Road Trippin’ - Guide to Greater Tampa Bay
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Road Trippin’

Road Trippin’

10 Destinations to visit on one tank/charge 

St. Augustine 

Must-try dining 
  • Breakfast: The Blue Hen Cafe 
  • Lunch: The Floridian 
  • Dinner: Collage 

With more than 42 miles of sandy beaches and enough historical attractions to captivate visitors for days on end, it is no wonder the oldest city in North America is consistently voted a top travel destination.  

St. Augustine’s deep Spanish history is seen throughout the historic town’s style and architecture. Two of the most popular relics from the past are the Colonial Quarter and towering Castillo de San Marcos, both of which can be explored via the Old Town Trolley or Ripley’s Sightseeing Train.  

Flagler College is not just a private college in the middle of downtown, but a historical landmark, as well. It is housed in the former Ponce DeLeon Hotel, which developer Henry Flagler built in the late 1800s as a luxury resort. See the former hotel in all its splendor on one of the public tours, with its gold-plated fixtures, intricate wood carvings, paintings, mosaics and elegant Spanish design. 

Fans of the greatest game are in luck. The Ancient City boasts a myriad of golf courses for all skill levels and budgets, including the nearby Players Championship course at Sawgrass, to satisfy all golfing desires.  

If coming face-to-face with prehistoric reptiles sounds better, enjoy an excursion to the St. Augustine Alligator Farm. Zip over the exhibits with their aerial obstacles or Pirate and Treasure Museum. Delve further into history at the Fountain of Youth and drink from the same springs that inspired explorers of all creeds to traverse the high seas in hopes of eternal life.  

Round out a fun-filled trip with a tour of the St. Augustine Distillery, bites and beverages at the adjacent Ice Plant Bar, a walk down the shelly St. Augustine and Vilano beaches or a haunted ghost tour. Not just for history lovers but rather full of adventure for all kinds of interests, simply pick the path to fun in St. Augustine. 


Must-try dining  
  • Breakfast: The Gathering Cafe 
  • Lunch: Ivy on the Square 
  • Dinner: Stirrups at the World Equestrian Center 

Known as Horse Country for its ties to Triple Crown winners and thoroughbred pedigrees, the rolling hills of lush green grass and ancient oaks have also served as the backdrop for a number of Hollywood productions.  

The World Equestrian Center in Ocala is one of their two locations in the country, and the largest equestrian complex in the US. Their indoor and outdoor arenas offer places to shop, eat, stay and, of course, watch some racing. From their Summers End Horse Show to their Winter Spectacular Show and everything in between, the World Equestrian Center has something for everyone. 

The City of Ocala is the gateway to the woods and lakes that make up the Ocala National Forest, which includes the largest sand pine forest in the world. Sand pines, live oaks and limestone canyon cliffs join forces at Canyons Zip Line and Canopy tours, where two to three hours can be spent gliding high up among the trees, taking in the sights from a bird’s-eye-view on more than a mile of interconnected zip lines.  

Ocala is not just rich in natural beauty, but cultural beauty as well. On campus at the College of Central Florida, the Appleton Museum of Art sits on 44 wooded and landscaped acres in the scenic area. The 81,610-square-foot museum is clad in travertine marble and houses a permanent collection of more than 24,000 works of art that represent 5,000 years of artistic creativity by cultures from around the world.  

The Appleton is accredited by the American Alliance of Museums and throughout the year has special exhibitions, hosts programs by visiting artists and scholars and offers studio art classes for all ages. The hours are 10 a.m. to 5 p.m. Tuesday-Saturday, and noon to 5 p.m. Sunday. For more information, visit  

Still have some energy to explore? Enjoy a horseback tour with one of these fabled steeds or simply slow things down and catch a double feature at Ocala’s Drive in Theater, one of the few remaining drive-in theaters in the country, ideal for a unique date night. 


Must-try dining 
  • Breakfast: Briar Patch 
  • Lunch: Hillstone 
  • Dinner: Bull and Bear at Waldorf Astoria Hotel 

For the seemingly few people who have not already been at least once, Orlando is on almost everyone’s bucket list — and for good reason. The Theme Park Capital of the World has it all. The thrills of visiting the Wonderful Walt Disney World, Universal Studios, SeaWorld Orlando and Discovery Cove are real, but they are only the beginning of the city where having fun is a way of life. 

