What could be better than blissfully riding your bike on a tropical island, with palm trees swaying around you and the ocean nearby as you ride? If that sounds good to you, then keep reading to learn more about two such islands off the Southwest coast of Florida. Gasparilla Island (Boca Grande) and Anna Maria Island are popular with cyclists.
I recently had the pleasure of bike riding on Boca Grande and Anna Maria Island. When cycling on these sun-drenched isles, you are never far away from white-sand beaches, local restaurants and shops, and glitzy waterfront estates. Gasparilla Island and Anna Maria Island are distinctively different kinds of places, but each makes for an enjoyable cycling experience.
Both islands are e-bike friendly. I saw plenty of other e-bikes during my visits and no signs prohibiting them. No hassles or rude comments either. If you ride a traditional bike instead of an e-bike, you will be glad to know these trails are flat and smooth. You’ll be fine.
TIP: While bicycling on these islands sure beats a day at the office any season of the year, the best time to bike ride here is from late fall to to early spring, November through April. Temperatures are pleasant, humidity is down, and nuisance bugs are mostly dormant. Summers in Southwest Florida are long and humid. On the other hand, the benefit of riding in the summer is that the warm Gulf of Mexico water will be just right for a swim. While winter weather is ideal for cycling, it is also the “high season” in Southwest Florida, so expect higher lodging prices, waiting lines at popular restaurants, and traffic delays.
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See Related Story: “Florida’s Pinellas Trail: A Success Story That Keeps Growing“
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Now let’s look at what it’s like to bike ride on Boca Grande (Gasparilla Island) and Anna Maria Island.
Gasparilla Island (Boca Grande)
Located on the Gulf Coast between Sarasota and Fort Myers, Boca Grande is a refreshing throw-back to Old Florida. There are no high-rise condos here. No traffic lights. Not even a Publix supermarket or a gas station. It’s laid back, but in an elegant and relaxing way.
Boca Grande is both historic and highly affluent. It is the main settlement on seven-mile-long Gasparilla Island. When most people talk about visiting this island, they simply say they visited Boca Grande, not Gasparilla Island.
Just how affluent is Boca Grande? According to realtor.com, the average home for sale recently listed for $3.7 million. This is the kind of tropical island where the 1 percent vacation or live. The island and some of its older establishments like to boast about former presidents, movie stars, and other VIPs who have vacationed or owned homes there. Even driving onto the island isn’t free. There’s a $6 toll on the causeway.
The island is perfect for leisurely cyclists. A paved and scenic bike trail runs nearly the entire length of the island. You can visit most of the Boca Grande’s better-known landmarks by bike, including Gasparilla State Park, the historic Gasparilla Inn & Club, downtown shops, beaches galore, and even two lighthouses. Gulf Coast beaches parallel the trail, just a few blocks away, giving you ample opportunity to take a diversion for shelling, sunbathing, or swimming.
One unusual feature of this rail-trail is that cyclists share the path not only with pedestrians but with golf carts. Golf carts are a popular means of local transportation here, along with bicycles. The bike trail, as well as most streets on the island, are approved for golf cart travel.
The only other place where I have shared a trail with golf carts was in The Villages, Central Florida’s huge retirement community with more than 100 miles of golf cart paths where bicycles are also allowed. On the Boca Grande trail, I found golf cart drivers for the most part to be kind and considerate toward bicyclists, especially if you act the same way toward them. Sharing the trail worked surprisingly well.
On the north side of the island, just after crossing the causeway from the mainland, the bike trail begins at Kappy’s Market, a popular local store that is a combination of a deli, convenience store, souvenir stand, and pharmacy.
While this is as far north as the trail goes, I ventured further north into an upscale residential community that occupies the northern tip of Gasparilla Island. Riding along lightly traveled Gulf Shores Drive and adjacent streets, you see stunning high-end homes with beautiful landscaping. It’s a good way to squeeze in a few extra miles on your ride.
As you head south on the island from Kappy’s Market, the bike trail takes you past residential communities and some businesses. While some sections are sunny, much of trail has at least some shade cover. That will help if riding in the warmer months of the year.
One drawback of this trail is the number of curb cuts for cross streets, plus entrances to neighborhoods and businesses. If you want a remote trail where you can ride at top speed for fitness purposes, this isn’t the trail for you. The good news is that traffic is relatively light. I rarely encountered motorized vehicles at crossings, except in the downtown district. Further, bikes are so common here that motorists are accustomed to them and courteous.
If starting on the north end, downtown is about two thirds of the way down the trail. The Gasparilla Inn is just a short block or two off the trail and is worth a stop. If you want a high-end meal, you can stop at the Gasparilla Inn’s dining room or nearby at The Pink Elephant, a historic restaurant operated by the Gasparilla Inn that has served many presidents and other dignitaries over the years. Other popular downtown restaurants include Temptations, Scarpa’s Coastal, and the Loose Caboose.
