Ever dream of boating and sunbathing in a remote oasis? Mansions with swimming pools dipping into canals, charming shops selling cheerful resort wear, and regal dining surrounded by reading nooks awaits you in Boca Grande. 

Located on Gasparilla Island, you drive across an arched toll-bridge and are greeted by a row of shops. The secluded mystic attracts second homeowners who fall into two types of travelers.

The seasonal residents from colder climates who include software developers and electronics inventors, computer company owners, and elected officials. For snowbirds, the high season begins at Christmas and lasts until after Easter, with stragglers staying until May.

The area also draws in second homeowners who want to get away from the larger cities on the weekends. This includes those with a passion for fishing who visit throughout the year. 

Boca Grande is unique in that it is naturally barren. It floats on the Gulf where the breeze is scarce, so the temperatures can soar. Pirates once hid on the island, giving the streets their clever names. The ground is arid and covered in gray stones.

The most common critters are raccoons and iguanas. Interestingly, the residents sued a farmer up North for his killing birds destroying his crops because they wanted the birds to migrate to their area for birdwatching. Yet, they paid over a million dollars to eradicate their iguana population. A few surviving iguanas thrill tourist by peaking out from overflow drains leading into the canal and sunbathing on the manicured lawns, but not without disgruntled remarks by the residents.

A Family Destination with a Romantic Twist

It is an outdoor sports arena for families — happy, holiday-loving tribes dressed in flashy linens and boat shoes. The vacationers keep within their polished-cotton shorts and color coordinated socks mainly at their homes. When they venture out, it is for church, boating and sun-walking. Labradors are a golf cart accessory, and everyone introduces himself to his neighbor’s dog. 

The social time is family time. The community puts together festivals for each holiday. Even Halloween is given a wholesome sense of escape from the world. Whether you are visiting for Thanksgiving or Easter, make sure you pack appropriate costumes and accessories for the kids and pets.

The romance is in the fact the setting lends itself for appreciating one another. It is the type of place where you take a long breath, and reach out, with one person beside you to take your hand. 

Where to Stay

Most accommodations are waterfront homes with swimming pools and golf carts as staple items. If you prefer hotels, the Gasparilla Inn & Club has the most personality and amenities, but does not allow pets. This Old Florida flavor offers both cabanas and state rooms. The grounds provide for light golfing and social events.

Another favorite choice of mine, especially if you are traveling with pets, is The Innlet, located at the marina for the fisherman who wants a hot meal and a dip in a pool. Pets are welcome. 

Dining on the Go

Eating is not the main draw to the area, but I have a few suggestions for light meals. The Dolphin Cove Cafe offers take-out breakfasts in the traditional egg-combo entrees. They also have smoothies and you can modify the sandwiches if you prefer healthier meals. They only take cash, as do other places on the island.

Another good choice, in that there is one option for a vegetarian or vegan entree, is the 3rd Street Bistro. If you are a lobster eater, Newlin’s market provides take-out gourmet crackers and treats in addition to their fish selections.  

Gasparilla Sunset by J Wilder Bill

The fried-fish restaurant, South Beach, attracts daily crowds to witness the sunsets where the sky-scape is sure to change something inside you and spark up a romance. A more reserved clientele gathers at the Pink Elephant where the view offers less brilliance and the mood is less chatty. 

Dining begins and ends practically before dark. The moment the sun dips below the ocean, the sidewalks are rolled up for the night. If you are a night-owl, you have the options of site-seeing the houses along the winding canal streets or walking on the dark beaches.

For years, a shipwrecked vessel was left washed ashore, collecting tropical animals and unbroken shells. Overhead, the Milky Way is vivid, along with the constellations. 

Activities Aside from Napping

Things to do include sightseeing on airboats, birdwatching on powerboats, and sunset sailing. Daytime is for exploring nearby islands, some of which can only be reached via water transportation. The waters overflow with tarpons. Dolphins leap over the wake to say “hello” and birds carpet the inlets. The shallows comfort turtles and urchins.

In the early afternoons, the quaint shops get busy. Along with the resort wear stores, there are art and novelty shops. The best selection for kids is at the lighthouse museum. A man who worked on the phosphate docks that washed away long ago will share local legends with you.

How to Dress

Light dresses and flats, by all means. With the rocky terrain, no one wears heels of any kind. If you see flip flops instead of boat shoes, they are the resilient brands with thicker soles, rather than the frilly styles. Sarongs are worn with tee shirts.

Some wear light jackets during the winter months. Be prepared with a cotton sweater, closed toe-shoes, and jeans for the chilly evenings.

Boca Grande by J Wilder Bill
Boca Grande by J Wilder Bill

Children are oftentimes dressed up more so than the adults, especially for the festivals and holiday afternoon events. It is rare to see someone in a bathing attire. Instead, linens in soft neutrals are worn to church, and vivid resort wear is for shopping. Cocktail hour calls for less flashy outfits, and more respectable clean lines in softer colors. 

Canoodling Because…

What makes Boca Grande a place to cozy up to your loved ones, is the sense of seclusion.  It is a preserved town with twisted trees and silent community centers. Here, you plan your days around family. There are no distractions from being with the ones you care about the most. People tend to arrive and stay put, with one family member going out to pick up a newspaper or cup of coffee. The accommodations are for self-contained vacationing. 

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