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WESPISER DICKEY TEAMBARCLAY'S REAL ESTATE GROUP
Siblings Selling Sunshine
Southwest Florida local guide

Things to Do in Southwest Florida

Choose a beach walk, a nature outing, a historic tour, downtown dining or an island adventure. These ideas connect to the 40 destinations in our Local Attractions guide.

AI-created illustration of Mary and Ty enjoying Fort Myers River District
Mary and Ty · AI-created destination illustration

Property Tours & Market Updates

Explore our listing videos and the latest Southwest Florida market reports from Mary and Ty.

Team images are AI-created illustrations, not photographs documenting an on-site visit. Original 20 destination entries researched October 7, 2026; twenty additional entries researched October 8, 2026. Check each official website for current access, weather notices, hours, fees and reservations.

Beach walks, shells and sunsets

Choose one beach as your main stop. Add a picnic or nearby lunch, and leave time for a relaxed walk. Beach parking and shoreline conditions vary.

  • Sanibel Island: Walk the shoreline and look for empty shells; leave living shells and wildlife undisturbed.
  • Captiva Island: Pair a shoreline stroll with an early dinner, then enjoy the sunset.
  • Lovers Key State Park: Plan a beach walk and picnic; check current park access and available rentals before departure.
  • Boca Grande: Explore the village, enjoy lunch and finish with a beach stroll.
  • Tigertail Beach, Marco Island: Enjoy birdwatching and a beach walk; choose a route suited to the tide and your mobility.
  • Delnor-Wiggins Pass State Park: Pack a picnic and plan a relaxed shoreline walk after checking park alerts.
  • Stump Pass Beach State Park: Enjoy a beach walk and look for empty shells; verify current park access before traveling.
  • Clam Pass Beach Park: Enjoy the mangrove boardwalk and beach; check current tram and amenity availability.

Boardwalks, gardens and wildlife

Choose a garden, boardwalk, zoo or guided nature outing. Bring water and comfortable shoes. Wildlife sightings are never guaranteed; Manatee Park visits especially depend on seasonal conditions. Reserve guided tours and confirm meeting points.

History and a town lunch

Plan a historic or visitor-center stop, then enjoy lunch. Reserve boat excursions separately and check historic-tour schedules.

Island trips by boat

Confirm your outbound and return transportation before traveling. Cayo Costa requires particular attention to its current private-vessel access notice.

  • Keewaydin Island: Book a suitable boat trip and enjoy a beach walk with time reserved for the return journey.
  • Cabbage Key: Arrange boat transportation, enjoy lunch and allow time to explore before returning.
  • North Captiva Island: Plan a boat or ferry outing with beach time and an island lunch.
  • Cayo Costa State Park: Consider a private-vessel beach visit only after verifying current access and landing arrangements.

Dining, boutiques and galleries

Make a meal the centerpiece, then explore the surrounding village or downtown. Check official calendars for events and reserve popular dining times.

  • Fifth Avenue South, Naples: Browse shops and galleries, then enjoy a patio meal; check the official event calendar.
  • Captiva Island: Pair a shoreline stroll with an early dinner, then enjoy the sunset.
  • Boca Grande: Explore the village, enjoy lunch and finish with a beach stroll.
  • Fort Myers River District: Start with coffee, browse a gallery and enjoy a downtown meal; check current event listings.
  • Fishermen’s Village, Punta Gorda: Enjoy a waterfront meal and browse the shops; check the official calendar for events.
  • Matlacha: Browse artwork and gifts, then stop for a casual meal; check current business and event information.

Picnics and relaxed park outings

Choose a park for a picnic, a gentle stroll or a break in the shade. Confirm rental availability, trail conditions and current venue notices before planning extra activities.

A relaxed afternoon in the River District

Start with coffee, browse downtown galleries and choose a restaurant for lunch. Check the official district information for current events and allow time to enjoy the streets and public art.

Official River District information →

Build a day that fits you

Start with one main destination. Confirm transportation, access and reservations. Leave room for lunch and breaks, and keep a weather-friendly alternative available. For accessible routes, ask the destination directly about the facilities you need.

More museums, gardens and local history

Explore these ten additional destinations. Check current access, tour reservations and seasonal schedules before traveling.

Explore Southwest Florida with Mary and Ty

Mary Wespiser Dickey and Ty Wespiser are siblings and business partners at the Wespiser Dickey Team, Barclay’s Real Estate Group. Planning a move, selling a home, or exploring commercial property? We can help connect your real estate plans with the communities you want to know.

Call (812) 212-2633

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