Things to Do in Ft. Myers
You're not just staying in Fort Myers. You're staying in the heart of it.
Cracker Cow Cottages sits in the Historic River District, one of Southwest Florida's most walkable, vibrant, and storied neighborhoods. The Caloosahatchee River runs alongside it, the same river that drew Thomas Edison and Henry Ford to spend their winters just blocks from where you'll be sleeping.
Today the River District is a thriving mix of historic architecture, waterfront dining, craft cocktails, local boutiques, and a genuine sense of community that the resort strips and chain hotels simply can't replicate. On any given week you might stumble into a farmer's market under the bridge, an evening Art Walk, a live concert at Centennial Park, or a ghost walk through streets that have more than a few stories to tell.
This is a neighborhood worth exploring. Here's where to start.
Right Outside Your Door
Centennial Park — Right on the river. Live concerts, open green space, and some of the best sunset views in Fort Myers.
Coastal Dayz Brewery — A laid-back local brewery worth an evening. Great beer and good people.
The River District — Dining, shopping, live music, and history all within a short stroll. myriverdistrict.com has the full rundown.
Publix — For the essentials!
Where to Eat
Fort Myers' Historic River District has quietly become one of Southwest Florida's best dining neighborhoods. From a James Beard nominated kitchen to a slice of Brooklyn on Second Street, there's something worth sitting down for every night of your stay.
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2262 First Street
If you're going to splurge once this trip, make it here. Chef Brad Kilgore — James Beard nominated — blends Japanese and Italian cuisines in a way that shouldn't work but absolutely does. Reserve ahead.
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2200 Edwards Drive at the Luminary Hotel
An open kitchen, outdoor seating, and some of the freshest seafood in the district. Farm to table done right, right on the water.
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2122 Second Street at Broadway
One of Fort Myers' most beloved institutions. Two historic homes connected by a lush courtyard, serving elevated Southern cuisine that's been drawing locals for decades. Go for a special occasion or just because.
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2214 Bay Street
Down-home Southern cooking done with care. The kind of place that makes you slow down and order dessert even when you said you wouldn't.
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2224 Bay Street
Four floors of history and a rooftop that earns the climb. A Fort Myers landmark with great food and even better views.
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1300 Hendry Street
Right on the water with the kind of laid-back energy that reminds you you're in Florida. Perfect for a long lunch or a casual dinner watching the river go by.
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2200 Edwards Drive at the Luminary Hotel
The best breakfast in the district, full stop. Get here early on weekends — locals know about this one.
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2207 First Street
Handcrafted burgers, cold beer, and a garage theme that's more fun than it sounds. A crowd pleaser for families and groups.
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2282 First Street
Fresh Gulf seafood in a relaxed setting. Great oysters, great happy hour, great excuse to stay for another round.
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2112 Second Street
Cozy brick-walled dining with a Brooklyn soul in the heart of Fort Myers. Don't miss the upstairs dessert bar.
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1520 Hendry Street
Scratch-made pizza, made fast. Simple, satisfying, and exactly what you want after a long day at the beach.
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527 Hendry Street
A neighborhood staple with a relaxed vibe and a menu that hits the spot every time.
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2736 Edison Avenue
A Fort Myers institution that's been feeding locals longer than most places have been open. Classic comfort food with genuine history behind it.
Where to Drink
Whether you're in the mood for a craft cocktail on a rooftop, a cold beer under the stars, or a tequila in a speakeasy you had to find first — the River District has a night out for every kind of traveler. This neighborhood knows how to have a good time without trying too hard.
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2200 Edwards Drive — top of the Luminary Hotel The highest perch in the River District with Caloosahatchee River views to match. Elevated cocktails, a stunning space, and the kind of sunset that makes you book another night.
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Look for the hidden entrance — that's part of the fun. Once you find it, settle in for exceptional tequila, light bites, and the satisfaction of knowing not everyone does.
