America's Best Small Beach Town Is an Old Florida Gem With Crystal-clear Waters and a Scenic Bike Path

While the state of Florida welcomes almost 140 million visitors each year, only a small portion of them make their way to serene Gasparilla Island and its main hub, Boca Grande. This upscale yet down-to-earth community on the Gulf of Mexico is just the right amount of under-the-radar, except when it comes to its role as “tarpon capital of the world."

In the words of Nikki Heimann, manager of The Pink Pony — an island-favorite ice cream shop opened in 1988 by her grandfather — the stoplight- and franchise-free community is “like stepping back in time.”

“Our beaches are stunningly clean and our water is usually clear and sparkling, with a bountiful variety of sea life,” she says. “A big allure is game fishing in our deep-water pass for tarpon. We have two well-maintained historical lighthouses with a museum and state park on the south end, and a smooth bike path that runs the whole length of the island, so many people enjoy renting a golf cart or bicycle to spend the day cruising around. It’s a great place to visit if you’re looking for peace, tranquility, and quiet time.”

Beyond its looks, Boca Grande is resilient. Along with much of Southwest Florida, especially Sanibel and Captiva islands to the south, it was devastated by Hurricane Ian in September 2022. The Pink Pony reopened soon after the storm, but other establishments were not so fortunate. “Many iconic features of our landscape are gone forever," Heimann says. "Everyone around here has their story and struggle that they’re going through. We are just thankful we didn’t get washed out.”

Back in action, Boca Grande remains a captivating place to visit — a tranquil respite from the frenetic pace of our modern world (and many parts of Florida) with a beachy, small-town allure. In fact, Travel + Leisure rated it the best small beach town in the country in 2023. Find out why for yourself by exploring the village by golf cart, bike, or your own two feet.

The Best Times to Visit 

Like many beach towns in Florida, Boca Grande is a seasonal destination. “Most people enjoy coming to the island during our busy ‘social season’ when the town is bustling with activity and the Florida sunshine is a delightful reprieve from the winter snow up north,” Heimann says. This period lasts from approximately Thanksgiving to spring break.

“Then, we roll into tarpon season, when the fishing families come to town and enjoy the island through summertime,” she continues. “Many downtown businesses close during August and September, so that’d be the time to come if you like to sweat in solitude.”

While mid- to late summer is a crowd-free, quieter time in Boca Grande, you may have trouble securing a stay, as the Gasparilla Inn closes annually from mid-July to early October. However, other hotels stay open, and there are assorted vacation rentals available. When planning your visit, remember that the best time to visit Florida, in general, is spring and winter as hurricane season lasts from June 1 through Nov. 30 each year, so there’s always a chance of storms during the summer and fall. 

Things to Do

As one might expect of America’s best small beach town, the best things to do in Boca Grande are in, around, or on the water — namely, fishing, shelling, boating, beaches, and biking. Heimann says the number one thing she recommends is not so much an activity but an experience: enjoying a sunset either on the beach or a paddleboard. Other things to do include climbing the Gasparilla Island Lighthouse (known locally as the “range light”) and heading to Gasparilla Island State Park for swimming, snorkeling, or fishing. Keep an eye out for the tarpon that often jump and roll in the deep waters of Boca Grande Pass. Or, for more tarpon time, go during the annual World’s Richest Tarpon Tournament, a tradition dating back to the early 1980s. Thousands of dollars in prize money is on the (literal) line.

You can see much of what Gasparilla Island has to offer on the Boca Grande Bike Path. The island is only seven miles long and a half-mile across at its widest point, and this 6.5-mile path runs past highlights like Banyan Street, the Boca Grande Historical Society, and the pretty-in-pink Johann Fust Community Library. The north end is close to Glass Bottom Rentals, where Heimann recommends renting a clear kayak to paddle around the old railroad trestles nearby.

Try to score an invite to the members-only Useppa Island; otherwise, a day trip to Cayo Costa should scratch the island-adventure itch. It’s accessible only via boat or kayak, with a ferry service available from several mainland locations.

Where to Stay

Gasparilla Inn & Club 

The Gasparilla Inn & Club represents old Florida at its finest, striking the perfect balance between ritzy and relaxed. The inn has a variety of accommodation options, from rooms and suites in The Main Inn to private cottages and two- to four-bedroom villas. Guests can take part in a range of activities, from golf to croquet, fitness classes, and spa treatments. The inn has four eateries — just be sure to pack with the dress code in mind.