Known as the City Beautiful, Orlando is home to more than 100 lakes, nearly 150 beautiful parks, gardens and recreation areas, hundreds of natural and manmade attractions, a thriving downtown, major league sports and international shopping and outlet malls.  

See it all from above. Breeze across the skyline in an Orlando Balloon Rides hot air balloon or glide with Aerostat Adventures over tropical landscapes. After touchdown, get moving with rentals from West Orange Trail Bikes & Blades and cruise Florida’s popular 22-acre West Orange Trail on rollerblades or bicycles. 

Zip through the Everglades’ headwaters on a Boggy Creek Airboat Adventure and look out for Florida’s original inhabitants. See alligators from land at the 110-acre wildlife preserve, Gator Spot, and seek out the rare leucistic white alligator. Go-karts and arcade games are next door at Fun Spot America’s multi-level go-kart tracks. 

Time to check out the unique parks and lakes of Orlando and feed the swans at downtown’s Lake Eola Park. Swan paddleboat rides are available there as well. Get the bait ready — the fish are biting at Bill Frederick Park at Turkey Lake, one of Florida’s top fishing spots. Next, grab a book and blanket and refresh under lush trees at Loch Haven Park and then check out the nearby Orlando Museum of Art and Orlando Science Center. The day ends with the best sunset spectating perch at Lake Underhill Park.  

Rather go for a walk? Stroll through the charming Thornton Park. It is known for boho boutiques, organic juice bars and stylish eateries. 

The nightlife is always buzzing in Orlando, from the multicolored lights of the Wheel at ICON Park at night to the flashy attractions along International Drive to the bars and clubs lining the downtown streets. Day or night, the good times never rest in Orlando. 

Space Coast 

Must-try dining 
  • Breakfast: Jimmies U.S. 1 
  • Lunch: Fishlips Waterfront Bar & Grill  
  • Dinner: Dixie Crossroads 

Cape Canaveral and the Kennedy Space Center on Merritt Island showcase America’s ambition and determination to get to the moon and beyond. 

The place where the nation launches and builds satellites and constructed the infrastructure that has made the International Space Station a celestial reality is open for exploration. At the hub of the Human Space Program, visitors can enjoy launch and training simulators, the Hubble Space Telescope theater, the U.S. astronauts Hall of Fame and the revered Rocket Garden that pays homage through relics and tours to the Mercury, Gemini and Apollo space programs that put America on the galactic map.  

Do not forget to pay respects at the Space Mirror Memorial, the towering national monument honoring the fallen astronauts who reached for the moon and landed among the stars..  

After a day in space, get grounded again at the Manatee Sanctuary Park and encounter this endangered species in its natural habitat. For the avid fishermen out there, the Space Coast is paradise, famed for an abundance of popular inshore sportfish like red drum, spotted sea trout and snook. 

After working up an appetite for some good seafood, head over to Cape Canaveral and eat at any of the channelside restaurants for dinner and a show: A table out on the decks will score patrons a view of the cruise liners coming into port. 

Fort Myers   

Must-try dining 
  • Breakfast: McGregors Cafe 
  • Lunch: Downtown House of Pizza 
  • Dinner: Wisteria Tea Room & Cafe 

Submerge into rich historical moments of America before leaning into the grand sandy beaches of this shimmering shoreline city in Southwest Florida.  

Fort Myers flaunts history and beauty with a 25,000-square-foot museum, botanical laboratory and giant banyan studded gardens at the Edison & Ford Winter Estates atop the banks of the Caloosahatchee River. The city has roots as the home of Calusa Native Americans and a destination of explorer Ponce de Leon. 

Today’s adventure-driven visitors reap the riches of Fort Myers Beach, running from north Bowditch Point Park to Lovers Key State Park. The Pier at Fort Myers Beach and Times Square, directly behind the pier, are dotted with surf shops, unique shopping, outdoor dining and a length of sunbathing-worthy waterfront offering volleyball and watersports. It is a perfect spot for all family members to relax. 

After 2003, The historic downtown area was brought back to life after decades of neglect. It is considered the river district combing waterfront homes and a walkable area for shopping, dining and entertainment. You can enjoy a crafted cocktail at The Standard, eat fresh seafood at the waterfront Oxbow Bar & Grill, listen to jazz music at The 86 Room, walk the monthly art and music walks or smoke a cigar at the World Famous Cigar Bar just to name a few.  

