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overhead shot of white lounge chairs and two ping pong tables surrounded by greenery at manasota key resort in florida

You know you’ve been humming along, maybe even screaming the lyrics alto voice in the shower, possibly muttering them as you drove your car around town. “I need to forget, so take me to Florida.” You’ve sung with meaning, doing your best Taylor Swift, bellowing soulfully, totally empowered into your hairbrush microphone. You’ve screeched the words in an uncertain soprano full blast. Oh, yes, The Tortured Poets Department had you at “Florida.” So, you gathered your besties, rented a vintage car — a convertible — and hightailed it to the Sunshine State.  “I need to forget,” you crooned together. “So take {us} to Florida,” you all howled, slightly off key. Your harmonies wafted down the road in the wind. Embarking on a road trip to Florida with Swiftie power had become an act of liberation. So off you rambled to the state’s southwestern corner to warble your way through a trio of fascinating destinations. From St. Pete/Clearwater known for its vivacious Gulf Coast beaches (with powder-sugar sand and emerald green waters) and buzzy food and arts scene to Manasota Key, located on the southernmost tip of Sarasota County (a haven for kayakers, shell seekers, and sunset buffs), this itinerary also takes you to Fort Myers and its bevy of culture-rich neighborhoods, eye-catching architecture, history, and pristine beaches. 

overhead shot of white beach chairs facing a body of water in florida
Courtesy of Manasota Key Resort

Day 1-2

Fly into St. Pete–Clearwater International Airport, which serves the Tampa Bay Area — and grab the coolest vintage convertible with the longest body and the biggest fins you can find. Escape Swiftie style into this storybook beach town with its trendy downtown and retro-beach scene. Slather on sunscreen, as St. Pete’s boasts an average of 361 sun-dappled days a year. 


Where to Stay

What could be more ideal for launching your girlie getaway than a pink castle? Renovated, historic, full of stories that could easily become Taylor Swift lyrics The Vinoy Resort & Spa, an Autograph Collection hotel, has chic rooms, a stellar spa, a clover-shaped pool, and tennis courts. Take time for a reset massage or results-driven facial. 

Where to Eat and Drink

Brunch at Concrete Jungle (Salmon Benedict or Chicken and Waffles) or Wild Child (Turkish Eggs or Avocado Toast). Dine at No Vacancy, the ideal hotspot for classic Florida seafood bites (think Under the Sea Nachos with lobster and shrimp), as well as punch bowls and tropical cocktails. End evenings at buzzy Dirty Laundry where waiters serve mojitos in pitchers. 

Shopping

When ready to shop, stroll down Central Avenue. Pop into trendy ZaZoo’d for unique decor and cool Ashe Couture for fun clothing. Brutique, a bar-cum-boutique has libations as well as bar accessories. Go to Crislip Arcade, a renovated 1926 arcade packed with vendors, including Merchant which sells quality, hand-crafted, Florida-made gifts.

closeup shot of a seashell on sand in florida
Courtesy of Fort Myers and its islands, neighborhoods and beaches

What to Do

Book an extravagant cabana hangout on St. Pete Beach, courtesy of The Cabana Club, a fun company that takes the hassle out of lugging your encampment to the sand. They’ll carve out an elegant spot complete with all your beach-day accessories. Later, find time for Clearwater Beach where Pier 60 awaits, abundant with calorie-burning activities for those so inclined — such as paddleboarding. Stay for the famous sunset enhanced by the presence of performers, musicians, fire breathers, and dancers. 

DAY 3 – 4: Manasota Key 

Driving distance to Manasota Key: 1 hour and 20 minutes 

Partake of island time on this unspoiled barrier island in south Sarasota County, just south of Venice and northwest of Englewood. A true hidden gem that envelops travelers into the serenity of nature, it stretches for 11 miles, edged by captivating white-sand beaches. Don’t miss Stump Pass State Park, a fisher’s paradise, where visitors regularly find an array of seashells and washed up shark teeth. 

a bedroom with white sheets at manasota key resort in florida
Courtesy of Manasota Key Resort

Where to Stay

Meld some Jimmy Buffet barefoot luxury into your Taylor-esque trip at oceanfront Manasota Key Resort, recently re-imagined to further showcase the island’s natural setting.  Positioned among native plants, with sparkling private beaches and two pools (not to mention lawn games), the breezy retreat excels at supporting guests in their quest to connect with nature — including paddleboard adventures to view manatees and dolphins in the bay, pelican, egret, and osprey spotting, kayaking, and more. 

