5-day Trip to St. Augustine Itinerary

Start your day with a kayak tour of the St. Augustine waterways and spot dolphins and manatees with St. Augustine Dolphin and Manatee Paddle or Kayak Tour. Afterward, grab a quick snack at Whetstone Chocolates of St. Augustine.

Enjoy a boat cruise along the Matanzas River and explore the historic sites with St. Augustine Boat Cruise and Electric Golf Cart Tour. For lunch, try the fresh seafood at The Conch House Restaurant.

Experience the thrill of a pirate show with St. Augustine The Black Raven Rum Runners Pirate Show (21+). Afterward, head to Ice Plant Bar for craft cocktails and a unique speakeasy atmosphere.

Start your day with a visit to the Lightner Museum to explore its eclectic collection. For breakfast, try the Cuban cuisine at Columbia Restaurant. Afterward, visit the St. Augustine Pirate and Treasure Museum.

Enjoy a leisurely lunch at Harry's Seafood Bar & Grille and then explore the St. Augustine History Museum to learn more about the city's past. Take a stroll through the Colonial Quarter and experience life in the 18th century.

Dine at Preserved Restaurant and savor their farm-to-table dishes. Afterward, take a St. Augustine Haunted Pub Crawl and discover the city's haunted bars and taverns.

Start your day with a visit to the St. Augustine Alligator Farm Zoological Park and get up close with these fascinating creatures. Enjoy a picnic lunch at Catch 27 and then relax on the beautiful beaches of St. Augustine.

Take a scenic drive to Fort Matanzas National Monument and explore the historic fort. For a sweet treat, visit Blackfly The Restaurant and try their famous key lime pie.

Enjoy a sunset cruise along the Matanzas River with St. Augustine Black Raven Sunset Cruise. For dinner, indulge in fresh seafood at The Reef Restaurant.

Start your day with a visit to the Lightner Museum to admire its extensive art collection. For breakfast, try the delicious pastries at Cellar Six. Afterward, explore the González-Alvarez House (Oldest House Museum Complex).

Enjoy a leisurely lunch at A1A Ale Works and then visit the St. Augustine Old Jail Museum Guided Tour to learn about the city's criminal history. Take a walk along St. George Street and browse the unique shops and boutiques.

End your trip with a delicious dinner at O'Steen's Restaurant, known for its famous shrimp. Afterward, take a St. Augustine Hop-on Hop-off Trolley Tour with Museum Entry to explore the city's landmarks one last time.