Get away from it all and escape to St. Augustine with your partner for a weekend that includes stunning scenery, historic beauty, and gorgeous sunrises and sunsets — all in the nation’s oldest city.
STAY // Start by booking a romantic stay at one of these historic inns:
The Collector Luxury Inn & Gardens is for adults only! Located in the historic district, the property contains nine historic buildings dating from 1790 to 1910. After an extensive renovation, the inn is now “a modern, sensory immersion in art, history, and romance.”
COUPLES PERKS:: Because the inn is directly in the heart of downtown, couples can take romantic strolls along brick-lined streets to nearby landmarks, restaurants, shops, art galleries, and the beautiful bayfront. Afternoon and late-night happy hour in the Well Bar and a mixology program that gives tips on making the perfect cocktail.
Carriage Way Inn Bed & Breakfast is a Victorian-style inn exclusively for adults age 21 and older. The historic home was built between 1883 and 1885 by Edmond Masters, a lead carpenter at Henry Flagler’s first Florida resort hotel, the Hotel Ponce de Leon. Masters built the home for his wife, Rosalie, and their daughter Grace, and he chose the very best structural woods for building: cypress, cedar, and heart of pine.
COUPLES PERKS:: Located in the historic district, the inn is walking distance to Saint George Street, architectural landmarks, art galleries, and the Castillo de San Marcos, the oldest masonry fortress in the continental United States. The inn serves a hot chef’s choice breakfast each morning and offers coffee, tea, and wine throughout the day.
HISTORY & ARCHITECTURE STROLL // Take your partner by the hand and stroll along the brick-lined streets of St. Augustine to view historical landmarks and buildings — the ancient city’s architecture tells the story of the city’s rich multicultural history!
Lightner Museum, completed in 1888 by Standard Oil co-founder Henry Flagler as Hotel Alcazar. This beautiful structure is built in the Spanish Renaissance Revival Style. Today it houses City Hall and the Lightner Museum with three floors of 19th-century art and collectibles once owned by Otto C. Lightner. Grab a bite at Cafe Alcazar, a restaurant that sits in the location of what was once the world’s largest indoor swimming pool.
BEST INSTAGRAM SPOTS:: The little bridge over the pond in the courtyard and the front fountain, with a view of Lightner Museum and the statue of Don Pedro Menendez de Aviles, the city’s founder.
Flagler College, once the Hotel Ponce de Leon, also built by Henry Flagler and completed in 1888. The Ponce is considered one of the finest examples of Spanish Renaissance architecture and was one of the most exclusive resorts of its day — one of the first in the US to be wired with electricity by Thomas Edison himself!
Take a tour to learn the history of the hotel and college, hear stories of the architectural heritage, and see the artwork that in this cultural landmark. Don’t miss the 68-foot domed handpainted ceiling in the grand lobby and the 79 Louis Comfort Tiffany stained glass windows in the dining room.
**Visit Flagler College’s website for updated information on tours during COVID-19.
BEST INSTAGRAM SPOTS: The Henry Flagler statue, the massive black iron gate, the frog fountain, the painted dome ceiling, and the Tiffany stained glass windows.
Casa Monica Hotel — built in 1888 by architect Franklin W. Smith in the Moorish Revival and Spanish Baroque Revival styles.
Governor’s House Cultural Center and Museum, circa 1710 and made of coquina, a native St. Augustine building material.
Trinity Episcopal Church — built in 1821, is the oldest protestant church in Florida.
Cathedral Basilica was built from 1793–1797. The original parish burned to the ground in 1586 by Sir Francis Drake.
Bridge of Lions — completed in 1927 and guarded by two Italian marble lions.
Castillo de San Marcos — completed in 1695 and is the oldest masonry fortress in the continental United States. Made of coquina, this native stone was mined from a quarry on Anastasia Island, which is now part of Anastasia State Park.
BEST INSTAGRAM SPOTS: All of the above locations are Instagram-worthy, with the Castillo the most visited and photographed location in all of St. Augustine.
ROMANTIC DINING // There are dozens of romantic restaurants in the historic St. Augustine area.
Catch 27, 40 Charlotte Street, downtown St. Augustine
Collage Restaurant, 60 Hypolita Street, downtown St. Augustine
Old City House Inn & Restaurant, 115 Cordova Street, downtown St. Augustine
Michael’s St. Augustine, 25 Cuna Street, downtown St. Augustine
Costa Brava, 95 Cordova Street, inside the Casa Monica Hotel
PRIVATE TOURS // To learn more about St. Augustine’s historic district, book a private golf cart tour with St. Augustine Gold Tours or St. Augustine City Tours. Tour guides know all the local stories and give guests an in-depth experience of the history and culture of the ancient city.
