Whether you’re a couple visiting the ancient city of St. Augustine, FL for the first time or planning a romantic date night as locals, our refined travel guide reveals the city’s charm, soul, and more authentic side—for couples seeking fun beyond the typical tourist path.
If you’re only in St. Augustine for one day, we’ve also included a bespoke curated itinerary to help you experience the spirit of St.Augustine during your brief visit.
Seal your love with a lock at Vilano Beach. We love to step away from the crowds and a love lock on Vilano Bridge is a quiet tradition for locals like us and tourists to slip away from the tourist path, elevated by panoramic views of Matanzas River and a stunning serene coastal horizon. Drive along the coast to find the pedestrian walkway over A1A in North Vilano Beach that is nicknamed the Love Bridge. And to top this romantic date off, it is perfect to stroll and swim at the beach, followed by and walking down to the Hyatt rooftop bar for a beverage with amazing ocean views.
Share sunset views and love letters at Freedom Park. One of our favorite places to watch the sunset is along the peaceful paved path at Freedom Park, where wide-open marsh views and glowing sunsets set the stage for an intimate moment. At sunset, we settle onto a bench and browse the whimsical love letter mailbox, filled with heartfelt notes from others who’ve passed through. It is quite a touching experience! You can use the provided pen and paper in the mailbox to write your own love letter—a poetic keepsake of your time together in St. Augustine.
Master the art of travel photography with your iphone. We loved learning how to capture striking, professional-quality photos—using just our phones, with Patricia at St. Augustine Photo Tours. Patricia is a local photography expert and her intimate, hands-on tour is designed especially for couples. It’s the perfect blend of creativity, history, and romance, with each frame telling the story of your journey together.
Canoe the inlets of Anastasia State Park. In the quiet of nature it is a truly unique time together. The sparking shallow waters of the Salt Run inlet—is truly romantic and rejuvenating, and a great place to experience a postcard-worthy view of the St. Augustine Lighthouse. And our must-do is to cap it off with a sun-soaked hour on the beach.
Step into our hidden world of Magic Hideaway. On Saturday nights, the historic Casa Monica Resort & Spa becomes home to one of St. Augustine’s most exclusive luxurious secrets—Magic Hideaway, an intimate speakeasy-style performance by world-renowned magician Bill Abbott. Tucked inside a private room, this immersive show combines close-up magic, mind reading, and elegant showmanship for a truly unforgettable evening. Sophisticated, surprising, and utterly enchanting—you’ll leave believing in magic. Our vision is to share a truly unique and personal experience with each and every guest.
Rent a moke or slingshot from Seaside Adventures (we do this every time we have guests visiting us!) or a vintage scooter from Saint City Scooters and explore the city’s magnificent historic streets with a sense of old-world flair. My family and friends always share this was one of their highlights. Time your ride with First Friday Art Walk for a cultural infusion of galleries, wine, and live music. You will see art and hear music that are very special and memorable – that’s what keeps us coming back every month.
Indulge in a Trio of Tranquility: Eastern Wellness Meets Luxury Spa
Begin with a traditional Chinese herbal foot and reflexology massage on Hypolita Street (a very strong massage that will loosen you up), then transition into a Himalayan salt cave for a detoxifying 60-minute escape at Salt Spa. I wish I could live there! Finish your rejuvenation journey with an aromatic massage at Poseidon Spa (very fancy and amazing service, making you feel like kings queens). Splurge on all three for the ultimate couple’s wellness experience, you deserve it!
Spend a half hour in cozy bliss petting exotic and cuddly creatures, and meet Latte and Mocha the resident Capybaras at this hidden gem. This is a very unique and memorable half hour. If you are a cat lover, be sure to visit Witty Wiskers (my personal favorite for it’s intimate venue) and Frisky Cat Cafes. Perfect for animal-loving couples – reservations highly recommended.
We absolutely loved our time with St. Augustine Sailing for an exclusive sunset cruise. It you are celebrating something special or life itself, we highly recommend you opt for a package that includes champagne and artisanal charcuterie as you enjoy breathtaking views of the city skyline and playful dolphins at dusk.
Wander off the beaten path, hand-in-hand, through uptown along San Marco Street’s elegant collection of vintage, antique, and designer shops. Highlights include: Cool and Collected: Mid-century modern treasures ( we have found many gifts here), Coastal Traders: Globally-sourced imports with character (we come here for our unique housewares and gifts for our friends). 360 Boutique: Sophisticated fashion with a European sensibility (fantastic designs from Italy and France and stunning delicate jewellery), and one of a kind finds at Snakebird Vintage. Stop for a bite to eat and drink at Hawaiin food truck call Hot Box, and Spinster Abbott’s
Only have a day in St. Augustine? You can still soak in the city’s rich history and romantic charm with our personally curated itinerary.
For the ultimate experience, stay at the iconic Casa Monica Resort & Spa—a luxurious landmark perfectly situated in the heart of the historic district.
We’re Bill and Rebecca Abbott, and we’re excited to share our personal favorite St. Augustine discoveries – from unforgettable dining and entertainment to the hidden gems that make this city magical.
