Anna Maria Island

This seven-and-a-half-mile isle includes Anna Maria to the north, Holmes Beach at the center and Bradenton Beach to the south. The Island Trolley connects them all. Aside from the beaches, there’s much to see and do on Anna Maria Island.

Arcadia

Old West meets Old South in Arcadia, home to the All-Florida Championship Rodeo, antiques stores and storied structures (an active historical society and Main Street Program keep things in town lively). You can observe barrel racing and bronco bucking during the rodeo, and there’s even a kids’ calf scramble and a shoot-out that recalls the rambunctious days of Arcadia’s turn-of-last-century cattle wars.

Bonita Springs

Shop amid waterfalls, palms and Mediterranean architecture at The Promenade or its counter, mega Coconut Point Mall. The Imperial River Boat Ramp provides access to the Great Calusa Blueway Paddling Trail and several local sites of interest: Follow the Blueway north of Bonita Springs to Estero and Koreshan State Historic Site, a former 19th-century Utopian community.

Bradenton

Bradenton’s vibe is scenic and refreshingly slow. In Downtown Bradenton, the Village of the Arts is filled with galleries, shops and cafes painted fuschia, lime and violet. Learn about Hernando DeSoto’s local landing at the South Florida Museum, Parker Manatee Aquarium and Bishop Planetarium complex. The Florida Maritime Museum at Cortez Fishing Village tells of the area’s angling heritage. Want more? Here’s a list of things to see and do in and around Bradenton.

Cape Coral

With skate, water and “family fun” parks (featuring mini golf, paintball and the like), Cape Coral caters to kids. But this city knows how to spoil nature-lovers, too. At Four Mile Cove Ecological Preserve, kayak or meander the boardwalk with an amazing walking tour to see wildlife. For the arts lovers in your group, check out the Cape Coral Arts Studio. Get inspired and get ready to laugh, cry and sing along at the Cultural Park Theater Co., putting on comedies, dramas and musicals the whole family will enjoy. Sports fans will cheer for Mike Greenwell’s Family Fun Park, where you can swing for the bleachers in the batting cages, race for the finish line in a go-kart or sink a hole-in-one on the minigolf course. When you’re all out of breath, take a break and find the big game on the big screen at the on-site sports bar.  Aquatic athletes and those who aren’t afraid to get a little wet will love the Sun Splash Family Waterpark – the largest waterpark in Southwest Florida, featuring more than 14 acres of aqua adventures.

Clewiston

Fishing isn’t the only thing that’s sweet in Clewiston, though its seat on Okeechobee bass fishing makes it a no-brainer here. Hire a guide out of a Roland Martin Marina (airboat tours run for those who prefer catching scenery to catching fish). Agriculture is the other attraction, and the chamber’s Sugarland Express gives visitors an up-close look at harvesting and processing for both citrus and sugar.

Englewood and Boca Grande

In downtown Englewood, wander amidst the boutiques, bistros and galleries along Dearborn Street, where a mural project makes the very buildings a canvas. Or, join thousands who come to the Englewood Farmers Market on Thursdays for fresh farm fare and interesting wares. In September, a restaurant week, Let’s Eat, Englewood, offers a rich diversity of dining options. Manasota Key is a barrier island where a variety of vacation rentals can be found along with a beautiful stretch of beach with all types of watersports activities, including paddling, kayaking and parasailing. Some of the area’s most memorable sights exist inside three state parks along its barrier islands: Stump Pass Beach, where you can sift the sand for shark teeth or fish for tarpon; Don Pedro Island, where boat-only access protects beaches; and Gasparilla Island, where you can tour the circa-1890 Boca Grande Lighthouse Museum. On Boca Grande, find more shopping, noshing and classic resorts with a coastal chic culture.

Everglades City

With Big Cypress National Preserve, Everglades National Park and the Ten Thousand Islands as neighbors, it’s not difficult to imagine what Everglades City stands for. If you can resist the call of the wild, duck into the Museum of the Everglades. From Everglades City, just follow the signs to reach Everglades National Park’s Gulf Coast Visitor Center. One-third of its 1.5 million-acre subtropical wilderness is waterlogged. Fish the flats, paddle the Everglades Wilderness Waterway Trail or take an airboat tour just outside national park boundaries – plenty of outfitters operate back in the “city.”

Fort Myers

Many Fort Myers visitors know that Thomas Edison and Henry Ford once were neighbors here . Tour Edison and Ford inventions, original antique cars and artifacts, at the Edison and Ford Winter Estates. Downtown, a statue at Centennial Park brings the visionaries back to life alongside their friend Harvey Firestone, and the Caloosahatchee River lends the area its nickname “The River District.” River cruises, art walks and the annual Edison Festival of Light (with a parade and science and engineering fair) unfold here. The 1908 Arcade Theater building, home to the Florida Repertory Theatre, demonstrates how the past can meld perfectly with the present.

Fort Myers Beach

Even the nights are bright here as crowds shift between souvenir shops, bars and restaurants on the strip. Times Square wraps it all into one and leads to Lynn Hall Memorial Park. Annual festivals include the American Sandsculpting Championship and the Fort Myers Beach Shrimp Festival. Carve out some quiet time at Lovers Key State Park.

