7 Fun Date Ideas in St Augustine for Couples

As longtime St. Augustine, Florida explorers, we’ve discovered countless romantic and unforgettable experiences for couples. From free adventures to unique paid activities, there’s something for everyone in this historical city. But to make it easy on you, we’ve boiled down our recs to just 7!

In this post, we’ve outlined some of the best things to do in St Augustine for couples. And with your wallets in mind, we’ve made sure to include a mix of free as well as paid options. From our favorite hiking spot to a spooky bar crawl, all of the following recommendations are Scho & Jo approved!

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Table of Contents

1. Hop on a Trolly Tour

Starting off with a classic St. Augustine activity, we can confidently confirm that the Old Town Trolley Tour is one of the top things to do in St Augustine for couples. We know, we know, it’s everywhere—but for good reason. It is really fun! And if you are interested in history, we found the trolly ride to be an incredibly informative experience.

Passing through the historic district’s cobblestone streets to the scenic waterfront, the trolley tour offers breathtaking views and fascinating stories narrated live. Learn about the city’s founding, its role in the Spanish-American War, and the people who’ve called it home throughout the years.

We’re big fans of the Old Town Trolley Tour because it’s a hop-on hop-off experience. This means you can explore on foot or take a break to eat whenever you like! If you need eatery recommendations, check out our favorite spots for breakfast as well as our go-to lunch and dinner joints.

Although Old Town Trolley Tours is the most popular trolley company in St. Augustine, Ripley’s Believe It or Not also runs their version, the Red Train Tours. We’ve written a guide that lays out everything you need to know about the St. Augustine Trolley Tours, comparing these two companies as well as offering some other options for tours in St. Augustine.

Old Town Trolley Tours start by the Old Jail and pass by over 100 attractions in St. Augustine. As a bonus, the company includes a complimentary ticket to the St. Augustine History Museum.

🚋 If you’re staying for 2 days or more, consider opting for their 2-day pass!

2. Explore St. Augustine by Foot

While walking might seem like a no-brainer, St. Augustine is so pedestrian-friendly that it deserves its own section. We love exploring the city on foot, and there are countless charming areas to wander through as a couple. Here are some of our favorites:

Historic Flagler College Campus – Admire the stunning architecture of Flagler College, once a grand hotel built by railroad tycoon Henry Flagler. We love strolling through the beautiful gardens and courtyards—especially when looking for a photo op.

Historic District Streets – Wander through the charming streets of the historic district, lined with colorful buildings, boutique shops, and quaint cafes. Our favorite streets are St. George Street, Charlotte Street, Aviles Street, Magnolia Avenue, and Bridge Street.

Castillo de San Marcos National M o nument – Explore this historic fort, one of the oldest continuously occupied European settlements in North America. Climb the ramparts for panoramic views of the city and the Matanzas River, or enjoy the waterside views by sitting on the wall on the water.
St. Johns County Ocean & Fishing Pier – Enjoy a leisurely walk along this iconic pier, offering breathtaking ocean views and the chance to spot dolphins and other marine life. On Wednesdays, one of our favorite Farmers Markets is held here from 8 am to 12 pm!

Watching the sunrise at Castillo de San Marcos fort.

🌅 For a truly unforgettable experience, try to catch the sunrise at Castillo de San Marcos.
The early morning light casts a magical glow over the fort and the surrounding area.

3. Step Back in Time at the Lightner Museum

If you’re looking for romantic things to do in St Augustine for couples, the Lightner Museum is a must-visit. This stunning museum, housed in the historic Hotel Alcazar, offers a captivating glimpse into the Gilded Age.

This museum is composed of three floors that are split between their permanent and temporary collections. They have a vast collection of artifacts, including elegant furniture, fascinating typewriters, intricate musical instruments, and more. The museum shows how visitors during that time were entertained through an inside pool, bowling alley, and more. We both are absolutely in love with their gardens, so don’t miss out on exploring those as well.

Plan to spend a good amount of time here—we spent about 2 hours exploring from start to finish. Afterward, we visited their Café for a quick refuel of coffee after our visit.

💡 Make sure to enjoy the grounds outside of the Lightner Museum as well!

4. Go on a ghost tour

As one of the oldest continuously occupied European settlements in North America, St. Augustine is steeped in history—and some say a healthy dose of the supernatural. So it should come as no surprise that this vibrant city is consistently ranked among the top 10 most haunted places in the United States.

To experience St. Augustine’s spooky side, consider embarking on a ghost or haunted tour. These guided walks and rides offer a thrilling and informative way to explore the city’s dark past.

