Robbie Caponetto

This colorful coastal village looks as if someone flew over South Florida and dropped a crayon box.

Think of Matlacha (pronounced MATT-luh-SHAY) as Mayberry meets Woodstock. Locals in town—and on the island that shares its name—offer the kind of warm welcome you'd expect from a small Southern town. But Matlacha's proximity to the Gulf of Mexico and its chill island vibe attract outdoor adventurers, as well as free-spirited artists and entrepreneurs who have set up shop here.

Come in July and you'll have the run of the place, with many spots open for limited hours; show up between December and April and the joint will be jumpin'. Either way, stop by Bert's Bar & Grill, snag a table outside on the dock, and get acclimated (bertsbar.com).

Getting out There
You'll soon discover that you're never far from a spot to dip a paddle here, as this area is part of The Great Calusa Blueway paddling trail, where local outfitters offer rentals and tours (calusablueway.com; carmenskayaks.com).

Capt. Jack La Plante of Captain Jack Boat Tours is a retired ship captain who first came here to deliver a yacht to private Useppa Island. Today, he has six boats and a successful tour business."We like getting involved in the community," says La Plante, who helps preserve the beauty of these island environs by volunteering to plant about 1,500 mangroves each year (captainjackboattours.com).

Fueling Up
Most of the attractions in downtown Matlacha are clustered along just a block or two. The Perfect Cup is a nifty little cafe and coffeehouse serving a creative menu for breakfast and lunch, with most items under $10 (239/283-4447). Try Irish Eyes—two poached eggs over spinach—or the Crabby Big Daddy omelet with lump blue crab, asparagus, and provolone. Grab a cup of coffee to go.

Shopping and Sugar
For something sweet, choose from 20 flavors of fudge at CW Fudge Factory (cwfudgefactory.com); that will get you through the short walk to Great Licks Ice Cream (239/282-2802), which serves local favorite Queenie's Ice Cream (queeniesicecream.com). Great Licks is adjacent to Island Visions Gallery & Gifts, with an eclectic selection of art, jewelry, and gifts (islandvision-stimeless.com). Find the work of over 120 Florida artists at Wild Child Art Gallery (wildchildartgallery.com), and buy fun, hippie-chick island wear at Frills Gallery (239/283-0192).

You can't miss Leoma Lovegrove Gallery & Gardens—just look for the bright green building with white mannequins on the roof. One of the area's best-known artists, Lovegrove is an Impressionist-Expressionist painter whose colorful works have inspired a line of merchandise at Bealls Florida Department Stores. Her work is also part of the private collection at the White House. She even "wrapped" one of Captain Jack's boats—you won't have any trouble spotting it at Lovegrove's dock (leomalovegrove.com).

Tucking In for the Night
Lodging here is not plentiful, but it's certainly not boring, either. Right on Pine Island Road are two rental cottages that back up to the Matlacha Pass Aquatic Preserve ($ matlacha-cottages.com). There is no fence between the waterfront backyards, so unless you don't mind getting cozy with the neighbors, bring friends and family along and rent both cottages. Just about everything downtown will be walkable.

 Robbie Caponetto

Angler's Inn ($ anglersinnmotel.com) has only a handful of units, but each one includes its own screened back porch overlooking a canal, and the owners provide complimentary grills, kayaks, bikes, and dockage. Janette and Karl Fraissinet, who bought this pet-friendly "botel" (boat dock/hotel) in 2014, have had so many guests who've checked in and not wanted to leave that they have to limit stays to 90 days.

If you want more luxe accommodations—hardwood floors, plush linens, a pool, and fine dining—head for Pine Island's secluded Tarpon Lodge, just a short drive from Matlacha ($$ tarponlodge.com). This old-school beauty is owned by the Wells family, who also own Cabbage Key Inn. The best food on the island can be found at Tarpon Lodge's restaurant and bar. Stay in the main house and you'll feel as if you've been offered a guest room in the home of wealthy relations. For more hotel-like lodging, book a stay in Tarpon's detached, 12-room Island House. Inside tip: Rooms 1 through 6 have views of Pine Island Sound, and Room 1 has an extra balcony.

After a few days on island time, you'll forget what it's like to be cold in winter—or why you ever saw the need for e-mail.