Mound House, a Calusa resting place, showcases history from 2,000 years ago. Tour the 30-feet high shell burial mound at Mound Key Archeological State Park. Historic downtown Fort Myers brings a different decade to enjoy. The 1920s art deco design, buzzing European curbside dining and the iconic Ford’s Garage restaurant make having dinner a destination event in this city center. 

More teaching moments in mind? Plenty of hands-on activities at the IMAG History & Science Center bring guests closer to the Calusa. Tour the IMAG aquarium and wind through weather and nanotechnology, too. Venture to the stars with planetary probing, meteorite collections and seven-days-a-week of planetarium shows at the Calusa Nature Center and Planetarium, only nine minutes from the IMAG. 

The Manatee Park, butterfly exploration and MLB Spring Training, featuring the Boston Red Sox and Minnesota Twins, will surely make for some one-of-a-kind memories in Fort Myers — this gorgeous Gulf-side city. 


Must-try dining 
  • Breakfast: Willow’s Cafe 
  • Lunch: The Garden Room Cafe’ at Shoogie Boogies 
  • Dinner: Siegfried’s Restaurant and German Biergarten 

Sarasota is a beach destination with 35 miles of white sand along the Gulf of Mexico, cultural attractions, nightlife and a district personality. Considered part of Southwest Florida, it is only a short, hour drive from St. Petersburg.  

Mingle at special events, volleyball tournaments and spring break festivities at Siesta Beach or picnic at family-friendly Lido Beach Park in mid-Lido Key. Caspersen Beach is prime for wildlife sightings, shelling and shark teeth finds, while Brohard Paw Park is perfect for a day with the dogs. 

Host to opera, symphony, classical ballet, film festivals, comedians and circus clowns, find cultural respite at the Sarasota Opera House. Spend hours with the circus world czar John Ringling and his wife, Mable, at Ca d’Zan at The Ringling. This Italianate estate brims with Renaissance-era paintings, the world’s largest circus in miniature, a unique sculpture garden, a circus museum and a historic theatre.  

Upscale shopping, eclectic galleries and restaurants are nearby at St. Armands Circle, and the bayfront sanctuary, Marie Selby Botanical Gardens, is not far away. Kids can climb through the caves and jump around the jungle while parents enjoy a trek through a lush, tropical oasis.  

The diversity of Sarasota does not stop at the dog beach or the opera. Downtown has great places to eat and an active nightlife with cabarets, comedy and local music. Old Florida adventures at Myakka River State Park journey through the same wetlands that Native Americans traversed over a century ago. Get a new perspective on an airboat ride through Lake Myakka’s alligator-laden waters. Whatever the getaway calls for, Sarasota has it all. 


Must-try dining 
  • Breakfast: Blueberry’s Cafe 
  • Lunch: Caffe dell’Amore 
  • Dinner: Mediterrano 

Naples has quickly become the pickleball capital of the world. Included in the transcendent elegance and beauty of Naples is East Naples Community Park. Its 68 courts welcomed 2,000 players from 47 states and 20 countries in 2021 for the first U.S. Open Pickleball Championship. With an average low temperature of 72 degrees, this Paradise Coast destination is a world-class wonder. 

Beyond the courts are the silky beaches and rolling waters flush with tropical fish, birds and other wildlife. Naples Beach, where Naples Pier is located, is a perfect place to start the day. Families love the access to playgrounds and showers available at Lowdermilk Beach Park near downtown and the serenity of Delnor-Wiggins Pass State Park’s undisturbed barrier island. 

The Florida Panther National Wildlife Refuge and Bird Gardens of Naples, home to wild parrots, make for more memorable tropical excursions. Naples Zoo at Caribbean Gardens is filled with giraffes, primates, pythons and a historic botanical garden. End the day with magical manatees on a Manatee Sightseeing Eco-Tour by boat. 

Any good trip calls for a journey into the world-class culture of Naples. Historic downtown boasts Fifth Avenue South and Third Street South, where high-end boutique shopping, exquisite dining and gallery shopping are endless. Antiques lovers will enjoy hunting for iconic pieces in the Naples Antique district and the classic ambience from Naples Philharmonic Orchestra. Both Luciano Pavarotti and Andrea Bocelli have performed with them. Or end the night with Opera Naples at Wang Opera Center. 