Where to Eat and Drink

Seaside, nosh authentic smoked barbecue at Sandbar Tiki & Grille (burgers and coconut mahi baskets) for lunch. In the evening, slip on sundresses and order up fancier American coastal cuisine at The Waverly, (Oysters Rockefeller, sushi, shrimp cocktails) which overlooks Englewood Beach. Look no further than Manasota Key Resort’s Beach Bar for sunset cocktails. 

Shopping

In the  area of Manasota Key and Englewood,  local boutiques, farmers markets (with regional produce and artisans), and beach-centric gift shops will tempt. Buy that new bikini at Barefoot Trader and the necklace to go with it at Inspired by the Sea.

kayaks lined up near a small shed on a beach in florida
Courtesy of Manasota Key Resort

What To Do

Bike or trek through Sump Pass State Park, resplendent with trails, a mangrove forest, and bone-white beaches. Kayak or standup paddle board through crystalline waters from Manasota Key Resort to Lemon Bay, where you can spot countless bird species, dolphins, and manatees along the way. Or, chill at the pool or beach and let Florida help you “forget” and “bury” your regrets — per Taylor’s Florida!!!.

DAY 4 – 5:  Fort Myers and its islands, neighborhoods and beaches 

Driving distance to Fort Myers: 1 hour and 15 minutes

Calling all mermaids — build your castle in the sand in Fort Myers, its stylish islands, and its swanky neighborhoods. Dubbed the ”Seashell Capital” for its uncanny trove of seashells ever tossed to shore by the waves, the fascinating area has urbane, ritzy appeal mixed with casual allure.  Dynamic, Sanibel brims with shops and eateries, while quieter Captiva imparts a more ocean village vibe. 

overhead shot of tween waters island resort swimming area in florida
Courtesy of Fort Myers and its islands, neighborhoods, and beaches

Where to Stay

The quintessential beach retreat ‘Tween Waters Island Resort & Spa occupies 13 verdant acres on Captiva Island. With cottages, suites, and studios that pepper the beach, the hideaway has historic gravitas and upscale appeal with an Olympic-sized swimming pool, acclaimed dining, everlasting live music, nearby adventures aplenty (parasailing, shell hunting cruises), and an on-site spa.  

Where to Eat and Drink 

Do a brewery hop when it’s time to take a break from the sun. Begin at Fort Myers Brewing Company, the county’s first microbrewery, which specializes in funky beer flavors such as rich “Chocolate Stout” with notes of dark roasted coffee. Next, to the rhythm of live tunes, sample small-batch brews at Point Ybel. Try famous sour ales like “Who Lives in A Pineapple Under the Sour.”

Shopping

Get your Taylor-like garb at The Franklin Shops, a historic two-story structure in the heart of downtown Fort Myers. It’s full of show-stopping independent vendors selling fashion, jewelry, art, home decor, gifts, and more. 

What to Do 

Wander Bowman’s Beach with a basket in search of sand dollars, Conch shells — even the rare Junoia shell. Source materials as you go for a Swiftie crew art project — perhaps a beach-themed Eras friendship bracelet to commemorate your Florida!!! vacay.  Become master seashell identifiers at The Bailey-Matthews Shell Museum & Aquarium, home to the rarest collection of seashells. It’s the USA’s  sole museum dedicated to these ocean treasures. For the car caper’s piece-de-resistance, take a charter tour on a catamaran-style tiki boat with Nautical Tiki Cruises. Onboard Bluetooth speakers will blast all the best Taylor songs while you sing along and dance the night away. Offering stops for swimming or island-hopping, plus the chance to glimpse dolphins which seem to leap in rhythm with Taylor tunes, the BYOB cruise puts you front and center for the spectacle for one of the region’s kaleidoscopic sunsets.

Featured image courtesy of Manasota Key Resort