Retiree Retreats
Coastal Charm and Cultural Gems
Florida’s retirees can enjoy a slower pace while discovering its cultural treasures. In St. Augustine, stroll cobblestone streets lined with historic architecture, tour the Castillo de San Marcos, and visit unique art galleries and history museums. Take a scenic cruise along Matanzas Bay for a relaxing start to the trip.
Further south, Sarasota offers the grandeur of The Ringling Museum, showcasing art and circus history, as well as peaceful walks through Marie Selby Botanical Gardens. The area is also known for theaters and cultural performances, making it a perfect stop for retirees who enjoy the arts.
Naples is a haven for luxury shopping on Fifth Avenue South, fine dining, and scenic boat cruises along the Gulf Coast. Travelers seeking a more natural escape can explore the vast ecosystems of Everglades National Park, spot wildlife, or take a dolphin-watching cruise in Marco Island.
3-Day Retiree Itinerary
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Morning: Walk through historic St. Augustine and tour Castillo de San Marcos
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Lunch: Dine at Columbia Restaurant in St. Augustine
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Afternoon: Browse local galleries and shops or take a scenic cruise
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Dinner: Waterfront dining at Aunt Kate’s
St. Augustine
01
DAY
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Morning: Explore Sarasota’s Ringling Museum
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Lunch: Enjoy a meal at Owen’s Fish Camp
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Afternoon: Stroll Marie Selby Botanical Gardens or catch a matinee performance
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Dinner: Savor fine dining at Indigenous
Sarasota
02
DAY
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Morning: Take a boat tour in Naples or Marco Island
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Lunch: Dine al fresco at The Dock at Crayton Cove
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Afternoon: Explore Everglades National Park with a guided tour
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Dinner: End with dinner at The Turtle Club in Naples
Naples
03
DAY
