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Things to do in St Augustine: 2 local trip ideas

2 ready-made day trips in St Augustine, Florida: cultural and romantic. Each one strings together a handful of stops in order.

Cultural trip

A Journey Through Historic St.

5 stops · about 8 hr 45 min of stops · ~$167 per person

Immerse yourself in the Gilded Age architecture, centuries-old colonial history, and vibrant Spanish-Cuban flavors of historic downtown St. Augustine, traveling entirely on foot.

  1. 1

    PK’s Roosevelt Room

    121 St George St, St. Augustine, FL 32084, USA
    PK’s Roosevelt Room, St Augustine

    Enjoy a gourmet breakfast like the signature eggs Benedict in an elegant, vintage-inspired dining room.

    ★ 4.7 on Google · about 1 hr 15 min · ~$22 per person · Directions
  2. 2

    Lightner Museum

    75 King St, St. Augustine, FL 32084, USA
    Lightner Museum, St Augustine

    Explore majestic Gilded Age decorative arts housed inside Henry Flagler's former 1888 Hotel Alcazar.

    ★ 4.7 on Google · about 2 hr · ~$20 per person · Directions
  3. 3

    Columbia Restaurant

    98 St George St, St. Augustine, FL 32084, USA
    Columbia Restaurant, St Augustine

    Indulge in award-winning Spanish-Cuban dishes in a courtyard filled with hand-painted tiles.

    ★ 4.4 on Google · about 1 hr 30 min · ~$35 per person · Directions
  4. 4

    Castillo de San Marcos National Monument

    11 S Castillo Dr, St. Augustine, FL 32084, USA
    Castillo de San Marcos National Monument, St Augustine

    Walk the ramparts of the oldest masonry fort in the continental United States and take in bay views.

    ★ 4.7 on Google · about 2 hr · ~$15 per person · Directions
  5. 5

    Collage

    60 Hypolita St, St. Augustine, FL 32084, USA
    Collage, St Augustine

    Conclude your cultural day with a critically acclaimed, intimate fine dining experience focusing on local seafood.

    ★ 4.7 on Google · about 2 hr · ~$75 per person · Directions
Romantic trip

A Day of Intimate Old-World

5 stops · about 7 hr 45 min of stops · ~$480 per person

Immerse yourselves in the timeless romance of St. Augustine with an elegant day of vintage-inspired dining, historic streets, a sunset sailing charter, and rooftop nightcaps overlooking the bay.

  1. 1

    PK’s Roosevelt Room

    121 St George St, St. Augustine, FL 32084, USA
    PK’s Roosevelt Room, St Augustine

    Enjoy a sophisticated, 1920s-inspired brunch of mimosa flights and elevated southern classic plates.

    ★ 4.7 on Google · about 1 hr 15 min · ~$45 per person · Directions
  2. 2

    The Drunken Horse St. Augustine

    56 Charlotte St, St. Augustine, FL 32084, USA
    The Drunken Horse St. Augustine, St Augustine

    Cozy up in a charming, hidden-courtyard setting for a romantic French lunch of sharing plates and fine wine.

    ★ 4.7 on Google · about 1 hr 30 min · ~$65 per person · Directions
  3. 3

    Schooner Freedom Charters

    111 Avenida Menendez, St. Augustine, FL 32084, USA
    Schooner Freedom Charters, St Augustine

    Embark on a breathtaking sunset sail aboard the city's premier tall ship with complimentary drinks.

    ★ 4.9 on Google · about 2 hr · ~$150 per person · Directions
  4. 4

    Collage

    60 Hypolita St, St. Augustine, FL 32084, USA
    Collage, St Augustine

    Savor an intimate, award-winning candlelit dinner nestled inside a romantic historic cottage.

    ★ 4.7 on Google · about 2 hr · ~$180 per person · Directions
  5. 5

    River & Fort Restaurant & Roof Top Lounge

    12 Avenida Menendez, St. Augustine, FL 32084, USA
    River & Fort Restaurant & Roof Top Lounge, St Augustine

    End your perfect night with rooftop craft cocktails overlooking the lit-up Castillo de San Marcos and the bay.

    ★ 4.3 on Google · about 1 hr · ~$40 per person · Directions

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