Here comes the fun part! We’ve crafted a selection of expertly curated, local-approved itineraries to help you experience an unforgettable day in St. Augustine, FL—tailored just for you and your partner. Ready to discover your perfect romantic adventure?
Love exploring nooks and crannies alive with centuries of history and the colorful personalities who once called them home? Do guided tours and uncovering fascinating—or even unsettling—tales and mysteries ignite your curiosity? Welcome to St. Augustine, a city rich with history, charm, intrigue, and ghost stories around every corner.
Begin your day with a leisurely stroll through St. Augustine’s historic downtown district, taking in iconic landmarks and immersing yourself in the city’s captivating past. In the afternoon, visit the Lightner Museum to admire exquisite art and learn more about the city’s heritage. Then, take a guided tour of Flagler College to marvel at its stunning Tiffany windows. For a unique experience, join a historic photo lesson with Patricia and learn how to capture exceptional images of St. Augustine’s architectural beauty using your phone.
For dinner, indulge in a full-course meal at Casa Monica’s Cordova Coastal Chophouse & Bar, where luxury and fine dining come together in an elegant setting. Conclude your evening with the mesmerizing Magic Hideaway show at the Casa Monica Resort & Spa, where master magician Bill Abbott will leave you utterly spellbound.
Local Tip: To avoid the crowds, plan your visit outside the busy Nights of Lights season from November through January, when St. Augustine attracts throngs of visitors eager to see the city illuminated.
Life truly feels like a beach in St. Augustine, Florida! If you’re a laid-back salt life enthusiast, this charming coastal town is the perfect retreat.
Begin your day with a serene morning stroll along St. Augustine Beach, collecting seashells and shark teeth while savoring the fresh ocean breeze. Bonus: Witness the breathtaking sunrise as it glows over the water—a rare and magical coastal experience.
For lunch, enjoy a light, flavorful meal followed by a leisurely hammock nap at Stir It Up, Beachcomber, or Sunset Grille, beloved local spots and favorites among beach lovers.
Time your visit with the tide and rent a bike from Island Life Bikes for a scenic ride at the end of St. Augustine State Park—keep an eye out for a family of sea turtles making their way along the shore.
In the afternoon, embark on a scenic boat tour with St. Augustine Sailing or Sabrage, offering stunning views of the city skyline from the water. Bonus: Don’t miss the impressive cannon firing demonstrations at the historic Castillo de San Marcos, held throughout the morning and afternoon.
As evening falls, indulge in an elegant dinner at the renowned Casa Monica’s Cordova Coastal Chophouse & Bar, where exquisite cuisine and a refined atmosphere await.
Complete your day with the enchanting Magic Hideaway experience at Casa Monica Resort & Spa—just steps away—featuring world-famous magician Bill Abbott’s mind-blowing magic and intimate mind-reading performances. A truly unforgettable finale to your beach side escape.
Local Tip: St. Augustine offers two premier beach destinations—Anastasia Island and Vilano Beach. Anastasia Island boasts a spacious pier perfect for a leisurely stroll over the water, while Vilano Beach, where the Matanzas Inlet meets the ocean, offers the unique opportunity to spot dolphins swimming just off its rugged rocky point.
What could be better than a light buzz paired with a plate of exquisite cuisine? Food enthusiasts visiting St. Augustine are treated to an impressive array of food and wine tours, alongside a diverse culinary scene that caters to every palate.
Begin your day with a visit to the San Sebastian Winery or the St. Augustine Distillery, where complimentary tours and tastings offer a refined introduction to local flavors. Bonus: Both are conveniently located next to the renowned Whetstone Chocolates, a celebrated chocolatier known for its handcrafted confections.
For a more immersive experience, join one of the expertly guided Tasting Tours—available by foot or shuttle—that showcase the very best of St. Augustine’s culinary delights.
When evening falls, reserve a table at Casa Monica’s Cordova Coastal Chophouse & Bar, famed for its elegant fusion of coastal and chophouse fare served in a romantic setting.
Complete your night with the intimate and spellbinding Magic Hideaway show at Casa Monica Resort & Spa, where romance, mystery, and world-class magic combine for an unforgettable finale.
Local Tip: Plan ahead for parking—while many venues offer on-site parking, the conveniently located two-story garage just across from the city gates provides easy access to downtown.
If you delight in bringing home unique souvenirs or timeless collectibles from your travels, St. Augustine offers a treasure trove of boutiques, galleries, and antique shops to explore.
Begin your morning wandering the charming streets—browse the exquisite art galleries along King Street, discover one-of-a-kind finds on St. George Street, and hunt for antiques in Uptown St. Augustine. Don’t miss the boutique shops on West King Street, where carefully curated selections await discerning shoppers.
For a true taste of local creativity, visit the St. Augustine Art Association to admire authentic, locally crafted artwork. Car enthusiasts will appreciate the nearby St. Augustine Classic Car Museum, showcasing the finest classic and vintage automobiles.
As evening approaches, indulge in a romantic dinner at Casa Monica’s Cordova Coastal Chophouse & Bar, where the ambiance is enriched by stunning Spanish and Moroccan influences.
Complete your day with the captivating Magic Hideaway show, conveniently located within the Casa Monica Resort & Spa—a spellbinding blend of mystery, romance, and intrigue.
Local Tip: For a truly luxurious experience in the heart of downtown, stay at the iconic Casa Monica Resort—you’ll feel like royalty from the moment you arrive.
It’s no surprise that we want you to experience St. Augustine in an unexpectedly romantic and magical way as a couple. We hope to welcome you at one of the upcoming Magic Hideaway performances.
Due to the intimate nature of the show, advance reservations are highly recommended.
