New Chat
Download App
Ask me about your trip!
There are no messages for this conversation.
5-Day St. Augustine Adventure with Historic Tours and Culinary Delights Itinerary
Last updated: 2024 Jun 14Historic Landmarks and Waterfront Wonders
Morning
Begin your St. Augustine journey with a hearty breakfast at Catch 27, known for its fresh seafood and local ingredients. Afterward, immerse yourself in history with a visit to the iconic Castillo de San Marcos National Monument, the oldest masonry fort in the continental United States. Explore the fort and enjoy the stunning views of the Matanzas River.
Afternoon
For lunch, head to The Florida Cracker Cafe for a taste of traditional Florida cuisine. Spend your afternoon at the St. Augustine Lighthouse and Maritime Museum, where you can climb to the top for panoramic views and learn about the area's maritime history. Afterward, take a relaxing Boat Cruise and Electric Golf Cart Tour to enjoy the city from both land and water.
Evening
As the sun sets, dine at River & Fort Restaurant & Roof Top Lounge for a memorable meal with a view. Cap off the evening with the enchanting St Augustine Nights of Lights Trolley Tour, a perfect introduction to the city's holiday charm (seasonal activity).
Bedtime
Find amazing hotels in St. Augustine.
4.76Castillo de San Marcos National Monument
Book Now
4.76Castillo de San Marcos National Monument
Book Now
4.82St. Augustine Lighthouse and Maritime Museum
Book Now
4.82St. Augustine Lighthouse and Maritime Museum
Book Now
Pirate Tales and Museum Marvels
Morning
Start your day with breakfast at The Drunken Horse St. Augustine, a cozy spot with a unique menu. Then, embark on the St. Augustine Hop-on Hop-off Trolley Tour with Museum Entry to visit key attractions such as the Fountain of Youth and the Old Jail. Take your time to hop off at the spots that pique your interest.
Afternoon
Enjoy a leisurely lunch at The Conch House Restaurant, known for its Caribbean-inspired dishes and waterfront dining. Afterward, continue your museum exploration with a visit to the intriguing Potter's Wax Museum, where lifelike figures bring history to life.
Evening
For dinner, savor the Spanish flavors at Columbia Restaurant, a St. Augustine institution. Cap off the night with the adults-only St. Augustine The Black Raven Rum Runners Pirate Show (21+), an interactive and entertaining experience on the high seas.
Bedtime
Find amazing hotels in St. Augustine.
4.61St. Augustine Hop-on Hop-off Trolley Tour with Museum Entry
Book Now
4.61St. Augustine Hop-on Hop-off Trolley Tour with Museum Entry
Book Now
4.67Potter's Wax Museum
Book Now
4.67Potter's Wax Museum
Book Now
Wildlife Encounters and Haunted History
Morning
Fuel up for the day at Mill Top Tavern and Listening Room, a local favorite with a historic ambiance. Then, spend your morning with the gentle giants on the St. Augustine Dolphin and Manatee Paddle or Kayak Tour in the beautiful waters of the Matanzas Bay.
Afternoon
Enjoy a casual lunch at The Backyard at Meehan's, a laid-back spot with a great outdoor atmosphere. Afterward, delve into the city's spooky side with the St. Augustine Ghosts and Gravestones Old Town Trolley Tour. This tour takes you to the most haunted locations in the city and provides a chilling glimpse into St. Augustine's past.
Evening
Dine at Prohibition Kitchen, where the vintage decor sets the stage for a memorable meal. After dinner, continue the ghostly theme with the St. Augustine Haunted Pub Crawl, which combines spirits of the otherworldly kind with the spirits you drink.
Bedtime
Find amazing hotels in St. Augustine.
4.27St. Augustine Dolphin and Manatee Paddle or Kayak Tour
Book Now
4.27St. Augustine Dolphin and Manatee Paddle or Kayak Tour
Book Now
4.24St. Augustine Ghosts and Gravestones Old Town Trolley Tour
Book Now
4.24St. Augustine Ghosts and Gravestones Old Town Trolley Tour
Book Now
Culinary Delights and New Year's Eve Festivities
Morning
Start your New Year's Eve with a delightful breakfast at Sangrias Wine and Tapas Bar. Afterward, take a stroll through the St. Augustine History Museum to gain a deeper understanding of the city's rich past.
Afternoon
Enjoy a leisurely lunch at Barley Republic, a gastropub with a wide selection of craft beers. Spend your afternoon exploring the city's sweet side with the St. Augustine Chocolate & Sweet Walking Tour with Tastings. Indulge in delectable treats while learning about the area's confectionery history.
Evening
Welcome the new year with the St Augustine New Years Eve Nights of Lights Pirate Cruise, a festive and lively way to enjoy the holiday lights (seasonal activity). After the cruise, head to Ice Plant Bar for a post-midnight toast and a late-night bite.
Bedtime
Find amazing hotels in St. Augustine.
4.14St. Augustine History Museum
Book Now
4.14St. Augustine History Museum
Book Now
5.00St. Augustine Chocolate & Sweet Walking Tour with Tastings
Book Now
5.00St. Augustine Chocolate & Sweet Walking Tour with Tastings
Book Now
Final Flavors and Farewells
Morning
Enjoy a relaxed morning at The Oak Room Restaurant and Lounge, where you can savor a sumptuous breakfast. Afterward, take a guided tour of the The St. Augustine Old Jail Museum, a fascinating look into the city's criminal history.
Afternoon
For your last lunch in St. Augustine, visit Castillo Craft Bar + Kitchen, a modern eatery with a focus on local ingredients. Afterward, take a self-guided stroll through the Colonial Quarter, where you can immerse yourself in the living history of the city's colonial past.
Evening
Conclude your St. Augustine adventure with a memorable dinner at The Backyard at Meehan's, where the warm ambiance and delicious food will leave you with fond memories of the city. Reflect on your trip as you enjoy your meal, and perhaps raise a glass to the next journey.
Bedtime
Find amazing hotels in St. Augustine.
4.62The St. Augustine Old Jail Museum
Book Now
4.62The St. Augustine Old Jail Museum
Book Now
4.72Colonial Quarter
Book Now
4.72Colonial Quarter
Book Now
Top St. Augustine Travel Videos
Adjacent Cities
Find the right stay during your trip.