Mid-October through mid-November will give you exceptional weather—generally warm and dry with humidity that’s not “low,” but still definitely lower than the summertime sauna—and it’s also before the holidays and the massive migration of retirees and snowbirds that happens during the winter. Although the best time for arts and culture events is during the winter (when those snowbirds—and their money—are around), there are still plenty of smaller, more local events in the fall. Did I mention the weather was nearly perfect this time of year?
In Sarasota, the Gulf Coast Beach Resort Motel is the oldest hotel on Lido Key and is located right on the beach; although the accommodations are far from luxurious, they’re clean and come with an added touch of kitschy history that’s incredibly appealing. The Wyvern Hotel in Punta Gorda is a stylish, perfectly located property with great service, nice rooms, and ridiculously reasonable rates.
Fried gator tail is so cliché, but it’s so delicious. The Gulf of Mexico has such an abundance of seafood that to come to this part of the state and not have freshly-caught and expertly-prepared fish means that you may very well have missed the entire point of your visit.
Spectator sports are few and far between in this part of the state, although baseball fans can enjoy MLB’s Grapefruit League spring training games in Bradenton, Sarasota, Fort Myers, and Port Charlotte. There are PGA and LPGA golf tournaments throughout the year as well.
St. Armand’s Circle in Sarasota is great for high-end boutiques and all-around experience; located on Lido Key, the Circle is pedestrian-friendly and packed with local shops and restaurants (although a few chains have snuck in). Naples offers lots of luxe stores and art galleries that would be appealing to the older, wealthier clientele that tends to vacation there.
Hands down, the Ringling Museum of Art and its surrounding complex provide the most essential, non-beach/non-“outdoorsy” destination in the area. The museum houses top-notch collections inside a space that is huge and beautiful, while the adjacent Circus Museum is far more entertaining and enlightening than it should be. However, the circus magnate’s mansion (Ca’ d’Zan), which is located on the back, waterfront-facing side of the property, is truly a sight to behold. Imagine all the most ostentatious affectations of wealth that a Gilded Age circus millionaire would apply to his home… and then you haven’t even begun to scratch the surface of the vainglories contained within Ca’ d’Zan.
Again, the Ringling Museum is highly underrated as an actual museum; its collections are stunning and several of them are routinely updated by a smart and modern curatorial staff. Naples is great for buying art—with dozens of expensive galleries and several well-attended annual auctions—but art there is often less concerned with being interesting than it is with being expensive.
The Everglades is the obvious and correct answer here; the vast expanses and near-total absence of development makes it excellent for spotting everything from gators and bears to wild hogs and, of course, multiple bird species. However, real birding aficionados will want to head for the J.N. “Ding” Darling National Wildlife Refuge on Sanibel Island or the Audubon-managed Corkscrew Swamp Sanctuary near Naples, where the winter months bring an incredible diversity of winged creatures.
The Myakka River State Park, between Sarasota and Venice, offers hiking and camping, and the Myakka and two lakes provide plenty of opportunities for fishing, kayaking, canoeing, and more. Of course, you can do all of these things in the Everglades as well, with the bonus of being able to get (very) far away from civilization. Additionally, even in more developed areas like Sarasota and Naples, there are still plenty of options for hiking, beaching, watersports, and boating.
