Flagler University

The Best Things to do in St. Augustine this Winter

Things to do in St. Augustine, the lightner museum in downtown for guilded age

Winter feels slightly different in Florida than in other parts of the country, so there are always so many fun things to do in St. Augustine, even from December through February when much of the US is covered in snow. It’s still all about sunshine here and temperatures hovering in the mid to high-60s. While that might not be bathing suit weather, you’ll still get by with shorts instead of a parka!

The historic downtown area of St. Augustine is a popular destination year-round, and parking can be a challenge. That’s where our St. Augustine Bed and Breakfast comes in as the best choice for lodging during your visit. We’re located within easy walking distance of all the top attractions, shopping, and restaurants in the historic heart of town—heading out on foot is the best way to explore! It also helps that you’ll find world-class amenities, beautifully appointed guest rooms, and the most welcoming and warm service from our professional staff.

Before you start filling your itinerary with all of the best things to do in St. Augustine, get your reservation on the books today!

Things to do in St. Augustine, a florida beach at sunset on a winter's day

The Best Things to do in St. Augustine This Winter

The history of St. Augustine is apparent at every turn, making it an important part of your visit as you hit these attractions and activities while you’re here. Strolling the streets of Old Town is like taking a step back in time, allowing you to visualize what this incredible city must have looked and felt like all those years ago.

  • St. Augustine’s historic district is the heart of the city and is the best place to start your adventures. You’ll find many of the most exciting things to do in St. Augustine in this very walkable area of the city. You’ll pass by buildings that date back to the 1700s or earlier. The architecture is fascinating, ranging from Spanish Colonial to Gilded Age extravagance. Our favorite historical stops are the Lightner Museum, the Ximenez-Fatio House, and St. George Street.
  • During your stay, one of the best things to do in St. Augustine is grab a front-row seat to the stunning sunrises or sunsets at the beach. Check out the Bayfront Walk for panoramic views of Matanzas Bay. From here, you’ll see sailboats, the Bridge of Lions, and the lighthouse. The trail begins at the headquarters of the Florida National Guard and concludes at the Castillo de San Marcos National Monument.
  • Washington Oaks Garden State Park is a lovely place to spend the afternoon in the winter. This peaceful park includes a formal rose garden, reflection ponds, and a beautiful shoreline covered in unique Coquina rock formations. It’s a great picnic spot!
  • For a quick and informative introduction to St. Augustine’s history, we recommend taking the Old Town Trolley Tour, which allows you to hop on and off at various places throughout the city. It’s one of the best things to do in St. Augustine to get a lay of the land and learn a few key historical details about the Oldest City.
Things to do in St. Augustine, the black and white stripped lighthouse
  • The St. Augustine Lighthouse and Marine Museum is a great space to learn about the maritime and nautical history of St. Augustine. From the top of the 165-foot-tall lighthouse, you’ll also enjoy exceptional views of Matanzas Bay and the Florida coast.
  • San Sebastian Winery is one of the best places to stop for a glass of wine. You’ll find complimentary winery tours and tastings a few blocks from the historic district seven days a week! Plan for lunch at The Cellar Upstairs Restaurant on its open-air deck.
  • The dinner options in St. Augustine are spectacular—the hard part is choosing where to go! Harry’s Seafood Bar and Grille serves up New Orleans-style dishes like jambalaya and gumbo with a twist. Collage Restaurant is known for its international cuisine with beautiful plating. And The Ice Plant is a vintage bar and restaurant known for creating craft cocktails paired with delicious farm-to-table food. This is just the tip of the iceberg for fantastic St. Augustine restaurants.
  • St. Augustine comes alive in the evenings with live music drifting through the cobblestone streets. Spending an evening with cocktails, smooth jazz, and your favorite person is by far one of the best things to do in St. Augustine this winter.
Things to do in St. Augustine, a spacious suite at our Bed and Breakfast in Florida

Elegant and Spacious Lodging in St. Augustine

We may be biased, but we truly believe that staying at the St. Francis Inn is one of the best things to do in St. Augustine. Not just because of our location, amenities, and comfortable guest rooms but also because our dedication to hospitality is unparalleled. You’ll feel pampered and doted on, whether at our exceptional complimentary breakfast service or our afternoon wine and appetizer “happy hour.” From the minute you arrive at our St. Augustine Bed and Breakfast, you’ll see why our guests return year after year to celebrate and relax in the lap of luxury.

Start planning your next getaway to Florida, filled with all of the best things to do in St. Augustine. Book today!

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Experience Nights of Lights

Stay two consecutive weeknights (Sunday-Thursday) between Nov 18, 2023 through Jan. 27, 2024 and receive a free Evening Nights of Lights Trolley Tour, including a pair of complimentary magical viewing glasses per guest.

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