Get Our Newsletter

Planning A Romantic Weekend in St. Augustine

Last Updated on October 31, 2023

Interested in a romantic weekend in St. Augustine? When it comes to old-world charm, St. Augustine is ideal for a romantic destination.

This centuries-old town is a great getaway for those wanting a change of pace combined with historical landmarks.

St Augustine Beach surfing at dawn.

It features beautiful beaches, eclectic dining, fresh seafood, and locally inspired farm-to-table restaurants.

There are some incredible things to do in St. Augustine for couples no matter where your interests lie.

Brick Street in St Augustine.
Source: St. Augustine

Adventure through old neighborhoods, walk along brick-paved streets, and meander down hidden alleyways.

A set of marble lion statues sit at the base of St. Augustine's Bridge of Lions

Walk from the Bridge of Lions to the Castillo de San Marcos. It is the centerpiece of St. Augustine’s historic district.

At sunset, join lovers and families as they walk the waterfront promenade.

Photo of a horse drawn carriage in St Augustine
Try a romantic carriage ride through St. Augustine

Consider a romantic carriage ride under the stars or even a moonlit evening champagne toast at the top of the St. Augustine Lighthouse.

Columbia Restaurant in St. Augustine, one of seven locations.
St. Augustine. Source: Columbia Restaurant

For foodies, a weekend in St. Augustine offers an endless selection of places to dine. Eat your way through the city’s multi-cultural history by dining on dishes with Spanish, British, French, Greek, and Minorcan flavors.

The Reef St. Augustine.
Source: The Reef St. Augustine

Many independently owned restaurants and taverns flourish in this town. You can sample the locally harvested datil pepper with its signature sweet burn, a bowl of flavorful Minorcan clam chowder, and a plateful of local shrimp.

Table of Contents

    Spending a Romantic Weekend in St. Augustine

    Two women at the Castillo de San Marcos.

    Settled by Spanish explorers in 1565, the “Historic Coast” is known for its history and charming touristy vibe. Trams circle historical landmarks as drivers regale visitors with stories noting their antiquity.

    Tours of every kind are available here. Find historic, food, wine, and even ghost tours – all uncovering the layers of the town’s enduring history.

    People loading a canon in to the Castillo De San Marcos.
    Source: Castillo De San Marcos

    You may even chance upon a random archaeologist excavating a new chapter of St. Augustine’s history.

    To make your weekend extra special – here are some ideas to help plan your next visit.

    Stay at St. Augustine’s Oldest Inn

     St. Francis Inn St. Augustine.

    It all begins with a romantic Bed & Breakfast Inn. This is one of the great things to do in St. Augustine for couples.

    There are many to choose from. St. Augustine’s oldest Inn, St. Francis, a charming bed & breakfast, dates back to 1791.

    This quiet retreat traces its beginnings from the Second Spanish Colonial period. The inn has 17 quaint rooms, appointed with unique antiques in relaxed comfort.

    St. Augustine's Oldest House building exterior.

    The inn is situated in a quiet neighborhood within easy walking distance of almost everything. This inn is also steps away from St. Augustine’s Oldest House.

    It includes a buffet breakfast, social hour, and late-night desserts that can be enjoyed in an intimate European courtyard.

    St Francis Inn Bed and Breakfast pool.
    Source: St Francis Inn Bed and Breakfast

    Added amenities include a swimming pool, parking, and complimentary bicycles.

    The next morning, rise and shine to a delicious homemade breakfast. Be on your way for your St. Augustine discoveries. 

    St. Francis Inn Address: 279 St George St, St. Augustine, FL 32084

    Bike Through St. Augustine History

    Biking in St Augustine.
    Source: Florida Parks

    Many St. Augustine inns have bikes available, including the St. Francis Inn. Find a bike, slip on a backpack, grab a map, or your phone. You can venture through the scenic neighborhoods of the old city.

    Bike through the historic district on Hypolita Street to the waterfront. Ride north along the sidewalk that parallels Avenida Menendez.

    Castillo de San Marcos.

    Next stop, Castillo de San Marcos. Take in a magnificent morning view at the Castillo de San Marcos, the oldest masonry fort in the continental U.S. Created from locally sourced coquina, a mixture of shell and limestone.

    The indestructible fortress took 23 years to build. It played a key role in protecting the Spanish. They ruled St. Augustine during the 17th and 18th centuries.

    Actors at the Castillo de San Marcos.

    Walk the grounds and meet the volunteer re-enactors who bring the fort to life. Hike to the top of the fortress and breathe in the fresh air under royal blue skies as you take in the 360-degree panorama.