Boca Grande Hotel

The quaint Boca Grande Hotel offers more laid-back accommodations on the north end of Gasparilla Island, near Uncle Henry’s Marina, but the closest public beach access is three miles away. The property has an outdoor pool, loungers that you can rent out and bring with you to the beach, and a guest laundromat for cleaning up before you repack your suitcase. Next door, you can grab a deli sandwich or ice cream from Kappy’s Market.

The Palmetto Inn

A sister to the Boca Grande Hotel, The Palmetto Inn is located in the Downtown Boca Grande Historic District and just a short walk from the beach. Built as a private residence in 1900, it’s now a charming inn with seven suites and some of the lowest in-season rates on the island.

The Innlet on the Waterfront

Located on the waters of the Boca Grande Bayou, The Innlet on the Waterfront is an unfussy charmer with about 30 waterfront and courtyard-facing rooms. Amenities include a pool, on-site restaurant serving breakfast and lunch, plus a full-service marina if you BYOB (Florida-speak for "bring your own boat"). Be on the lookout for manatees as you enjoy your breakfast on the patio of The Outlet.

Where to Eat and Drink

Gasparilla Inn

Guests of the Gasparilla Inn will be delighted to find that its restaurants are some of Boca Grande’s best. It has an elegant main dining room (open for breakfast and dinner), the casual Pink Elephant (open for lunch and dinner), and the atmospheric BZ’s, where the public and guests alike can enjoy beverages and snacks while taking in views of The Gasparilla Golf Club and Charlotte Harbor. The Beach Club is another favorite for poolside beverages and lunch but is reserved for inn guests and members only.

The Temptation Restaurant 

To experience Boca Grande like a local, order the fish of the day at The Temptation Restaurant. Signature dishes include crab cakes served with roasted shrimp sauce and pan-fried lemony-garlic snapper, while the daily special might be blackened tripletail or chargrilled pompano. The wine list is equally impressive.

Scarpa’s Coastal

Sister to the beloved, family-owned Scarpa’s Italian in Lakeland, Scarpa’s Coastal serves fresh Florida seafood with an Italian flair. It also offers an extensive wine menu with bottles imported from Napa Valley and Italy. Patrons rave about the crab cakes, pasta, and chicken dishes.

Eagle Grille and Miller’s Dockside at Boca Grande Marina

The Boca Grande Marina is home to two restaurants, Eagle Grille and Miller’s Dockside. At Eagle Grille, you’ll find a quieter setting with second-floor waterfront views, while Miller’s Dockside has a sports bar atmosphere right on the water. They have the same menu, full of fresh coastal cuisine like oysters, Gulf grouper, and shrimp.

Sisters Restaurant

It’s not vacation unless you go out for pizza at least once, and Sisters Restaurant is the place to do it. This homey spot offers classic Italian comfort foods to eat indoors or out — and, yes, it really is owned by twin sisters.

The Pink Pony

What’s a beach day without a stop for ice cream? The best place to grab a sweet treat is The Pink Pony, the kind of hometown ice cream shop that once rented out movies on VHS and developed photo film. Things are different now, but visitors can continue at least one generations-old Boca Grande tradition and stop in for hand-dipped Amish ice cream, sorbets, specialty sundaes, shaved ice, all-fruit smoothies, açaí bowls, and coffee drinks. The Pink Pony also has snacks, beer, wine, bagged ice, and souvenirs. And don’t miss Tortuga, the outdoor walk-up window serving authentic Mexican food behind the storefront.

Where to Shop

Boca Grande has local, family-owned shops selling souvenirs, art, clothes, and more. Heimann recommends Fugate’s — “a classic island gift store that has a little bit of everything,” she says. Or stop by Barbara Anne’s for a special piece of jewelry to commemorate your trip. 

At the family-owned Smart Studio Art Gallery & Shop (which has another location in Maine), you’ll find stunning local art, including original paintings, prints, driftwood sculptures, gifts, and home decor. Or, if you’re in the market for light tackle or outdoorsy clothing and accessories, stop by Boca Grande Outfitters.

How to Get There

Aside from the private Coral Creek Airport, which is less than 10 miles from Boca Grande, there are several public airports nearby. The closest is Punta Gorda Airport (PGD), about an hour away, which is serviced by Sun Country and Allegiant Air with nonstop flights from about 50 cities.

There’s also Sarasota Bradenton International Airport (SRQ) and Southwest Florida International Airport (RSW), both of which are about an hour and a half away, and Tampa International Airport (TPA), which is about two hours away by car. Boca Grande is over three hours from both Orlando International Airport (MCO) and Miami International Airport (MIA). No matter where you fly into, there’s just one road onto Gasparilla Island: the Boca Grande Causeway.