7 Things You Must Do on Your First St. Augustine Trip

There is SO MUCH to see and do in St. Augustine–just look through our blogs on ‘things to do’ and you’ll find a ton! But if this is your first trip, here is our list of 7 things you MUST do in St. Augustine.


If you’ve come to St. Augustine many times, you may want to check out our list of hidden gems in our city. But if you’re just discovering our town, or if you’re only here for a few days, and you want to see the real highlights, here are our suggestions:

Old Town Trolley in St. AugustineRide the Trolley.

There are two trolley tour companies in St. Augustine–Old Town Trolley (they’re the orange and green ones, and their closest stop is the Oldest House) and the Red Train (they’re red, obvs, and you can pick them up at the golf course on Avenida Menendez). Both trolleys have unlimited on/off privileges–you can ride the whole route to get an overview of the town, or you can use the trolley as transportation from one attraction to the other, hoping on and off as often as you’d like. Old Town Trolley has three day passes (a great deal if you’re staying that long) and the Red Trolley has a senior discount. They have very similar routes, and they both stop at all the big photo opp’s in town.

I often recommend riding the trolley once to get the lay of the land, and then using it as transportation from site to site. As you ride, you’ll see some of our most beautiful landmarks, including Memorial Presbyterian Church, built by Henry Flagler after his daughter died during childbirth. The church was recently named one of the most important architectural sites in the country.

Tour Flagler College.

I know, this isn’t a college tour for you…but seriously, take the tour, whether you have a high school senior in tow or not. This is my favorite tour–it starts in the lobby of the college, which used to be the lobby of the opulent, over-the-top, place to be seen Ponce de Leon Hotel. The lobby is magnificent, with carved wooden columns, a painted domed ceiling, a mosaic floor, and all the luxury you’d expect from a great Victorian era hotel. The tour takes you through the lobby, and back to the cafeteria, which is lined with floor to ceiling Tiffany Glass windows. You’ll also see some of the hotel’s old parlors, which still have some original decoration, and lots of great stories. Check out the beautiful courtyard too–the fountain is just beautiful. 74 King Street. www.flagler.edu.

The Castillo de San Marco fortVisit the Fort.

It’s hard to miss our fort, as the site takes up 20 acres right on the Matanzas Bay in our historic district! The Castillo de San Marco was built in the late 1600’s of coquina, a porous stone found on the Florida coast (fun fact: the oldest part of our bed and breakfast is also made of coquina. It is not a friendly surface to hang curtains or any kind of artwork). You can walk the grounds for free–it’s a beautiful park area, oftentimes full of elementary school students rolling down the grassy hill. And it’s right next to the seawall, which overlooks our beautiful bay. There is a fee to tour the inside of the fort, and I recommend it, just to see the construction more closely. There are cannon firings every Friday, Saturday, and Sunday; check their event calendar for specifics. 11 South Castillo Drive. 904.829.6506. www.nps.gov/casa.

Become a Pirate.

Not technically, of course…St. Augustine doesn’t have a great history with pirates. But they are a big part of our history, and there is no place better to learn about them than the Pirate Museum across from the fort. Pat Croce opened the museum in 2010 to share his AMAZING stash of pirate treasures with the world–he has an original flag from a pirate ship, actual pirate treasure, and extensive research on all the big name pirates of the time. To build the museum, he partnered with Disney, and there are some stunning animatronics in the displays (like the pirate who is sleeping in the front room and the pirate who has been beheaded in the middle of the museum). 12 South Castillo Drive. 877.467.5863. www.thepiratemuseum.com.

Dine in the Deep End.

Now, if you’re staying at our St. Augustine bed and breakfast, you might not need a big lunch. But save a little room so that you can enjoy a mid-day meal at the Café Alcazar. Café Alcazar is located in the Lightner Museum; you can access it from the back of the building, across from the Corazon Theater. Here’s the cool thing: the Lightner Museum is in the old and beautiful Alcazar hotel, and the café is in the old INDOOR POOL (emptied of water, of course). Many times there is a pianist or guitarist playing…once you hear it, you will insist that every concert be held in an empty cement pool. 25 Granada Street. 904.825.9948. www.thealcazarcafe.com.

storefronts along Aviles StreetWalk, walk, walk.

The best way to dine out for multiple meals a day is to walk it off! And there is no better walkable town than St. Augustine. From the inn, we recommend walking west on Bridge Street (Bridge is the street just to the north of the inn). From Bridge, take a right on Aviles Street (pictured at left). Aviles is the oldest street in the country, and today it’s lined with charming boutiques, restaurants, and art galleries. From Aviles, walk east on King Street, past the Plaza de la Constitucion. Cross Avenida Menendez to check out the Bridge of Lions, then take a left on the seawall and walk towards the fort. Don’t worry if you get lost–all the streets in St. Augustine are beautiful and worth a leisurely stroll.

Eat, eat, eat.

Southern Living recently named St. Augustine the best Foodie city of the South–and we have to agree! There are so many options in town–just ask us for a recommendation, or check out our blogs for the most romantic restaurants, the best restaurants on the water, our favorite seafood spots, or read our suggestions for a St. Augustine Foodie Weekend.

This list is a generic one of the must-sees in town. If someone asks us what they have to do on their vacation, this is the list we give them. But if you have specific interests–if you love music, or beer, or art, or fine jewelry–just ask us! We’re happy to make suggestions, and if we don’t know something ourselves, we can call someone who does.

We’re here to help you customize the perfect vacation for YOU!