    You’ll soon know why the Spanish built this immense fortress with a commanding view of the harbor. Capture the quintessential St. Augustine “selfie” standing inside one of the turrets or next to a cannon.

    Castillo de San Marcos Address: 11 S Castillo Dr, St. Augustine, FL 32084

    Bike past the Mission Nombre De Dios

     National Shrine of Our Lady of La Leche at Mission Nombre de Dios.
    Source: National Shrine of Our Lady of La Leche at Mission Nombre de Dios

    Continue pedaling north along Avenida Menendez (becomes San Marco Avenue, A1A) to the Mission Nombre de Dios. The landmark will be the towering 208-foot Great Cross overlooking Matanzas Bay.

    This location marks where Pedro Menedez de Aviles first landed. He claimed the area for Spain and the location of the first Catholic mass.

    Park at  National Shrine of Our Lady of La Leche at Mission Nombre de Dios.
    Source: National Shrine of Our Lady of La Leche at Mission Nombre de Dios

    But it’s a charming reconstructed chapel known as the Shrine of Our Lady of La Leche. It dates back to the 1600s and is tucked away within the shady park which makes it worth the stop.

    Enjoy some peaceful contemplation, find a bench, and enjoy your lunch.

    Mission Nombre De Dios Address: 89 A1A Scenic and Historic Coastal Byway, St. Augustine, FL 32084

    See More St. Augustine History

    Fountain of Youth Franciscan Mission de Nombre.

    Just a few blocks away will be your next stop. Situated in a quiet neighborhood, the Fountain of Youth Archaeological Park is the original site of the nation’s oldest city.

    It is located in the area first explored by Juan Ponce de Leon in 1513 and settled by Pedro Menendez de Aviles in 1565.

    This “old Florida” property includes the original “spring” or mythical “fountain of youth” and a mix of reconstructed settings that bring St. Augustine’s history to life.

    Fountain of Youth weapon demonstration.

    Walk through a Timucua family compound representing life in the Timucuan capital of Seloy, designed to recognize the Native Americans who inhabited the region thousands of years before the Spanish.

    Fountain of Youth Park.

    Here are other experiences you won’t want to miss:

    • Enter a reconstructed thatched 1587 Franciscan Mission Nombre de Dios that began the Spanish mission system in the New World.
    • Observe a blacksmith demonstrating the tools of the trade over a fire
    • Walk to the waterfront to see the replica of a Chalupa, a 16th-century Spanish utility boat
    • Witness a 16th-century cannon create a deafening boom as it is fired, and climb the Spanish watchtower overlooking Matanzas Bay, designed as an early warning system for enemy attacks
    • Visit with the costumed re-enactors – a Franciscan friar priest, a Timucua interpreter, and weapons demonstrators – all happy to share stories and tales of the period.

    Fountain of Youth Archaeological Park Address: 11 Magnolia Ave, St. Augustine, FL 32084

    Dining in St. Augustine

    St. Augustine's St. George Street.

    By now, you’ll be ready to relax over some noshes and cocktails so cycle back to historic Old Town.

    Park your bikes before walking the pedestrian-only St. George Street where shops, restaurants, pubs, wine bars, and sidewalk cafes line the street.

    St George Row.
    Source: St. George Street

    Find a place to relax and enjoy some people-watching. You’ll be amazed at the eclectic personalities that walk St. George Street.

    Look for local pirates, winches, and colonial soldiers, some from the Colonial Quarter exhibiting three centuries of Spanish (and British) colonial life.

    Bartender at St. Augustine Ice Plant Bar.
    St. Augustine Ice Plant Bar

    From there, deciding where to plan a St. Augustine dinner will be your biggest challenge. Seafood? The list is endless: But favorites for the fresh local fare include Schooners Seafood House or the classic Barnacle Bills for starters.

    Schooners Seafood House Address: 3560 N Ponce De Leon Blvd, St. Augustine, FL 32084
    Barnacle Bills Address: 1302 N Ponce De Leon Blvd, St. Augustine, FL 32084

    Food in a bowl.
    Source: Floridian St Augustine

    If you are hungry for a bit of savory deliciousness, try the Floridian Restaurant known for its seasonal and sustainable southern dishes.
    Floridian Restaurant Address: 72 Spanish St #3638, St. Augustine, FL 32084

    Columbia Restaurant 1905 salad and paella display.
    Photo credit: Columbia Restaurant Group/Facebook

    For Cuban food, the Columbia Restaurant dishes up real, authentic cuisine.

