FOR COUPLES
play, stay, eat
As local residents who make time for weekly date nights, we’ve come to know—and love—St. Augustine deeply. From timeless classics to hidden gems and exciting new spots, we’re constantly exploring what makes this city so special for couples.
Now, we’re sharing our personal favorites to help you craft a luxurious, romantic getaway filled with unforgettable moments, local charm, and a touch of magic.
personable, hidden gem, amazing memories
When we take time to play—whether at home in St. Augustine or while traveling—we’re drawn to experiences that are intimate, locally loved, and delightfully unexpected. The kind of places that feel like well-kept secrets, full of character and heart.
In a world that rarely slows down, these moments of connection and wonder are where we feel most present. For us, the best “play” is about savoring the experience and each other—creating memories that stay with us long after the night ends.
A Romantic, Luxury Magic Show—One of St. Augustine’s Best Date Night Experiences
Looking for one of the most romantic things to do in St. Augustine? Magic Hideaway is a luxurious, unforgettable experience designed with couples in mind. Whether you’re celebrating an anniversary, birthday, or planning a special St. Augustine date night, this intimate magic show offers something truly unique.
Hidden inside the historic Casa Monica Resort & Spa, the velvet-lined showroom sets the stage for world-class magician Bill Abbott, whose masterful sleight-of-hand and spontaneous wit leave guests amazed, laughing, and fully engaged. It’s interactive, up-close magic that happens right in the palm of your hand.
A local favorite for couples activities in St. Augustine, Magic Hideaway is an elevated evening of connection, wonder, and lasting memories.
Join us every Saturday night for one of the best date night ideas in St. Augustine.
wind in your hair, adventure, curiosity
One of our favorite local date ideas? Cruising the coast in a Moke from Sea Side Adventures. These open-air electric vehicles are effortlessly cool and incredibly fun to drive—perfect for a carefree day exploring St. Augustine together.
Whether you’re winding along the waterfront, heading to the beach, stopping at parks, or grabbing bites at your favorite local spots, the experience is a perfect blend of sun, music, and spontaneous adventure.
Top tip: It’s the kind of ride where holding hands just feels right.
glowing sand, calm water,
perfect sunset
When we have just a few hours—or even better, a full day—to unwind, we love escaping to Matanzas Beach on the Intracoastal Waterway’s west side.
A charming boardwalk guides you to soft, fine sand where tranquility awaits. We often wander to the right, seeking out a quiet nook nestled among driftwood trees. There, we set up our hammock, spread out a cozy blanket, and settle into our chairs with a good book and some soothing music.
The views are nothing short of spectacular, with sea turtles occasionally peeking through the water and dolphins playfully nearby. We spend the afternoon chatting, laughing, snacking, and soaking in the natural beauty—capping it all with a breathtaking sunset that leaves us in awe.
For couples craving a peaceful, romantic retreat where they can truly connect with nature—and with each other—Matanzas Beach is an unforgettable choice.
A Romantic Evening Under the Stars
Strolling hand-in-hand along cobblestone St. George Street in downtown St. Augustine is pure couple bliss—anytime, any season—with new sights and experiences waiting around every corner.
When live music fills the air at Colonial Oak Music Park, our evenings become truly magical. The majestic live oak tree adorned with softly glowing hanging lanterns creates a dreamlike ambiance perfect for romance.
The talented local musicians always deliver unforgettable performances, and we find ourselves dancing the night away beneath the stars. To top off the night, a sweet treat from Mayday Ice Cream makes the experience even sweeter.
For couples seeking a romantic night out with live music, dancing, and cozy charm, Colonial Oak Music Park is a must-visit St. Augustine destination.
hand in hand strolling, unique finds, sweet music
Every Saturday morning, we love visiting the Farmers Market at the St. Augustine Amphitheater—one of our most romantic and peaceful rituals as a couple in St. Augustine.
Strolling hand in hand beneath the canopy of live oak trees draped with Spanish moss, the market offers a picture-perfect setting to slow down and savor the moment together. The friendly vendors are passionate about sharing their unique, fresh goods, making each visit feel personal and special.
We pick up seasonal vegetables, locally raised meats, farm-fresh eggs, artisanal cheeses, fresh fish, and our favorite kombucha for the week ahead. Afterwards, we settle on the deck to enjoy charming live music while sipping our drinks—an ideal cozy spot to connect and enjoy a leisurely morning together.
For couples seeking a relaxed and authentic St. Augustine experience, the farmers market is a must-visit destination.
Sunset at Freedom Park: Watch the sky light up as you stroll hand-in-hand, then feed the gentle horses carrots and apples—an intimate and memorable moment.
Discover Local Charm: Wander through the unique shops and boutiques in West King Street, Uptown, and historic Downtown St. Augustine, perfect for leisurely exploration and finding one-of-a-kind treasures.
Beach Days: Spend sun-soaked hours at Vilano Beach and Anastasia State Park, ideal spots for couples to relax, swim, and enjoy the ocean breeze together.
