Romantic Getaway: Things to Do in St. Augustine for Couples

St. Augustine, Florida, offers a perfect blend of history, charm, and scenic beauty, making it an ideal destination for couples seeking a romantic getaway. Here’s a guide based on my most recent trip to St Augustine, including some of the best experiences for couples to enjoy together.

I was a guest of the St Augustine tourism board, Florida’s Historic Coast, but all opinions are my own. This itinerary assumes you have access to a car. St Augustine is an easy city to discover the old town by walking, but a car will be helpful if you want to get further afield, as I will recommend. 

St. Augustine from the water on a boat from St. Augustine Sailing

Table of contents: (Hide)

• Arrival 
• Day 1: Historical and Cultural Immersion
  • Morning
    • Visit the Castillo de San Marcos
    • Visit A Museum
  • Lunch
    • Smokin D’s BBQ
  • Afternoon
    • Old Town Trolley Tour
    • Fountain of Youth Archaeological Park
    • St. Augustine Distillery
  • Dinner
    • La Cocina International
• Day 2: Adventure and Relaxation
  • Morning
    • Anastasia State Park
  • Lunch
    • Salt Life Food Shack
    • St. Augustine Sailing
  • Dinner
    • The Columbia Restaurant
• When to Visit St Augustine

Arrival 

I am assuming that your first day will be a travel day, arriving in St Augustine sometime just before dinner time. Check into your hotel or B&B, get some dinner, and, as time permits, explore a bit of the old city near your accommodation.

Check-in to your Hotel

Carriage Way Inn B&B
Address: 70 Cuna St, St. Augustine, FL

I recommend you stay in the Old City, somewhere within walking distance from Castillo de San Marcos. I stayed in the Carriage Way Inn B&B and can highly recommend it for a romantic weekend for two. This is an adults-only establishment, so it is not suitable for a family trip to St Augustine. Carriage Way proudly proclaims its virtual monopoly on the award for the “Best Bed and Breakfast” going back to 2017.

Here, you will find a comfortable room with freshly baked cookies in the parlor, complimentary wine and sodas, and a delicious breakfast. It might not matter for a romantic weekend, but it also has fast enough internet for a travel blogger like me to get some work done. I stayed in one of the satellite properties, Centennial Inn, which is across the street, but had most of my breakfasts in the main Carriage Way building. 

Dinner

There are several great places for dinner in St Augustine. If you love fresh seafood with a southern twist in a scenic waterfront setting and you arrive before sunset, then I would head to Fish Camp. Get a seat out on the deck with a view of the sunset over the San Sebastian River. If a menu with phrases like “catch of the day,” “pan-fried,” and “seafood boil” gets you salivating, then this is the place for you.

St. Augustine Fish Camp
Address: 142 Riberia St, St. Augustine, FL

Day 1: Historical and Cultural Immersion

Morning

Visit the Castillo de San Marcos

As a history buff, I think that the Castillo de San Marcos is the one must-see destination in St Augustine. Is it particularly romantic? Maybe not. But the walls do allow for some great views of the water, including the sailboats that we will experience later in the trip.

This is the oldest masonry fort in the continental U.S. and one of the oldest buildings in the country. Construction started on the fort in 1672. The fort should take 30-60 minutes to visit; allow a bit more time if you want to take a ranger-led tour.

• Hours: 9 am to 5:15 pm (the last admission at 5 pm, closed on Thanksgiving Day and Christmas Day)
• Admission: $15 for adults (Only credit and debit cards are accepted for payment. This site is run by the National Park System, so the National Park Pass or the Golden Eagle Pass can also be used for admission)

Visit A Museum

After visiting Castillo de San Marcos, I recommend one of two museums. If you want more history or feel like your inner child is never far from the surface, I would cross the street to visit the Pirate & Treasure Museum. If we were talking about a trip with kids, I would say this is a required stop, but not on a romantic weekend. Go to this museum if the idea of learning more about pirates sounds like fun. If you want to touch an actual treasure chest, see one of the only remaining Jolly Roger flags, or learn about the likes of Blackbeard, then this is your museum.

St. Agustine Pirate & Treasure Museum

• Location: 12 South Castillo Drive, St. Augustine
• Admission: $19 for Adults
• Hours: 10 am to 7 pm (closed Christmas Day)

If you and your loved one’s vibe is a bit more refined, then I would recommend the nearby Lightner Museum. The Lightner Museum, located in the historic downtown district of St. Augustine, Florida, occupies the former Alcazar Hotel, which was built in 1888 by railroad magnate Henry Flagler. This Gilded Age resort hotel has been transformed into a museum housing an extensive collection of 19th and early 20th-century fine and decorative arts.

If you are a history buff, I highly recommend you also visit the smaller Fort Matanzas, which guarded the backdoor of St Augustine, and Fort Mose Historic State Park, which was the location of the first free Black settlement in North America. However, I will save writing about those for another blog post.