    Columbia Restaurant Address: 98 St George St, St. Augustine, FL 32084

    The Ice Plant Drinks.
    Source: The Ice Plant

    Head to the Ice Plant Bar, for handcrafted adult beverages and farm-raised food for a younger, hip vibe, that shares the building with the St. Augustine Distillery.

    Ice Plant Bar Address: 110 Riberia St, St. Augustine, FL 32084
    St. Augustine Distillery Address: 112 Riberia St, St. Augustine, FL 32084

    Farmer’s Market, Beaching It & A View From Above

    Bicycle on Anastasia Beach State Park

    Another planned day takes you over the St. Augustine Bridge of Lions to Anastasia Beach, to the Farmer’s Market, and for a majestic view from high above. This is one of the great things to do in St. Augustine for couples.

    The “oldest U.S. city” draws most travelers because of its rich history, but after visiting St. Augustine’s attractions you may be ready for a walk on the beach, and the local Anastasia State Park has one of the best.

    Anastasia State Park Address: 300 Anastasia Park Rd, St. Augustine, FL 32080

    Beach Walkway.

    Miles of gorgeous, wide-open beaches are accessed by long, wooden walkways across towering sand dunes. It’s a perfect and picturesque place to view the vast blue Atlantic as you breathe in the fresh salt air.

    Nearby is Salt Run, a tidal salt marsh with an upland hammock where you can observe coastal birds and wildlife.

    St Augustine Farmer’s Market

    St. Augustine Farmer's Market.

    If you happen to be in the area on a Saturday, wander through the St. Augustine Amphitheatre Farmer’s Market, located at the St. Augustine Amphitheatre.

    Grab your latte and walk along a row of tented purveyors offering fresh produce, coffee, breakfast, seafood, honey, and hand-crafted items as local musicians keep the vibe fun.

    St. Augustine Amphitheatre Address: 1370-1380 A1A Scenic and Historic Coastal Byway, St. Augustine, FL 32080

    Minorcan Clam Chowder from Osteens.
    Source: O’Steens Restaurant

    After a refreshing stroll on the beach, treat yourself to lunch at Osteen’s Restaurant, a local institution where folks line up for the simple menu of tasty fried shrimp, oysters, and local fish.

    Be sure to sample the Minorcan Clam Chowder, considered one of the best in town (cash only).

    Osteen’s Restaurant Address: 205 Anastasia Blvd, St. Augustine, FL 32080

    St. Augustine Lighthouse

    St. Augustine Lighthouse.
    Source: St. Augustine Lighthouse

    Next, are you ready to get your heart rate going? Most agree that there is something special about a lighthouse with towering shapes, unique history, and amazing tales of dedicated lightkeepers trudging up steep steps to help guide ships.

    The 219-step St. Augustine Lighthouse with its spiraling black and white stripes will continue your love affair with another maritime treasure.

    St. Augustine Lighthouse.

    Long ago built as a wooden sentry watchtower on the Matanzas Inlet, the first tower on U.S. soil to aid navigators became a predecessor to the current 149-year-old St. Augustine Lighthouse that still stands.

    The trip to the top is worth every step, especially for the breathtaking vista from high above.

    St. Augustine Lighthouse Address: 100 Red Cox Dr, St. Augustine, FL 32080

    Sunset Grille.

    For dinner, try the Sunset Grille for a view of the beach from the open-air deck and a taste of the “New Minorcan” chowder, a mix of New England and Minorcan chowder.

    Sunset Grille Address: 421 A1A Beach Blvd, St Augustine Beach, FL 32080

    Also on the island is the local neighborhood favorite eatery Gypsy Cab, where the house-made salad dressing is so popular, they sell it by the bottle.

    Gypsy Cab Address: 828 Anastasia Blvd, St. Augustine, FL 32080

    Aviles Street in St. Augustine.

    For a little nightlife, head back to town, to A1A Ale Works overlooking the Bridge of Lions, or a walk along Aviles Street, the oldest public street in the country, and home to late-night fun.

    A1A Ale Works Address: 1 King St, St. Augustine, FL 32084

    It’s “Whatever” Day – Pick and Choose

    Kayakers in St. Augustine.
    Matanzas Bay Eco-Tour

    Next, choose your own trail to round out your trip. Maybe it’s a tour of Flagler College, another day on a sparkling beach, or a kayak ride through a stunning preserve.

    Or you might want to continue eating your way through the Historic Coast.

    Flagler College Tour

    Flagler College.

    Built by oil magnate and railroad baron Henry Flagler as the Hotel Ponce de Leon, it now houses Flagler College.

