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Top 10 St. Augustine Date Night Ideas

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Fun and Unexpected Date Nights in the Nation’s Oldest City

While we’d never pass up a romantic stroll down the beach, there is so much more to explore in St. Augustine and St. Johns County than just the miles of sun-kissed sand stretching the length of Florida’s Historic Coast. From award-winning craft cocktails and dining to world-class bespoke experiences and surprising natural wonders, there is no shortage of amorous activities in St. Augustine. In fact, we might have to rename the Oldest City in America the Most Romantic City in America. 

Follow along as we run through some of our favorite hotspots and hidden gems that will have you falling head over heels.

Love Trees of St. Augustine

St. Augustine is home to an awe-inspiring floral phenomenon. Dubbed “Love Trees”, this rare marvel occurs when two trees grow in, through, or around one another. It is said that any couple who shares a kiss under one of these trees will share an everlasting love. So, be careful if it’s your first date!

The love trees are possible due to the temperate climate of St. Augustine, where the average temperature is a pleasant 70.2º. There are at least seven love trees spread around the walkable historic downtown.

Get Moving with Live Music 

This small town just south of 15,000 residents punches far above its weight when it comes to the live music scene. A lively community of local musicians can be found everywhere from breweries in Lincolnville to busking on cobbled streets. 

For a perfect date night, head to The Amp on Anastasia Island. This incredible venue hosts legacy acts like The Beach Boys and Ringo Starr, contemporary artists like Kacey Musgraves and The Killers, and guitar heroes like Jack White and Billy Strings (who has stopped by for multiple three-night residencies). You never know who might show up on their calendar next.

No show in town? Don’t miss local live music venues that have excellent entertainment. Notable local favorites include Prohibition Kitchen, Planet Sarbez, Casa de Vino 57, Bin 39, The Beacon, Stogies Jazz Club, Beaches, and Mill Top Tavern. 

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Delicious Drinks

If you’re looking for a sip of Love Potion No. 9, it’s hard to go wrong in St. Augustine. Dozens of different watering holes will beckon you and your date in with extensive wine lists and highly trained mixologists.

For those trying to get their tiki on, there’s no better spot than Boat Drinks on St. George Street. Just a few steps away is River & Fort and the view from their unbelievable rooftop patio—time your arrival here for a sunset sip. If a one-of-a-kind cocktail experience is what you’re after, cross the Bridge of Lions and saddle up at Odd Birds Kitchen and Cocktail Lounge. Finally, if you want some privacy, visit The Well on the grounds of The Collector Luxury Inn and Gardens.

Gourmet Dining Around Every Corner

If we were to list out every restaurant we loved in St. Augustine, this blog would be approximately 10,000 words long. So, until we publish our Michelin Guide-style version of Moby-Dick, here are three restaurants that will serve as the perfect backdrop for your next date night. 

Sainte-George is an under the radar restaurant in the thick of the historic downtown; take in a candlelight dinner inside or a romantic meal for two on their balcony. Also downtown, you’ll find Michael’s Tasting Room, with a menu that changes seasonally housed in a beautiful building originally built in 1764. Last, but certainly not least, is Llama Restaurant. Reservations at this small, Peruvian restaurant are difficult to come by, but so worth the effort.

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Set Sail with St. Augustine Sailing

If you’re looking to woo the mode adventurous type, a private sail aboard one of St. Augustine Sailing’s pristine yachts may be just the ticket. This family-owned business knows everything there is to know about the waters around St. Augustine and are more than willing to share their secrets with you. 

Various experiences include private sunset sails and sailing lessons for all skill levels.

Ghost City Tours

Hold your date a little tighter, there’s a chill in the air. As the Oldest City in America, it is no surprise that St. Augustine has no shortage of spooks and specters. Skip the scary movie and let the talented guides of Ghost City Tours and Ghosts and Gravestones show you and your date around the hidden side of St. Augustine.

You know what they say…’til death do us part.

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WhichCraft Candle Parlor

For a truly unique experience, plan your next date night with a stop at WhichCraft Candle Parlor. Select your fragrances and make a one-of-a-kind candle in one of the most unique settings in northeast Florida. 

WhichCraft offers public and private sessions, witch is perfect for the next time you double date in the Ancient City.

Play a Round of Putt-Putt

Florida is the golf capital of the world, and St. Augustine just might be the mini-golf capital of the world. With multiple courses to choose from, mini golf is a classic date night for the young and the young at heart.

Tee it up at Ripley’s Bayfront Mini Golf—Florida’s oldest mini golf course! Or, if you find yourself closer to the beach, explore the pirate ships and fun obstacles of Anastasia Miniature Golf and Fiesta Falls Miniature Golf.

An Educational Date Night in St. Augustine

This might come as a shock, but Florida’s Historic Coast is chock full of history! Explore the past and present of St. Augustine with your date at local museums like the Governor’s House Cultural Center and the Oldest House Museum Complex.

Impress your date with gilded age splendor at the Lightner Museum. This eclectic collection features highlights from estate of collector Otto C. Lightner, all housed in the opulence of Henry Flagler’s former Alcazar Hotel.

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Sweet Treats for Sweethearts

If it’s dessert you’re looking for, you won’t have to look too hard in St. Augustine. You can satisfy the sweet tooth of you and your sweetheart at a number of cafés where “dessert before dinner” isn’t just a joke, it’s a way of life. 

You’ll find frozen treats at Mayday Ice Cream and The Hyppo. Pop into Choco-lattes if you’re hunting for a baked good or you want to extend the night over a fresh cup of coffee. Wine, cheese, frozen custard, bon-bons, and Amish-made icecream? Look no-further than Bovine. Or, if French-inspired chocolate is what you’re after, hit up Claude’s Chocolates. 

Welcome Home to St. Augustine

Whether you’ve just started thinking about life in St. Augustine, or if you’ve lived in the Ancient City your entire life, we want to make your time here unforgettable. The Newcomer Group cannot wait to share our passion with you. Feel free to check out our up to date real estate listings or give us a call at (904) 599-5633 for more information about living in St. Augustine.

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