Nature Walks: Explore the serene beauty of Washington Oaks Gardens State Park, with its stunning landscapes and romantic walking trails.
Live Music Scene: Experience the vibrant local music scene featuring incredible artists like Bad Dog Mama, Jolie, Sam Pacetti, and Romona and the Riot—perfect for an unforgettable date night.
First Friday Art Walk: Immerse yourselves in St. Augustine’s creative energy with the monthly Art Walk, showcasing local artists and galleries.
Film Nights: Enjoy unique cinematic experiences with the St. Augustine Film Society, a great way to unwind and enjoy thought-provoking films together.
St. Augustine Trolley Tour: Relax and explore the city aboard the charming trolley, guided by some of the best and most knowledgeable local guides—an easy and fun way to see the highlights.
luxurious venue, excellent location
and exceptional service
Each month, we take turns planning a romantic two-night getaway within a five-hour drive of St. Augustine. When choosing accommodations, we prioritize venues that offer not only comfort but also visual inspiration—places that feel both elegant and inviting.
Location matters deeply; we seek properties nestled in the heart of vibrant towns or cities, within easy walking distance of fine dining, live music, and local attractions that pique our curiosity.
Above all, exceptional service is essential. It’s what allows us to truly unwind, feel cared for, and enjoy every moment of our stay.
Pulling up to the iconic Casa Monica Resort and Spa in downtown St. Augustine, we were immediately captivated by the building’s rich history and opulent architectural details.
From the moment valet greeted us to the instant we stepped beneath stunning gold-leaf archways, surrounded by carefully curated art and elegant design, a sense of calm and inspiration washed over us. The staff’s warmth and professionalism made us feel genuinely cared for throughout our stay.
The resort offers everything a couple could desire for a romantic escape: a serene poolside retreat, exclusive access to the South Ponte Vedra Ocean Club, and effortless steps to downtown’s best dining, shopping, and entertainment.
Indulge in exquisite meals at the renowned Cordova Coastal Chophouse, unwind at the Poseidon Spa, or explore the resort’s extraordinary Grand Bohemian Art Gallery. Saturday evenings and Sunday brunch come alive with top-tier live music, and of course, the resort is home to St. Augustine’s most unforgettable couples’ experience—the intimate Magic Hideaway magic show.
Nestled on charming, cobblestone-lined Cordova Street in historic downtown St. Augustine, The Collector Inn is a true hidden gem—surrounded by sweeping palms and exquisite landscaping.
From the moment we stepped onto the grounds, we were transported into the lap of luxury. Our first stop was the serene Well Bar and Gardens, where the friendliest staff attended to our every need as we savored expertly crafted cocktails infused with fresh herbs from their own garden.
Every room is thoughtfully designed with elegance and comfort in mind, offering a romantic, adults-only retreat. Whether unwinding with a great book amidst the stunning gardens or simply enjoying each other’s company, the Collector Inn promises a stay that feels both intimate and utterly fulfilling.
You can’t miss The Local as you cruise along A1A—the retro pink and white façade always brings a smile. The playful, vintage-inspired rooms perfectly blend fun with comfort, while their seamless contactless digital check-in adds a modern touch.
Nestled in an unbeatable island location, The Local is close to some of our favorite local eateries and just a short bike ride from both Anastasia State Park and downtown St. Augustine. Couples will appreciate their charming pool, stylish bikes, and convenient partnership with Anastasia Fitness right nearby.
With so much to explore and a variety of uniquely themed rooms, you’ll want to return again and again—trying them all along the way.
Located in the heart of historic downtown St. Augustine, Carriage Way Inn invites couples to step back in time. Crossing through the charming cobblestone Carriage Way, we immediately felt embraced by the warm, carefully preserved historic décor.
The attentive general manager welcomed us with genuine hospitality, ensuring every detail of our stay was personal and memorable.
Perfect for couples seeking a romantic and intimate retreat, Carriage Inn combines timeless elegance with heartfelt service—making it a cherished choice for romantic stays in St. Augustine.
When the call of the beach is irresistible, Embassy Suites St. Augustine Beach answers with effortless style and comfort. From the moment valet welcomes you, the bright, inviting foyer—with lush plants and cozy seating—sets the tone for a truly romantic couples’ getaway.
With stunning ocean views visible upon entry, the resort offers an array of relaxing spots that invite playful exploration: from plush couches and fireside chairs to serene beach-side lounges. Their complimentary 5pm happy hour adds a delightful touch of fun to the day.
Choosing between the pool and oceanfront is a delightful dilemma—both are enchanting settings perfect for unwinding together. Cap off your evening with a romantic walk along the moonlit beach, a signature experience here.
Every detail of this luxurious resort, paired with attentive, impeccable service, makes Embassy Suites a top choice for couples seeking a memorable romantic beach getaway in St. Augustine.
exceptional flavor , unique and adventurous experience
and top notch service
When we can craft excellent meals and cocktails at home, dining out has to truly wow us. For a romantic evening, we seek cozy, intimate settings that invite connection. We delight in tasting fresh, exciting flavor combinations—culinary creations that surprise our palates and offer something we simply can’t or don’t make at home.
