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Florida STAYcation Picks: Our Favorite “Drivecations” to Explore

As we began exploring the possibility of taking a family vacation, I noticed that my criteria had certainly changed from a year ago when I was planning a surprise European vacation. I was hesitant to fly, yet I still desperately wanted to get away to make summer memories with the kids.

I began searching for places we could drive to that wouldn’t be too crowded. I wanted private beaches and spacious villas with kitchens so I could cook in and not have to eat out for every meal. Outdoor activities and wide-open spaces were a high priority on my new list.

Having the entire state of Florida as our backyard and Georgia and South Carolina as neighbors, I soon realized that everything I was looking for a perfect vacation was right here.

Tampa happens to be the perfect location for a “drivecation.” Sneak away on a Friday, hit the road with your little roadies and make a b-line for any one of these adventures that will make you so glad you took the trip.  

Westgate River Ranch and Rodeo: 100 miles east

Category: Outdoor Adventure, Peaceful, Eco-Florida, Old Florida

You might be familiar with the Westgate brand from its collection of Orlando resort hotels, but Westgate also has an incredible dude ranch right in the heart of Florida!

Escape from city life in this vast Central Florida backcountry and wear your kids out on fresh air and good clean fun before bedtime. Spend the day adventuring on the 1,700-acre Westgate River Ranch, reminiscent of when ranchers and cattle controlled the rich Florida land. For younger kids, try touring the property on horseback, fishing at the catch and release pond, skeet shooting or mini golfing. 

Conestoga Ranch Glamping Resort at Westgate River Ranch
Conestoga Ranch Glamping

This Conestoga ranch glamping resort is a great mix of Luxe/Rustic retreat, with equal parts adventure and creature comforts (and quite a few creatures as well!). Bottom line, if you’re on the hunt for a truly unique Florida ranch vacation, Westgate River Ranch is your million star resort,

Pro Tip: Make sure you book a stay over a Saturday night so you can attend the Saturday night rodeo! 

An old Florida staycation adventure to Crystal River: 62 miles north 

Category: Water Adventure, Peaceful, Eco-Florida

staycations and drivecationsJuly 1 to mid-September is prime Gulf Coast scallop season; hunt for your own succulent treasure when you head out onto Kings Bay from the Plantation on Crystal River with your very own boat and captain. A mask, fins, snorkel and bag are all you need for this activity.

Once you’ve found your limit, take the scallops back to the Adventure Center where they will help shuck them and the chef at West 82 will cook them for you! Wind down by watching the sunset over the Bay and relaxing in your spacious villa. 

Pro Tip: Your guides can lend you a mask, fins and snorkel, but consider bringing kids their own. Bring an underwater camera or GoPro to capture the fun too!

Anna Maria Island: 64 miles south

Category: Beach Adventure, Peaceful, Eco-Florida

Florida STAYcation Picks: Our Favorite "Drivecations" to ExploreBook a 2-bedroom suite plus kitchen at the Waterline Marina Resort & Beach Club, just a block from Holmes Beach, which you’ll have pretty much to yourself as the public beaches are much further away. Take the free trolley to downtown Anna Maria Island for dinner at the Sandbar, where you can eat on the beach and watch the sunset right from your table.

Guess the sunset time right and you win a bottle of champagne! The next morning, have Kayak Jack deliver a paddle board to you for the day and later, walk to The Feast for lunch and to Small Town Creamery for a sweet treat. 

Related: Three Perfect Days on Anna Maria Island

Pro Tip: Get up early, pick up doughnuts from the Donut Experiment and drive to Anna Maria Island Pier to catch the sunrise. The pier is closed right now for renovations, but there is plenty of parking in the morning to park and enjoy this view!

Captiva Island: 176 miles south 

Category: Water Adventure, Beach Adventure

staycations and drivecations“Florida’s Tahiti” is the jewel in the crown of Gulf coast barrier islands. Enjoy it from the South Seas Island Resort that sits amidst 330-acres of wildlife preserve. Rent a golf cart to take full advantage of the resorts’ 2.5 miles of private beaches, pools, water slides and of course, the majestic Gulf sunsets!