You will find bike racks scattered through the downtown district.
Going south from downtown, the trail ends at Gasparilla State Park, which bikes can enter for only $2. The park features an old lighthouse, a museum, and beaches.
While in the area, you may also want to check out the nearby 8.5 mile Cape Haze Pioneer Trail in Charlotte County or the 2.5-mile Punta Gorda Harborwalk. Back on the mainland, you’ll find your usual Florida mix of supermarkets and other stores for your necessities.
Anna Maria Island
Drive two hours north from Boca Grande and you will find another of Florida’s true gems, Anna Maria Island. Located off the coast of Bradenton, between Tampa Bay and Sarasota, the island includes three towns — Anna Maria, Holmes Beach, and Bradenton Beach.
Anna Maria Island shares many similarities with Gasparilla Island. Both are seven miles long. Residents on both islands have tried to preserve the “Old Florida” feel, including building height restrictions that prohibit high-rise condos and hotels. Both islands are affluent, with median home prices recently of $1.2 million on Holmes Beach and $2.3 million in the town of Anna Maria, according to realtor.com.
Unfortunately for cyclists, Anna Maria Island lacks a consistent trail network. You can’t ride a single trail uninterrupted from one end of the island to the other like you can on Boca Grande. Riding here means being comfortable with a combination of road and trail riding. Keep in mind, however, that this is a resort island, where speed limits are low and bikes are common. The main road, Gulf Drive, has bike lanes along most of the island, and intersections are well marked. Or you can do what I prefer and find parallel residential roads to the main road, which keeps you out of traffic most of the time when no trail is available. To me, that reduces the stress level and makes for a quieter ride.
While not perfect, riding this beautiful island is still a pleasure. It definitely has the feel of a beach town (or actually three beach towns) and the island homes are lovely. One of my favorite parts of this ride was exploring the upscale and nicely landscaped neighborhoods, few of which are gated. I rode the northern section along North Shore Drive and past Bean Point Beach, took South Bay Blvd. to its dead-end point, and explored the Key Royale community where most homes have a water view. It may require spending time studying GPS or maps, but if you plan it well, most of the island is easily accessible by bike, with only occasional interaction with unpleasant traffic.
People come to Anna Maria Island primarily for its world-class beaches. If you like white, soft sand and warm Gulf waters, Anna Maria Island is your type of place. Manatee Beach Park is the most popular public beach, with ample parking and good facilities. Compared with ultra-upscale Boca Grande, Anna Maria Island does feel in places more like a typical beachside tourist town, especially in Bradenton Beach. There are more of the old-style beach rentals and souvenir shops here than on Boca Grande.
If you grow weary of cycling, you can catch the free Island Trolley, which is bike-friendly (you can store your bikes onboard while you ride) and runs the entire length of the island.
One of the benefits of being a tourist town is that there are plenty of restaurants and shops to explore. I enjoyed lunch at Ginny’s & Jane E’s Cafe and Gift Shop, a popular spot with locals and tourists. They are also known for their smoothies, shakes, and ice cream. You may need to add some extra miles to your bike ride after enjoying this restaurant’s treats!
Another benefit of visiting Anna Maria Island is the choice of nearby places to bike ride. Coquina Beach, on the very southern tip of Anna Maria Island, has a popular bike trail. It’s not a long trail but worth exploring. On the nearby mainland, Robinson Preserve has a 2.5 mile paved bike trail. Go further south to Sarasota and Venice and you can pick up one of Florida’s finest bike trails, the Legacy Trail and the adjoining Venetian Waterway Trail. Together, the two trails offer 20 miles of continuous cycling.
While in the area, put your bike aside and enjoy the beautiful beaches and water sports. Or indulge in Sarasota’s famous upscale shopping and dining, including legendary St. Armands Circle. For a scenic car ride along the beachfront, try driving the barrier islands south from Anna Maria through Longboat Key to their end at Sarasota. It’s a beautiful ride that is worth taking time to enjoy. Some of this section is also bike-friendly, but conditions vary from place to place.
Give Island-Style Bike Riding a Try
Bicycling and small islands just seem to go together. That is certainly the case in Florida, from Amelia Island off the coast of Jacksonville to Key West. Gasparilla Island and Anna Maria Island may not be as famous for cycling as those better-known resort islands, but either island can make a great day trip or a week-long vacation.
If you’ve got the money, these islands may even suit you for a winter getaway retreat or year-round residence. If you move there, be sure to let me know when your guest bedroom is ready.