    Developed as a high-end luxury hotel designed to attract well-heeled tourists when it opened in 1888, it remains one of the most impressive buildings in the city to this day.

    Flagler College.
    Source: Flagler College

    The student-led “legacy” tour (10 am – 2 pm daily) is considered one of the best in St. Augustine.

    You’ll get the Flagler history while being led through the courtyard, gardens, gilded domed Rotunda, and the “Hogwarts-style” dining room with Tiffany windows.

    Flagler College Address: 74 King St, St. Augustine, FL 32084

    More Beach Time

    Anastasia Beach in St. Augustine.

    For more beach time you can choose from plenty of beaches, but one of the best is Villano Beach, accessed via A1A over the Usina Bridge.

    Hang with the locals, kick back, watch the surfers and kiteboarders, or just wander aimlessly scanning for beach treasures and shark teeth. This is your place to let it all go.

    Aunt Kate's On the River Minorcan Clam Chowder.

    For lunch, dinner, or even a cocktail follow the locals to a legendary eatery for old Florida dining, Aunt Kate’s On the River.

    This waterfront restaurant overlooks the scenic Tolomoto River setting the stage for tasty seafood dishes dating back to a time when Henry Flagler ferried his hotel guests out for oyster roasts.

    Aunt Kates Restaurant.
    Source: Aunt Kate’s Restaurant

    Continuing this legacy and celebrating the area’s Minorcan (also spelled Menorcan) heritage, the restaurant is still serving fresh seafood, traditional Menorcan Pialu (rice) dish, datil cornbread, gator tail, and the prized local Menorcan clam chowder.

    Aunt Kate’s on the River Restaurant Address: 612 Euclid Ave, St. Augustine, FL 32084

    Luvin O Van.

    Another great stop is the Luvin’ O-Van food truck. The owner of the former Hot Shot Bakery, Sherry Stoppelbien, runs this truck with the same great food, at a different location.

    Luvin’ O-Van Address: This food truck moves often. Their location can be found on the Luvin’ O Van Facebook Page.

    Beaches at Vilano shrimp and steak.
    Source: Beaches at Vilano

    Beaches at Vilano is another restaurant on the Intracoastal Waterway at the base of the Vilano Bridge. Dig your toes in the sand while watching the sunset as locals ride up by boat or wave runner.

    Enjoy a Key West vibe with live music on the deck and don’t miss the datil pepper fish & grits.

    Beaches at Vilano Address: 254 Vilano Rd, St. Augustine, FL 32084

    Get Close to Nature on a Kayak

    Man kayaking in St. Augustine.

    Affectionately known as the GTM, (Guana Tolomato Matanzas National Estuarine Research Reserve), this unique ecosystem offers a chance for kayakers to enjoy a slice of northeast Florida’s pristine nature in a vast, stunning estuary.

    Join Ripple Effect guided eco-tours to experience local wildlife while paddling through tidal creeks in a protected marine nursery.

    You may even chance upon bottlenose dolphins, sea turtles, migrating birds, and bald eagles while quietly paddling through this Florida treasure.

    St. Augustine Distillery

    St. Augustine Distillery.

    The St. Augustine Distillery, located in a renovated 1917 ice plant, hosts free tours where handcrafted small-batch spirits (vodka, rum, gin, and whiskey) are distilled.

    Learn about Florida’s spirits-making history and the artisan distilling process.

    St Augustine Distillery Tasting.
    Source: St Augustine Distillery

    You’ll even enjoy an adult beverage tasting following the tour.

    St. Augustine Distillery Address: 112 Riberia St, St. Augustine, FL 32084

    And one more idea: A Ghost Tour

    St. Augustine's Haunted Pub Crawl.

    It doesn’t need to be Halloween in the Nation’s oldest city for you to enjoy a ghost tour.

    St. Augustine is one of the best places to go for a paranormal experience.

    Ghost Augustine.
    Source: Ghost Augustine

    Hipster Haunted Pub Crawls, food and wine tours, trolley and train adventures, and traditional graveyard haunts are just a sample of the offerings.

    Ghost Adventure Car.

    And most of the guides are certified (yes, certified) to share stories of death, murder, and mayhem.

    There’s no doubt that St. Augustine’s fascinating history embedded with culture, fine epicure and fun makes Florida’s Historic Coast a great choice to create your own love story – over and over again.

    For more romantic Florida options check these out:

    For more Authentic Florida St. Augustine stories:

    Here are a few more St. Augustine inns to add to your list:

    Leave a Comment