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The outdoor spot the River District didn't know it needed. Live music, wide screen TVs for the game, high end food trucks, and open air energy that's hard to leave. Great for groups.
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1406 Hendry Street
Handcrafted cocktails, great wines, draft beers, and shareable plates in a setting that feels both relaxed and refined. A solid go-to for any night of the week.
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2226 First Street
Fresh Mex, strong margaritas, and a lively atmosphere that gets going early and stays that way. Perfect for a casual night out.
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Located in Patio De Leon A social craft beer spot tucked into one of the River District's most charming outdoor spaces. Pull up a chair, order something local, and stay awhile.
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2225 First Street
Coal fired pizza and cold drinks in a setting with personality to spare. A great spot to land after a long day.
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2224 Bay Street
Four floors of history topped off with one of the best rooftop bars in Fort Myers. Worth going back to for drinks even if you already ate here.
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8502 Hendry Street
It calls itself world famous and nobody's arguing. A Fort Myers institution for a reason. Come for a cigar, stay for the stories.
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Right down the street from the cottages — because sometimes the best bar is the one you can walk home from.
Coffee & Bakeries
Fort Myers' independent coffee scene punches well above its weight. Every one of these is locally owned, thoughtfully run, and worth the detour.
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2011 Bayside Pkwy
Certified organic coffee, house-made syrups, freshly baked goods, and a warm, unhurried atmosphere right in the heart of downtown. The kind of place you walk into for a coffee and stay for an hour. A brand new gem and already a neighborhood favorite.
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2400 First Street, Suite 104
Raw juices, smoothies, organic coffee, vegan meals, and açaí bowls — all locally sourced and thoughtfully made. Great for guests who eat clean without wanting to compromise on flavor. Don't miss the salads and wraps.
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2281 Main Street
A community-first coffee shop rooted in locally sourced beans and genuine hospitality. Simple, intentional, and consistently excellent. One of the best spots in the district to slow down over a really good cup.
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1520 Broadway, Suite 107
Florida's first CBD marketplace — but don't let that overshadow the genuinely great coffee, craft beer, food, and good-vibes atmosphere. A one-of-a-kind spot that's very much Fort Myers.
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4125 Cleveland Ave
A cozy hidden gem tucked inside Edison Mall with homemade pastries, Cuban coffee, and a vintage atmosphere that makes it feel like a discovery. Worth the short drive.
Shopping & Local Experiences
The River District isn't just a place to eat and drink, it's a neighborhood worth wandering. Independent boutiques, local makers, a non-profit gallery, and a flower bar where you can build your own bouquet.
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2200 First Street
One location, over 100 shops across two floors — fashion, jewelry, art, home décor, handmade goods, and everything in between. A two-story emporium built into a beautifully restored 1937 building. The number one shopping stop in the River District and easy to lose an afternoon in.
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1414 Dean Street
An elevated bohemian gift shop with a soul. Every item is hand-selected — crystals, jewelry, candles, home décor, and gifts for people who appreciate something with originality. One of the most distinctive shops in downtown Fort Myers.
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2281 First Street
Consciously sourced apparel, natural body care, crystals, art, and locally made products. A calming, beautifully curated space for those drawn to holistic wellness and thoughtful gifting.
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2273 First Street
USA-made coastal soaps, body butters, bath bombs, cleansers, and serums, all in a fun, sensory shopping experience. Perfect for gifts or stocking up for the rest of your trip.
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1518 Jackson Street
A mother-daughter run boutique with a thoughtfully curated collection of women's clothing, from casual chic to elegant. Known for personalized service and finding you the perfect piece.
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1516 Jackson Street
Build your own bouquet, browse dried herbs, teas, and biodegradable greeting cards embedded with wildflower seeds. A one-of-a-kind shop that feels as good to be in as it does to shop.
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2265 First Street — Arcade Building
An award-winning non-profit gallery showcasing over 50 local artists in a stunning SoHo-style space with 12-foot ceilings, distressed brick walls, and creaky wooden floors. A must-see.
