Valentine’s Day falls on a Friday this year, making it the perfect opportunity to spend a romantic holiday in the nation’s oldest city. And the city of St Augustine is steeped in historic architecture, quaint cobblestones, eclectic shopping, and delicious dining— it’s the ideal date night destination. 

Here are a few ideas to bring the magic of St Augustine to your Valentine’s Day this year. 

The Raintree
With a roaring fireplace and a koi pond, the Raintree is an uptown, old school restaurant tucked inside an ornate Victorian home. Offering an intoxicating blend of Mediterranean, Asian, and American cuisine, the Raintree is the ideal spot to bring your sweetheart for an unforgettable Valentine’s Day dinner. They even have a special V-Day menu, including mouth-watering items like Seafood Thermidor, Filet Mignon, and Lasagna Puttanesca. Top it off with a decadent Creme Brulee, Key Lime Pie, or Chocolate Mousse. Reservations are required. 

Odd Birds Bar
Pull up a plush bar stool at the Odd Birds Bar, an eclectic and refreshing spot with a constantly changing and innovative craft cocktail menu. Odd Birds prides itself on inviting guest bartenders who enjoy experimenting with new flavors and taste combinations. Come to Odd Birds with a spirit of adventure and an open mind— and try something new this Valentine’s Day with someone you love. Who knows— it may just become “your” drink!

Horse Drawn Carriage Ride
Score some major romance points by booking a horse-drawn carriage ride through the cobblestoned streets of historic downtown St. Augustine. You’ll feel like you’ve stepped back in time at the sound of the clip-clop of horses hooves. The knowledgeable guides will bring the city’s history to life with fun and interesting St. Augustine stories. 

Go For a Sail
Book an enchanting, private cruise aboard a gorgeous, fully-equipped sailboat. Hop aboard a vessel at St Augustine Sailing— then sit back, relax, and enjoy a beautiful daytime sail or a romantic sunset voyage. It’s the perfect way to St. Augustine from a new angle, and to enjoy the relaxation of being on the water together. 

No matter what time of year, it’s always the right time to visit St Augustine. But there’s no doubt that the city comes alive with opportunities for romance during Valentine’s Day. Consider spending the holiday in this enchanting city— it may quickly become your annual tradition.