Out on the Town: Date Night in St. Augustine
There’s something undeniably romantic about St. Augustine. Maybe it’s the cobblestone streets and centuries-old architecture, or the glow of lantern-lit alleyways after sunset. Or it could be the ocean breeze drifting through the historic district as you walk hand in hand, weaving through art galleries and courtyards that feel frozen in time.
No matter what romance means to you, St. Augustine sets the stage for the perfect date night. Whether you’re planning an anniversary getaway, a special vacation with your partner, or just a night out while you're visiting, this stunning coastal city is full of romance.
From rooftop cocktails to moonlight sails, St. Augustine offers creative ways to connect. Below, we’ve rounded up the best date night ideas to help you enjoy your perfect evening.
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Classically Romantic Date Night Ideas
Horse-Drawn Carriage Ride Through the Historic District
There’s nothing quite like seeing the city from a horse-drawn carriage. Cozy up under a blanket and clip-clop your way past the Plaza de la Constitución, along Aviles Street, and across the iconic Bridge of Lions. If you’re looking for a date night straight out of a love story, this is it.
St. Augustine Lighthouse & Maritime Museum
Maybe it’s all those Nicholas Sparks novels about people falling in love in a quiet coastal town, but there’s just something about lighthouses that feels romantic. Head to the St. Augustine Lighthouse and Maritime Museum and climb the winding stairs to the lookout deck. From there, enjoy sweeping views of the Atlantic, the Matanzas Inlet, Anastasia Island, and the St. Augustine bayfront. After you’ve taken epic pictures from the top, spend some time exploring the museum and grounds.
- Address: 100 Red Cox Dr, St. Augustine, FL
- Hours: Daily, 9 AM – 6 PM
- Admission: $17.95 per adult
San Sebastian Winery + Rooftop Music
Housed in one of Henry Flagler’s historic railway buildings, San Sebastian Winery offers a romantic blend of history, wine, and rooftop dining. Start with a free self-guided tour and tasting, then head up to The Cellar Upstairs—a third-floor venue with live music most weekends, plus a bar menu on the patio from 3–9 PM featuring sliders, cheese plates, and more.
For a full evening out, enjoy lunch or dinner indoors, or elevate the experience with the five-course chef’s pairing menu, created by Chef Norberto Jaramillo and Chef Sebastian Sikora. It’s one of the most elegant date night options in the city.
- Address: 157 King St, St. Augustine, FL
- Tasting Hours: Mon–Sat 10 AM–6 PM, Sun 11 AM–6 PM (last tasting at 5 PM)
- Dining: Lunch 11–3, Dinner 5–9 (Tue–Sun)
- @la_cocina_at_the_cellar on Instagram
Sunset Picnic on the Beach
Want something low-key? Pick up snacks and wine, grab a blanket, and head to one of the best beaches in St. Augustine for an incredible sunset picnic on the sand. Watching the sky turn vibrant shades of pink and orange as the sun dips below the horizon is an incredibly romantic way to spend an evening. Take some time to enjoy each other's company, stroll along the shore, and let yourself be fully in the moment - no phones, no distractions, just you and your special someone.
Unique Date Night Ideas in St. Augustine
Ghost Tours in the Historic District
We don’t save ghost tours just for Halloween here in St. Augustine. In a city so alive with history and lore, taking time to learn about its storied past is a must if you’re looking for a memorable and unique date night. Several companies offer nightly walking tours through the historic district, sharing stories of long-lost lovers and haunted inns.
Schooner Freedom Full Moon Sail
Plan a night to remember when you book a moonlight sail aboard the Schooner Freedom, one of the most unforgettable date night experiences in town. It’s BYOB, lasts about 1.5 hours, and includes soft live music and quiet conversation under the stars.
- Rates: $55 per person
- Sails: subject to Bridge schedule
- Dates: March 13-May 31: 8:45 PM | June 1 – August 14: 9:15 PM | August 15 – November 2: 8:15 PM
13 Keys Scavenger & Mystery Hunts
Want something interactive and fun? The 13 Keys Scavenger and Mystery offers customizable experiences where you solve clues across the city. Choose from historical themes, haunted hunts, or even romantic quests. It’s a playful way to explore hidden parts of town and learn something new about each other along the way!
Cheers to Forever at the Fountain of Youth
Tucked beneath ancient oaks and winding paths along Magnolia Avenue lies a spring once believed to grant eternal youth. According to legend, the Fountain of Youth can turn back time—or even stop it altogether. So, if you’re walking hand in hand with someone you’d never want to grow old without, this might just be the most fitting stop in St. Augustine.
Take a sip together and indulge the thought of a world where forever really exists. Who knows? Maybe it does, and it starts right here.
