Guide To A Romantic Weekend in St. Augustine

Discover the magic of wintertime in St. Augustine and embark on a historical “Transportainment^®” adventure!

Book a Room at a Luxurious Bed and Breakfast

There’s nothing more romantic in St. Augustine than a stay at a bed and breakfast; especially if it’s one that overlooks the water and dates back 100 years. When planning your romantic St. Augustine getaway, make it unforgettable by booking your stay at the Casablanca Inn of St. Augustine. It is an ideal setting to rekindle your romance or spark a new one, with elegant suites and rooms that offer gorgeous views of the Matanzas Bay, whirlpools, private porches, sundecks, and beautiful antique furnishings. After a day of exploring the ancient city, spend the evening of your private porch gazing at the water as yachts sail into the bay and the sun begins its descent in the distance.

Explore the City Aboard the Old Town Trolley

Grab your lover’s hand and a seat aboard the orange and green trolley. Sit back, relax and enjoy the narration from your expert guide who will entertain and amuse the two of you with stories and fascinating facts about the history of St. Augustine. The trolley will take you past more than 100 different points of interest, including the Spanish Quarter, St. George Street, Castillo de San Marcos, the Fountain of Youth and many of Henry Flagler’s most treasured architectural wonders. For a truly romantic St. Augustine experience, hop off at the Bay View stop and take a horse-drawn carriage ride.

Picturesque views of the Castillo de San Marcos, the peaceful sounds of the harbor and the balmy breezes will set the mood for memories that you’ll always hold in your hearts.

Indulge in Chocolate and Wine-filled Experiences

Next to the two of you, nothing goes better together than wine and chocolate. And you can sample both in romantic St. Augustine. For a delicious experience, take a chocolate tour at the Whetstone Chocolate Factory. You’ll learn all about the history of chocolate, how they make it and the differences between white, dark and milk chocolate varieties. You’ll also get to indulge in some of their creations. For a special treat, get two straws and share a frozen hot chocolate together.

Then, head just next door to the San Sebastian Winery for a taste of some of the finest American wines and the most unique ones made from hybrid and muscadine grapes. Take a tour and then stop in at the Cellar Upstairs Wine and Jazz Bar above the winery. Snuggle your honey as you sip a glass of wine, listen to live Jazz and Blues and take in wonderful views of the city.

Celebrate Eternal Love at the Fountain of Youth

What better way to celebrate your love for each other than a visit to the original site where Ponce de Leon sought the secret to eternal youth, the Fountain of Youth. Inside the coquina building, among the beautiful natural scenery, you’ll see the original spring of eternal hope that has flowed for centuries. The centerpiece of Ponce de Leon’s archaeological park, the Spring House holds majesty that has captured the attention of visitors since 1868. Share a drink of the water together and create a romantic St. Augustine memory that will stand the test of time.

Witness Breathtaking Views Atop the St. Augustine Lighthouse

One of the most romantic things to do in St. Augustine, the Sunset/Moonrise Tour of the historic St. Augustine Lighthouse will take your breath away. After climbing the 219 steps together, hold hands as the sun makes a fiery display across the sky over the shimmering water. Then, enjoy a champagne toast and steal a kiss as the moon begins to rise above you.

Take a Stroll Along the Beach

St. Augustine is known for its gorgeous beaches and nothing says romance like a stroll hand-in-hand along a sandy shore. There are several great beaches that are just perfect for a quiet walk, including Vilano Beach which is often less crowded. Stop and relax for a moment at the Vilano Pier, where the two of you can take in the pretty skyline of downtown St. Augustine and each other.