Lightner Museum

• Location: 75 King Street, St. Augustine
• Admission: $19 for adults
• Hours: 9 am to 5 pm (last admission at 4 pm, closed on Thanksgiving Day and Christmas Day)

If you prefer things that are just plain weird, the original Ripply’s Believe It Or Not Museum is the obvious choice. Ripley’s Believe It or Not! is the first and oldest Ripley’s Odditorium, opened in 1950. It is located in the historic Castle Warden, a building dating back to 1887 that was once a hotel frequented by Robert Ripley himself. The museum spans three floors and features over 800 exhibits, including a range of bizarre artifacts and oddities collected from around the world, including shrunken heads and a replica of the International Space Station made from match sticks.

Ripley’s Believe It or Not!

• Location: 19 San Marco Avenue
• Admission: $24 for adults (purchase tickets, money-saving discounts)
• Hours: 10 am to 6 pm

Lunch

Smokin D’s BBQ

I had some of the best BBQ I have eaten at Smokin’ D’s BBQ in St Augustine. This is not a fancy place. You will likely be eating on a picnic table outside or on a bench, looking out at the San Sebastian River. This is a place to go with someone who will love you even if you get some BBQ sauce on your face.

Owner Cameron Perrott has brought the business his father Daryl started (the original D in Smokin’ D) closer to downtown. He clearly inherited his father’s zeal for what makes good BBQ. This is a restaurant for people who like meat, particularly smoked meat. Good BBQ takes time, so I recommend lunch instead of dinner because they will start running out of some dishes late in the day. 

On Wednesdays, their normal menu expands with “Wet Wednesday.” This is the only time the restaurant will serve meat from the previous day. They add a tangy sauce to the meat and serve it on a sandwich. If you can, throw in a side of Grandma’s moonshine pickles.

I should also say that Cameron changed my mind about a white BBQ sauce. I told him that I had never found one that I liked. That is no longer true. When I return, I will get some of that smoked turkey with white sauce… and I would have bet you good money that I would never say that phrase.

• Location: 1409 N Ponce De Leon Blvd, St Augustine
• Hours: Wednesday – Monday. 11 am to 7 pm… or until sold out

Afternoon

Old Town Trolley Tour

The Old Town Trolley Tour provides an overview of the city and allows visitors to learn more about St. Augustine and its unique American history. The tour features 22 stops at more than 100 points of interest, including iconic landmarks like the Castillo de San Marcos, Flagler College, and the Lightner Museum. The open-air trolleys provide an excellent opportunity for taking photos and enjoying the view.

Each trolley is narrated by a knowledgeable driver who shares interesting stories and historical facts about the city’s rich past, making the tour both educational and entertaining. The full loop takes approximately 90 minutes, and trolleys run every 15-20 minutes. 

The trolley ticket includes free admission to the St. Augustine History Museum, a complimentary shuttle to local hotels, and a beach shuttle service to the Alligator Farm and the beach. The tour operates daily from 9 am to 4:30 pm.

Hop off at Stop #22 to visit the Fountain of Youth.

Fountain of Youth Archaeological Park

This park became a tourist attraction in 1868 when Henry H. Williams purchased the land and began promoting it as the Fountain of Youth. It might still be a tacky roadside attraction if it were not for the third owner of the park, Walter B. Fraser, who emphasized the site’s historic roots. 

Since Ponce de Leon didn’t actually discover the Fountain of Youth… your actual mileage will vary on whether drinking the water with your sweetie will be a good alternative to growing old together. Hey… it’s worth a try.

More importantly one this site in 1565, Pedro Menéndez de Avilés founded the city of St. Augustine at the site of the native Timucua village of Seloy, which is now part of the park. This makes it the oldest continuously occupied European-established settlement in the continental United States. It is also the original site of the oldest of the Spanish Missions in the New World. Archaeological excavations have uncovered significant remains from this early period, including Spanish fortifications and artifacts from both the Spanish settlers and the Timucua people.

Today, the park offers a variety of educational and entertaining activities, including exploring the Timucuan village, participating in archaeological digs, and viewing re-enactments of historic events.

• Location: Address: 11 Magnolia Ave, St. Augustine
• Hours: 9 am to 6 pm (last ticket sold at 5 pm)
• Admission: $23 for adults

St. Augustine Distillery

The St. Augustine Distillery is a locally owned artisanal distillery housed in a restored historic ice plant building dating back to 1917. Founded by 20 local families with a mission to create world-class spirits and enrich the community, the distillery opened its doors to the public in 2014 after several years of preparation and restoration efforts. The distillery uses locally sourced ingredients to produce award-winning spirits, including bourbon, rum, gin, and vodka. 

Bourbon requires at least 3 years of aging, so they started producing gin, rum, and vodka because those require less aging. They won awards for their gin, rum, and vodka, but I think it is fair to say that their true love is bourbon.

Distilling is still relatively new as a legal business in Florida, and their stills, “Bessie” and “Ella,” are the first two legal stills in the state since prohibition.

