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Plan a family vacation to Southwest Florida for everything under the sun

Last updated 6th October 2024

Southwest Florida family vacations are warm and sunny year round. Sabrina Pirillo recently discovered quite a few other reasons why this lovely coast is irresistible to Canadian families.

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Naples Pier, Southwest Florida family vacations

It’s no secret that the Sunshine State is a favourite destination for Canadian families, it’s a vast playground of family fun filled with tons of activities and hidden gems waiting to be discovered along the way. But in southwest destinations like Naples and Punta Gorda, the possibilities for turning family moments into memories are practically endless.

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Fifth Avenue, Naples

Naples takes Florida family vacations off the beaten track

Situated on the Gulf of Mexico in Southwest Florida and referred to as Florida’s Paradise Coast, Naples is known for its family adventures and wild outdoor explorations.

Its world-famous Everglades National Park is the only subtropical mangrove wilderness in the US, home to endangered wildlife, as well as over 350 species of birds. And both Fifth Avenue South and Third Street South are highlights for Naples’ shopping in the historic downtown area, alongside plenty of places to dine beachside.

Is there anything more iconic than an Everglades’ airboat tour

There’s nothing like a beautiful Florida breeze whipping through your hair as you glide along the water across 104 hectares of private grasslands on an airboat through the Everglades. Wooten’s Everglades Airboat Tours adds a unique riding style through this vast ecosystem as their captains are like Vin Diesel in the Floridian version of Fast and the Furious Florida Drift! And don’t forget to keep your eyes peeled for movement in the water.

Enjoy a two-part immersive tour beginning with spotting a range of wildlife and then heading to an island for shelling with Marco Island Boat Tours. This tour is perfect for the whole family and starts by boarding an open-air boat and taking in the scenery of the 10,000 Islands National Wildlife Refuge while you head out and search for dolphins and wading birds with an expert naturalist.

Depending on the season, manatees, dolphins, sea turtles, bald eagles, ospreys, herons, egrets, pelicans, rosette spoonbills, as well as numerous species of fish and shore birds can be spotted. During the second half of the tour, marvel at Marco Island, the most family-friendly of the barrier islands, from Kice Island—an uninhabited barrier island—where you’ll spend time searching for beautiful seashells.

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Scoping out the Naples neighborhoods on the trike tour

Even getting about is more fun on Southwest Florida family vacations

Back on land, if an electric bike and a tricycle had a baby, they would produce a trike. Trike Tours USA offers a unique experience exploring the natural beauty and neighbourhoods of Naples on a 90-minute guided tour. Knowledgeable guides navigate through the heart of the city stopping at places like Naples Bay Landing Park, Millionaires Row and Old Naples along the way.

Famished for family dining? Get a taste for Southwest Florida 

Worked up an appetite from all the adventure? After your trike tour, stop in the Old Heart of Naples on Third Ave South and dine alfresco at Barbatella. Here, a rustic menu of Italian staples from abundant charcuterie trays to veal parmesan, pasta, pizza, salads and a Nutella pizza for dessert will leave you full and satisfied!

For dinner, let Executive Chef, partner and winner of Food Network’s “Chopped” championship, Kayla Pfeiffer, tantalize your tastebuds with what is described as her familiar and New American cuisine. Bicyclette Cookshop offers dishes like Caviar bumps paired with a pack of crunchy Bugles to roasted branzino, and even offers a Happy Meals menu for the little ones, plus it’s just a ten-minute drive from a hotel oasis.

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Beachfront Ritz-Carlton Naples, Southwest Florida

Ritz-Carlton Naples adds luxury and leisure to Florida family vacations

A celebrated beachfront icon, the newly transformed Ritz-Carlton Naples delights with signature experiences on Florida’s Gulf Coast beaches. Enjoy the feeling of refined luxury while the comfort and familiarity of a home shape an epic family vacation stay. Relax in expansive suites with extraordinary ocean views by booking a bi-level suite for optimal space. The suites feature a living area and a sofa bed with a separate bedroom, bathroom and balcony on the bottom level.

Located in the new Vanderbilt Tower, the spacious Club Lounge is spread out over 4,000 square feet and features a full-service bar, a whimsical kid’s club with toys, books, games and more, and offers five meal presentations, with fare that includes elaborate breakfast spreads, and sushi rolls, crudité, sandwiches, soups, charcuterie and more later in the day. There are also canisters full of snacks and coolers loaded with soft drinks and juices, available 24/7.

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View of the family pool, Ritz-Carlton Naples

Endless family pool fun in the year-round Florida sun

Once everyone is fueled up, head out and explore the property.

The Game Room houses video games, table tops and vintage arcade style entertainment; the gated Family Pool area (which can be seen from the bi-level suites) is only a few steps from the beach, where you can grab a bite at Gumbo Limbo Beach Bar & Restaurant and enjoy the sunset. Guests also have a complimentary shuttle to Naples’ sister property, Tiburon. Just down the road, it features waterpark fun at The Reservoir, which offers several poolside attractions including waterslides, a winding river and a children’s splash area.

