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A Weekend Itinerary for Gainesville, Florida

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Check out our itinerary for Gainesville, Florida. You'll be surprised at how many cool offerings this Florida city has to offer!

Gainesville is a fun-filled city between Orlando and Tallahassee in Alachua County, Florida. Besides being home to one of the state’s most exceptional educational facilities (University of Florida), Gainesville is a cultural city with a theater, museums, art, and extraordinary tours.

When people ask what cities I recommend visiting in the Sunshine State, Gainesville always tops my list. Here is my weekend itinerary for Gainesville, Florida.

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gainesville florida weekend itinerary

Arrive in Gainesville

Arrive and check-in your hotel. Chain hotels are abundant in Gainesville, and the Doubletree by Hilton is my favorite. It has a college town vibe, upscale hotel amenities, and is in a great location.

Gainesville also has a Bed and Breakfast District, well-known for the number of historic bed and breakfasts found there. I’m crazy about the Magnolia Plantation Bed and Breakfast Inn, which has impeccable service, gorgeous rooms, a cool setting, and a fantastic breakfast. 

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Join in the fun of pedaling a 12-seater bike around the streets of Gainesville aboard a Florida Fun Bike. Enjoy a history lesson while getting some exercise as you ride on your own private tour or join a group outing and mingle with others. The owners, Amber and Derrick, are fantastic tour guides and do an excellent job of showcasing Gainesville’s downtown and nightlife.

Gainesville has great street art and murals to take in, evening branching out to electrical boxes. World-renowned artists, as well as local ones, have contributed to Gainesville’s eclectic 352 Walls art scene. You will see several of these scenes during your Florida Fun Bikes outing.

Taking a Florida Fun Bikes excursion in Gainesville is definitely a great way to mingle and have many laughs for the evening.

The Top Restaurant is one of Gainesville’s most popular dining options. Situated in the heart of downtown, this hip restaurant is where you go to be seen, have fantastic cocktails, and eat amazing food.

Try the Fried Kimchi Cauliflower or Garlic Shrimp for starters and go with the Spicy Peanut Tofu or Belgian Style Trout for the main course. Save room for dessert because the Carrot Cake and Vegan Chocolate Cake are quite memorable. 

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A Full Day in Gainesville

Head over to Maple Street Biscuit Co. where the biscuit combinations are out of this world. I love the Sticky Maple (fried chicken, bacon, pure maple syrup) and The Squawking Goat (fried chicken, fried goat cheese medallion, pepper jelly).

Oh heavenly day those dishes at Maple Street Biscuit Company in Gainesville.

After breakfast, you may want to burn some calories or enjoy nature while taking some pictures as you hike through Sweetwater Wetlands Park or Prairie Paynes. If you are lucky like me, bison and alligators might be rearing their heads for your photo ops. Sweetwater Wetlands is also home to many migratory birds. Both are great places to connect with nature. 

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Fun and funky describes the decor and atmosphere at Satchel’s Pizza, but foodies approve the creative pizza combinations, crisp and healthy salad, and craft soda sampling. Satchel’s also has fun desserts, and whether you are hungry enough for them or not, be sure to browse the menu. 

This is the signature salad, loaded with goodies, from Satchel's Pizza in Gainesville.
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A new and unique attraction in Gainesville is the Cade Museum. A world-class venue for doing, not seeing, this hands-on learning experience will be unlike anywhere else. The Cade Museum fosters creativity and invention and recognizes its opportunities in Gainesville through its legacy contributor, Dr. Cade, the inventor of Gatorade, among many other things.

The Cade Museum features maker stations and open labs as well as classes that require a reservation. This steel and concrete building is breath-taking and looks perfect in its Depot Park setting.

If the kids are along on your trip, they will love taking advantage of Depot Park’s impressive playground equipment. Drop in the Pop A Top Corner Store for a glass bottle soda and snack after playtime is finished.

If you are without kids, consider riding a bike in this neighborhood, as there are lots of cool things to see.