Simple works, too. Grab dinner at Celebration Park Naples, filled with food trucks serving seafood, barbecue and fusion cuisine along the waterfront.  

Whether it is an easy weekend or extravagant vacation beyond the sugary beaches, the activities, arts and environment of Naples are where visitors can suit up for any occasion. 

West Palm Beach 

Must-try dining 
  • Breakfast: Loic Bakery Cafe Bar 
  • Lunch: Hullabaloo 
  • Dinner: Pescatore Ristorante 

Punch that ticket for a three-hour, 40-minute Amtrak train ride directly from Tampa Bay and relax all the way to the luxury of West Palm Beach. A vibrant community with colorful neighborhoods, celebrated beaches and upscale shopping, West Palm Beach continuously offers exciting eateries, lots of adventure and a refined sense of living. 

Henry Flagler’s segue into hotels and railroads originally drew those to visit West Palm Beach and sister city Palm Beach. Today, more than 8 million visitors annually swim the celebrated waters of Palm Beach, postcard perfect Lake Worth Beach or Peanut Park’s clear turquoise waters. Get a unique ocean view at the John D. MacArthur Beach State Park sitting on an Atlantic Ocean barrier island or join scuba and free divers spending the day diving at Ocean Reef Park. Dog enthusiasts pick Juno Beach, and sun bathers get cozy with a rental cabana or lounge chair at Oceanfront Park on Boynton Beach. 

See Also

There are plenty of family adventures, too. Shipwreck Cove and 190 species of ocean inhabitants tantalize at the South Florida Science Center & Aquarium, as does a round of mini golf at its Conservation Course. For more animal interaction, rides and splashing around make way for Lion Country Safari, part drive-through safari, part adventure park and all parts a roaring good time. A lazy river, wave pool and more make plunging into Rapids Waterpark a very cool idea. 

Add one last stop at Henry Flagler’s Beaux-Arts Whitehall grand mansion, built in 1902, before going to West Palm Beach Antique Row for shopping and dinner. Find quaint European eateries like Belle & Maxwell’s and Rosemary Square offers more familiar faire, as well as one-of-kind shops. West Palm Beach will always remain a favorite weekend getaway. 

Greater Gainesville  

Must-try dining 
  • Breakfast: Afternoon 
  • Lunch: Paramount Grill 
  • Dinner: Spurrier’s Gridiron Grill 

Hop on northbound Interstate 75, driving straight into Greater Gainesville in just two hours, and spend a day, a weekend or even a whole week in the Gator Nation.  

Greater Gainesville is so much more than the home of the prestigious University of Florida. It is also Old Florida, a busy city, a fun downtown, a natural haven and a cultural epicenter all at once. 

Enjoy the excitement of college football at Ben Griffin Hill Stadium and more than 75,000 roaring fans chomping down on years of tradition. Then, get lost in big city culture or natural elements found everywhere in the area. Rock the night away, enjoy Dance Alive National Ballet or take a seat at any of the dozens of professional theatrical performances at the Hippodrome Theater or Curtis M. Phillips Center for the Performing Arts.  

Start the excursion off at one of Greater Gainesville’s sparkling gems, The Cade Museum of Creativity & Innovation, which will excite the family while discovering fascinating scientific inventions. Learn about the University of Florida’s famed hydration invention, Gatorade, and even talk to astronauts at the Hubble International Space Station.  

Next up are the Florida Museum of Natural History and the Butterfly Rainforest. Travel through Florida’s history of flora, fauna, fossils and historic people and enjoy special exhibits that sometimes include a T-rex or two. Celebrate lepidoptera and biodiversity with more than 80 species of butterflies and moths in the Butterfly Rainforest or experience the daily release of butterflies and the world’s largest moth, the Atlas moth. 

Just as charming as the athletic and arts scenes are the peaceful natural springs and habitats surrounding Greater Gainesville’s seven municipalities. Start the day with a bike ride, hike or walk along the pristine paths and extended trailways, preserves and nature parks that wind through Greater Gainesville.  

