Over the years we have enjoyed visiting St. Augustine, Florida, many times both before kids, and as a family. Every trip is fun, but there is just something special about the way they do Christmas. As the oldest city in America, it already feels like a step back in time, but during the holiday season, it transforms into a festive blend of twinkling lights, cheerful trolley rides, and Southern charm.
From historic streets lined with holiday décor to quirky museums and Atlantic beaches, St. Augustine offers a joyful escape perfect for families, couples, and anyone looking to slow down and savor the season. The perfect temperatures of December in Florida make it a pleasure to walk through downtown, enjoy the talented musicians on street corners, or watch the sun rise over the ocean comfortably.
Nights of Lights: A Sparkling Tradition
At the heart of St. Augustine’s holiday charm is the Nights of Lights celebration, an award-winning tradition that bathes the city in more than three million white lights from mid-November through January. Inspired by the Spanish custom of placing candles in windows, this glowing display turns the entire historic district into a twinkling bit of magic.
Walking through the ancient streets, you’ll see palm trees wrapped in lights, historic homes aglow, and storefronts decorated with timeless style. It’s a holiday tradition you won’t want to miss.
All Aboard the Holly Jolly Trolley
To take in the magic of the lights in style, hop on the Holly Jolly Trolley also known as Old Town Trolley’s Nights of Lights Tour. This seasonal tour offers a festive way to explore the historic district, complete with holiday music, complimentary cookies, and warm cider. Riders are given 3D viewing glasses that make the lights sparkle even more.
Whether you’re visiting with little ones or looking for a romantic evening ride, this open-air trolley is a must-do and one of the best ways to experience the spirit of St. Augustine during Christmas.
What if riding with a large group on the trolley isn’t your thing? If you prefer something more in keeping with the historical feel you could opt for a horse drawn carriage tour, a private escorted gold cart tour, and even a boat tour.
A Stop at Ripley’s Believe It or Not!
For something a bit more whimsical, we recommend a visit to Ripley’s Believe It or Not!, one of the city’s most fun and family-friendly museums. Located in a historic castle-like building, Ripley’s is full of strange artifacts, mind-bending exhibits, and just the right amount of holiday flair. During Christmas, the building is lit up as part of Nights of Lights, adding to the celebration. It’s a memorable stop that kids and adults will enjoy.
Anastasia State Park (and Beach)
A visit to Anastasia Beach during the winter months is something I highly recommend. The cooler season may not be typical beach weather, but that does not mean you should skip it. The shoreline is peaceful, the crowds are fewer, and the crisp air makes for a refreshing walk along the sand. Even on cooler days, the sun shines brightly, creating a beautiful setting for collecting shells, enjoying the sea breeze, or simply taking in the natural beauty. St. Augustine’s beaches in winter have a charm all their own, and Anastasia Beach is the perfect place to experience it.
Where We Stayed: Homewood Suites by Hilton St. Augustine San Sebastian
We stayed at the Homewood Suites by Hilton St. Augustine San Sebastian, and it made the perfect home base for our holiday adventures. Set along the San Sebastian River, this all suite hotel offers a blend of comfort and convenience. Each room includes a full kitchen and spacious living area, which makes it easy to spread out and feel at home, especially if you are traveling with family.
The location could not be better. It is a short drive or even a pleasant walk to the historic downtown, yet the hotel sits in a quieter corner, away from the late night bustle. That balance meant we could easily explore the shops, restaurants, and attractions during the day, then return to a calm and restful spot at night.
One of our favorite perks was the complimentary breakfast each morning, perfect before heading out to sightsee. The property also has a pool and outdoor spaces overlooking the river, which gave us a chance to unwind between outings. Parking was convenient and stress free, another plus in a busy destination like St. Augustine.
On-Site Amenities & Activities at Homewood Suites by Hilton St. Augustine San Sebastian
This hotel is designed with comfort in mind, making it a great choice for families or travelers planning a longer stay. Each suite features a fully equipped kitchen, and the property offers:
- Heated outdoor pool
- Fitness center
- Free Wi-Fi
- BBQ grills
- A cozy riverside patio
- Complimentary hot breakfast every morning
While the hotel doesn’t host its own events, its location puts you right in the middle of everything happening in town.
Dining & Location Perks
Though there is no restaurant on site, the in-room kitchens were ideal for preparing light meals or snacks and the hotel is just steps from several delightful places to eat. You’ll find the San Sebastian Winery within a short stroll, along with Carmelo’s Pizzeria and Bog Brewing Company close by. Just across the river in the historic district you can enjoy standout dining such as La Cocina at the Cellar Upstairs (fine dining), The Blue Hen (casual), or Foxtail Coffee Co (coffee shop). We absolutely loved dining at Columbia Restaurant in St. Augustine, and I highly encourage you to give it a try for its incredible Spanish and Cuban inspired flavors in a beautiful historic setting. With so many options for dining shopping and sightseeing nearby you are unlikely to ever go hungry.
What Makes This Hotel Special?
The Homewood San Sebastian strikes a rare balance: it is close to all the holiday action yet still feels peaceful and tucked away. The suites are spacious and comfortable, giving families plenty of room to relax and spread out. With scenic views of the river and thoughtful amenities like full kitchens and living areas, it feels more like a vacation rental than a standard hotel stay. It was exactly what we needed to unwind between holiday outings while still having the convenience of being near all that St. Augustine has to offer.
Top 3 Reasons to stay at the Homewood Suites by Hilton St. Augustine San Sebastian
- Comfort & Space – Suites with kitchens make it ideal for longer stays or traveling with family.
- Festive Fun Nearby – You’re only minutes from trolley tours, Nights of Lights, and holiday attractions.
- Riverside Serenity – Enjoy the charm of downtown with the peace and quiet of the San Sebastian river from the pool deck.
Average Price Per Night
- Weeknights: $170–$220
- Weekends & Holidays: $230–$275
(Prices vary with demand—booking early for Christmas is highly recommended.)
Whether you’re looking to stroll among lights, hop on a cheerful trolley ride, explore something strange at Ripley’s, or simply relax by the river, St. Augustine is the perfect place for a cozy Christmas getaway. This has become one of our favorite family holiday traditions.
If you are thinking about planning a holiday vacation in St. Augustine or anywhere else, I would be delighted to help. Whether you are looking for a cozy getaway, a family adventure, or a festive escape filled with lights and local traditions, I can take care of the details so you can simply enjoy the experience. Reach out to me and let’s start planning a trip that is memorable, relaxing, and stress free
If you are ready to explore St. Augustine, take a look at my affiliate link on Viator. It is a great place to browse and book your favorite experiences, from tours to activities, so you can make the most of your trip.
