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Pirate Adventures and Culinary Delights in St. Augustine Itinerary
Last updated: 2024 Jun 14Arrival and Waterfront Exploration
Morning
Arrive in St. Augustine and start your day with a delightful breakfast at Maple Street Biscuit Company, known for its unique biscuit creations.
Afternoon
After breakfast, take a leisurely stroll along the Waterfront and Downtown area. Visit the iconic Castillo de San Marcos National Monument and explore the historic fort. For lunch, enjoy fresh seafood at Cap's on the Water with views of the Matanzas Bay.
Evening
In the evening, embark on the St. Augustine Black Raven Tropical Sunset Cruise. Enjoy the beautiful sunset views while experiencing a taste of pirate life with live entertainment. For dinner, savor a meal at Sunset Grille overlooking the water.
Bedtime
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![Visit Castillo de San Marcos National Monument in St. Augustine](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/68/d1.jpg)
4.76Castillo de San Marcos National Monument
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![Visit Castillo de San Marcos National Monument in St. Augustine](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/68/d1.jpg)
Castillo de San Marcos National Monument
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![Visit St. Augustine Black Raven Tropical Sunset Cruise in St. Augustine](https://cdn.getyourguide.com/img/tour/33f3da0be5e48d102d471768cb9d3d1d47cda53f892bc96d2f426347381a5196.jpg/21.jpg)
4.22St. Augustine Black Raven Tropical Sunset Cruise
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![Visit St. Augustine Black Raven Tropical Sunset Cruise in St. Augustine](https://cdn.getyourguide.com/img/tour/33f3da0be5e48d102d471768cb9d3d1d47cda53f892bc96d2f426347381a5196.jpg/21.jpg)
St. Augustine Black Raven Tropical Sunset Cruise
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Pirates, Ghosts, and Spirits
Morning
Start your day with a hearty brunch at Harry's Seafood Bar & Grille, a local favorite known for its Southern cuisine.
Afternoon
Dive into the pirate history of St. Augustine with the St. Augustine Black Raven Rum Runners Pirate Show (21+). After the show, continue the theme with a visit to the St. Augustine Pirate and Treasure Museum. For a late afternoon pick-me-up, enjoy a coffee at The Kookaburra, a cozy cafe.
Evening
For a unique experience, join the St. Augustine True Crime Guided Pub Crawl. Explore the darker side of the city's past while enjoying drinks at local pubs. End the evening with a sophisticated dinner at Collage Restaurant, known for its fine dining and artistic presentations.
Bedtime
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4.17St. Augustine Black Raven Rum Runners Pirate Show (21+)
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![Visit St. Augustine The Black Raven Rum Runners Pirate Show (21+) in St. Augustine](https://cdn.getyourguide.com/img/tour/9f56c77763688bd009d499c24bbc6dd2522a6491a9bf256cfc30ddfbd5e599d2.jpeg/21.jpg)
St. Augustine Black Raven Rum Runners Pirate Show (21+)
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![Visit Mt. Cook Day-Tour Christchurch to Queenstown in St. Augustine](https://cdn.getyourguide.com/img/tour/59eff3d370f28.jpeg/21.jpg)
4.03St. Augustine Pirate and Treasure Museum
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![Visit Mt. Cook Day-Tour Christchurch to Queenstown in St. Augustine](https://cdn.getyourguide.com/img/tour/59eff3d370f28.jpeg/21.jpg)
St. Augustine Pirate and Treasure Museum
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![Visit St. Augustine True Crime Guided Pub Crawl in St. Augustine](https://cdn.getyourguide.com/img/tour/63f7b5d5db3cf.jpeg/21.jpg)
3.86St. Augustine True Crime Guided Pub Crawl
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![Visit St. Augustine True Crime Guided Pub Crawl in St. Augustine](https://cdn.getyourguide.com/img/tour/63f7b5d5db3cf.jpeg/21.jpg)
St. Augustine True Crime Guided Pub Crawl
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Historical and Haunted Sites
Morning
Enjoy a leisurely morning with a brunch tour at Columbia Restaurant, a historic eatery serving up traditional Spanish cuisine.
Afternoon
Explore the historical sites of St. Augustine with a visit to the Fountain of Youth and the Castillo de San Marcos National Monument. Dive into the city's haunted past with the St. Augustine Ghosts and Gravestones Old Town Trolley Tour. For a light afternoon snack, indulge in the sweet treats of the St. Augustine Chocolate & Sweet Walking Tour with Tastings.
Evening
As the night falls, participate in the St Augustine OId Jail After Dark Paranormal Investigation for a spine-chilling experience. Afterward, have a casual dinner at The Floridian, a farm-to-table restaurant with a cozy atmosphere.