LaBelle

Along the scenic Caloosahatchee River and not far from Lake Okeechobee is the friendly, historic town of LaBelle, known for its Curtis Honey House, country architecture, citrus farms and Swamp Cabbage Festival. Once a center of cattle raising and still popular with Florida cowboys, LaBelle offers visitors a glance at the state’s rich heritage.

Lehigh Acres

A town built on rest and relaxation, you can fish, golf and paddle here. Nearby Hickey’s Creek Mitigation Park includes a fishing pier, canoe and kayak landing and hiking trails amid pines, marshes and cypress swamps where alligators, tortoises and otters thrive.

Longboat Key

This island respite between Bradenton and Sarasota is known for its luxurious appeal. Chef-owned and operated (and oh-so-sophisticated) Euphemia Haye and The Haye Loft are loved locally for their globally inspired selections, dessert lounge and live music. 

Marco Island

Resorts here specialize in an island experience — without leaving the U.S.  The area is famous for its wide, soft sand beaches, and an array of both upscale and Old Florida style dining opportunities. This is the gateway to the world-famous Everglades and the Ten Thousand Islands, both perfect for daytrips to see unspoiled natural attractions, bird watching and wildlife viewing. 

Naples

One luxe label isn’t enough to support this discerning destination, so five-star and luxury resorts dot the area. Golf is debonair, as is the scene along Fifth Avenue South and Third Street South, where the carefree congregate in vogue galleries, boutiques and eateries. Artis-Naples is the home to The Baker Museum and the Naples Philharmonic. Dining is plentiful and enhanced with many locally owned restaurants, featuring award-winning chefs and everything from gourmet to Floribbean flavors.

Nokomis

You’ve likely heard more about its more well-known neighbors Sarasota and Venice, but Nokomis fills some of the space between. It has a jetty for fishing, and you can surf near there, too. Nokomis Beach and North Jetty Park call to toes-in-the-sand types.

North Port

North Port features biking, hiking, riding and Warm Mineral Springs, a modern-day health spa with a history dating back 10 thousand years.

Palmetto

High-rising Riviera Dunes Marina may symbolize the Palmetto of late, but waterways and an agricultural museum suggest the town’s beginnings. Tour the Manatee County Agricultural Museum, the 1914 Carnegie Library and a 1935 schoolhouse at Palmetto Historical Park. Emerson Point Preserve evidences natural Palmetto; paddle or bike past beaches and canals thick with mangroves.

Port Charlotte and Charlotte Harbor

These scenic locations are nestled along the north side of Charlotte Harbor where the Peace River joins the expansive waters. You’ll find recreational lands, fishing charters, paddling outfitters, and a focus on outdoor activities. The area is a boating and fishing center, with access to miles of waterways and prolific fishing, and a reputation as the Tarpon Capital of the world. The Murdock area a bit north of the harbor is a growing commercial center, with shopping areas, office complexes, financial institutions, theaters, restaurants and accommodations.

Punta Gorda

Its perch on the south side of Charlotte Harbor and the Peace River never goes unnoticed by anglers and nature-seekers. It also inspires resident and visiting artists, who have fashioned a creative hook for this fishing village. More than 30 hand-painted murals depict local flora, fauna and founders. On and around Marion Avenue, you can shop and lunch amid the arts (and palms, old-style street lamps and brick streets), and harborside Fishermen’s Village is a lively place with more of the same. USA Today’s 10 Best named Punta Gorda the #2 Small Town Food Scene.

Sanibel Island

You can see more of Sanibel on two wheels than on four; try a bike ride on 25 miles of of paved trails.  Or hoof it, and check out some of the best parks, walking trails, and biking areas Southwest Florida has to offer. Make sure to explore the Botanical Gardens at Sanibel Moorings as well as the J.N. “Ding” Darling National Wildlife Refuge, which makes up a large portion of Sanibel Island, protecting the largest undeveloped mangrove ecosystem in the United States. 

Sarasota

The arts are the keepers of this city by the bay. Become a patron of the opera, ballet or theater (the Asolo Repertory Theatre Company performs in a 19th-century opera house originally from Dumferland, Scotland). Visual arts are a cornerstone of The John and Mable Ringling Museum, where the awe-inspiring Rubens Galleries are part of a large collection and display of European art. The museum also features a stunning variety, from antiquities to Asian and American as well as contemporary art. Ca’ d’Zan, the Ringlings’ Venetian-style winter mansion, is another look-don’t touch stunner, and a circus museum on the grounds tells of Sarasota’s big-top heritage. Appreciate the city’s historic architecture, named, appropriately, the Sarasota School style; the bright-hued buildings of Towles Court Artists Colony house galleries and studios. Downtown, Pineapple Avenue and Main Street are known for its restaurants and annual events. At St. Armands Circle, shop and snack all the way to the beach.

Siesta Key

Despite its sleepy name, energy underscores Siesta Key. The lush, 8-mile long barrier island of Siesta Key is tropical living at its best, with watersports, nightlife, and the nearby Gulf State for eclectic shopping and dining with an international flavor.

Venice

Well-preserved Mediterranean Revival structures and beautiful water views are responsible for the Venetian vibe here. Browse the museum at The Triangle Inn and tour the Venice Train Station, both restored since their 1927 completion. If prehistory is your passion, make plans to visit during the annual Shark’s Tooth Festival. North of Venice is Oscar Sherer State Park, with an abundance of nature and wildlife.