Above all, exceptional service transforms a meal into a mini escape—making us feel pampered and cared for, if only for a brief, cherished moment.
always a stunning experience
Having savored nearly every dish on their exceptional menu, we can confidently recommend the Saddleback Pork Chop—featuring sumac, fennel chutney, apple salad, and rich pork jus—as a standout. They also serve some of the finest steaks in St. Augustine.
The attentive staff and expertly crafted cocktails, especially the Espresso Martini, elevate every visit. The décor blends exquisite art with cozy, comfortable seating—perfect for an intimate date night.
For a truly memorable evening, reserve a table during live piano performances by their talented house pianist, Bo. Afterwards, complete your night with the unforgettable Magic Hideaway show, just steps away.
our weekly date night
After a busy day of work and sports, our favorite way to unwind is a stroll over to Blackfly Restaurant, where we settle into the cozy bar for a perfectly crafted dry gin martini with three olives and share a wood-fire pizza.
This hidden gem is so exceptional, we’re tempted to keep it our secret. A beloved local hot spot, Blackfly consistently delivers outstanding food, impeccable service, and a welcoming atmosphere.
The friendly team makes us feel instantly relaxed the moment we step through the door—ideal for couples seeking a laid-back yet memorable dining experience in St. Augustine.
delicate and great wine list
We’re passionate about great wine, and visiting La Nouvelle to let their expert sommelier thoughtfully pair our meals is always a special treat. Whether on intimate dates, celebrating with friends, or marking special occasions, this charming French-inspired restaurant never disappoints.
The Steak Au Poivre with Frites is a must-try, perfectly complemented by their curated wine selections. Though we rarely order dessert elsewhere, the delicate orange mousse nestled in a white chocolate crust is irresistible—we savor every exquisite bite.
Relax on the porch and let yourself be transported to the romance of France, creating a truly unforgettable romantic French dining experience in St. Augustine.
a stunning sunset experience
Few experiences rival the romance of watching a breathtaking sunset while enjoying a memorable dinner. Caps On The Water delivers that pure magic, and we’ve returned many times to savor it.
Located just a short drive from downtown St. Augustine in Vilano Beach, this waterfront gem offers exceptional food and attentive service. The peel-and-eat shrimp are a standout starter, while the Vanilla Grouper—served with horseradish, wasabi-crusted flash-fried mashed potatoes, fried spinach, and a delicate vanilla rum sauce—is a dreamy main course that perfectly caps off the evening.
For couples seeking a romantic dinner with stunning views, Caps On The Water is an unforgettable choice for sunset dining near St. Augustine.
intimate and exceptional flavors
For couples seeking a serene escape, Drunken Horse offers the perfect setting to unwind and truly enjoy each other’s company. Tucked away on Charlotte Street, this charming spot transports you to another world, especially when seated on the enchanting back patio surrounded by lush elephant ear plants.
Their tapas-style French plates are as visually stunning as they are delicious—each dish thoughtfully crafted to delight and surprise your palate. The professional, attentive service creates a calming atmosphere, allowing you to relax fully and savor intimate moments together.
An ideal choice for couples looking for a romantic, off-the-beaten-path dining experience in St. Augustine.
Eats:
Chez L’Amour — Home to the best jazz musicians in Northeast Florida, with mind-blowing décor and delicious, creative tapas and craft cocktails crafted by the talented Chef Ellie.
Boat Drinks — Known for the best smash burger, rum cocktails, and outstanding service. Their lively outdoor bar is a favorite spot, and don’t miss the soft-serve delight at Cookiebird just across the street.
Sarbez — Perfect for decadent grilled cheese, a laid-back patio vibe, and a Tempeh Reuben with jalapeño that wins every time.
Osprey Tacos & Old Coast Ales — A weekly date night favorite with live music, the best queso in town, and authentic street tacos.
Tasting Tours — Run by a passionate, knowledgeable team—try a tour during your week here for a unique culinary adventure.
Casa De Vino 57 — A cozy garden setting featuring excellent wines, charcuterie, and live music from local favorites like Sam Pacetti and Jolie.
Llama Restaurant — Quaint and intimate with expertly executed Peruvian dishes; their appetizers are a must.
Breakfast:
Buena Onda — A couple’s favorite with a Potato Frittata Sandwich and Rose Latte that brighten the day.
Roosevelt Room — Sit at the bar sipping mimosas and indulge in their eclectic menu—you’ll want to try everything.
Bar Citra — The perfect chill spot with inviting décor, where the “pretty toast” is simply unforgettable.
Drinks:
St. Augustine Distillery Tour — A fantastic date idea featuring expertly crafted bourbons and spirits.
Spinster Abbott’s — Bright and comfy, with a relaxed Florida vibe, great beers, and a vintage bodega to explore.
Tini Martini Bar — Romantic and fun, especially at night with twinkle lights and tiki torches, overlooking the harbor.
Sogno Restaurant — One of our favorite wine bars; ask the sommelier-owner Stacy Critell for a perfectly paired glass.