For a full day of peace and quiet, pack your beach chair, a good book and cooler and have Captiva Cruises take you to Cayo Costa State Park. 

Pro Tip: Pack bikes, helmets and fishing rods to save a few bucks on the trip! 

Fort Lauderdale: 275 miles southeast

Category: Outdoor Adventure, Exploration, Water Adventure

staycations and drivecationsStart your vacation before you even arrive by driving across Alligator Alley and taking an Airboat Adventure out of Sawgrass Recreation Park to glimpse the Everglades—a unique habitat of 1.5 million acres of subtropical wetlands.

The Lago Mar Beach Resort and Club boasts one of the largest private beaches in Broward County, and the sunrise from this coast are spectacular.  Rent a canoe or kayak from Whiskey Creek Hideout at Dr. Von D. Mizell-Eula Johnson State Park and grab a quick bite from the Waterfront Bar and Eatery. With plenty of 2-for-1 LauderDeals happening in Fort Lauderdale now through September (including the Sawgrass Recreation Park Airboat Adventure), you can paddle-board, fish and scuba dive for half the price! 

Pro Tip: Visit Sunny.org for all the details on their 2-for-1 activities and download the pass book!

Key West: 422 Miles South

Category: Beach Adventure, Water Adventure, History, Eco-Florida

staycations and drivecationsBegin your stay in paradise when you check in at the Casa Marina Key West, A Waldorf Astoria Resort, home to the largest private beach on Key West. Build sand castles and relax in a hammock by the water or enjoy a Barefoot Billy’s dolphin excursion that leaves right from the resort.

Take the Old Town Trolley to the Key West Lighthouse and don’t forget to take your picture by the Southernmost Point Buoy. Enjoy dinner on the beach at Salute! On The Beach at Higgs Beach. Break up your drive home with a few nights at the Cheeca Lodge and Spa in Islamorada. Here, you can enjoy a complimentary paddleboard or book a 2-hour snorkeling trip right from the resort to see the second-largest coral reef in the world. 

Pro Tip: Build in one full day to check off a day excursion to the Dry Tortugas National Park, accessible by charter sea plane or ferry. Spend the day exploring Fort Jefferson and the surrounding natural habitats.

South Walton: 420 miles northwest

Category: Beach Adventure, Eco-Florida

Florida STAYcation Picks: Our Favorite "Drivecations" to ExploreTake scenic Route 30A west along the emerald coast of Florida’s Panhandle and feel the softest sugar sand beaches beneath your feet. The 16 coastal towns that make up South Walton are each unique in design, each with a  different vibe, and some are more budget friendly than others.

Rosemary Beach is our family’s favorite costal destination. Bring bikes to explore the farmer’s markets, playgrounds, boardwalks and four state parks in the area. Book a junior suite with a Gulf view at the Hilton Sandestin Beach Golf Resort and Spa and enjoy bunk beds for the kids and sunsets from your private balcony.   

Related: Getaway Itinerary: Beach Hopping in South Walton

Pro Tip: If you can, explore the 16 eclectic communities that make up South Walton. Each is unique and you might just find your next idyllic vacation spot. Definitely enjoy lunch at Airstream Row in Seaside, the town where “The Truman Show” was filmed.

St. Augustine Florida: 176 miles northeast

Category: Beach Adventure, History

Florida STAYcation Picks: Our Favorite "Drivecations" to ExploreThe oldest city in the United States is only hours away, making this an easy “field trip” that everyone in the family will enjoy! Dive into history at 300-year-old Spanish-built forts like the Castillo de San Marcos and Fort Matanzas.

Climb to the top of St. Augustine Lighthouse, a 165-foot tower with spectacular views of the coast. Walk through historic St. George Street and grab a cool treat at Hyppo Gourmet Ice Pops before checking out the Lightner Museum, formerly the Alcazar Hotel built by Henry Flagler in 1888. 

