St. Augustine Historic Bar Crawl

Our original walking tour combines St. Augustine history with relaxed stops at some of our favorite local pubs and restaurants. Led by a local guide who is part historian, part new friend, part drinking buddy, you’ll explore the city’s historic streets and architecture while hearing the stories and characters that shaped America’s oldest city. The route changes regularly, allowing us to highlight different partner establishments depending on the day and season. While beer lovers will feel right at home, each stop offers beverage options beyond beer, which may include wine, cider, cocktails, hard seltzers, THC-infused drinks, or non-alcoholic selections. Food is included during the experience, making this a fun, social, and well-paced way to enjoy St. Augustine’s history. If you’re looking for an exciting and unique way to experience St. Augustine’s history while discovering favorite local spots you might never find on your own, this is the walk for you.

1. 1

   Dog Rose Brewing Co.

   45 min

   Your experience begins at Dog Rose, located in the historic Lincolnville neighborhood on the south side of St. Augustine’s historic district. This vibrant, locally loved spot is the perfect starting point for our Historic Bar Crawl, blending neighborhood charm with a relaxed, welcoming atmosphere. While Dog Rose is well known for its creative craft brews made on site, beer is just one of many options available. Guests can also choose from a variety of wines, hard seltzers, cider, THC-infused beverages, and non-alcoholic beers, so everyone can find something they enjoy, regardless of taste or preference. Your guide will meet you here, introduce the experience, and help you select your first drink before heading out to explore St. Augustine’s rich history.

2. 2

   Stop 2

   Pass by

   Both Prince Achille Murat (nephew of Napoleon Bonaparte), and American poet Ralph Waldo Emerson stayed here in the 1820's to fight a bout of illness. This 1790 coquina house is a great example of Second Spanish period architecture.

3. 3

   Father Miguel O'Reilly House Museum

   Pass by

   With parts of the structure dating back to 1691, the O'Reilly House is St. Augustine's oldest standing home. Father Michael O'Reilly moved into the house in 1785 and was a leading figure in the construction of the Cathedral. Upon his death in 1812, he willed the house to Catholic Church. It is now operated as a museum by the Sisters of St. Joseph.

4. 4

   Stop 4

   10 min

   Extending south from the Plaza to Bridge Street, Aviles Street is one of the narrow, brick lined, historic streets of the city which has retained much of its colonial character.

5. 5

   Plaza de la Constitucion

   Pass by

   The plaza has been a central part of St. Augustine since 1573 when it was first laid out by the Spanish Royal Ordinances.

6. 6

   Stop 6

   Pass by

   The narrowest street in the city! Built only 7 feet wide to make it almost impossible to steal gold being transported from the ships to the Royal Spanish Treasury.

7. 7

   Castillo de San Marcos National Monument

   Pass by

   The oldest and largest masonry fort in the continental United States. Finished in 1695 and survived 2 British attacks. It is not part of the National Park Service.

8. 8

   St. George Street

   Pass by

   Starting at the Old City Gates and extending to historic Lincolnville, St. George Street is the center of shopping, entertainment, historical sites, attractions, and restaurants.

• Wheelchair accessible
• Service animals allowed
• Not recommended for travelers with spinal injuries
• Not recommended for pregnant travelers
• Not recommended for travelers with poor cardiovascular health
• Travelers should have at least a moderate level of physical fitness

For a full refund, cancel at least 24 hours before the scheduled departure time.