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Pull up an adirondack chair and settle in at one of Tampa’s favorite summertime escapes, the laidback Anna Maria Island. (Courtesy of Bradenton Area Convention and Visitors Bureau)

5 Destinations Tampa Locals Escape To

Leave of Absence

by Terry Ward
March 21, 2024
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It’s a beautiful thing to feel at once rooted in a place you love and also free and inspired to travel the world. There is just as much to experience and explore out there after all as there is waiting to welcome us home. As much as we love where we live, when summer arrives, more than a few people in Tampa decide to skip town for a change of scenery and a different sense of place in some of our favorite destinations in the United States and abroad.

From Highlands and Cashiers in North Carolina–where you should hardly be surprised if you bump into a Tampa neighbor at a waterfall or favorite haunts like Calders Coffee Cafe–to the Florida Keys during the sweet days of lobster mini-season, the Rocky Mountains, Italy and our city’s backyard beachy paradise on Anna Maria Island, these are a few of the treasured places where Tampa residents take a leave of absence come summer. 

Caribbean-hued seas and powder white sands are the backdrop for a stroll along Anna Maria Island. (Courtesy of Bradenton Area Convention and Visitors Bureau)

Anna Maria Island 

The secret is out about Anna Maria Island, but those of us in Tampa have long been enamored with the small-town charm and incredible sand-spun beaches of our backyard paradise. 

“I describe the island as having something for everyone,” says South Tampa mother of four Christy Vicari, whose company, Sunrise Bay Properties, offers vacation homes in Holmes Beach and Bradenton Beach. “It’s laid back like a true beach town with that beachy-vibe feel,” she says. “You won’t see any high-rises…which is part of its magic and allure.”

An idyllic day on Anna Maria Island might see you kicking things off with coffee and a cinnamon bun in the cheerful surroundings of Ginny and Jane E’s Cafe and Coastal Store before renting a golf cart or pedaling a bike to explore the island’s piers and cute shops and cafes along Pine Avenue. Come sunset, there’s no better spot than The Sandbar to enjoy a grouper sandwich and raise a margarita to the Gulf Coast good life with your toes in the sand. 

Surrounded by emerald green mountains, Lake Glenville, in North Carolina’s Jackson County, offers respite from the Florida heat. (Courtesy of Jackson County Tourism Development Authority)

Highlands and Cashiers, North Carolina 

“We love the simple mountain life for two months out of the year,” says South Tampa resident Lauren Basil about escaping to her family’s vacation home in Highlands, North Carolina, where she spends summer days tubing with the kids on pretty Lake Glenville and braving the chilly waters of local waterfalls. 

“My perfect day in Highlands is going on a hike with my family, exploring, eating good food and then curling up by the fire at the end of the day,” she says. 

Slip sliding away a beautiful summer’s day at Sliding Rock in Cashiers, North Carolina. (Courtesy of Jackson County Tourism Development Authority)

On the highest plateau of the Appalachian Mountains in North Carolina, roughly 600 miles north of Tampa (count on about 8.5 hours if you’re driving), Highlands has a temperate rainforest climate that’s a welcome respite from Florida’s summer heat. 

Consider making the elegant Old Edwards Inn & Spa, a Relais & Châteaux property right in town, your base for exploring the area’s hiking trails, scenic drives, golf courses and cute surrounding mountain towns like Cashiers. If you’re on an adults-only retreat, Half-Mile Farm, with cabins or rooms in a historic farmhouse overlooking Apple Lake, is a true treat. 

A road trip along the Overseas Highway through the Florida Keys beckons during July’s Lobster Mini Season. (Courtesy of The Florida Keys and Key West)

Florida Keys 

We can source our share of fresh stone crabs from local purveyors in the Tampa Bay area from mid-October to May 1. But come the last Wednesday in July, there’s no better place to be than the Florida Keys to celebrate harvesting and feasting on the Sunshine State’s other favorite crustacean. 

For two busy days during the lobster mini-season (this summer’s dates fall on July 24 and 25), Tampa families make places like Marathon, Key Largo and Islamorada their base of operations for diving the cerulean seas for their limit of spiny lobsters–both to enjoy in the moment at waterfront feasts and for filling freezers back home.

The early bird gets the worm during a sunrise paddle on Islamorada. (Courtesy of The Florida Keys and Key West)

“The Florida Keys are such a special spot to our family, as it brings us all together and our love for the water and just simply living that carefree, salt-in-your-hair and sun-in-your-face Florida life,” says Ashley Stutevoss of South Tampa, who decamps with her husband and kids to a family cottage on Big Pine Island every July. 

If you lack your own family address in the Keys, consider a stay at iconic Florida Keys resorts where you can BYOB (bring your own boat) like Reefhouse Resort & Marina on Key Largo, Hawks Cay Resort on Duck Key and Parmer’s Resort on Little Torch Key in the Lower Keys. 

Snow-capped peaks surrounded by so much green make Breckenridge as appealing in summer as wintertime.

Colorado and Utah 

Our favorite western ski towns like Breckenridge, Colorado, and Park City, Utah, come calling during the summer months, too, for hiking through meadows of wildflowers, enjoying mountain views from a cabin hot tub, mountain biking and more. 

New last summer in Breckenridge, The Carlin is the town’s only “restaurant with rooms,” offering four exquisite suites and different experiences on its three stories, among them Tavern Underground pub, for burgers, fish tacos and the like, and the more buttoned-up “Restaurant,” with its raw bar and wood-fired oven. 

In Park City, consider registering the kids for an outdoorsy day camp. Join the locals at favorite events like the Summer Concert Series at the outdoor amphitheater in Deer Valley and Park City’s biggest outdoor dinner party, Savor the Summit, in June. 

Villa Cipressi’s courtyard overlooks the property’s grand gardens and Lake Como. (Courtesy of R Collection Hotels)

Italy 

An advantage of school getting out so early in Tampa for summer compared to elsewhere around the country means we can get over to Europe before the bulk of the tourist crowds descend on the continent in July and August.

June is prime season to experience France, Spain and Italy–our favorite–before everyone else arrives and temperatures are still mild. 

Consider renting a house in Tuscany’s wine country, heading to Portofino or the Amalfi Coast to live the Mediterranean lifestyle or relaxing lakefront in northern Italy at Lake Como with a hideaway property like Hotel Villa Cipressi as your summertime address.   

Along the Portofino coast in Rapallo, Grand Hotel Bristol beckons with some of Liguria’s most stunning views. (Courtesy of R Collection Hotels)

Want more inspiration? Check out Where to Go in 2024. Looking to advertise, click here.

Tags: anna maria islandColoradoflorida keysItalynorth carolinaTerry Wardtravelwhere to go
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