Don't Miss These Regular Events:
The River District comes alive on a regular rhythm — check myriverdistrict.com for current dates and schedules!
Weekly Farmer's Market
Fresh local produce, vendors, and community under the bridge
Art Walk
First Friday of every month. Galleries open late, artists on the streets, shops buzzing
Music Walk
Third Friday of every month. Live performances and strolling musicians throughout the district
Centennial Park Concerts
Free outdoor concerts on the river. One of Fort Myers' best kept regular events
Edison & Ford Winter Estates Tours
Step inside the winter homes of two of America's greatest minds, just minutes from your cottage
Ghost Walks
The River District has stories. Some of them are best heard after dark
Getting Around
One of the quiet perks of staying in the Historic River District is that you may not need your car as much as you think. Dinner, drinks, coffee, shopping, live music can be found on foot from the cottages. But when you're ready to venture out to the beaches, the Everglades, or beyond, here's how to get there.
Getting Here
Southwest Florida International Airport (RSW) — 16 miles, roughly 20 minutes
Punta Gorda Airport (PGD) — 25 miles, a good option for budget carriers
Rental Cars
Budget — 2807 Fowler St & RSW Airport
Enterprise — 905 Boy Scout Dr
Taxis & Ride Share
Southwest Florida Transportation Group — 239-275-TAXI
Uber and Lyft are both active in Fort Myers
Public Transit
LeeTran — Lee County's bus system with 20 routes and 1,467 stops throughout the area. Track schedules and departures in real time on the Moovit app.
Bike Rental (a great way to explore the River District)
Pedego Electric Bikes — 2059 Altamont Ave
Fort Myers Schwinn — 3630 Cleveland Ave
Golf Cart Rental
Island Carts — Looking for an even easier way to get around? These street legal golf carts are the way to go! Island Carts make it easy and fun, and will even drop off and pick up the carts for you! Advice from Fort Myers Police Department: always have your license on you and park in a parking spot!
Please note: I’m not affiliated with any of these companies or services.
Beaches
The Gulf Coast beaches of Southwest Florida are some of the most beautiful in the country — warm water, soft sand, and enough variety to fill an entire trip. For more details, check out the official beach website.
Fort Myers Beach
15 miles from the cottages
The classic Gulf beach experience. Soft white sand, warm turquoise water, and a lively strip of dining and bars nearby. Great for a full beach day with everything you need within reach. Go on a weekday if you want a little more breathing room.
Bowditch Point Park (Hidden Gem)
North tip of Fort Myers Beach
One of the best kept secrets on the island. Tucked at the quiet northern end of Fort Myers Beach, Bowditch offers stunning sunsets, dolphin sightings, and excellent shelling without the crowds. Parking is remarkably affordable at around $2–3. Worth the trip every time.
Lovers Key State Park (Best All-Around)
Just south of Fort Myers Beach
If you only make it to one beach, make it this one. Just $8 per car gets you an uncrowded stretch of stunning Gulf beach, kayak rentals, nature trails, wildlife watching, snorkeling, and a shuttle to the sand. One of Southwest Florida's most complete outdoor experiences.
Lighthouse Beach Park — Sanibel Island (Shelling)
The gateway to Sanibel's world-famous shelling scene. Calm, clear water, a beautiful historic lighthouse, and some of the best conditions for finding shells on the island. This is where the famous Sanibel Stoop begins — the hunched-over shuffle of every shell hunter on the lookout for their next perfect find.
Bowman's Beach — Sanibel Island (Best Shelling on the Island)
Considered one of the finest shelling beaches in the world. Whelks, tulips, and dozens of species wash up here regularly. Less crowded than the lighthouse end of the island, more rewarding for serious shellers. Set aside a few hours and bring a bag.
