12 Cities in 12 Months Exploring Florida One City at a Time

Alexandria

Florida Travel | Travel | US Travel

August 9, 2023

12 Cities in 12 Months Exploring Florida One City at a Time

Florida, my home state, yet so many places left unseen after all these years. Since we’re staying in Florida, every city on the list is a year-round destination.

Come back every month for us to expand on a new city, with its must-sees, and where to stay!

1. Destin

Destin has become a top family destination and #1 on my list because we’ve never been! It’s hard for me to make a drive longer than an hour to go to any Florida beach, but I hear this is well worth the trip! Known for its beautiful white sand beaches, boardwalk, and streets meant to be explored by bike! Destin is the ultimate beach town with several smaller towns around to explore, like Seaside, Florida.

Don’t Miss: Henderson Beach State Park, The Village of Baytowne Wharf, Gulfarium Marine Adventure Park, Destin Commons

Where to Stay: Alys Beach or Henderson Beach Resort.

2. St. Augustine

St. Augustine has been a quick family vacation favorite since I was little. The “oldest city in the US” was established in 1565 and it takes you back in time with its cobblestone streets and old buildings. One of the best things about St.Augustine is that it’s entirely walkable!

Don’t Miss: Castillo de San Marcos National Monument, Lightner Museum, Flagler College’s Hotel Ponce de Leon, St.George Street, St. Augustine Lighthouse, St.Augustine Distillery

Where to Stay: Casa Monica Resort & Spa or Embassy Suites by Hilton.

3. Miami

Miami has been a getaway destination for me for years and years. We’ve spent many weekends with all our kids at the Fontainebleau, watching Miami Heat games, and taking in all the vibes South Beach is giving out. We are lucky to have Miami, with some of the finest restaurants and resorts in the world, so close to us! It’s such a vibrant lively city, full of history and truly a city with something for everyone!

Don’t Miss: Wynwood Walls, South Beach, Cuban food at Versailles, Vizcaya Museum & Gardens, Española Way, Bal Harbour Shops, TimeOut Market

Where to Stay: Acqualina Resort, JW Turnberry or Fontainebleau

4. Key West

Key West is a picturesque subtropical paradise! The clear blue waters make it a prime spot for scuba diving, fishing, snorkeling, boating, and having some major fun in the sun! Key West can be a place to party, the perfect place for a romantic getaway, or your next family vacation. If you take the drive from Miami to Key West, you can stop at all the other beautiful keys along the way! Key Largo, Marathon, and Big Pine Key are some of my favorites. Surprisingly, Key West doesn’t have the best white sand beaches since they are smaller and scattered. My recommendation is Bahia Honda State Park on Big Pine Key or Sombrero Beach in Marathon to get your sandy beach fix.

Don’t Miss: Dry Tortugas National Park, Duval Street, Ernest Hemingway Home and Museum, Mallory Square, Conch Tour Train, Key West Butterfly & Nature Conservatory

Where to Stay: Margaritaville Beach House, Kimpton Key West or Casa Marina

5. Amelia Island

A true hidden gem in Florida, Amelia Island is only about 40 minutes NorthEast of Jacksonville. “The Isle of Eight Flags” Amelia Island has been under control of 8 different countries since its founding in 1562. It is home to more beautiful Florida beaches, historic charm (Florida’s oldest bar!), so many outdoor activities to keep your family going, and a couple amazing beach resorts. Amelia Island is a classic picturesque beach town, good enough to be the backdrop of some big-time movies like G.I Jane! This quiet island is known for being less crowded and more low-key than other islands around Florida, but that definitely doesn’t mean there’s less to do!

Don’t Miss:The tallest sand dune in Florida at American Beach, shark tooth hunting at Fort Clinch Beach, Boneyard Beach, horseback riding on the beach, fishing off the pier at Amelia State Park, grabbing a drink at the Palace Saloon, grab lunch at Cafe Karibo and much more in downtown Fernandina Beach

Where to Stay: Omni Amelia Island or Ritz Carlton Amelia Island

6. Sarasota

This might be my favorite city on this list and one we frequent often! Sarasota is home to some of the best beaches in the US (totally unbiased) and only about an hour from Tampa. The clear blue waters and white sand beaches of Anna Maria Island, Lido Key, and Siesta Key will never disappoint. One of my favorite things to do in Sarasota is have dinner in St.Armands circle, then walk over to Lido Key to catch the sunset. Sarasota may have a small beach town vibe, but is actually rich in history and italian-influenced architecture. When you’re down for a “non-beach” day, there are several stunning museums and gardens to visit. Most notably, the Ringling Museum is home to the jaw dropping art collection of the circus co-founder, John Ringling.

