For the 50+ Traveler

The best way to describe Boca Grande would be to say it’s an “old Florida” town that sits within a 7-mile long strip of land known as Gasparilla Island. Known for hospitality and charm, it’s also a natural beauty. Visitors come here for world-class sport fishing, the historic downtown, and dazzling white-sand beaches.

About 100 miles south of Tampa, the barrier island of Gasparilla has been the playground for the rich and famous since the 1900s. Boca Grande, its largest town, attracted wealthy winter residents such as the Rockefellers, Vanderbilts, and the du Ponts (among other notables) to its stunning shores for sport fishing. Later, these famous men made a fortune from phosphate mining; it was discovered in the Peace River just above Punta Gorda, 20 miles east of Gasparilla Island. The savvy industrialists invested in the new enterprise, and the valuable mineral was shipped out from Boca Grande’s harbor by schooner (and later rail). The elites were called “Beachfronters” because they built their homes near the Gasparilla Inn and Club, right on the beachfront. It was the beginning of the heydey on Boca Grande.

Aerial view of Boca Grande, Florida.

Things To Do In Boca Grande

Just as in the past, sport fishing is the draw in Boca Grande, but there are other reasons to visit the village that is only 3 miles long. Here’s a shortlist of suggestions to keep you occupied but also leave plenty of time to relax on the beach.

Gasparilla Outfitters exterior, Boca Grande.
Jeanine Consoli

1. Catch A Tarpon

Boca Grande is known as the spot for “the world’s greatest tarpon fishing,” and you’ll want to work with a knowledgeable guide like Captain Sandy Melvin at Gasparilla Outfitters. Gasparilla Outfitters specializes in booking charter fishing trips in the Boca Grande area and represents many of the finest local guides for a great day out on Boca Grande Pass. Sandy has been guiding people since 1987, and his primary goal is your satisfaction.

2. Paddle A Glass-Bottom Kayak

Glass Bottom Rentals launches from a cove with calm, shallow water. This makes an easy start for a paddleboard or kayak to get out to the Boca Grande sandbar and nearby islands. The sparkling clear water is perfect for glass-bottom kayaks, which are also available to rent. We chose the glass-bottom kayaks and loved viewing all the sea creatures swimming underneath. The mackerel were jumping out of the water, and dolphins were swimming nearby. Some seasonal tours include turtles and manatees.

The sandbar is a popular spot for boaters to meet, hang out, and spend the afternoon enjoying a swim, some music, and the Florida sunshine.

Gasparilla Adventures exterior, Gasparilla Island.
Jeanine Consoli

3. Rent A Bicycle Or A Golf Cart

Gasparilla Adventures has what you need for a day or more while visiting Boca Grande. There’s nothing like feeling the breezes coming off of the ocean while you ride along miles of bike paths, admiring the scenery. It’s a fun way to see the points of interest on the island while you stop and marvel at the gorgeous trees on Banyan Street, the two lighthouses, and of course, the incredible beaches. If you would rather look like a local, rent a golf cart instead. It's the primary mode of transportation and makes the trip a whole lot easier. They have carts for four or six passengers.

4. Golf At The Gasparilla Inn And Club

The Gasparilla Inn and Club has hosted famous guests since 1913. Today, members and guests who stay at the Inn can play on the course with no tee-times. The Gasparilla Golf Club constantly challenges players because the championship course, designed by Pete Dye, is an “island within an island.” The par 72, 6,837-yard course features eco-friendly native grasses and five different tees on each hole to suit various play levels.

Banyan trees on Banyan Street, Boca Grande.
Jeanine Consoli

5. Visit Banyan Street

Banyan Street is an attraction because it’s really breathtaking no matter what time of day you choose to visit. It is located in the historical district just south of downtown. The street was designed in 1914 by landscape architect Carl Rust Parker. The block is lined on either side with Ficus benghalensis (Banyan trees) and runs perpendicular to the Gulf of Mexico. The massive canopy creates a tunnel effect, and the sunsets here are magical.

6. Tour Two Lighthouses

Why would a tiny barrier island have two lighthouses? One was lit in 1890 at the Boca Grande Pass, the deepest natural port in Florida. It was needed to light the way into Charlotte Harbor and played a huge role throughout the island’s history, especially during World War II. Today, it’s part of Gasparilla State Park and has a museum that opened in 1999. It also won the “Best Looking Lighthouse” award from Florida Monthly Magazine. The second began its life in Delaware and was transported to Gasparilla Island in 1927. A 4th-order Fresnel lens was installed and lit in 1932, and it was used to help ships sail through the Boca Grande Navigational Channel to Charlotte Harbor. It is located mid-island at Gasparilla Island State Park. It was restored and is now available for docent-led tours.