Pro Tip: Stay at the Ponte Vedra Inn and Club, about 40 miles north on AIA from St. Augustine, or at the Peyton House, which is one step from the Atlantic Ocean beach and close to the resorts’ Surf Club. 

Orlando: 95 miles east

Category: Relaxation, Outdoor Adventure, Eco-Florida

Florida STAYcation Picks: Our Favorite "Drivecations" to ExploreAlmost all theme parks will open in limited capacity by early to mid-July. Some require tickets and reservations, but there are so many other things to do if you head an hour east. At Wild Florida, you can experience the Everglades via an airboat without the long drive south.

Orlando Balloon Rides will take your family on an unforgettable hot air balloon ride over Central Florida. Book an entire home or villa for your family at Reunion Resort that comes with more amenities than a Disney vacation. Spend the day playing golf, foot golf (think golf but with a soccer ball), relaxing by the pools or playing in the water park, all without leaving your resort. If you must leave, Cocoa Beach and Kennedy Space Center are only an hour away for a day excursion. 

Pro Tip: Save a day to explore one or more of the seven state parks in a 50-mile radius of downtown Orlando. We enjoyed the refreshing crystal-clear waters of Blue Springs State Park. Bring a pool noodle!

Miami: 294 miles south

Category: Water Adventure, Outdoor Adventure, Exploration, Eco-Florida

Florida STAYcation Picks: Our Favorite "Drivecations" to ExploreWhile soaking up the rays on Miami Beach, take in a few sights that might make you rethink Miami as a family-friendly destination rather than a party scene.

Check into The Palms Hotel & Spa and relax with direct access to the beach or rent a private tiki cabana poolside—very Miami style!

Take in the murals of Wynwood Walls or panoramic views of Biscayne National Park from the 65-foot lighthouse at Key Biscayne and stop in Coconut Grove for dinner at Glass and Vine. After your kids have worked off some energy at Peacock Park, grab a brew from Panther Coffee for the ride back to Miami Beach. 

Pro Tip: On your way down, take advantage of day trips to see the Everglades or visit Fort Lauderdale.

Cocoa Beach & Cape Canaveral: 145 miles east

Category: Water Adventure, Outdoor Adventure, Eco-Florida

Florida STAYcation Picks: Our Favorite "Drivecations" to ExploreHop across Florida to Cape Canaveral to see real rocket ships, tour launch pads and learn about space from the experts at NASA.

Take a private surfing lesson when you stay at the Westgate Cocoa Beach Resort in Cocoa Beach or hit the waves and boogie board all day. Ride the 335-foot lazy river at Wakulla Falls Water Park or pick up a game of volleyball at the world-famous Cocoa Beach Pier. We loved eating at SeaDogs, but there are many places at the Pier to grab something to eat and drink.

Pro Tip: Bring boogie boards for the beach and plan a day trip to Merritt Island Wildlife Refuge. Pick up a map from the visitor center and drive up Black Point Drive or walk the trails to see all the amazing wildlife on the island.

Related: Go See a Rocket Launch and Explore Kennedy Space Center with the Kids: A Florida Bucket List MUST! 

Florida STAYcation Picks: Our Favorite "Drivecations" to ExploreBeyond the Sunshine State, but Worth The Drive:

Blue Ridge Mountains: 611 miles northeast

The mountains are calling. VRBO a picturesque mountain cabin on the outskirts of Asheville close to the Blue Ridge Mountains.

Pick up a trail guide and choose a few trails that younger kids can do (we hiked Flat Rock and Craggy Gardens). Drive along the Blue Ridge Parkway and stop to take pictures or just soak up the view from above. Stroll along Main Street in downtown Hendersonville and enjoy dinner outside at Never Blue. Fresh air and walking are good for the soul! 

Pro Tip: The Biltmore Estate will never disappoint so add that to your list of things to do before you leave the area.

