1. Sunken Gardens (St. Petersburg)
One of St. Petersburg's oldest tourist attractions, Sunken Gardens has been welcoming visitors since the 1930s, when it grew out of a drained lake bed turned lush botanical garden. Today, families can wander winding paths through tropical plants, koi ponds and flamingo habitats inside a piece of living St. Pete history. 1825 4th St. N, St. Petersburg
2. Heritage Village (Largo)
Spread across 21 acres in Pinellas County's Heritage Park, Heritage Village is an open-air museum featuring more than two dozen historic structures, from a Cracker farmhouse to a railroad depot, relocated and restored to tell the story of Pinellas County life from the 1800s to the early 20th century. You can walk right into the past, admission is free. Bonus: Heritage Village is celebrating their 50th anniversary this year. Stop by and wish them a happy birthday! 11909 125th St. N, Largo
3. Ybor City (Tampa)
Just across the bay, Ybor City offers a walkable history lesson in cigar-rolling, immigration and Tampa's industrial boom. Stroll the brick streets of this National Historic Landmark District, visit the Ybor City Museum State Park, and grab a Cuban sandwich while you're at it. Bonus points for spotting the neighborhood's famous roaming chickens. Ybor City Museum State Park, 1818 E 9th Ave., Tampa
4. Gulfport Historic Waterfront District
This small, walkable beach town on Boca Ciega Bay has kept its old Florida charm, with a historic casino building, waterfront park and a laid-back main street lined with local shops and eateries. It's a low-key way to introduce kids to Florida's early 20th-century resort-town roots while still leaving time for a splash in the bay. Beach Boulevard S, Gulfport
5. Sacred Lands
Sacred Lands preserves and interprets the site of a centuries-old Tocobaga Indian mound, offering families a rare chance to connect with the deep Indigenous history of the Pinellas peninsula long before European settlement. It's a quiet, reflective stop and a meaningful reminder of who called this place home first. 1700 Park Street North, St. Petersburg
6. St. Petersburg Shuffleboard Club
Founded in 1924, the St. Petersburg Shuffleboard Club is the oldest and largest shuffleboard club in the world and a colorful piece of the city's history as a haunt for retirees and snowbirds long before it became a hip multigenerational hangout. Grab a court, learn the rules and let the kids discover a game their great-grandparents might have played right here. 559 Mirror Lake Dr. N, St. Petersburg
7. Sponge Docks & Spongeorama (Tarpon Springs)
Tarpon Springs is home to the highest concentration of Greek heritage in the country, built on a sponge-diving industry dating to the 1880s. The free Spongeorama museum tells that story through historic photos and a short film, and the adjacent Sponge Docks make for an easy waterfront stroll with Greek bakeries and sponge boats docked just steps away. 510 Dodecanese Blvd., Tarpon Springs
8. Fort De Soto Park's Historic Batteries (Tierra Verde)
Best known for its beaches, Fort De Soto also holds a piece of military history: coastal artillery batteries built around 1900 and added to the National Register of Historic Places in 1977. Explore the old fort structure, then cool off at the beach or rent kayaks to paddle the mangroves. 3500 Pinellas Bayway S, Tierra Verde
9. The Don CeSar, "The Pink Palace" (St. Pete Beach)
You don't have to book a room to appreciate the Don CeSar's storied past. Built in the 1920s and added to the National Register in 1975, the pink Mediterranean-style hotel is a Gulf Coast landmark families can admire from the grounds, lobby or beach out front. Grab a drink at the poolside bar or just a quick photo op. 3400 Gulf Blvd., St. Pete Beach
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Bonus: History + A/C
When the Florida heat (or a sudden summer storm) sends you looking for air conditioning, these two spots deliver both comfort and a deep dive into the region's past:
Tampa Bay History Center (Tampa) — 12,000 years of regional history through interactive exhibits covering Florida's first peoples, Spanish explorers, cigar workers and more. Don’t miss the Touchton Map Gallery, with Florida maps dating back to the 1500s. 801 Old Water St., Tampa
St. Petersburg Museum of History — the city's oldest museum, with exhibits spanning Tocobaga settlements, the Gilded Age tourism boom and St. Pete's role in the world's first scheduled commercial airline flight. 335 2nd Ave. NE, St. Petersburg
Shuffle Tampa — Not historic, but undeniably Florida: this indoor shuffleboard and entertainment venue puts a modern spin on the same game St. Pete made famous, with air conditioning and snacks to match. 2612 N. Tampa St., Tampa
Located in Disston Heights to the west of downtown, this unassuming 1960s ranch-style house was the final home of Jack Kerouac, the legendary Beat Generation writer. The home was added to the city’s list of locally designated landmarks in 2022. Intimate house shows performed in Kerouac's living room have featured touring artists Caleb Caulde, Alice Wallace, and David Dondero. Check their schedule for upcoming happenings.