The 21,000-acre Paynes Prairie Preserve State Park is a National Natural Landmark. This savanna ecosystem puts explorers close to bison, wild horses, tropical birds and Florida’s omni-present alligators. Other popular parks include Sweetwater Preserve, a woodland park with wetlands, where dozens of native birds visit. Find sandhill cranes, purple gallinules and great blue herons among the mix. 

Botanical enthusiasts will thrill at the 68 acres filled with 24 major collections along Kanapaha Botanical Gardens 1 ½-mile walkway. It provides places for kids to play, koi to feed and giant Victoria water lilies — known to reach an 8-foot expanse — to awe over. 

Take a time out and enjoy the view from one of the classic Southern rocking chairs on the visitor’s center porch before cooling off in one of the area’s many alluring natural springs. Float, kayak or canoe in the cool, crisp waters of Alexander, Blue, Ginnie, Ichetucknee, Juniper, Otter, Poe, Salt and Silver Glen Springs or popular local favorite, the K.P. Hole. Picnicking and camping are available, too.  

Healthy eating options abound in Gainesville. Ranking site Niche named it one of the “2021 Healthiest Places to Live in Florida” by the abundance of farm-to-table options. Farm fresh is not a cliché, with family farms providing fresh fruits, vegetables and more to many of the area’s restaurants, including the area’s specialty: watermelon.  

Tasty comfort food and delicacies are everywhere in Greater Gainesville. From Spurrier’s Gridiron Grill, Prime & Pearl Steakhouse, Alpin Beer + Wine’s casual French Bistro, Paramount Grill in downtown Gainesville, to great brunch Afternoon or sushi at Dragonfly Sushi, there is no shortage of options for even the pickiest palates. 

After an indulgent dinner, it is time to end the day with some incredible live music in this city where history runs deep. Home to Bo Diddley and Tom Petty, Greater Gainesville does not disappoint, with talented acts across genres. Options from grassroots to the 55-member Gainesville Orchestra are endless. 

Bo Diddley’s Plaza on a Friday night is full of free concertgoers and a fun vibe. Rock out at the Heartwood Soundstage, where nationally recognized bands often play. Enjoy the classics, orchestral, symphonic, quartets, trios and more at the Curtis M. Phillips Center for Performing Arts. The first-rate fine arts venue offers international ballet, Broadway and theater. It is positioned next to the 40,400-square-foot Harn Museum of Art, home to the works of Claude Monet and presidential portraitist Kehinde Wiley, pottery collections and so much more. 

Only two hours up the road, taking the drive to explore Greater Gainesville’s Gator Nation, nature, fine art, museums, Old Florida history, gastronomic and musical pleasures is well worth the drive. 


Must-try dining 
  • Breakfast: Louisiana Lagniappe 
  • Lunch: Bitterroot food and spirits 
  • Dinner: McGuire’s Irish Pub of Destin 

Not to be overlooked, this hidden seaside gem along Florida’s Emerald Coast is one of the Sunshine State’s finest locales for golf, nature trails and general coastal revelry. Destin is the quintessential slice of Floridian heaven. 

Positively rife with top-notch beaches, Destin’s aquamarine waters are crystal clear, edged by soft white sands and lofty, natural dunes. Visitors will never feel landlocked, as the thin strip of beachfront is flanked by the calm Gulf of Mexico on the south side and the wide Choctawhatchee Bay to the north. Be sure to check out the gorgeous natural coastline at Henderson Beach State Park. 

Water sports are an obvious choice for Destin’s active population. Naturally encouraged by the abundant waterways, jet skiing, dolphin excursions, fishing and parasailing are go-to ventures for visitors and veterans alike. Meanwhile, scenic vistas abound for golfers at Destin’s famous courses. Country clubs and championship courses are unbelievably plentiful, including the famous Kelly Plantation Golf Club, an 18-hole waterfront wonderland established on a former turpentine plantation.  

Need a break from the sun? There are plenty of restaurants, nightlife venues and shops to mix things up. Destin Commons, for instance, is an outdoor plaza rich with diverse retailers and sizzling seafood restaurants. Historic Fort Walton Beach is abuzz, year-round, with folks getting their fill of breweries, cafes, farmers markets and shining local crafts soaked deep with Fort Walton’s curious quaint flavor. 

Despite the distance, Destin is an absolute must-go. An adorable beach town, it is the perfect vacation destination and first taste of Florida for those heading down to the Sunshine State. 

By Rose Derkay and Shelley Akins.

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