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

Alexandria
Florida Travel | Travel | US Travel
January 5, 2024

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, FL
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.

2. St. Augustine

St. Augustine Florida
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!

3. Miami

Miami
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!

4. Key West

Duval Street in Key West, Florida
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.

5. Amelia Island

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

Palace Saloon

6. Sarasota

12 Cities in 12 Months - 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.
12 Cities in 12 Months - Sarasota
12 Cities in 12 Months - Sarasota
12 Cities in 12 Months - Sarasota

7. Tampa

Tampa
Tampa
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.

8. Everglades National Park, Homestead

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!
Everglades National Park, Homestead

9. Winter Park

Winter Park Florida
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.
Winter Park Florida

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

10. Orlando

Orlando Florida
Orlando seems like a no brainer when it comes to cities to visit in Florida. Almost everyone I meet out of state tells me they’ve been or plan on going to Disney World. While Disney World is a top notch vacation, there is so much more to explore! Did you know Orlando was the watersports capital of the world?! You could easily spend weeks here without getting bored, although you will get very tired. There are about 480 resorts in the Orlando area, so picking which one to stay at may be your hardest part of this adventure.
Orlando Florida
Orlando Florida
Orlando Florida
Don’t Miss: Universal Studios, Universal City Walk, Disney World, Disney Springs, Orlando City soccer game, Discovery Cove, Aquatica, The Wheel at ICON park, Orlando Magic Basketball, Nona Adventure Park, Andretti Indoor Karting, The Mall at Millenia, SeaWorld, Abracadabra Ice Cream Factory, GatorLand, Wonderworks, Blue Springs State Park

Where to Stay: JW Marriott Bonnet Creek, Omni Championsgate, Loews Sapphire Falls, Four Seasons Orlando, Gaylord Palms

11. St. Petersburg

St. Petersburg FL
St.Petersburg gives you the best of two worlds: a busy downtown city and beautiful Florida beaches. Downtown St.Pete is one of my favorite areas and is thriving with museums, bars, trendy restaurants, unique shops, and entertainment for the whole family. Put on your walking shoes, grab a scooter, or book a segway to explore. A short 9 miles away from downtown, is the sunshine, sand, and beach! I was married on St.Pete Beach so it also holds a special place in my heart. The Don Cesar, the “pink palace”, was built in 1928 and is such an iconic place to stay or spend the day.
St. Petersburg FL
St. Petersburg FL
St. Petersburg FL
Don’t Miss: Trolley Pub Brewery Tour, Vinoy Park, Mural Tour, St.Pete Pier, Sunken Gardens, Kayaking in Weedon Island Preserve, Dali Museum, Book an Afternoon Tea at Toast the Hostess, Immerse yourself in art at Fairgrounds, Tiki Cruise

Where to Stay: The Don Cesar, Tradewinds Island Resort, The Vinoy, or AC Marriott Downtown

12. West Palm Beach

West Palm Beach, FL
This cute seaside oasis is known for its unique boutiques, sidewalk cafes, gardens, nightlife, and waterfront fun.The Palm Beaches collectively are known as America’s First Resort Destination. The Palm Beaches take up 47 miles of shoreline and are made up of 39 small beach towns. West Palm Beach, one of those 39 towns, is home to some of the best upscale chic restaurants like Ristorante Santucci, Galley, Table 26, and Pistache French Bistro, and Lola 41.
West Palm Beach, FL
Don’t Miss: The Square, Mounts Botanical Gardens, Worth Avenue, Tour Flagler Museum, Lion Country Safari, West Palm Beach Food Tour, Have Brunch at Restoration Hardware, Grandview Public Market, Peanut Island, Municipal Beach, Society of the Four Arts Gardens

Where to Stay: The Breakers, Eau Palm Beach, or The Colony

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