In this new era of masks and social distancing, meeting the “right” person can be harder than ever. So spending quality time together on a first date is more important than ever. Here are a few places in this ancient and spectacular city of St. Augustine that you can explore together — as you explore each other’s personalities and compare tastebuds!

1.Lightner Museum: Want a place that feeds the mind, body, and (romantic) soul? Check out what’s on offer at the former Alcazar Hotel, built in 1888 by Henry Flagler. Originally named “St. Augustine’s Lightner Museum of Hobbies,” the Lightner Museum opened in 1948 to display the collections of artwork, antiques, and curios of Chicago publisher Otto C. Lightner. Today, the museum has plenty of collections worthy of a walk-through, including the former Russian and Turkish baths. After spending some time meandering the museum halls, digesting the art and objects, you and your date can head on down to what was formally the largest indoor pool in the world for a scrumptious lunch at the Café Alcazar. Don’t worry: the pool is drained so no soggy sandwiches here!

2. Ice Plant Bar and St. Augustine Distillery: A few drinks can loosen your mood. But finding out where they come from and how they are made can sharpen your mind. Located in a stunningly restored ice plant from the turn of the century, the distillery offers a free tour that includes a video and then a walk-through to see how the facility makes tasty handcrafted, locally-sourced, award-winning rum, bourbon whiskey, gin, and vodka. After a taste-testing, you can head over to the Ice Plant Bar and Restaurant – located in the same building – to really indulge. The waiters, who are decked out in 1920s flair, can suggest even more inventive beverage concoctions with heirloom sugar cane to accompany the tasty farm-to-table dishes. This is surely one way to break the ice on a date!

  3. San Sebastian Winery: Taking a complimentary wine tour at the San Sebastian Winery is an ideal way to spend time getting to know each other. You’ll be able to talk plenty as you walk through the 18,000-square-foot wine production facility, which features everything from fermentation to bottling. When you come to the end, you can enjoy some wine tasting before heading up to Cellar Upstairs Bar and Restaurant, offering outdoor dining. It not only has delicious local wine and beer, as well as a great menu, but also features some of the best live music and sunset views in the city.

  4. St. Augustine Lighthouse & Maritime Museum: One way to get the heart racing even faster is to walk up the 219 steps that lead to the top of the Lighthouse together. At the top, you can enjoy spectacular views of the city and ocean. If you go during one of the Lighthouse’s events, you can even enjoy complimentary champagne, hors d’oeuvres, and dreamy moonlights. When you head back down to get grounded, you can pop over to the World War II-themed eatery, the Tin Pickle, for a delightful picnic style lunch. The winding staircase shouldn’t knock the wind out of you – but maybe your date will!

5. Ghost Tour: Get your pulses racing with the  Augustine Ghost Tour. A master storyteller will enthrall you with spooky tales about the incredible history of the Nation’s Oldest City. This may be a perfect opportunity to grab hands and share some jitters! Afterwards, there will be plenty of restaurants to choose from that offer soothing, yummy foods. You may also want to hit Scarlett O’Hara’s which houses its very own “ghost bar.” To find out the story, ask any of the bartenders or waitstaff while navigating the rich deliciousness the menu offers.


Here’s to a date you won’t forget anytime soon!