- Address: 11 Magnolia Ave St. Augustine, FL 32084
- Hours: Daily 9 AM to 6 PM
- Price: $22.95 per adult
Best Date Night Spots in St. Augustine for History and Art Lovers
Lightner Museum
Inside the former Alcazar Hotel, the Lightner Museum houses collections of 19th-century art, antiques, and curiosities. It's quiet, atmospheric, and perfect for wandering hand in hand.
- Address: 75 King St, St. Augustine, FL
- Hours: Daily 9 AM–5 PM
- Admission: $19 per adult
Self-Guided Stroll Through the Historic District
You can’t visit the Nation’s Oldest City without exploring the charming lanes of the Historic District. Wander famed areas like Charlotte Street, St. George Street, and Aviles Street, stopping in at the various art galleries and quiet cafés. Don’t miss Magnolia Avenue and Bridge Street—both great for photo ops, thanks to shaded courtyards and romantic backdrops.
With history and charm around every corner, this date night idea invites you to embrace the fun of discovering something new with the one you love. Maybe you’ll find a perfect keepsake, enjoy the best meal of your trip, or just lean into a night of new experiences with your favorite person.
Castillo de San Marcos
Walk the grounds of the oldest masonry fort in the U.S., take in views of the bayfront, and watch the changing of the guard if you visit at the right time. While this may not seem like the most romantic site, it’s a truly remarkable landmark to behold. And if you’re with someone who loves history and learning, it’s like visiting a living museum full of ancient tales. Take a picnic and enjoy the views, or visit at golden hour and get fantastic photos.
- Address: 1 S Castillo Dr, St. Augustine, FL
- Hours: Daily 9 AM–5 PM
- Admission: $15 per adult
The Ice Plant + St. Augustine Distillery
Located in a historic ice plant from the early 1900s, this spot serves up handcrafted cocktails, a moody ambiance, and one of the best bar menus in town. Stop by the St. Augustine Distillery for a free tour and tasting before heading upstairs for dinner or drinks.
- Address: 110 Riberia St, St. Augustine, FL
- Hours:
- Mon - Thu: 11:30 AM - 12:00 AM
- Fri: 11:30 AM - 2:00 AM
- Sat: 10:00 AM - 2:00 AM
- Sun: 10:00 AM - 12:00 AM
Date Night Restaurants in St. Augustine
Sometimes the perfect date night doesn’t need an itinerary, just a table for two, soft lighting, and a meal you’ll remember long after your vacation ends. St. Augustine has no shortage of romantic dining options where you can settle in, slow down, and enjoy both the food and the company. Whether you prefer a rooftop view, candlelit lighting, or an ocean breeze, these restaurants are favorites for couples looking to keep it classic.
- River & Fort Rooftop Lounge – Southern-inspired fine dining with views of the bayfront and Castillo de San Marcos.
- Forgotten Tonic – Intimate and stylish, offering elevated American comfort food and craft cocktails.
- The Floridian – Seasonal Southern cuisine with a fresh, local twist in a casual yet charming setting.
- Raintree Restaurant – Upscale Continental fare in a restored Victorian home, known for romantic ambiance.
- The Reef Restaurant – Oceanfront dining on Vilano Beach with a seafood-forward menu and quiet beachside views. Perfect if you want something away from the crowds of downtown.
Keep the Food Theme Going with a Guided Experience
Corks & Forks Tour
This guided food and wine tour takes you to some of the best restaurants and hidden gems in town. Perfect if you want to sample a little of everything without having to make all the decisions yourself.
Whetstone Chocolates Tasting Tour
Because what’s more romantic than chocolate? Book a behind-the-scenes tour and tasting at this beloved St. Augustine chocolatier.
Picture-Perfect Romantic Spots in St. Augustine
If you’re planning to pop the question, celebrate an anniversary, or surprise your partner with a moment they’ll remember forever, these spots feel made for milestone moments.
Bridge of Lions at Sunset:
Watch the sailboats pass beneath the bridge, stay for golden hour, or plan a proposal during the Fourth of July fireworks over the water.
The Plaza de la Constitución:
Visit in winter during Night of Lights for one of the most magical date night backdrops in Florida.
St. Augustine Lighthouse Grounds:
Even if you don’t climb it, the surrounding park and view make a beautiful spot for photos and memorable moments.
St. Augustine Beach:
There’s no wrong time to visit the beach, but early morning and twilight walks are especially romantic. Book a secret photographer who can capture all the magic.
Plan Your Perfect Date Night in St. Augustine
Featured Property: Barefoot Trace 410
Whether your love story is just beginning or you’re celebrating decades together, St. Augustine offers unforgettable ways to reconnect, explore, and enjoy each other’s company. And when the night winds down, there’s nothing better than heading back to a cozy rental just steps from it all.
At Coastal Realty Vacation Rentals, we’ve welcomed couples for years to our award-winning properties. Choose from Oceanfront, Oceanside, or our Premier/Luxury vacation rentals, and enjoy the best prices on your selection. We can’t wait to welcome you on your romantic St. Augustine getaway.
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