All the Feels: Three Days of Adventure
In a destination like Fort Myers, where natural wonders flow seamlessly around unique cultural gems, it’s easy to indulge in your adventurous side. Every waterway, every trail and every beach seems to stand out with something incredible to discover. If you’re searching for the best ideas to push out of your comfort zone, check out this three-day getaway itinerary in Southwest Florida, where a long weekend can turn into your trip of a lifetime.
Day 1
Captivated by Cape Coral
Hundreds of miles of freshwater and saltwater canals meander through Cape Coral, creating an idyllic backdrop where exhilarating adventures await. A vacation rental overlooking a canal is an excellent choice for families and groups of friends, and some even come with the boat included from your own private dock.
Head out for a day of boating adventures, whether that's spotting dolphins (which never fails to surprise and delight), reeling in a prize catch or exploring the area's underwater world. Whether island hopping or bar hopping, you'll discover plenty of places to expand your taste buds' horizons, from the infamous Dollar Bar on Cabbage Key to a variety of food trucks at Slipaway Food Truck Park & Marina, to Next Door at Tarpon Point Marina, which according to Gulfshore Life Food Editor Andrew Atkins, is an experience where you should "...abandon your expectations. There is no point in having them. They will be blown away before you've worked your way through the appetizer."
Excitement on land also awaits at Sunsplash Family Waterpark. Rush down multiple waterslides and try to stay standing in the new 12,000-square-foot Paradise Cove wave pool. A new 16-foot movie screen sets the stage for “dive-in” movie night with the whole family. Or get the party started at Wicked Dolphin Distillery, named the #1 craft rum distillery in the nation by USA Today's 10BEST readers' poll 2025. Enjoy a free tour - tastings included! - and then indulge in some more fruity libations at their Wicked Garden tiki bar.
Day 2
High Adrenaline on Fort Myers Beach
Get ready for thrills on Fort Myers Beach. Follow the wind and water on a parasailing adventure, zip around in a Jet-Ski or gather a group for a banana boat ride. If you’re feeling rowdy, Salty Sam's Pirate Cruise is all about swashbuckling fun. Go on a family cruise or try the adults-only version.
At the base of the bridge, Times Square is filled with lively crowds and endless entertainment. Pop into a beach bar for live music and drinks, wander between food truck favorites, and watch street performers in action. Sunset is an especially spectacular time to gather, with clear views from the beach to see the sun sinking into the Gulf waters. Dine on the patio at Nervous Nellie's on a Sunday night and you'll be treated to a free concert at adjacent Bayside Park.
Feeling really adventurous? Hop aboard the Key West Express and enjoy a day trip to quirky Key West, where the local watering holes are always filled with interesting characters.
Day 3
Thrills in Fort Myers
If you're ready to step out on the town, look no further than downtown Fort Myers. Explore an ever-growing playground of bars and bites, including stylish rooftop bars and speakeasies. Start your night at Oise, where you're sure to taste something for the first time ever. The menu is filled with Executive Chef Brad Kilgore's unique fusion of Japanese and Italian cuisine. Taste and see why he was nominated for a James Beard award and was named a Best New Chef by Food & Wine.
After dinner, stretch your mind even more at a play performed by The Laboratory Theater of Florida, an innovative organization dedicated to taking artistic risks and known for its cutting edge productions.
Venture to the Hertz Arena for a thrilling evening of world-class comedy, concerts and other top national performers. This arena is also home to the Florida Everblades, a professional minor league hockey team who won the Kelly Cup finals three years in a row (2022-2024). They're sure to come back fighting after their near miss as champions in 2025. The action-packed hockey season runs from October through April.
Head to south Fort Myers for a paddle through Bunche Beach Preserve's network of mangrove tunnels with Kayak Excursions. You'll be transported to a magical world with unique creatures at every turn, from scurrying fiddler crabs and leaping mullet to incredible wading birds like the Great Blue Heron and Roseate Spoonbill. In the cooler winter months, you're likely to see manatees swimming near these mangrove forests as well.
Ready to chase new adventures? It just feels right in our islands, beaches and neighborhoods. Explore more itineraries and start planning your trip to Fort Myers today.