Don’t Miss: Lido Key Beach, St. Armands Circle, Myakka River State Park, Siesta Key Beach, Ringling Museum of Art, Mote Marine Laboratory & Aquarium, Ca’ d’Zan, Bayfront Gardens, Owen’s Fish Camp, and my personal favorite, Anna Maria Island.

Where to Stay: The Ritz Carlton Sarasota or The Resort at Longboat Key Club

7. Tampa

Home sweet home! I was raised in the suburbs of Tampa, dropped off at Busch Gardens to act as childcare over multiple summers, and currently in amazement of the downtown area transforming to that big city feel. Tampa is full of rich history dating back to 1513, but its year to start shining is 2023! Tampa recently landed a spot on Time Magazine’s 2023 World’s Greatest Places and if that’s not enough to convince you this city is becoming something great, I don’t know what will. While we have beautiful beaches right in our backyard, there’s some major fun to be had in the city. One of my many favorite things to do in Tampa is eat. The burger at Boulon is something I tell everyone to try, a Cuban sandwich from The Columbia is not one to miss, and the Sunday Market at Wat Thai Temple is such a unique foodie experience. Two personal favorite restaurants of mine (take it from a local) are Rome+Fig and Rocca.

Don’t Miss: Tampa Riverwalk, Armature Works, Sparkman Wharf, The Florida Aquarium, Ybor City Trolley, The Tampa Theatre, Bern’s Steakhouse Dessert Room, Salt Shake on the Bay, International Mall Plaza, MidTown, Brunch at Oxford Exchange, Hyde Park Village, Curtis Hixon Park, eBoats Tampa, Kraken Cycleboats, Gasparilla Pirate Invasion every January.

Where to Stay: The Tampa EDITION or Marriott Waterside

8. Everglades National Park, Homestead

Everglades National Park is the largest subtropical wilderness in the US sitting pretty with 1.5 million acres! This gorgeous park has several different ecosystems within it, including freshwater marshes and mangrove swamps. There are 3 different entrances to the park; Gulf Coast, Shark Valley and Ernest Coe areas. I highly recommend making this National Park a day trip during your Marco Island or Miami beach stay. While all the sights and sounds are amazing, the mosquitoes are not. Make sure you pack your family some DEET insect repellent, and long loose-fitting clothing!

Don’t Miss: Seeing a manatee, American Crocodile, and Florida Panther, which are all on the endangered species list! The Sunrise Mangrove Tunnel Kayak Tour with Shurr Adventures, Pahayokee Overlook boardwalk and Shark Valley Observation Tower, Everglades Airboat Tour with Everglades Safari Park, Everglades Alligator Farm, Download the very useful map and plan guided tours using the NPS website.

Where to Stay: Like many National Parks, you’ll have to choose which side to stay on. JW Marriott Marco Island, Baker’s Key Resort Key Largo, Mandarin Oriental Brickell

9. Winter Park

This little city near Orlando has put itself on the map in recent years and has become a foodie’s paradise along with an amazing place to spend some time outdoors. Winter Park has an old-world charm and is a perfect place to get away from the city or tourist traps of Orlando for a quick weekend getaway.

Don’t Miss:Winter Park Chain of Lakes Paddle Boarding, Kraft Azalea Garden, BBQ and craft beers at The Ravenous Pig, Boutique shopping on Park Avenue, Dining at Michelin recommended Prato,
Winter Park Village, Scenic Boat Tours, Hannibal Square, Mead Botanical Garden

Where to Stay:The Alfond Inn at Rollins College or The Grand Bohemian

Coming up…

Orlando
St.Petersburg
West Palm Beach

Share 12 Cities in 12 Months - Exploring Florida One City at a Time on Pinterest!

Copenhagen Travel Guide – Everything You Must Do, See, and Eat

Copenhagen has been rated “the happiest city in the world” multiple years in a row and we went deep in the drenches to see why. We traveled to Copenhagen for a soccer trip, but luckily had ample time to get to explore this fabulous city in between practices and games....

Anna Maria Island Travel Guide

Anna Maria Island has my heart. We “beach week” here every year to kick off summer. There’s not many things better than a week spent being complete beach bums and welcoming the summer with sandy feet and sun kissed skin. Anna Maria Island is located on the Southwest...

Traveling to XCaret Mexico

What you need to know before you go XCaret Park is an eco-theme park in Playa del Carmen, Mexico. It’s not your typical theme park and there aren’t any roller coasters. Instead, there are underground caves to swim in, rope courses through the jungle, ocean adventures,...

« Older Entries

Get My Free State Bucket Lists

We want you and your family to follow right along with us! I’ve created some AWESOME bucket lists for my family and wanted to share them! You can download them right to your phone.