St Augustine First Time Visitor Guide + Itinerary

Table of Contents

What to Do & What to See in St. Augustine

For our St. Augustine first time visitor guide, we’re narrowing down and simplifying, since the city has so much to offer, that it can be a little overwhelming trying to figure out what to see and do on your first visit. If you only have a short time to visit or if it’s your first time in this historic city, there are few things you just can’t miss. We’ve compiled a list of the must-visit attractions along with an itinerary to visit and experience while you’re here. One great thing about St. Augustine is that the tourism or historic district is fairly compact and easy to navigate.


Figuring out where to park in an unfamiliar city can be daunting. We’ll make it easy and recommend just a few great places to park. 

  • Historic Downtown Parking – Visitors Center:
    • 1 Cordova Street, St. Augustine, FL
    • Park here since you can get free info and maps from the Visitors Center….there’s also restrooms as well. From here you can hop on a Trolley or walk to most places around town.
  • Park at Old Town Trolley:
  • Street or metered parking: In the off-season (October – February), you’ll find numerous metered parking around the area.


old town trolley tour


  • St. Augustine Trolley Tours are a great introduction to the city since these tours provide narrated historic overview of the city. You can hop on and off at different stops and use this as transportation while you’re here.
  • There are two types of Trolleys in St. Augustine. 

St. Augustine Trolley Stop Map Printable

    • Red Train Trolley: This tour is not a hop on hop off and is more or less a tour. We recommend the Old Town Trolley Hop on Hop Off versus this tour.


If you love history….you’ll love being historic in St. Augustine! The city was founded in 1565 by Spanish explorers and is the oldest continuously-inhabited European-established settlement in the United States. We recommend experiencing Savannah’s historic past by walking in the same alleys, pathways and houses of those who have gone before. 

  • Lightner Museum: Opened its doors in 1880’s as another one of Flagler’s hotels, Hotel Alcazar, with what was at the time the largest indoor swimming pool in the world! Its architecture is amazing. The building features soaring ceilings, and enough marble to refill a quarry. More than 20,000 items are on display from a collection of Chicago’s publisher Otto C. Lightner who bought the hotel and later give it to the city. Eat lunch in the wonderful Café Alcazar (in the deep end of the drained swimming pool). Wonderful food and such ambiance.
  • Villa Zorayda: is located at 83 King Street next to the Lightner Museum. Built in 1883 by the eccentric Boston millionaire Franklin W. Smith as his winter home, it was inspired by the 12th-century Moorish Alhambra Palace in Granada, Spain.
  • Riverboat Narrated Cruise: The Savannah River was a crucial artery that supplied the city and was the reason…and still is a major reason why Savannah is relevant today. Tour is included with TourPass
  • Historic or Ghost Walking Tours: Walk by and learn about why this or that is significant and all the amazing tidbits and facts on these tours. Tour is included with TourPass
  • Castillo de San Marcos: The oldest masonry fort in the continental USA. This National Park site can be visited. Admission is not included with Tour Pass.
  • Spanish Military Hospital Museum: Their fully guided presentation will take you back to the colonial Spanish days of medicine with both surgical and apothecary demonstration. Your journey to the past begins as our skilled surgeon performs surgical demonstrations. Watch as our Apothecary creates medicines and discover how colonial herbs were the origins of some of the most popular medicines today.
  • Fountain of Youth: The original site of the Nations oldest city. Located in the area first explored by Juan Ponce de Leon in 1513 and settled by Pedro Menendez de Aviles in 1565, historic St. Augustine is the oldest successful European settlement in the United States. Colonial America started right HERE, 55 years before the Pilgrims landed on Plymouth Rock, and 42 years before Jamestown! With a long, rich history spanning nearly 500 years, the Fountain of Youth Park will delight and amaze you. Whether you visit for an hour or take all day, our 15 waterfront acres will provide you with hours of enjoyment.
  • Old Jail Museum: Listed in the National Registry of Historic Places, The Old Jail is a must-visit when in St. Augustine! Built to look like a hotel in the Romanesque Revival style and painted in an unassuming color, visitors will find that the Old Jail has been renovated to give tourists a glimpse into the daily lives of St. Augustines most notorious prisoners living under the penal system of the 19th and early 20th centuries. Costumed actors tell tales of the jail and its occupants, and even book you as an inmate! Additionally, the Old Jail has a large collection of weapons and artifacts for you to inspect up close and is one of just a few prisons of its kind still standing that makes for a great day of sightseeing on a historical adventure.


A visit to St. Augustine wouldn’t be complete without strolling along one of the many beautiful beaches which are only about 10 minutes drive time from downtown. Check-out our St. Augustine Spring Break & Beach Guide for more info



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