Updated on January 18, 2018.


The sun rising over St. Augustine Beach.

St. Augustine is one of the most romantic places in Florida. In fact, it made the list of the Top 50 Romantic Destinations Around the World, by U.S. News & World Report. Therefore, when planning your next Valentine’s Day or romantic getaway, keep the Nation’s Oldest City in mind. Whether you’re in a relationship, celebrating years of marriage, or going on that very first date, St. Augustine has activities for all types of romance.

Watch the Sunrise on the Beach

Head to the beach. One factor contributing to St. Augustine’s title as one of the most romantic places in Florida is that the sun rises to the east – A.K.A. right over the historic coast. So, start your Valentine’s Day or romantic getaway off on the right foot. Is there a better way to spend a morning with your loved one than by watching the sunrise over one of our pristine beaches? Sure, you might have to wake up a little bit earlier than usual, but the view will be worth it.

Enjoy the Early-Morning Charm of Downtown

Cozy up on the bayfront at Casablanca Inn for brunch and listen to the quiet splashes of Matanzas River while you watch the sailboats sway back and forth. Take time out of your morning routine to slow down and enjoy conversation, coffee, and pastries at one of St. Augustine’s many coffee shops and breakfast restaurants. This way, you get to enjoy the city in the quiet of the morning before the hustle and bustle of the day.


A quiet morning on the bayfront.

Lounge in our Greens

Depending on the weather, St. Augustine has some fantastic picnic spots. Whether it be on the lush grass under the Great Cross,  lounging by the bayfront near the Castillo de San Marcos National Monument, in the middle of various historic monuments in the Plaza de la Constitucion, or on the court of what used to be the Alcazar Hotel. St. Augustine’s colonial architectural style and old-time feel create a naturally beautiful and romantic venue. Therefore, fancy dinners and expensive jewelry won’t make or break your celebration in one of the most romantic places in Florida: the Nation’s Oldest City.
A picnic is a great, affordable way to skip lines and enjoy a beautiful view all at once. If you don’t want to cook, you can pick up some delicious meals from food trucks and cafes around town. A few of our suggestions include Crave Food Truck, Uptown Scratch Kitchen, Flavors Eatery, and Stir It Up.

Wine and Dine

St. Augustine is full of award-winning restaurants and bars. St. Augustine has everything from lively pubs to intimate dinner spots to uniquely themed bars. No matter the style of dining you’re in search of, St. Augustine has it all. However, it is always best to call well in advance to double check a restaurant’s hours and see if they take reservations.

Experience St. Augustine

A tour is a great way to explore St. Augustine. There are several romantic tours to take with your partner that last year round. Saddle up for a romantic carriage ride through the city, a pub crawl for a laid-back, fun time, or an intimate scenic cruise on the water, St. Augustine has it all.

Romantic Date Ideas:

  • Tours by The Tasting Tours. The Tasting Tours host various tours throughout the year that are sure to spark flames in any partnership: Wine and Horse Carriage Rides, Wine and Food Tours, and many more.
  • Enjoy the moonrise, with champagne, during a Sunset Moonrise tour atop the Nation’s Oldest Port: St. Augustine Lighthouse and Maritime Museum.
  • Cruise the Matanzas River and beyond with Schooner Freedom Charters Sunset Sails.


  • Always call ahead to see how long the wait will be.
  • Prepare a backup plan in preparation for weather changes.
  • Go with the flow and have fun!

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Change is inevitable, so please verify hours, prices and important information before embarking on your Old City adventure.
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