Beach in Boca Grande, Florida.

Best Beaches In Boca Grande

While all the beaches have sugar-white sand and the Gulf of Mexico’s warm, turquoise waters lapping the shoreline, here are two beaches to visit when on Boca Grande.

1. Gasparilla Island State Park At The Boca Grande Pass

Gasparilla Island State Park has everything mentioned above, plus it is a great spot to see where the Gulf of Mexico meets Charlotte Harbor. This is the spot where the fishermen hang out, and it's impressive to watch them at work. There are amenities and the historic lighthouse, which offers tours.

2. A Beach Close To Town

The local beach between Fourth and First streets has plenty of public parking for your golf cart, bike, or car. It is only one block from town, making it the perfect place to spend a few hours and head into town for refreshments. It is a local favorite for watching the sunset, and while you wait for nature's magnificent show, you can collect some lovely shells as you wander along the beach.

Best Hotels In Boca Grande

As you can imagine, Boca Grande is under the radar, and that’s what makes it a hidden gem. The options are to stay at a historic inn or rent from a reputable local firm. Your vacation should be in the hands of people who know how to make the most of your time in paradise.

1. The Gasparilla Inn & Club

The Gasparilla Inn & Club is a Historic Hotel of America Landmark Inn. Since opening in 1913, the gracious hospitality offered at The Gasparilla has never changed. The Inn has a variety of accommodation options, including 142 luxury rooms, activities, and amenities. The resort offers golf, a beach club, spa, salon, tennis, croquet, marina, shopping, a fitness studio, and rentals for your own adventures on Boca Grande.

2. Boca Grande Vacation Rental Agency

Boca Grande Vacations is a recommended rental agency with a team that can help vacationers find the perfect match for their stay and answer any questions about Boca Grande.

South Beach Bar and Grille, Boca Grande.
Jeanine Consoli

Best Restaurants In Boca Grande

1. The Pink Elephant

Affectionately known as “The Pink," this casual lunch or dinner spot is a favorite for the past 60 years. They are known for craft cocktails and fresh local seafood. Dockage is available for boats up to 45 feet.

2. The Temptation Restaurant

The Temptation Restaurant is one of the most popular dinner places on the island. While the food is considered upscale, the vibe is still casual. The Temp has served “old Florida” cuisine, which includes fresh, locally caught seafood, meat, poultry, and pasta, since 1947. The Caribbean Room features small plates, but you can order the full Temp menu if you prefer. Reservations are advised.

3. South Beach Bar And Grille

After biking around the island, we stopped in at the South Beach Bar and Grille. This waterfront restaurant is right on the Gulf of Mexico and offers casual dining at its best for lunch and dinner. You can sit inside, on the covered deck, or right on the beach in your cover-up and enjoy all the breathtaking views of the water. The menu is vast, with a focus on fresh seafood and everything else you can think of. They have a fully stocked bar with frozen cocktails and a full list of beer and well drinks. They often have live entertainment and pastel-colored Adirondack chairs to enjoy the spectacular sunsets.

Pro Tips

Downtown Boca Grande has some great stops for shopping and snacks. If you need quality shirts, shorts, bathing suits, sunglasses, or a beach hat, head to Boca Grande Outfitters. They have everything you might need for outdoor sports like golf and tennis, for every member of your family, and even items like collars and leashes for your dog. They also offer guides, lessons, and equipment for saltwater fly fishing, including any tackle you might need.

In need of coffee, tea, breakfast, or lunch? How about a smoothie made with real fruit or homemade ice cream? Head to the Pink Pony. They have an outdoor sitting area to enjoy whatever you purchased. If your dog needs something yummy, they have ice-cool frozen yogurt treats for your furry family member.

When the bridge was built connecting Boca Grande to the mainland in the 1960s, the city experienced a brief economic downturn, but generations of visitors who always knew what a stunner she was never left or returned over the years to make this place their second home. Many celebrities call it home, too, but the locals let them relax in peace and don’t bother them with photos or autograph requests. They just blend in like regular people. It’s why real estate here consistently ranks among the most expensive in America.