suggested itinerary:
- Coffee downtown
- Explore murals
- Visit The Dalí Museum
- Lunch at the pier
- Beach stop
- Rooftop drinks before driving home
Explore Florida’s East Coast Beaches
Florida’s east coast has an entirely different vibe from the Gulf Coast.
The water is brighter blue, the beach towns feel more energetic, and there’s a unique mix of beach culture, nightlife, shopping, and dining.
One of the best ways to experience it is by doing a mini beach-town crawl.
Start your morning in Deerfield Beach before heading north toward Delray Beach to explore Atlantic Avenue’s restaurants, bars, boutiques, and coffee shops. Continue toward West Palm Beach or Singer Island for beautiful beaches and waterfront dining. We love to ogle at the mansions on the A1A!
This makes a great:
- Couples day trip
- Girls’ weekend
- Beach + shopping day
- Spontaneous overnight getaway
Everglades City: A True Old Florida Experience
If you want something that feels worlds away from modern Florida, head to Everglades City.
This tiny waterfront town is packed with Old Florida charm and surrounded by some of the most unique ecosystems in the country.
Spend the day taking an airboat ride, exploring the mangroves, spotting wildlife, or kayaking through the backwaters before stopping for fresh seafood at places like Camellia Street Grill or Triad Seafood.
It’s slower-paced, scenic, and one of the best reminders that Florida still has pockets of untouched beauty.
Loop Road: One of Southwest Florida’s Best Hidden Gems
For an unforgettable Old Florida adventure, spend the day exploring Loop Road through Big Cypress National Preserve.
Loop Road is one of the best hidden gems near Southwest Florida and offers incredible wildlife viewing, fishing, photography, and scenic driving all in one trip.
The road winds through cypress forests, marshes, and remote Everglades landscapes where you’ll regularly spot:
- Gators
- Wading birds
- Turtles
- Deer
- Otters
- Wild hogs
It’s also become a favorite local spot for fishing along the roadside canals. You’ll often see anglers catching bass while massive gators sun themselves nearby.
The drive itself feels like stepping back into old Florida. Some sections are gravel, but most vehicles can handle the road comfortably if driven slowly.
Suggested itinerary:
- Grab breakfast before heading east
- Cruise Loop Road slowly with plenty of stops
- Fish along the canals
- Pack a cooler for lunch
- End the day with dinner in Everglades City or Chokoloskee
If you’re looking for a peaceful day surrounded by nature, this may be one of the most underrated adventures in all of Southwest Florida.
One of the best parts about living in Naples, Bonita Springs, or Fort Myers is that incredible experiences are only a short drive away. Whether you’re snorkeling in the Keys, exploring a rooftop in Miami, wandering the streets of St. Pete, or spotting gators deep in the Everglades, Florida is full of unforgettable adventures waiting just beyond Southwest Florida!