Then, for your evening meal, I can recommend Nolita. On-site at the Ritz-Carlton, it draws inspirations from New York-style Italian classics (the clue is in the name) with artisan pastas and dishes inspired by family recipes.

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Southwest Florida family vacations on perfect Gulf Coast beaches

The Charlotte Harbor Gulf Island Coast, Punta Gorda and Englewood Beach

Punta Gorda/Englewood Beach is Florida’s charming natural paradise located on the Southwest Gulf Coast and is spotlighted by more than 1300 kilometers of pristine unparalleled shoreline, including captivating river passages, a mangrove-edged aquatic preserve, and more than a dozen miles of natural Gulf beaches.

This coastal community sits between Tampa and Naples and surrounds the state’s second-largest harbor. The Charlotte Harbor Gulf Island Coast includes the areas of Don Pedro Island, Englewood-Cape Haze, Port Charlotte and Charlotte Harbor, as well as Punta Gorda. And its combination of excitement and adventure, along with a chilled vibe, makes for a very family-friendly getaway destination.

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Sunseeker Resort, Southwest Florida family vacations

Soak Up the Sun at Sunseeker Resort

Opening its doors in December 2023 is Florida’s premier Gulf Coast Oasis: Sunseeker Resort Charlotte Harbor. Escape to this relaxing waterfront destination where everything you need for classic Florida family vacations is at your fingertips. Stay in one of the bright 785 guestrooms or in one of the 189 signature Sunsuites™ that feature floor-to-ceiling windows overlooking the Charlotte Harbor.

With 20 restaurants to choose from, your dining options are endless. This includes 11 food options from Harbor Yards Food Hall home to a diverse range of fares available throughout the day, two poolside options (Reflections Pool & Bar is on the ground floor with views of the harbor) and a restaurant at the golf course. The property also features boutique shops and a provisions store for all your snacking needs.

Fresh coastal fare awaits at Waterside Table Restaurant. Situated between the Sunseeker’s tropical pool oasis and the coastal views of Charlotte Harbor, the menu offers everything from poolside fare, to stacked Sunseeker Kid Cakes for breakfast, shared plates, starters, sandwiches, salads and more.

Discover outdoor adventure in Englewood and Charlotte Harbor

SUP Englewood gets the aquatic juices on Southwest Florida family vacations by letting you dive into adventure and take a paddling trip through Lemon Bay at Don Pedro State Park. By kayak, curious minds discover sea stars, live shells, hermit crabs and encounter manatees, dolphins and navigate trails through mangroves while learning about the importance of preservation and conservation with a Florida Master Naturalist.

In Punta Gorda, take a 90-minute eco-tour aboard a swamp buggy with Babcock Ranch Eco-Tours. With open windows and expert guides narrating your experience, get back to nature as you spot alligators, birds, deer, birds of all types and even wild hogs and turkeys as well as the historic Cracker Cattle. The tour goes through four different ecosystems of Florida, including the Telegraph Cypress Swamp.

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Fishermen’s Village, Punta Gorda © Visit Florida

Dining and dancing on Southwest Florida family vacations

In Englewood, indulge in an extensive and diverse menu of southern Florida fare and beachfront dining at Lock ‘N Key Restaurant & Pub.

Then head across the street and go shark tooth hunting, sit on the sandy beach, take on some waves or enjoy the basketball courts and playground at Englewood Beach.

Serving the community since 2009, Laishley Crab House is another Punta Gorda favorite, this time located on the Peace River waterfront, and offering stunning views along with its fresh seafood.

From Laishley Crab House, head down to the waterfront and board Red Tiki Tours. Their spacious 14′ x 28′ vessel features plenty of space to move around or even dance, if you dare. Alternatively, views of wildlife, a gorgeous sunset and the twinkling city lights from the water will mesmerize you. So sit back, relax, sip on a refreshing beverage and listen to music—or singalong to your favourite karaoke songs—as you cruise along the scenic shoreline.

Don’t miss Fisherman’s Village. Punta Gorda’s one-stop-shop superstructure, it’s part waterfront mall, part marina and part resort, featuring shops, boutiques, restaurants, spacious vacation suites, harbor cruises and live entertainment, as well as hosting special events throughout the year. Then, at the end of the village you’ll find Harpoon Harry’s, an open air, boat-casual seafood restaurant located on Charlotte Harbor where they serve a large array of seafoods, along with salads, sandwiches and cocktails.

Finally, just a short walk from Fisherman’s Village, the Military Heritage Museum is a thrilling experience for families. Not only does it house 1000s of fascinating artefacts, it features flight simulators, interactive displays, and a laser shooting range, as well as a 247-seat theater. And don’t worry about strolling past, you can’t miss the museum, just look out for the big Huey Helicopter right in front of it!

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