All the Feels: Three Days of Reconnection
Whether you're sharing experiences with your partner on a couples getaway or passing down your favorite memories and traditions on a family vacation, Fort Myers is all about building everlasting connections. Get inspired by ideas in this Southwest Florida itinerary designed to make you feel reconnected. From exploring the beach to dynamic downtowns, it just feels right to spend quality time together.
Day 1: A Day on the Water
Start your day with a swim or a group paddle at Bunche Beach Preserve. It’s stunningly serene, but also leaves plenty of room for playtime. Stick around for the sunset as it sinks over San Carlos Bay and Sanibel Island off in the distance.
Lawless adventures take on a comedic twist on Salty Sam’s Pirate Cruise. Sail into the Gulf on a fun-filled outing, whether you’re looking for swashbuckling fun with kids, an adults-only voyage with a bottle of rum or an all-ages sunset cruise.
Feast on all your favorites right by the marina. Parrot Key Caribbean Grill offers a taste of the Caribbean in Southwest Florida. Share a platter of peel-and-eat shrimp, dive into a basket of fried seafood or swap bites of your entrees while enjoying the waterfront views.
Day 2: Reconnect in the River District
A morning on the shaded boardwalk of Six Mile Cypress Slough Preserve is an invitation to be in the moment. Hear the echoing calls of birds, the occasional rustle of an egret, and enjoy space to reconnect through meaningful conversation or companionable silence.
Toss aside your schedule and go take a stroll through the historic Fort Myers River District. The neighborhood is packed with activities so you connect over shared interests – whether that’s admiring historic architecture and exploring art galleries, carving out time to visit the IMAG History & Science Center, or catching a show at the Florida Repertory Theatre.
From rooftop bars with sweeping river views to buzzing sidewalk cafes, downtown dining and nightlife has offerings to match every craving. A touch of romance awaits at The Veranda — a landmark restaurant housed in a pair of 1900s homes. Engage in meaningful conversation as you enjoy the warmth of the outdoors or the elegant dining room while you indulge in Southern coastal cuisine with an extensive wine list.
Day 3 - Bond on Sanibel Island
Set out for a day of discovery on Sanibel Island’s 25 miles of bike trails. One of the breezier trails is along Periwinkle Way, connecting Lighthouse Beach to Tarpon Bay Road. An easy stop is Periwinkle Place, where the shops are wide open and ready for browsing — pick out some coastal clothing and seaglass-inspired accessories, and grab a bite of casual island cuisine at Blue Giraffe.
Head to Tarpon Bay Beach to enjoy leisurely time together on the sand and in the water. A naturalist-led Kayak Trail Tour is an ideal way to learn about the coastal ecosystem and wildlife as you paddle through the mangrove forest along the Commodore Creek Trail.
Journey north for an unforgettable experience at the newly reopened Bubble Room on Captiva Island. You’ll be talking about the nostalgic and quirky decor in every room, their signature bubble bread and the towering orange crunch cake. Next door is Boops by the Bubble Room, an equally charming space with an old-fashioned soda fountain, Love Boat ice cream and the Bubble Room’s famous cakes.
From reconnecting with your loved ones to sharing unforgettable adventures, all the feels are here. Explore more itineraries, and get ready for it all to Just Feel Right in Fort Myers.
