Though many tourists visit Florida for Miami’s world-class nightlife or the family-friendly epicenter of Orlando, the state’s Southwest corner offers quieter destinations with more breathing room for sinking into a slower pace.
In Lee County, Fort Myers Beach and the Sanibel and Captiva Islands are ideal for mellow getaways, digital detoxes, or just a relaxation reset. Those destinations and other hotspots like Coconut Point (in Estero), Bonita Springs, and Cape Coral are all within an hour of each other by car, making for stress-free, smaller day trips.
This summer, I destination-hopped through Southwest Florida for an easygoing, unhurried getaway — here’s where to stay, what to do, and top places to eat.
How To Spend Three Days Around Southwest Florida’s Gulf Coast
Where To Stay
If you’re a solo traveler or couple, The Hibiscus House of Fort Myers is a charming small bed-and-breakfast in the River District. If you haven’t stayed at a B & B before, this mother-daughter-owned hideaway will make you a believer. The rooms are cozy and comfortable with thoughtful touches, and the service makes you feel at ease. The home also runs a cafe on the first floor during the day, perfect for grabbing a morning pick-me-up.
Mother-daughter vacationers or bestie duos may also love The Hibiscus House, or a stay at the Hyatt Regency Coconut Point Resort and Spa. The latter is a top choice if you want an upscale escape for a few days. The two-level spa (albeit under renovation until this fall) includes treatment rooms, magnesium vitality pools, and steam and sauna rooms. Ideal for multigenerational groups, the resort has an on-site lazy river, waterpark, outdoor games, and seven restaurant and bar options. Additionally, guests can easily receive help planning off-property excursions, and the Saltleaf Golf Preserve is just next door. Families or friend groups would have a good time there, or at the Margaritaville Beach Resort Fort Myers Beach.
Day 1: Check In And Chill Out
Since this Southwest Florida itinerary is all about prioritizing slow travel and ease, don’t feel like you have to hit the ground running. On arrival, take it easy by resting and relaxing at your hotel of choice. Unpack, settle in, and enjoy the amenities of your stay.
Once you’re ready for some sun and social time, chill poolside or visit one of the region’s many beaches. Your options include Fort Myers Beach, Siesta Key Beach, and Bonita Beach Park, to name a few. But if those options aren’t your vibe, consider visiting a spa as the ultimate kickoff to your trip. You also have the option of hitting up a course for some twilight golf in the afternoon.
For dinner, keep things simple by dining in or near your accommodations.
Day 2: Tap Into Max Relaxation And Restoration
Use day two to make the most of the destination’s natural beauty. Wake up early and try to catch the sunrise. Take a boat on an early cruise before the sun starts beating down, and stop for some shelling at the Sanibel or Captiva Islands. If you’re on a guided tour, they might be able to take you to a more remote spot to treasure hunt for shells. Use the opportunity to enjoy a device-free moment as you walk the beach, focusing on nothing but picking the best shells.
While you’re out on the Gulf’s open water, keep your eyes peeled, as it’s an incredible time for wildlife viewing. You don’t need to be a seasoned bird watcher to spot ospreys, bald eagles, egrets, and pelicans — they’re easy to find. And in the water itself, some manatees and dolphins may swim along. Just don’t forget to pack lunch and some snacks if you’ll be spending hours on the boat.
After freshening up, head to Matanzas On the Bay for dinner. You’ll feast on coastal fare while enjoying beautiful sunset views over the water.
Day 3: Enjoy Downtown Fort Myers/The River District
End your unhurried Southwest Florida itinerary in Fort Myers – more specifically in Downtown and its River District. Have a retro-styled breakfast at Ella Mae’s Diner. The establishment’s proud namesake, Dr. Ella Mae Piper, was a local Black entrepreneur and philanthropist. During her lifetime between the 19th and 20th centuries, she used her passion for community and the success of her entrepreneurship to support churches, fellow business leaders, scholarships, and the building of Dunbar Community School.
After that, have an artsy day and unleash your inner creativity. Visit the Arts For Act Gallery and the exhibits at the Sidney & Berne Davis Art Center. Grab a quick bite to eat at Turo Tacos, then head to Azaleas On The Corner for a wine tasting and art class. And before the sunlight fades, weave in a stop at Centennial Park for waterfront views and great photo ops.
Dinner at Oise Ristorante is a must. The restaurant’s unique and flavorful menu, featuring Japanese and Italian fusion, measures up to its stunning interior. Moreover, the waitstaff is intentional and warmly attentive. Afterward, enjoy a leisurely night stroll in the downtown area. If you’re up for it, do some bar hopping, visit a cigar lounge, or head to Escondido Lounge, a 1920s Prohibition-era-inspired speakeasy.