Here are some of our favorites:

Classic Ghost Walking Tour – This 1.5-hour walking tour takes you by foot through Old Town’s most haunted locations by night. Visit spots from the Old Cemeteries to Castillo de San Marcos. This tour has operated since 1998 and is award-winning! They even offer paranormal tools to rent and take with you on your tour.
Haunted Pub Crawl – If you’re looking for unique night-time things to do in St Augustine for couples, a haunted pub crawl is a must-try. Explore the city’s dark history as you visit historic pubs and enjoy delicious drinks. Your guide will share chilling tales of ghosts of bar managers long passed and strange occurrences in some of the most infamous locals of St. Augustine. This tour has a duration of approximately 2 hours.
Haunted Trolley Tour – Take a spooky twist on the traditional trolley tour with this “Ghosts and Gravestones” Trolley Tour! As you ride through the city under the moonlight, your guide will share chilling stories of ghosts, hauntings, and paranormal activity. This tour lasts for about 80 minutes. It’s a great option if you don’t want to walk after a long day of exploring St. Augustine.

5. Enjoy a Sunset Boat Tour

One of the most romantic things to do in St Augustine for couples is to embark on the Sunset Boat Tour. Glide through the calm waters of the Intracoastal Waterway as you take in the stunning views of the city’s historic landmarks and lush marshes—all while listening to a knowledgeable guide on board with you.

Pushing offshore from St. Augustine and continuing onto Dolphin Bay, bottle-nosed dolphins are often seen on this 1-hour cruise—so keep your eyes peeled! Pass underneath sites such as the famous Bridge of Lions and sail next to downtown St. Augustine, breezing by the Spanish fort.

🥂 Although food and drink aren’t provided, you’re allowed to bring a boat-friendly snack and beverage!

6. Go on a Hike at Guana Tolomato Matanzas Reserve

For the more adventure-bound couples, we recommend going hiking in the GTM Reserve. This nature reserve is located just several miles north of St. Augustine, so if you have a car and are looking to hike near St. Augustine, this reserve is a must! With its diverse ecosystems, stunning landscapes, and abundance of well-kept trails, it’s the perfect spot for a couples hike.

There are two ways to pick out which route you’d like to go on:

Ask in the Visitor’s Center – Their friendly guides will be more than happy to provide you with a physical map and some recommendations. The Visitor’s Center is open from 9 am – 4 pm Tuesday to Saturday, closing Sunday and Monday.
Plan in advance with AllTrails – We like picking out trails beforehand with the AllTrails app, searching for and downloading a route based on difficulty, length, and rating. This is particularly helpful when we visit and the Visitor’s Center is closed.

Beyond hiking, this park’s trails are also fit for mountain bikes or any bike with wide tires. Birders are also common frequenters of this area, as it is a protected habitat teaming with wildlife like bald eagles, hawks, and woodpeckers!

If you arrive by car, they do require a small fee for parking ($3.00 during our visit), but there is no entrance fee to enter the GTM Reserve itself.

🎒 We recommend packing bug spray, water, and food if you plan on spending the day!

We love using AllTrails to download maps offline so we can always stay on the trail. Sign up for AllTrails+ so you too can download maps offline before your hike!

7. Wrap up your day with drinks and live music

After a day of exploring St. Augustine’s historic sites and natural beauty, there’s nothing quite like winding down with a delicious drink and live music. St. Augustine’s vibrant nightlife scene offers a variety of options to suit every taste and mood. From must-try restaurants to sophisticated bars, this city has what it takes to end the day on a high note.

Here are some of our favorite spots to grab a drink and enjoy some music:

La Cocina at the Cellar Upstairs – Located above the San Sebastian Winery, this rooftop bar offers food and drink, panoramic views of St. Augustine, and toe-tapping live music from Tuesday through Sunday.
- Location: 157 King St, St. Augustine, FL 32084
- Hours: 11 am – 9 pm Tuesday – Sunday (Closed Monday)

Dog Rose Brewing Co. – Dog Rose Brewing Co. is a vibrant craft beer haven that caters to both beer enthusiasts and those seeking live music in St. Augustine. With darts, shuffleboards, indoor seating, and a spacious outdoor patio, Dog Rose is the perfect spot for more of a laid-back date night.
- Location: 77 Bridge St, St. Augustine, FL 32084
- Hours: 12 pm – 10 pm Everyday (Open until midnight Friday and Saturday)

Forgotten Tonic – Voted #1 Bar on Aviles Street in 2023, Forgotten Tonic is a stylish bistro offering a delightful menu of small plates, main courses, and expertly crafted alcoholic and non-alcoholic cocktails. With a sophisticated atmosphere, live music offerings, and unique decor, it’s the perfect spot for a romantic date night.
- Location: 6 Aviles St, St. Augustine, FL 32084
- Hours: 11 am – 11 pm Everyday (Open until 12 am Friday and Saturday)

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