Itching to get out of town, Lakelanders? Skip those pesky airport security lines and jump in your car for a road trip to St. Augustine instead. From its winter light festival in the historic district to the tableside-crafted salad at The Columbia — we’re spilling all the details on how to have an unforgettable time in “The Nation’s Oldest City.”
📍 Essential info
Drive time: ~3.5 hours
Year city was established: 1565
Est. population: 15,500+
Don’t worry, be capy — this cafe is one of just a few of its kind in the world.
Photo by @britbritbreaker
🎟️ Experience
Old Town Trolley Tours
There are nearly 500 years of history to be explored in St. Augustine, so learn from the pros on a guided tour. Old Town Trolleys will take you to sip from the Fountain of Youth, sightsee at Castillo de San Marcos, or even ghost hunt at the Old Jail — all while narrating your trip.
Nights of Lights
St. Augustine transforms into a winter wonderland from November to January. Head to the historic district to see 20 blocks illuminated with millions of holiday lights. It’s free to enjoy on foot, but you can also book a sightseeing tour by boat, horse-drawn carriage, or trolley.
The Capybara Cafe
Book a time slot at this newly opened cafe to meet capybaras Mocha and Latte. You’ll get up close and personal with these friendly rodents that are native to South America while learning all about wildlife conservation. Win-win, right?
Trust us, this is one salad you’ll want to order on vacation.
Photo by @abbyallenleach
🍽️ Eat
Columbia Restaurant
If you love this eatery’s Ybor City location, pay a visit to the one in St. Augustine’s historic district. We always start our meals with the “1905" Salad, made tableside, along with a pitcher of sangria. You’re on vacation, after all.
Alms + Fare
For lighter bites, hit this bakery for breakfast. Everything on the menu here is gluten- and dairy-free, and naturally sweetened. A maple cinnamon latte would pair perfectly with a freshly baked muffin before a day of exploring.
Cafe Alcazar
Make a reservation to have lunch in this casual fine dining restaurant, located inside what was once the world’s largest indoor swimming pool. You’ll find Greek + Mediterranean influences on the menu, plus locally sourced ingredients. After your meal, visit the adjoining Lightner Museum.
If you’re looking for a poolside stay, think pink and go for The Local.
Photo by @annamariaschmidt_
🏨 Stay
The Local
Forget what you know about motels — this spot was voted the No. 1 motel in the country on USA Today’s 10Best list. Book a few nights here and enjoy the retro-style rooms + pool that are sure to end up on your Instagram after your trip.
Couples Tropical Getaway
Just imagine enjoying morning coffee while feeling the sea breeze on a balcony each morning of your vacation. Bring your sweetheart with you to this rental home just 200 ft from the boardwalk to St. Augustine Beach.
Casa Monica Resort & Spa
For a truly historic trip, stay at this hotel first built in 1888 and once owned by Henry Flagler. It’s located within a few blocks of many downtown attractions + offers a spa, on-site restaurant, and heated pool.
St. Augustine’s streets are rich in history and Spanish influence.
Photo by @victoriabardega
Wait a minute, Lakelanders. Before you head out the door, find the cheapest places to fill up your gas tank and stock up on road trip snacks from bodega Market. Also, bookmark this map so you have no trouble finding all of our recommendations while visiting St. Augustine.
🚗 Cruise
No matter where the highway takes you, our road trip must-haves will ease your journey as you make your way to your destination.
- With more than 23,000 location-based audio stories, Autio’s Unlimited Plan: Lifetime Subscription is your perfect companion offering mini podcasts about the history, culture, and geology of areas you drive through.
- You’ll stay fully charged up and connected with this 4-in-1 retractable car charger that has iPhone compatibility and secure plug-in capability.
- Rock a comfortable sweatshirt and pants set for the road featuring a cozy elastic waistband and marshmallow-soft fabric.
- Keep your tailbone supported during lengthy drives with a thick memory foam cushion that is machine washable and gives complete postural support.
- Avoid getting stranded with a dead battery by packing this portable car jump starter that gives up to 50 jumps in a single charge — no flagging down a stranger needed.
- Easy to clean and leak-proof, this collapsible car trash can gives you 2 gallons of storage capacity to keep your vehicle free from clutter.
