Kick off your time in Naples by sightseeing around town. Start with a morning sightseeing cruise for a view of town from the water. See the millionaire mansions of Port Royal and pristine Keewaydin Island, all while keeping an eye out for dolphins, Florida manatees, and seabirds. Continue exploring on your own in the afternoon. Stroll down Fifth Avenue, see the collection of tropical plants at the Naples Botanical Garden, or head to Naples Beach and Pier for some fun in the south Florida sun. Families might head to the Naples Zoo, while history buffs should plan a visit to the the Revs Institute, home to a collection of vintage cars, boats, motorcycles, and aircraft. Have dinner along Fifth Avenue South before heading back to the pier for sunset.

Naples and its surroundings teem with outdoor adventure, and today you have time for one or two favorite Florida activities. Spend the day stand-up paddleboarding through the mangrove estuaries of protected Delnor-Wiggins Pass State Park, Jet Ski through the waters of Ten Thousand Islands, head offshore for some deep-sea fishing, or paddle the waterways of Everglades National Park by kayak. Most of these activities can be done in half a day, so you can pick two—one for the morning and another for the afternoon—or spend half a day relaxing on the beach or by the pool. In the evening, set sail on a sunset cruise in the waters of Naples Bay.

When it comes to activities and attractions about an hour outside of Naples, you have choices. You could spend the day shelling and birdwatching on Sanibel and Captiva islands, touring the Edison and Ford Winter Estates in Fort Myers, soaking up the sun on the beaches of Bonita Springs, canoeing or fishing on Marco Island, or exploring the planned community of Ave Maria. No matter how you choose to spend your day, head back to Naples for your final night. Enjoy a picnic dinner on the beach at sunset, or book a table at a waterfront restaurant with a view—the perfect setting for a farewell toast.