Day Trip: Edison & Ding — Fort Myers in a Day
~60 miles south, about 1 hour
Head south on US-41 through the Tamiami Trail corridor and cross the bridge into Fort Myers. The morning belongs to the Edison & Ford Winter Estates — 21 acres of riverfront grounds where Thomas Edison tended what was once the world's largest private botanical garden.
Afterward, cross the causeway to Sanibel Island, one of the finest shelling beaches in North America. Bowman's Beach, on the island's quieter western end, is worth the extra drive. On the way back, stop at J.N. "Ding" Darling National Wildlife Refuge for a late-afternoon tram or kayak tour through mangrove tunnels teeming with roseate spoonbills.
Where to eat: Ford's Garage for lunch, Doc Ford's Rum Bar for a sunset drink, Blu Sushi if you want to linger into the evening.
Tips: Leave Sarasota by 8am. Check the Sanibel Tide Chart app — low tide is best for shells. The causeway backs up on weekends, so a weekday works better.
2-Day Trip: Naples & the Everglades Edge
~100 miles south, about 2 hours
Drive south through Fort Myers and settle into Naples for the night — one of Florida's most polished small cities, where Fifth Avenue South delivers good restaurants within walking distance of the Gulf. Spend your first afternoon at Naples Pier and the Baker Museum at Artis-Naples.
Day two, push east on US-41 into Big Cypress National Preserve and the Fakahatchee Strand, a primordial swamp where ghost orchids bloom and Florida panthers still roam. The Clyde Butcher Big Cypress Gallery — a working studio inside the preserve — is a worthwhile stop for anyone interested in Florida's wild interior. End the day with an airboat ride at Everglades City before looping back north.
Where to eat: Campiello for dinner on night one, USS Nemo for fresh seafood, Stan's Idle Hour in Goodland if you want something more local and strange.
Where to stay: Inn on Fifth (Naples) puts you walking distance from everything. Note: summer rates drop significantly and the crowds thin out — an underrated time to go.
7-Day Loop: Keys to Crystal River
~600 miles, circular route
This is the full journey — a counterclockwise loop through the region's wildest corners.
Day 1 — Marco Island: Drive south through Fort Myers to Marco Island, a barrier island with a fishing-town feel and some of the best shelling on the Gulf coast.
Days 2–3 — The Everglades & Florida Keys: Push into the Everglades via Flamingo, then take Card Sound Road (the toll road most people skip) into Key Largo. It's one of Florida's most scenic drives. Spend two nights in Key Largo or Islamorada — snorkeling, dive shops, and stone crab at sunrise. Dinner at Marker 88 on the water.
Day 4 — Big Cypress & Corkscrew Swamp: Cut north and spend the morning at Corkscrew Swamp Sanctuary, an ancient cypress cathedral managed by Audubon. The boardwalk feels like walking through deep time. Then push toward the Tampa Bay area for the night.
Day 5 — St. Petersburg & Tampa: A 90-minute detour to the Dalí Museum in St. Pete is worth every minute. Dinner on the Tampa Riverwalk at Bern's Steak House, if you're into that kind of thing (you should be).
Days 6–7 — Tarpon Springs & Caladesi Island: Loop back through Tarpon Springs, a Greek sponge-diving community unlike anywhere else in Florida. Stop at Hellas Restaurant for lunch. Then drive south along the Suncoast and finish with a swim at Caladesi Island — routinely ranked among the best beaches in the country — before heading back to Sarasota.
Where to stay along the route:
Keys: Playa Largo Resort (Key Largo)
Naples area: Trianon Old Naples
Tampa/Dunedin: Fenway Hotel
Tampa: Hyatt Regency Tampa
All three routes work as standalone trips or building blocks. The 7-day loop is best broken up with a couple of slow nights in the Keys before the long drive back up the Gulf coast.
