Why should tourists have all the fun? One of the benefits of living in a place where everyone else vacations is that you’re never far from some of the most amazing destinations, no matter the time of year. Whether you go for a long stay or a long weekend, just make sure you don’t miss any of these incredible destinations, which we believe make for the best vacations in Florida.

1. Anna Maria Island
Flickr/Carol VanHook
Facebook/Harrington House Beachfront Bed & Breakfast
Where to stay: Harrington House Beachfront Bed & Breakfast. This upscale bed and breakfast on the much-loved Anna Maria Island offers gourmet breakfasts, free bike and kayak rentals, and much more.

What to do: Try absolutely anything water-related and peruse the shops at the Historic Green Village. And for something else altogether, you can rent a scooter and explore the island.
2. Key West
Flickr/Joe Parks
Flickr/Aidan Wakely-Mulroney
Where to stay: Avalon Bed and Breakfast on Duval Street. This unpretentious B&B is a tropical paradise, two minutes from the beach.

What to do: There's too much to fit here, but here are a few must-see recommendations: The Hemingway Home and Museum, Dry Tortugas National Park, and the Sunset Celebration in Mallory Square.
3. Amelia Island
Flickr/Evangelio Gonzalez
Facebook/Elizabeth Pointe Lodge
Where to stay: Elizabeth Pointe Lodge. Guests rave about this 1890s Nantucket-style hotel. It's full of history, but has every modern convenience, as well.

What to do: Visit Fort Clinch State Park and the delightful historic district, full of impressive Victorian architecture. Learn more about all there is to explore when you visit Amelia Island.

4. Captiva Island
Flickr/Lori Howe
Facebook/Jensen's On The Gulf
Where to stay: Jensen's On The Gulf. Friendly and intimate suites and cottages with sundecks featuring jaw-dropping views of the Gulf of Mexico.

What to do: Head to Doc Ford's Rum Bar & Grille for a tasty meal, or try The Bubble Room if you love all things weird. Visit J. N. "Ding" Darling National Wildlife Refuge for some stunning wildlife, but spend most of the time on the gorgeous, unspoiled beaches of Captiva and nearby Sanibel. Many folks agree that when it comes to the best vacations in Florida, it's hard to beat a trip to Captiva Island.

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5. St. Augustine
Flickr/Matthew Paulson
Flickr/Rob Bixby
Where to stay: Old Powder House Inn. If you're going to stay in St. Augustine, you should definitely stay in one of their many bed and breakfasts. We recommend The Old Powder House Inn. You'll be right in the middle of everything, with a gorgeous room and delicious breakfast.

What to do: Visit the Castillo de San Marcos and Flagler College, tour the local winery or distillery, and choose from a number of excellent restaurants. You'll quickly discover why St. Augustine is one of the best historic towns in the U.S.
6. Cedar Key
Flickr/Monik Markus
Flickr/Lara Cerri
Where to stay: The Cedar Key Bed & Breakfast. This historic inn is both beautiful and laid-back, like the town itself.

What to do: Try the World Championship Clam Chowder at Tony's Restaurant and tour the Cedar Key Historical Society Museum.
7. Destin
Flickr/David Kosmos Smith
Flickr/{just jenniver}
Where to stay: Henderson Park Inn. This inn is located only a couple of minutes away from one of the most beautiful stretches of beach in the country. Children are not allowed, but guests receive a breakfast buffet, picnic lunches, afternoon tea, and sunset cocktails. You can also borrow pretty much anything you need for the beach for free.

What to do: There are fun boardwalks like the Village of Baytowne Wharf for shopping and dining, but you're going to want to spend most of your time at the beach. Here's more on what makes Destin one of the top vacations in Florida.

8. Gainesville
Julie Fletcher via Flickr/VISIT FLORIDA Editor
Flickr/Allen Forrest
Where to stay: Magnolia Plantation Inn. This house and its grounds are full of Victorian charm and are located near all the shops and restaurants in downtown Gainesville.

What to do: Gainesville might be best known as the home of the University of Florida, but that's far from all it has to offer. Try some of the best pizza in Florida at Satchel's (or choose from many other restaurants) and visit Devil's Millhopper Geological State Park, Paynes Prairie, and the Kanapaha Botanical Gardens if you're a nature lover. Nearby Micanopy has lots of history and top-notch antique shopping.

Do you agree that these are some of the best vacations in Florida? What other beautiful places in Florida should we add to the list? Please leave your comments below — we’d love to hear from you!

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More to Explore

best vacations in Florida

Beth C. | May 16, 2021

What are some must-visit places in Florida?

If you love exploring Florida, you'll essentially never run out of places to visit. The state is both large in size and brimming with fun things to do. At the top of the list is, of course, Key West. No matter the time of year you visit, you'll enjoy some tropical weather and authentic beach vibes. For something a bit more off-the-beaten-path, you can plan a visit to Mount Dora, considered to be one of the coolest small towns in the state. Whether you're taking a walk through Grantham Point Park or checking out the Renninger's Antique Center & Flea Market, you'll find there's plenty to do.

What are the best Florida getaways?

Looking for a beautiful Florida resort getaway? Look no further than Captain Hiram's Resort. Located in the Sebastian area, this beautiful waterfront destination will make you feel as though you've been temporarily transported to the Caribbean. It's the perfect place to relax beachside. For another kind of tropical getaway, the Dry Tortugas won't disappoint. Located 70 miles off the coast of Key West, this national park promises to impress with its sapphire-blue waters.

What are the most amazing things to do in Florida?

If you're wondering about the most amazing things to do in Florida, you'll want to add Silver Glen Springs to the top of your list. It's here that you can enjoy one of the best swimming holes in Florida. Tucked away in the heart of Ocala National Forest, this stunning spring-fed swimming hole boasts clear water that you'll find to be perfectly refreshing any time of the year. Learn more about what awaits you at Silver Glen Springs.

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Featured Addresses
Anna Maria Island, Florida, USA
Key West, FL 33040, USA
Amelia Island, Florida 32034, USA
Captiva Island, Florida 33924, USA
St. Augustine, FL, USA
Cedar Key, FL 32625, USA
Destin, FL 32541, USA
Gainesville, FL, USA