Turner Beach — Captiva Island (Sunsets & Shelling)
Captiva's iconic sunset beach. Come in the late afternoon, find a spot in the sand, and watch the Gulf put on a show. Excellent shelling with over 30 species spotted regularly, plus casual dolphin sightings that never get old. A perfect way to end any day. (Check out Captiva’s South Seas Resort and Tween Waters — a day pass gives you access to parking, beach access, restaurants, pools and shops! Contact each resort for more details.)
Looking for lounging and pool time? Here are some past guests favorite options!
Brightwater Lagoon in North Ft. Myers
The Luminary Hotel in the River District
Adventures
Fort Myers is the perfect jumping-off point for some of Southwest Florida's most unforgettable experiences. The water, the wilderness, and the wide open Gulf are all within easy reach.
On the Water
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One of the more quietly unforgettable things you can do in Southwest Florida. The historic fish shacks off Pine Island sit on stilts over the water — paddling around them at sunrise or sunset is the kind of experience that doesn't photograph well but never leaves you.
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A local outfitter running guided eco tours through the mangroves with dolphins, manatees, and birds around every bend. Great for all skill levels and one of the best ways to see the real Florida that most visitors never find.
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The area's premier tour company covering just about everything — dolphin cruises, shelling trips to Cayo Costa, sunset sails, and fishing charters. Book in advance during season. Worth it.
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Rent a kayak or canoe at the visitor's center and slip into the mangroves. Egrets, herons, roseate spoonbills, and kingfishers are waiting around every bend. One of the top wildlife experiences on Sanibel and genuinely spectacular any time of year.
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The largest expanse of primordial wilderness between Naples and Marco Island. Take a guided kayak tour through mangrove tunnels, small hidden bays, and across active mud flats — or a guided boat tour to hidden spots on the Bay. Wild, remote, and worth every paddle stroke.
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There's no better way to experience the Florida Everglades than gliding across the water on an airboat. Several excellent operators on the western side of the Everglades south of Naples will give you the thrill of the visit while educating you on the wildlife and waters of the Glades.
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The western portion of the Everglades has excellent campgrounds for both RVs and tent campers. Some are accessible only by guided kayak tour — you paddle in and camp on the sand. Others are open to the public year-round.
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In Florida there's fishing, and then there's fishing for tarpon in Boca Grande — the self-proclaimed Tarpon Fishing Capital of the World. If you fish, this belongs on your bucket list. If you've never fished, this might be the trip that changes that.
Beyond the Shoreline
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Florida's only warm mineral spring sits at a consistent 85°F year-round. With a high mineral content the spring is considered therapeutic and offers a genuinely unique passive recreation experience. A worthwhile detour for something completely different.
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The Peace River in Southwest Florida is a virtual graveyard for prehistoric creatures. Fossils of the giant megalodon — the carcharodon shark that grew to 55-60 feet — have been found here. Rent a canoe or kayak, take a tour with an experienced fossil hunter, or wade the shallows on your own. Open year-round.
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A 90-minute tour through four unique Florida ecosystems including the Telegraph Cypress Swamp. Wildlife sightings are plentiful and you'll get a close look at the Florida Cracker cattle — one of the oldest and rarest breeds in the United States. A genuinely special experience that connects you to the history of this land.
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Dating to 1893, this fascinating site preserves what remains of an intrepid community — mostly women — who settled here at the turn of the 20th century. They followed an eccentric New York physician, believed in the Hollow Earth theory, and built their New Jerusalem in Southwest Florida. Strange, compelling, and completely worth an afternoon.
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Take the water taxi from Pine Island Marina out to Cabbage Key — a tiny island off the coast accessible only by boat. The Dollar Bar Saloon is already legendary before you arrive. Good food, cold beer, a fun crowd, and the kind of rustic coastal atmosphere that only exists in places like this.
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It doesn't happen every night, but when it does you'll never forget it. The Green Flash is an elusive optical phenomenon that appears at the exact moment the sun dips below the horizon. The Green Flash Waterfront restaurant on Captiva is the place to be — enjoy a meal dockside as you anticipate the moment. And if it eludes you tonight, there's always another sunset guaranteed tomorrow.