I’ve always felt blessed to live in a state that has so much to offer. We have culture and nature in spades, and how fun is it to jump in one’s car for a quick road trip when the mood strikes? The quieter months are a great time to get out and explore this beautiful part of the country. Here are a few spots that top my list, and make sure to say hi to our Sotheby’s friends if you go. (I’ve included links to affiliates’ web sites here.)
Boca Grande
The legendary Gasparilla Inn & Club reopens for its 107th season in October. Multi-generational families return year after year for its old-fashioned charm from the front porch’s rocking chairs to pastel, preppy décor. Its current stewards are doing a tremendous job in ensuring its placement within the Historic Hotels of America and the National Trust for Historic Preservation.
As if one of my favorite West Coast getaways couldn’t get any better, its Gulf-side accommodations debut in winter. The Beach Cottages’ spacious residences feature full kitchens, elevators and two to four bedrooms. A new fitness center opens beforehand. Doubling its size makes room for a yoga studio and exercise pool as well as a Zen garden and pickleball courts to meet demand for the fast-growing pastime.
Visitors can still dine at the inn’s multiple venues in the meantime. The Pink Elephant serves dinner nightly and lunch on weekends. Popular items are Thai-spiced, tempura-fried grouper and signature, rum-laced ice cream cocktails for an after-dinner drink and dessert in one. The Outlet restaurant and Inn Bakery are more daytime options.
https://the-gasparilla-inn.com/
Bonus Tip: If you want to know where the tarpon are biting, call captain Tommy Locke. The champion fly-fishing guide and sixth-generation Floridian also helps clients catch good eating species such as snapper, grouper, pompano, redfish and trout from his ultra-nimble Chittum skiff. I’m hooked.
http://www.tommylockeoutdoors.com/
Pop by Gulf to Bay Sotheby’s, too.
https://www.gulftobaysothebysrealty.com/eng
Marco Island 
Another fantastic destination on the Gulf of Mexico with big news is the JW Marriott Marco Island Beach Resort. Its $320 million renovation premiered last year for a much more luxurious experience in line with Florida’s elevated hospitality scene. The top-to-bottom revamp introduced an adults-only tower, Paradise by Sirene, with 94 rooms and suites, rooftop pool and beach butlers. Its exclusive Tesoro restaurant’s spacious deck overlooks the Gulf for a Greek Isles vibe.
All guests are welcome at the new 10K Alley, a mega-entertainment zone with games for kids of all ages. The property also offers two nearby golf courses and is in the midst of replacing the turfgrass at its 36-hole Hammock Bay Golf Course designed by Peter Jacobsen and Jim Hardy. The $4.8 million project wraps up in October. The Robert Cupp, Jr.-designed Rookery at Marco course is available to play now.
https://www.marriott.com/hotels/travel/mrkfl-jw-marriott-marco-island-beach-resort/
Pop by Premier Sotheby’s, too.
https://www.premiersothebysrealty.com/
Florida Scenic Highway 30A
Dotted with new urbanist developments like Seaside and Rosemary Beach, this stretch of the Florida Panhandle wins accolades for its chic design mixed with laidback lifestyle. Home rentals range in all sizes, and every good and service are within walking distance to ditch the car upon arrival. Grab a beach cruiser and your beach chair and spend quality time with family and friends on one of the world’s most gorgeous swaths of sand.
In Seaside, browse the latest titles at Sundog Books, try on new swimsuits at Ophelia and share a bottle of vino and tapas at 45 Central Wine & Sushi Bar. In Rosemary Beach, sip stiff punch drinks on Pescado’s rooftop deck, shop Southern tastemaker Ashley Gilbreath’s home selection at Parish, and play tennis on the Racquet Club’s green clay courts. Both communities have outposts of Amavida Coffee & Tea for a caffeinated pick-me-up.
Pop by Scenic Sotheby’s, too.