7 day itinerary for Saint Augustine Florida

Itinerary

Day 1: Arrival and Historic Stroll

Welcome to Saint Augustine! Start your trip by checking into your accommodation and freshening up. In the afternoon, take a leisurely stroll through the historic district. Immerse yourself in the city's rich history as you explore landmarks like the Castillo de San Marcos, the oldest masonry fort in the continental United States. Don't forget to visit the Lightner Museum, housed in the former Alcazar Hotel, which showcases an impressive collection of art and artifacts.

For dinner, head to a romantic restaurant like Collage or The Floridian. Enjoy a delicious meal while savoring the charming ambiance of the city.

Day 2: Wine Tasting and Sunset Cruise

Indulge in a day of wine tasting at the local wineries in the St. Augustine area. Start your day at San Sebastian Winery, where you can take a tour, learn about the winemaking process, and sample their award-winning wines. Afterward, visit the nearby St. Augustine Distillery for a tasting of their handcrafted spirits.

In the evening, embark on a romantic sunset cruise along the Matanzas Bay. Enjoy breathtaking views of the city's skyline as you sip on a glass of wine and watch the sun dip below the horizon.

Day 3: Nature and Beach Day

Escape the city and immerse yourself in nature at Anastasia State Park. Spend the day hiking through the park's trails, exploring the pristine beaches, or renting a kayak to paddle along the salt marshes. Pack a picnic lunch and enjoy a romantic meal surrounded by the beauty of nature.

In the evening, head back to the city and dine at a waterfront restaurant like Cap's on the Water. Indulge in fresh seafood while enjoying the serene views of the Intracoastal Waterway.

Day 4: Jazz and Nightlife

Get ready for a day filled with jazz music and vibrant nightlife. Start your evening by visiting the Jazz Club of St. Augustine, where you can enjoy live performances by talented local musicians. Sip on a cocktail and let the smooth melodies transport you to another era.

Afterward, explore the city's vibrant nightlife scene. Visit local bars like Prohibition Kitchen or The Ice Plant for craft cocktails and a lively atmosphere. Dance the night away or simply enjoy the vibrant energy of the city.

Day 5: History and Ghost Tour

Immerse yourself in the city's haunted history with a ghost tour. Explore the dark alleys and historic buildings as your guide shares chilling tales of the city's past. Choose from various tour options, such as the Ghosts & Gravestones Tour or the Ghostly Experience Walking Tour.

In the evening, dine at a haunted restaurant like The Columbia Restaurant, known for its delicious Spanish cuisine and ghostly encounters. Keep your eyes peeled for any paranormal activity while enjoying your meal.

Day 6: Romantic Carriage Ride and Fine Dining

Experience the charm of Saint Augustine with a romantic carriage ride through the historic district. Snuggle up with your loved one as you listen to the clip-clop of the horse's hooves and take in the sights and sounds of the city.

For dinner, indulge in a fine dining experience at a restaurant like Michael's Tasting Room or The Raintree. Enjoy a candlelit dinner featuring exquisite cuisine and impeccable service.

Day 7: Departure

On your last day, take some time to relax and reflect on your wonderful trip. Enjoy a leisurely breakfast at a local café before checking out of your accommodation. If time permits, visit the St. Augustine Lighthouse and Museum for panoramic views of the city and a glimpse into its maritime history.

As you bid farewell to Saint Augustine, take with you cherished memories of jazz music, fine wine, romantic moments, and the rich history that makes this city truly special. Safe travels!