Beaufort, South Carolina: 369 miles northeast

Florida STAYcation Picks: Our Favorite "Drivecations" to ExploreSouth Carolina’s second-oldest city is conveniently located between Charleston and Savannah along the Intracoastal Waterway. Check into your room at the Beaufort Inn and head to Blackstone’s Café to enjoy a traditional Southern breakfast.

Explore the waters with Beaufort Kayak Tours, then cool off at Hunting Island State Park, which boasts five miles of uncrowded beaches and nature trails as well as the state’s only publicly accessible lighthouse. Use the complimentary bikes from the inn to ride to the 10-mile Spanish Moss Trail, built over an old railroad line. Satisfy your sweet tooth at famed The Chocolate Tree, as seen in “Forrest Gump.”

Pro Tip: Jump in your car to find one of Beaufort’s quintessential road-side spots like the Shrimp Shack. The family-owned business has been frying up the best shrimp burgers around for more than 37 years. Chow down on made-to-order fried shrimp, shrimp burgers, crab cakes, flounder, clams, scallops and even fried chicken.

Florida STAYcation Picks: Our Favorite "Drivecations" to Explore

Smoky Mountains: 610 miles north

Drive north for just about a full day to visit the Great Smoky Mountains National Park in Tennessee and North Carolina. Stay off the beaten path by renting a cabin in Bryson City, North Carolina and access the park via Deep Creek.

Hike to see the waterfall at Juney Whank Falls, go gem mining in Bryson City, canoe in calm parts of the Nantahala River or level up your adventure by whitewater rafting with the Nantahala Outdoor Adventure Center. Disconnect for a while as you explore one of America’s greatest treasures: our National Parks and all their majestic glory. 

Pro Tip: Book your cabins early as they get very full in summer months!

Hilton Head, South Carolina: 374 miles northeast

Florida STAYcation Picks: Our Favorite "Drivecations" to ExploreHead for the Lowcountry of South Carolina and settle in at Hilton Head Island. There are several resorts, but a staff favorite is the Sea Pines Resort which features every-thing from hotel rooms, townhomes and single-family homes with your own pool.

This is a great option for families looking to distance themselves from others. Go for a bike ride along the many trails throughout the entire island.

There are more than 80 miles of intertwining trails. You can even ride your bikes on the beaches of hard packed sand. Tennis and golf are other popular activities as is a leisurely stroll through Harbour Town in Sea Pines Resort.

Pro Tip: Rather than bringing your own bikes, consider renting them from one of the numerous bike rental companies!

Lake Lanier, Cummings, Georgia: 491 miles north

Florida STAYcation Picks: Our Favorite "Drivecations" to ExploreFor those who want to camp but haven’t taken the plunge to purchase all the gear, head to Cummings, Georgia, and stay with the Georgia Glamping Company.

They have blended all the elements of a family camping trip with the amenities of a luxury hotel to create the perfect mix of an outdoor luxe vacation that will leave your family with all the memories of camp life.

Add on extras like a propane grill, fire pit, paddle boards or kayaks to make it easier to just show up and enjoy the time you have together. 

Pro Tip: Visit GaGlamping.com to book this Glamping destination with gorgeous Lake Lanier views. Spots won’t be available for long!

PHOTO CREDITS: Blue Ridge Mountains, St. Augustine, Cocoa Beach, Fort Lauderdale, Anna Maria Island: Marisa Langford – Beaufort, SC: Beaufort-Port Royal CVB – Captiva Island: South Seas Island Resort – Westgate River Ranch: Westgate River Ranch – Miami: The Palms Resort and Spa – Reunion Resort: Reunion Resort – Crystal River: Plantation at Crystal River – Rosemary Beach: Visit South Walton Florida – Key West: Cheeca Lodge and Spa – GA Glamping Company: The Wanderpreneurs – Smokey Mountains: Sommer Stiles – Hilton Head: Laura Byrne.

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