Visitors to the St. Augustine Distillery can enjoy free self-guided tours and tastings seven days a week. Enjoy a VIP tour and learn about the craft of distilling. The experience is both informative and delightful, and you’ll also have the opportunity to taste award-winning spirits.

Serious bourbon fans can take a Certified Bourbon Steward Course that was created in collaboration with The Stave & Thief Society.

• Location: Address: 112 Riberia St, St. Augustine
• Hours: 9 am to 6 pm, 11 am to 6 pm on Sundays (last ticket sold at 5 pm); guided tours run on the half-hour from 10:30 am to 5:30 pm.
• Admission: $23 for adults

Dinner

La Cocina International

What goes better than an afternoon in a distillery? Dinner above a winery. La Cocina International is located above the San Sebastian Winery. The restaurant’s patios offer wonderful views of the city, and it is perfect for a romantic dinner. 

Norberto Jaramillo, the executive chef of La Cocina International, emphasizes “local and sustainable ingredients with a technique-based approach.” That’s all well and good, but more importantly, the food is delicious. The restaurant was fairly new when I visited, but don’t be surprised if you need a reservation when you visit.

I had the Pear salad (Wine-poached Asian pears, artisan baby greens, mandarin wedges, blue cheese, caramelized pecans, and raspberry vinaigrette) and the Peri Peri Chicken (organic chicken breast served over a savory spinach cream sauce, accompanied by roasted potatoes and heirloom carrots). Both were wonderful. The menu also includes shrimp, fish, pasta, and steak dishes.

• Location: 157 King St., St Augustine
• Hours: Tuesday – Sunday, 11 am – 9 pm

Day 2: Adventure and Relaxation

Morning

Anastasia State Park

You didn’t think I would make an itinerary for St. Augustine and leave out the beach, did you? For some people, the beach is all they need in their itinerary, and that’s fine. St. Augustine offers a four-mile stretch of beautiful beach at Anastasia State Park. I visited the beach at low tide, when you can rent bikes and ride on compact wet sand near the ocean. As you can see from my video, you can easily have an entire mile of beach to yourself if you are willing to walk or bike a bit. 

You can also rent kayaks and stand-up paddleboards in the park to explore Salt Run. I learned two things about this: First, it is a better activity for high tide. Second, for some of us, a “stand-up paddleboard” is just a paddleboard.

The beach also has popular campgrounds. My St. Augustine host, Barbara,  said that the best time to camp at Anastasia State Park is when there is a great concert at the adjacent St. Augustine Amphitheatre. 

• Location: 300 Anastasia Park Rd, St. Augustine
• Hours: 6 am to 8 pm

Lunch

Salt Life Food Shack

• Location: 320 A1A on the Beach
• Hours: Sunday – Thursday: 11 am – 10 pm, Friday – Saturday: 11 am – 11 pm

St. Augustine Sailing

The perfect way to end a trip to St Augustine is on the water. What better way to do it than on a sailboat with St. Augustine Sailing?

St. Augustine Sailing offers an exceptional way to explore the scenic waters of Florida’s historic coast. Based at the Camachee Cove Yacht Harbor, this sailing charter company provides a variety of experiences, including private charters, sailing lessons, and sunset cruises. 

Our sail included a wonderful box lunch which was also made by this family-run business.

• Location: Address: 3076 Harbor Dr, St. Augustine
• Hours: 9 am – 8 pm

Dinner

The Columbia Restaurant

For your last dessert on your trip, I recommend the Columbia Restaurant. Don’t get me wrong, I also recommend them for dinner but listen carefully… you must leave room for dessert… especially their chocolate bread pudding.

The Columbia Restaurant is renowned for its authentic Spanish-Cuban cuisine and historic ambiance. Established in 1905, it is Florida’s oldest restaurant. It is known for its signature dishes, such as the 1905 Salad, paella, and Cuban sandwiches, all prepared with time-honored recipes. The restaurant’s ornate decor, featuring hand-painted tiles and vintage photographs, adds to its unique charm.

I had to try the 1905 salad, which is made at the table. It is a good salad to split with your sweetheart (remember dessert). The salad is a blend of crisp iceberg lettuce, ripe tomatoes, julienned ham, Swiss cheese, Spanish olives, grated Romano cheese, and freshly made garlic dressing.

I am more of a fan of Cuban food than Spanish food, so I ordered El Combo de Cuba (roast pork, boliche, empanada de picadillo, platanos, black beans, yuca, and yellow rice). Unfortunately, it was so good that it jeopardized my whole dessert plan. But… I soldiered on.

• Location: 98 St. George St, St. Augustine
• Hours: 11 am to 10 pm

When to Visit St Augustine

I visited St Augustine in July when I was in the area. If you are a local and are used to the hot, humid Florida summers, then it is certainly enjoyable this time of year. But for me, I would probably have enjoyed the weather better in the spring or the fall when the temperatures and humidity were a bit lower than in the 90s. The graph above will help you determine the best weather for your trip. May has the advantage that it is not in hurricane season.