Exploring Hidden Boating Trails: Offshore Adventures in Florida

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A family boating adventure helps build lasting memories. Discover the best hidden boating trails during offshore adventures in Florida.

Going on a boating adventure with your family is an opportunity you shouldn’t miss. It’s a unique experience that your kids will treasure for the rest of their lives. You can also sail around Florida with your friends, enjoying every second of the trip and taking full control of your itinerary. Either way, hiring a boat and planning your journey around places you can visit this way is always a solid plan. Here are a few hidden boating trails you could use as a starting point while planning.

Treasure Island

Watching a sunset over the Gulf of Mexico is a unique experience, so getting a boat rental in Treasure Island, Florida, is a great idea. This can be a uniquely fun experience for the entire family and one of the most cherished memories for years to come.

Treasure Island Beach, Florida. Photo by Peter Etchells via iStock by Getty Images

While you’re at it, you have to visit its incredible beach. The beach is wide and arguably one of the best places for kite-flying, making it one of the best options for families with children. Once you disembark, you can also consider another form of sailing and hire a kayak or a paddle board from a local vendor.

Boca Ciega Bay is an amazing place, with some archeologists claiming it was inhabited even by prehistoric Native Americans. Once you visit, you will understand why someone might choose to stay there.

Treasure Island Hippo Slide is four stories tall, making it one of the largest in the world. If you’re traveling with children, this is one of the things they’ll want to see.

Sand sculpting is an ancient and underappreciated art. Well, if you visit Treasure Island at just the right time, you might get a chance to see it during Sanding Ovations. This is the world’s largest sand sculpting festival and is a spectacle. Still, professionally made sand sculptures can last for months, meaning you can still enjoy the sight even if you’re a bit late.

Florida Keys

The US is a huge country, spanning the depth of an entire continent, so if you ever want to brag about traversing the entire place, you need to visit Key West (its continental southernmost part). This alone would be a reason enough to visit this area.

On your way from Treasure Island, you can also visit Sanibel.

Visit Sanibel Island on your way to Key West. Photo by Vito Palmisano via iStock by Getty Images

Once in Key West, you’ll definitely want to visit the Hemingway Home and Museum. If a person who traveled the world and was considered to be one of the greatest minds of his era chooses to make this place his residence, isn’t it, at least, worth a visit? For anyone who admires Hemingway, this is a must-visit, and it’s a great place to learn something about the arguably most famous American author.

Hemingway House in Key West. Photo by Michelle Maria via Pixabay

Dry Tortugas was a pirate base during the 1600s and 1700s. From here, Caribbean pirates attacked merchant shipping coming to the Gulf. For anyone interested in the history of piracy, this is one of the most important landmarks. This park has 100 square miles of open water and seven small islands. Its name (meaning turtles in Spanish) derives from an abundance of sea turtles present here at the time of discovery.

Port Charlotte Harbor

People who can’t decide between freshwater and saltwater adventures owe it to themselves to visit Charlotte Harbor. You don’t have to choose here since you’ll have access to both.

Night sky stargazing is one of the oldest human nighttime activities, and there’s no better place to do so than in Port Charlotte. If night catches you in the open sea, you can see the night sky in a completely different light.

Chester Roberts Park in Port Charlotte, Florida. Photo by Wiltser via iStock by Getty Images

Stump Pass Beach offers year-round swimming and sunbathing. In addition, there are shelling, hiking, and even picnicking opportunities everywhere. The length of your stay depends on the conditions.

Fisherman’s Village may not sound like much, but when you visit it, you’ll soon realize it has 30 boutique shops and five restaurants, making it a formidable tourist hotspot. One might argue that pound-for-pound, it’s one of the best small resorts on the continent.

If you’re a fan of anything army or warfare-related or a history buff, you owe it to yourself to pay a visit to the Military Heritage Museum. Just be cautious; it’s easy to lose track of time while visiting.


One of the main reasons Sarasota sometimes misses these lists is that it’s so close to Tampa Bay and Charlotte Harbor, both of which often make these lists. Well, today, we’ll fix this great injustice.

Fishing near Sarasota is some of the best in the US. This is why, if you’re visiting the place, you owe it to yourself to try it. For avid fishermen, visiting Sarasota can be an event you’ll plan your entire vacation around.

Sarasota, Florida. Photo by Sean Pavone via iStock by Getty Images

You might also find it interesting that Sarasota is considered the world’s shark tooth capital. The answer is more surprising than you think. Namely, this is one of the places where the most fossilized shark teeth were discovered. So, if you’re looking for personalized souvenirs, this is the location for you.

The biggest problem with trying to time your visit to a place around a festival is that there’s usually little room for this type of flexibility. This makes Sarasota ideal—there’s always some festival around.

Lastly, you should visit an oyster bar. Here, you can try some of the tastiest, freshest oysters in the world and wash them down with some incredible local beverages.

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Your Offshore Adventures in Florida

At the end of the day, while boating may not be for everyone, the only way to know for sure is to try it. The best thing about it is that it offers the same amount of leisure and adventure, making it a perfect choice for those traveling in groups where individuals can’t make up their minds about the nature of the trip. We invite you to explore Wander With Wonder to get more ideas of things to do on and off the water in Florida. We also have more great suggestions for fun family vacations.