Explore Southwest Florida's Nature and Historic Charm in Two Days

From kayaking through mangrove tunnels to touring a 2,000-year-old Calusa shell mound, this itinerary showcases the best of Fort Myers and beyond.

Published on Feb. 24, 2026

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Discover the natural wonders and historic sites of Southwest Florida with this two-day itinerary. Explore Sanibel Island's famous shelling beaches, paddle through the 'Ding' Darling National Wildlife Refuge, and tour the Mound House to learn about the region's indigenous Calusa tribe. Then head to Fort Myers Beach, Bonita Springs, and Boca Grande to experience the area's charming small-town vibes, local cuisine, and world-class tarpon fishing.

Why it matters

Southwest Florida is known for its stunning natural beauty, from pristine beaches to lush mangrove forests. This itinerary highlights the region's diverse ecosystems and rich history, providing visitors with an immersive experience that goes beyond the typical tourist attractions.

The details

The two-day itinerary starts on Sanibel Island, where visitors can search for the 'Sanibel Six' seashells at Bowman's Beach, then fuel up on brunch classics at Over Easy Cafe. Next, they'll explore the 'Ding' Darling National Wildlife Refuge, a sanctuary for migratory birds, by foot, bike, car, tram, or kayak. After indulging in a slice of the iconic Orange Crunch cake at the Bubble Room on Captiva, they'll visit the Bailey-Matthews National Shell Museum & Aquarium. The second day takes them to Fort Myers Beach, Estero Island's Mound House, Lovers Key State Park, and the Wonder Gardens in Bonita Springs, before ending the trip with world-class tarpon fishing in Boca Grande.

  • The best time to visit Southwest Florida is from November to April, when the weather is cool, dry, and minimally humid.
  • Summer is also a great time to visit, with lower prices and fewer crowds, though the region does see afternoon thunderstorms during this season.

The players

Annabelle Tometich

A writer and author who has always called Southwest Florida home, Tometich spent 18 years as a journalist, food writer, and restaurant critic for the Fort Myers News-Press. Her first book, 'The Mango Tree: A Memoir of Fruit, Florida, and Felony,' won the Southern Book Prize for Nonfiction in 2025.

J.N. 'Ding' Darling National Wildlife Refuge

A world-famous sanctuary for migratory birds and part of the largest undeveloped mangrove ecosystem in the U.S.

Bubble Room

An iconic restaurant on Captiva Island known for its giant, decadent cakes, including the signature Orange Crunch.

Bailey-Matthews National Shell Museum & Aquarium

A museum on Sanibel Island that houses a collection of more than 600,000 shells from throughout the world and the centuries.

True Tours

A company that offers ghost tours, history tours, and sightseeing excursions in downtown Fort Myers, sharing the rich history of the area.

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What they’re saying

“We native to the islands, beaches, and neighborhoods of Fort Myers like to say that we live where everyone else vacations.”

— Annabelle Tometich

What’s next

Visitors can continue exploring Southwest Florida by booking a charter to go tarpon fishing in Boca Grande, a world-class destination for the sport.

The takeaway

This itinerary showcases the diverse natural beauty, rich history, and charming small-town vibes of Southwest Florida, providing visitors with an immersive experience that goes beyond the typical tourist attractions.