Bedtime
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![Visit Fountain of Youth in St. Augustine](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/6a/99.jpg)
4.82Fountain of Youth
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Fountain of Youth
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![Visit Castillo de San Marcos National Monument in St. Augustine](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/68/d1.jpg)
4.76Castillo de San Marcos National Monument
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![Visit Castillo de San Marcos National Monument in St. Augustine](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/68/d1.jpg)
Castillo de San Marcos National Monument
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![Visit St. Augustine Ghosts and Gravestones Old Town Trolley Tour in St. Augustine](https://cdn.getyourguide.com/img/tour/56e9e653671b1.jpeg/21.jpg)
4.24St. Augustine Ghosts and Gravestones Old Town Trolley Tour
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![Visit St. Augustine Ghosts and Gravestones Old Town Trolley Tour in St. Augustine](https://cdn.getyourguide.com/img/tour/56e9e653671b1.jpeg/21.jpg)
St. Augustine Ghosts and Gravestones Old Town Trolley Tour
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![Visit St. Augustine Chocolate & Sweet Walking Tour with Tastings in St. Augustine](https://cdn.getyourguide.com/img/tour/60d330db2d787.jpeg/21.jpg)
5.00St. Augustine Chocolate & Sweet Walking Tour with Tastings
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![Visit St. Augustine Chocolate & Sweet Walking Tour with Tastings in St. Augustine](https://cdn.getyourguide.com/img/tour/60d330db2d787.jpeg/21.jpg)
St. Augustine Chocolate & Sweet Walking Tour with Tastings
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![Visit St Augustine OId Jail After Dark Paranormal Investigation in St. Augustine](https://cdn.getyourguide.com/img/tour/57212fb66edc9331.jpeg/21.jpg)
4.57St Augustine OId Jail After Dark Paranormal Investigation
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![Visit St Augustine OId Jail After Dark Paranormal Investigation in St. Augustine](https://cdn.getyourguide.com/img/tour/57212fb66edc9331.jpeg/21.jpg)
St Augustine OId Jail After Dark Paranormal Investigation
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Outdoor Adventures and Culinary Delights
Morning
Start your day with a refreshing kayak tour at sunrise with the St. Augustine Kayaking Sunrise Tour. Afterward, enjoy a relaxed breakfast at Mojo's Tacos.
Afternoon
Spend the afternoon exploring the natural beauty of the area with the St. Augustine Alligator Farm Zoological Park and the Old Florida Backwater Kayak Adventure Near St. Augustine. For lunch, savor the flavors of the South at Harry's Seafood Bar & Grille.
Evening
End your day with a premium spirits tasting and pairing at the St. Augustine Distillery Premium Spirits Tasting & Pairing. For dinner, indulge in a culinary experience at Catch 27, known for its fresh seafood and farm-to-table dishes.
Bedtime
Find amazing hotels in St. Augustine.
![Visit St. Augustine Kayaking Sunrise Tour in St. Augustine](https://cdn.getyourguide.com/img/tour/6284e551478bc.jpeg/21.jpg)
5.00St. Augustine Kayaking Sunrise Tour
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![Visit St. Augustine Kayaking Sunrise Tour in St. Augustine](https://cdn.getyourguide.com/img/tour/6284e551478bc.jpeg/21.jpg)
St. Augustine Kayaking Sunrise Tour
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![Visit St. Augustine Alligator Farm Zoological Park in St. Augustine](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/6f/92.jpg)
5.00St. Augustine Alligator Farm Zoological Park
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St. Augustine Alligator Farm Zoological Park
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5.00Old Florida Backwater Kayak Adventure Near St. Augustine
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Old Florida Backwater Kayak Adventure Near St. Augustine
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5.00St. Augustine Distillery Premium Spirits Tasting & Pairing
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St. Augustine Distillery Premium Spirits Tasting & Pairing
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Cultural Immersion and Departure
Morning
On your last day, take a guided tour of the Lightner Museum and the Father Miguel O'Reilly House Museum to immerse yourself in the cultural heritage of the city. Enjoy a farewell brunch at The Blue Hen, a charming restaurant with a focus on local ingredients.
Afternoon
Spend your final hours in St. Augustine with a leisurely walk through the Colonial Quarter and a visit to the González-Alvarez House (Oldest House Museum Complex). Pick up some souvenirs at the local shops and take in the last moments of this historic city.
Evening
As you prepare to depart, have a relaxed dinner at Athena Restaurant, known for its Mediterranean cuisine. Reflect on your adventures in St. Augustine and savor the memories before heading to the airport.
Bedtime
Find amazing hotels in St. Augustine.
![Visit Lightner Museum in St. Augustine](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/6b/a4.jpg)
4.71Lightner Museum
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![Visit Lightner Museum in St. Augustine](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/6b/a4.jpg)
Lightner Museum
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![Visit Father Miguel O'Reilly House Museum in St. Augustine](https://media.tacdn.com/media/attractions-content--1x-1/0b/27/6c/d1.jpg)
4.92Father Miguel O'Reilly House Museum
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Father Miguel O'Reilly House Museum
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![Visit Colonial Quarter in St. Augustine](https://media.tacdn.com/media/attractions-content--1x-1/0b/df/bd/80.jpg)
4.72Colonial Quarter
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![Visit Colonial Quarter in St. Augustine](https://media.tacdn.com/media/attractions-content--1x-1/0b/df/bd/80.jpg)
Colonial Quarter
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![Visit González-Alvarez House (Oldest House Museum Complex) in St. Augustine](https://media.tacdn.com/media/attractions-content--1x-1/0b/39/ad/b0.jpg)
4.93González-Alvarez House (Oldest House Museum Complex)
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González-Alvarez House (Oldest House Museum Complex)
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