Oldcity Offers Romantic Date Ideas In St Augustine

Men's Dating

OldCity.com Helps Couples Get Romantic On Dates in Historic St. Augustine

Suzanne Wentley

Written by: Suzanne Wentley

Suzanne Wentley

Never bored, Suzanne Wentley is a freelance writer, marketing professional, yoga teacher, energy worker, pet sitter, full-time traveling minimalist, and vegetarian. Her favorite dates include a creative cocktail (preferably made of local fruit and without a plastic straw), laughter, and a beautiful sunset over the sea. Her website is thelovelightproject.com.

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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The Short Version: St. Augustine, Florida, is the oldest city in the United States, and it certainly takes visitors back in time. Couples can embark on romantic strolls down cobblestone streets, enjoy quiet candlelit dinners, and spend nights at charming bed and breakfast establishments. OldCity.com highlights activities, accommodations, and adventures in the popular tourist destination. The site also shares a list of ideas for romantic dates, wedding proposals, and even milestone anniversaries. History is around every corner, and couples may be surprised at some of the hidden gems in the historic town.

St. Augustine, Florida, founded in 1565 by Spain, is considered the oldest city in the United States. It would be another 55 years before the Pilgrims landed on Plymouth Rock.

The area of St. Augustine was first discovered in 1513 by Juan Ponce de Leon, a Spanish explorer and conquistador who was searching for the mythical Fountain of Youth. While he never found it, the Spanish established the first colonial settlement in St. Augustine.

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OldCity.com offers plenty of options for those who want to visit St. Augustine.

For the next 200 years, the Spanish city would clash with pirates and then with the English colonies. In the 1700s, the town became a final stop on the Underground Railroad and escaped slaves found their freedom in the Spanish colony. After Florida joined the union in 1845, St. Augustine began its evolution into the modern yet historic wonder it is today.

Couples can certainly see their share of relics and artifacts on a date in the city. And OldCity.com adds to that list with new and exciting ideas for planning a date in the city.

The website helps visitors plan trips to St. Augustine to explore both its modern culture, unique cuisine and its rich history.

Today, visitors can still experience parts of the town that the Spanish settlers created hundreds of years ago, including narrow, cobblestone streets and houses with unique balconies. It has 36 original buildings from colonial times and another 40 reconstructed properties. One original structure is the picturesque Castillo de San Marcos, a stone fortress built to protect the city against the onslaught of British forces looking to take over.

Unique Date Ideas in America’s Oldest City

Couples who love romance and history have plenty to do in St. Augustine. A memorable date may start with a trip to America’s first colony, the Fountain of Youth Archaeological Park. It is the site of the 1565 settlement, created by the Spanish Admiral Don Pedro Menéndez de Avilés.

The property is located on 15 waterfront acres, and it’s the only place to sip from Ponce de Leon’s Spring of Eternal Hope. Couples can drink from the spring waters to try their luck living forever young for a lifetime.

Other activities that promote a romantic visit is the Small Indulgences European Day Spa & Salon, which offers couples massages, and a Bridal Package, seven days a week. A stop by Whetstone Chocolates can keep the relaxation going. The chocolatier offers tasting tours that teach visitors about the history of the business as they sample dark, milk, and white chocolates and cocoa nibs.

Screenshot from OldCity.com
Couples can find a variety of fun activities in historic downtown St. Augustine.

Couples looking for a bird’s eye view of the city can book a tour with First City Helicopters. The daytime and sunset tours are perfect for enjoying the beauty of nearby Anastasia State Park and taking in stunning views of the entire city. Many couples choose the romantic evening tour to pop the big question.

Those looking to add a little more mystery to date night often get a psychic reading at The Golden Gypsy right in the heart of downtown. Couples can enjoy live painting and receive a Tarot card reading, a palm reading, or a reading of the runes. The establishment also offers sunrise and sunset yoga classes.

Pack a Bathing Suit To Enjoy Nearby Beaches

Exploring the historic downtown can make for a charming date, but St. Augustine is also home to some of the best beaches in the state. From Guana River State Park to the north to Crescent Beach to the south, visitors shouldn’t miss the area’s long stretches of beautiful sand.

It’s easy to imagine the Spanish ships entering the area from the sea and crossing the Intercoastal Waterway, which naturally separates the mainland from the barrier island. Its public beaches are just a couple of blocks from delicious restaurants and popular bars.

Photo of St. Augustine area beach
OldCity.com can help couples choose which of the area’s beautiful beaches they want to visit.

Visitors can download the St. Johns County “Reach the Beach” app to prepare for the day. They can quickly find beach driving conditions, facility locations, lifeguard information, and emergency contacts through the app.

And unlike many destinations up north, visitors can drive on many of the beaches, including on Vilano Beach, St. Augustine Beach, and Crescent Beach. The daily pass for driving costs $10 for residents and nonresidents, with a 50% discount for handicapped and active military.

St. Augustine Beach, located on Old A1A Beach Boulevard, is less than five minutes from historic downtown. Its white sands connect with the St. Johns County Pier, which is a blissful place to walk hand in hand and watch for dolphins jumping in the water. Many active visitors also enjoy fishing off the pier or playing volleyball in the courts nearby.

Anastasia State Park and Recreation Area is a must-see for nature lovers. The 1,700-acre property is a protected bird sanctuary that offers five miles of sandy beaches with a bathhouse and nature trails. Admission is just $8 per vehicle.

St. Augustine is a Dynamic Date Destination in Florida

St. Augustine offers a wide range of accommodations for all tastes because it is such a popular place to visit. The Carriage Way Inn Bed & Breakfast has been voted the best B&B in St. Augustine four years in a row — including 2020. It’s located in the heart of the historic district, making it easy to walk around and explore local sites. It also offers aromatherapy towelettes and complimentary beverages upon arrival.

The Beachfront Bed & Breakfast is an adults-only location overlooking the ocean. It’s just 10 minutes from downtown and has suites with elegant linens and a refrigerator — perfect for extended stays.

Those who want a taste of history often stay at 44 Spanish Street Inn. The establishment was built in the 1920s in the heart of downtown. The small boutique inn features charming porches and brick courtyards just steps from the best shopping and restaurants.

Speaking of restaurants, St. Augustine is also a foodie paradise. Many couples reserve a table for Sunday Brunch at the Raintree Restaurant, a restored Victorian home built in 1879. Like so much of Florida, the restaurant is casual yet elegant.

The Spanish Bakery & Café is a popular lunch spot with outdoor picnic tables where visitors can enjoy authentic Spanish empanadas, soups, salads, and sandwiches. For a seafood fix, stop by the Kingfish Grill, which also has a full-service bar and seasonal entertainment right on the water.

Planning ahead will make a getaway or date that much better, so couples should consult OldCity.com’s comprehensive calendar of events to see what’s happening when they’re in town. From November 20, 2021 through January 31, 2022, visitors can enjoy the popular Nights of Lights, which brings the city to life with beauty and love.

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