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Dinner and Nighttime Activities

Emiliano’s Cafe is one of our favorite eateries in Gainesville. Choose from delicious Latin fusion (Mexican to Spanish) dishes at this quaint restaurant with outdoor seating. The Pollo Mole is sure to satisfy or have a taste of Mofongo, a traditional Puerto Rican staple that Emiliano’s does to perfection! You can also opt for the smaller portions on the tapas menu. Don’t miss the martinis and authentic mojitos.

A vibrant college town wouldn’t be the same without a happening cultural center, which in Gainesville is referred to as “The Hipp.” The Hippodrome State Theatre is in a spectacular historic building, and powerful performances grace the stage around 340 days per year. I couldn’t agree with their tagline more: “The Hipp. It’s close to home, but far from ordinary!”.

You can read more about Emiliano’s Cafe in this Gainesville Food post. 

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Pop by the Swamp Head Brewery or FishHawk Spirits Distillery for a cold beer or adult premium whiskey sampling. My favorite choices from Swamp Head Brewery are Midnight Oil (a coffee stout) and Wild Night (honey cream ale). Whiskey isn’t the only thing on the menu at FishHawk; the Blueberry Vodka is magnificent!

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Cookiegazm has taken Gainesville by storm, as it delivers into the wee hours of the night. Choose from provocative cookie titles and enjoy your warm treat, half gooey in the center, and drenched with an array of toppings. My favorite is La Cookieta, a peanut butter cookie topped with banana, dulce de leche, and condensed milk.

Note: Cookiegazm is closed during the summer months. 

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Take a Gainesville Food Tour

Before leaving Gainesville, consider taking a food tour. Gainesville Food Tour is one worth trying. Join married couple Caroline and Ryan and stroll the downtown streets as you hear an arsenal of stories about Gainesville’s interesting past. You will stop at five to six local eateries for a taste of the city.

On my brief tour, the stops were Liquid Ginger (Pad Thai), Loosey’s (Baconator slider and fries), and the Sweetwater Branch Inn (French toast casserole). This food tour is a tasty and educational way to spend the afternoon.

(Note: food tours are not offered in the summer months)

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Special Events in Gainesville

  • January/February: Hoggetown Medieval Faire
  • March: Gatornationals, Hot Rod Association, Spring Garden Festival, Kanapaha Botanical Gardens, India Fest at Santa Fe College, Primavera
  • April: Primavera, Santa Fe College Spring Arts Festival, Orange & Blue Game
  • May: Cade Prize Awards
  • June: Kids Triathalon, taste of HOME
  • July: UF Fanfares and Fireworks, Micanopy July 4th Parade, Alachua: “The Largest Small Town Fireworks Display in America”, Restaurant Week
  • September: Gator football begins, Art Festival at Thornebrook
  • October: Heart of Florida Asian Festival, Annual Florida Bat Festival, Butterfly Fest, Downtown Festival and Art Show, Micanopy Fall Harvest Festival, Punk Fest, Boo at the Zoo
  • November: Univ. of Florida Homecoming
  • December: Cane Grinding Day, Christmas Tree Lighting
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Monsta Lobsta Lobster Roll from the food truck rally at High Dive.

Hoggetowne Medieval Faire

The Hoggetowne Medieval Faire takes place on two back-to-back weekends at the end of January/early February each year. Thousands of people come out to enjoy jousting matches, incredible costumes, a human chessboard, medieval village, puppeteers, shopping, international food, and more at this incredible Renaissance event.

The festival has been running for over thirty years now. If your travels bring you to Gainesville during this time, it is certainly worth checking out.

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Gainesville: More Than Gators

Florida locals know Gainesville as the home of the Gators, arguably the state’s favorite team, but there is so much more to this city.

From the long list of abundant art and history museums to the unique opportunities, food tours to fun bikes, and everything in between, Gainesville is a place you’ll want to explore.

We hope you enjoy the itinerary for Gainesville that includes many of our top picks.

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The Carriage House at the Magnolia Plantation B&B.

Gainesville Photo Gallery

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Travel writers getting a sneak peek of the Cade Museum. Vicky (Buddy the Traveling Monkey), Me, Charles (McCool Travels), Julie (Fun in Fairfax), and Lori ( ).
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The Carriage House at the Magnolia Plantation B&B Inn.
Gainesville's historic bed and breakfast district features many great places to stay during your visit.

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