Curator’s statement
Step back in time to the era of pirates and explorers in search of the New World and the Fountain of Youth. St. Augustine, Florida, is renowned for its pristine beaches and intriguing, dark history. As a city founded in the 1500s, it’s only fitting that it has its fair share of frights.
The Fora Difference
Book with Jennifer to access exclusive perks and experiences on your trip.
Killer perks
Free upgrades, spa credits and more—we got you
Personalized recs
Customized travel planning for your style
Insider knowledge
Expert advice from people who’ve actually been there
Where to stay
Unlock perks by contacting Jennifer to book your trip.
Day 1: Welcome to Florida
You will fly into Jacksonville Airport and enjoy a 45-minute ride to the quaint town of St. Augustine, Florida. Once you arrive, check into your spooky accommodation and get settled — it's sure to be a frightful stay!
After unpacking, feel free to explore downtown. St. Augustine is known for being an extremely walkable city, making it easy to navigate. Many people get around by walking or renting bikes, and the fall weather is perfect for outdoor adventures. For dinner, stop by one of the local restaurants to enjoy fresh seafood that was likely caught and served the same day.
To finish off the night, you can choose to take a boat tour and watch the sunset or head in early to relax and prepare for the adventures ahead.
Day 2: Forts and frights
Wake up and grab breakfast because we have a busy day ahead! We’ll kick off our adventure by visiting the historic Castillo de San Marcos. This fort is one of the oldest and best-preserved in the United States, boasting over 450 years of history — and yes, it has its fair share of ghosts. If you’re lucky, you might catch a live weapon-firing demonstration during your visit.
Exploring the fortress can work up quite an appetite for some delicious Spanish food, and I have the perfect spot for lunch.
Once you’ve enjoyed your empanadas, head toward downtown to visit the famous Cathedral Basilica of St. Augustine. Stroll through the beautiful courtyards and marvel at the stunning artwork inside, which reflects the city’s ancient history.
Just a block away from the church is the magnificent Lightner Museum. Originally built in the 1800s as a luxurious hotel resort, it now houses an impressive collection of art and artifacts. Feel free to explore the museum and delve into the history of the area through the years.
As the night comes to a close, you can choose to dine at one of the lovely local restaurants or embark on a delightful dessert tour.
Day 3: Coastal creeps
Bring a beach bag because today we’re heading to the coast! Start your morning with a hearty breakfast before visiting one of the most haunted locations in the United States: the St. Augustine Lighthouse. This site has been featured on numerous paranormal tours and is sure to give you goosebumps.
After your lighthouse adventure, head over to the Alligator Farm Zoological Park, where you can enjoy some family fun and even feed some gators!
Once you’ve had your fill of alligators, grab some delicious tacos at a local restaurant. Then, unwind with a relaxing beach day to cap off your thrilling adventures.
As the evening approaches, you can choose to wind down early or opt for an adults-only night at the Black Raven Tavern. Enjoy a drink while watching a lively pirate show on a pirate ship, or visit one of the local distilleries for a gin tasting experience!
Day 4: Heading back to reality
Wake up and rent a bike for an early morning stroll through the charming streets of St. Augustine. Enjoy the beautiful sights of the city as you soak in the moment before heading back to Jacksonville. Eat, shop, take photos and relish the lovely Florida weather.
If you have enough time, stop by the Fountain of Youth Archaeological Park to discover what Ponce de León sought in the New World.
After your morning adventure, check out of your hotel and make your way back to Jacksonville Airport for your departure home.
Day 5: Events and tours
St. Augustine during the fall offers a variety of events throughout the city. You'll find plenty of ghost tours, as well as family-friendly activities and fun options for adults. Additionally, local golf courses nearby make it an ideal destination for a bachelor party or getaway.
Need to know
If you wish to stay longer or extend your trip to other Florida destinations, feel free to let me know! These hidden gems of Florida are perfect for families who love to adventure and relax.
I customize this trip completely to your taste, if you wish to bring kids I can even make it kid friendly and spooky!
Let's talk about customizing this itinerary for you. Or, about other destinations.
Travel Advisor
Jennifer Demarta
Get in touch with Jennifer
Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.
You can normally expect a response from Jennifer within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).
This itinerary is part of our ongoing series on travel to St. Augustine. For more travel tips, check out Fora Advisor Natalia Eldridge’s guide, A Weekend in St Augustine, Florida.