For the truly romantic, travel back in time on a horse-drawn carriage tour. Country Carriages and Southern Carriages tour guides narrate St. Augustine’s rich history, covering 450 years from the founding of the city by the Spanish in 1565, through colonial times, the Gilded Age, and into the modern era.
Take a day trip to Anastasia Island to experience sunrise at St. Augustine Beach and sunset at an iconic attraction.
SUNRISE // Travel over the Bridge of Lions to Anastasia Island for a day at St. Augustine Beach. We recommend viewing an amazing sunrise from the shore at the St. Johns County Ocean Pier (completed in 1939, with recent renovations and gorgeous views). The location offers free parking, beach access, public restrooms, and outdoor showers for washing off the sand.
Also on site: The pier ($2 each for sightseeing), a gift shop with snacks and drinks, and a visitor center.
BEST INSTAGRAM SPOTS: The pier, from underneath with crashing waves or on the pier with views of the ocean.
The St. Augustine Beach Art Studio & Gallery is located in the large building to the right of the pier. Find stunning artwork and photography by local artists on display.
Enjoy a day relaxing in the sand and surf and then head to lunch at one of these popular beach eateries: The Beachcomber, Sunset Grille, Little Margie’s, Mango Mangos, Back 40 A1A, Stir it Up, and Salt Life Food Shack.
SUNSET // The top of the St. Augustine Lighthouse is a romantic spot, with breathtaking views of the St. Augustine area and the Atlantic Ocean. Couples often climb in the evening just before sunset. The 1874 Lighthouse tower is also one of the most popular spots for marriage proposals. Hours are 9 AM to 6 PM seven days a week, with extended summer hours.
BEST INSTAGRAM SPOTS: The spiral staircase and stunning views from the top.
THE VIEWS // Cap off the evening with gorgeous views on the rooftop at San Sebastian Winery located in one of Henry Flagler’s former East Coast Railway buildings.
Florida is the birthplace of American wine! French Huguenots who settled North America around 1562 made wine from the abundant wild Muscadine grapes they found growing near present-day Jacksonville. Enjoy San Sebastian wines and appetizers at The Cellar Upstairs Bar and Restaurant, with outdoor seating and rooftop views of St. Augustine’s historic towers.
Saint George Street is the “main street” of historic St. Augustine, with shops and restaurants tucked in around every corner.
DISCOVER & SHOP // Saint George Street is the main thoroughfare for foot traffic (vehicles are not allowed) in the historic district and boasts many attractions, boutiques, art galleries, restaurants, and fun souvenir shops.
The City Gates — An iconic landmark, The City Gates were built in 1808 from coquina, the naturally forming, local building stone mined from a quarry on Anastasia Island. The gates have endured while the city has changed around it.
Oldest Wooden School House— While the exact date of construction is unknown, the Oldest Wooden Schoolhouse first appears on tax records in 1716.
Pena-Peck House — The Pena-Peck House dates back to 1750 when King Ferdinand VI of Spain ordered it built for the Spanish Royal Treasurer. Tours are offered daily.
Colonial Quarter — A living history museum where guests can learn about blacksmithing, view a live musket demonstration, and climb the wooden watchtower for amazing views of the Castillo de San Marcos and the bayfront.
BEST INSTAGRAM SPOTS: Stand in the middle of Saint George Street and take great pics of the street, shops, and the balconies above. Views of the fort and bayfront from the wooden watchtower at the Colonial Quarter, the giant oak tree in the beautiful Colonial Oak Music Park, and ringing the school bell in the garden at the Oldest Wooden Schoolhouse. Great downtown restaurants include The Floridian, A1A Ale Works, St. Augustine Seafood Company, Prohibition Kitchen, and The Roosevelt Room.
OLDEST STREET // Aviles Street is the oldest mapped street in the U.S. — filled with art galleries, shops, restaurants, and historic attractions. The Spanish Military Hospital Museum, the Ximenez-Fatio House Museum, and the Saint Augustine Historical Society Library are great locations for learning more about the oldest city.
DISTILLERY & ICE PLANT // Take a free tour of the St. Augustine Distillery Company and learn how Florida-made craft spirits are created. Housed in the historic Ice Plant building that was originally built as a power plant in 1905 and expanded in 1917 into the first Florida facility to generate commercial block ice. After the tour, dine at The Ice Plant restaurant and enjoy farm-to-table cuisine and craft cocktails.