St. Augustine, FL - Weekend Itinerary


We just came back from a quick weekend getaway to St. Augustine, FL had such a great time. We booked the hotel back in January, knowing that life was going to be hectic over the next couple months and we would appreciate a moment to de-stress. If you're wondering what the heck there is to do in St. Augustine, I’ve included our itinerary and was sure to share if we felt it was a “must do”. Enjoy!

Where we stayed

We stayed at an equally adorable and quaint bed and breakfast in the heart of the historic district (Literally, it is in the middle of the two oldest streets in the nation) called Victorian House. We had never stayed in a bed and breakfast, but it was a requirement for us when we started looking for accommodations. Part of what makes St. Augustine so special is the history, so we chose authenticity over luxury. We stayed in the Juli Room which is their most economic room for 2. For starters, we arrived almost at midnight and we felt terrible about it (unlike a hotel, this felt a lot like staying at someone’s house and I didn’t think to advise them that we’d be checking in late). The owner, Anthony, left me a detailed message and was kind enough to leave me a hand written letter with my keys - welcoming me to the Victorian House and providing instructions. We made it to our room easily and were smitten with it. Original hardwood floors, small bathrooms, antique furniture and décor on every inch of the space. They serve breakfast every morning from 8-930am in the dining room and it was DELICIOUS everyday. They provided us a map with instructions, their cell numbers in case we needed anything, and just amazing service. The most you’ll walk to anything from this location is 15 minutes, so we barely used our car. The location in itself is amazing and the nightly rates were competitive. I will say, the bed and breakfast life is one with little privacy and this old house echoed every single noise - In other words, be considerate and don’t expect a luxury hotel stay. I also would not stay here with children - again, you will keep everyone up just by talking.

What we did

Lighthouse & Beach - Nice but not necessarily must-do

The first thing we knocked out was the lighthouse. It is just over the A1A bridge, in the Anastasia State Park. It was a bit chilly so we didn’t stick around to see the beach much (we’re from Miami, beaches aren’t a huge deal to us). That being said, we heard that going up the lighthouse was a must so we knocked this bad boy out first. It’s almost 15 stories up so take your walking shoes and a bottle of water. You get a beautiful view of the marina and the old city across the way. The lighthouse is black and white with red trim, feels like every lighthouse you’ve ever seen depicted in a painting. Your ticket up also gets you entrance to some exhibits, a museum in the keeper’s house, and the on-site archaeology office where you can see some original items they’ve recovered in the area. It was really cool but I wouldn’t say it was a must-see for us, just because we have a lot of this back at home too. What stood out to us most was the keeper’s house where you learned about the life of the lighthouse keeper, and the archaeology area where you can speak to them of the team about their work. The actual beach and lighthouse was nice, but necessarily a must-do.

San Marcos Castillo - Must do (With demonstration)

Following our exhausting but worth it trek up and down the lighthouse, we parked our car back at the B&B and walked to the San Marcos Castillo (The historic fort). They’ve opened up almost all the rooms in the fort with historic artifacts, displays, interactive videos and more. You’re able to wander the grounds freely and they even do a weapons demonstration with a cannon shot every hour on the hour. If you’re going to stick around for the demonstrations, this is a must-do.

Old City - Worth walking, museums may not be worth it

After we knocked out two big attractions, we decided to walk the historic area (old city) and get to know the city a bit. We didn’t do any of the museums, but we enjoyed walking the colonial quarters and seeing the oldest schoolhouse and house as well as the oldest streets and city gates. Flagler college is architecturally impressive and the area is filled with small bars and shops attracting the young crowds. There are quite a few historic houses in the old city, marked with plaques. I encourage you to stop and read, take in the history and enjoy strolling. The houses are right on the streets in these areas, with a lot of little hidden gems and areas to find and enjoy. We didn’t feel the museums were worth it, but walking it is a must-do.

St. George’s Street - Must do

The bulk of your time will probably be spent here. For every moment we thought the town seemed empty, we’d turn the corner on St. George and suddenly find a bustling crowd. St. George’s street is in the center of the historic district and is parallel to Avandia Menendez (street running around the ocean). It’s full of small boutiques, souvenir shops, bars, restaurants, ice cream parlors and more. This is also where you find some museums (like the pirate museum and wax museum), the oldest wooden schoolhouse, and the entrance to the colonial quarters attraction. We walked this street often and enjoyed our strolls here. The Oak is an outdoor venue serving drinks and some pretty great live music. We came here after dinner one night and really enjoyed the ambience, it was a cool place to hang out for a bit. For places to eat on St. George’s, check out our places to eat section on this post.

St. Augustine Distillery - Must do

This distillery just opened their doors in 2014, using the old ice plant factory that used to generate ice for the city of St. Augustine. They’re award winning for their bourbon, and they offer a free tasting and tour of their facility. The people here had such a great energy to them which made us want to stay for a tour and hangout. They’re passionate about what they make, and it was so refreshing to see a local business literally hand crafting and hand bottling goods in small batches. In addition to bourbon, they also make vodka, rum, and gin. We’re honestly not much into alcohol, but we truly enjoyed our experience here and will say this was an absolute must-do.

Whetstone Chocolate Factory - Must do

Yup, that’s right. A chocolate factory. I’ll save you the read and just say, you NEED to do this. Whetstone chocolates are local right in St. Augustine, and they specialize in artisan chocolates which means they do it all by hand and with loving tender care. With your tour ticket comes a tasting of 5 chocolates, each more delicious than the last. We learned about how chocolate is made, had a chance to actually walk the local factory and see people at work, and got chocolate wasted in the process. Make sure you get their gator bait, it’s a bunch of nutty goodness bathed in their best selling Aviles milk chocolate. WORTH . IT.

The Corazon Movie Theatre - Good place to go for a movie night

We were tired and it was raining, so we decided to walk to the nearest movie theatre and catch a film. This theatre is family owned, which made it completely different than any theatre experience we had had. For 20 bucks we bought two movie tickets, nachos, and a drink. The theatre itself was a large movie screen with a bunch of patio chairs in front of it. I absolutely loved every second of our time here, so if you can wrap your head around a different type of experience - give this place a chance.

Fountain of Youth - Must do

I honestly fought Adam on visiting this place. I thought it was just going to be a baby spring in the middle of a basic park, and didn’t get what all the hoopla was about. Welp, I was wrong. Not only is this the original location of colonization that eventually led to the forming of the USA, but there is all kinds of historical artifacts and exhibits that make this worth it. Weapons demonstrations, cannon shooting, blacksmith at work, the original spring that you can drink from and the stone cross, a planetarium, a reenactment of the Indian reserve, it was all pretty darn cool. It’s a $15 entrance and you can honestly spend the whole day here with all the shows and things to see. There's also a TON of peacocks. We have plenty of those in Miami too, but they were in season so we saw many of them with their feathers puffed up and it was a site to see. We only spent a couple hours here, but it’s definitely a must see.

What we ate

Burrito Works Taco Shop - Must eat

Ok. Adam and I are total taco fanatics, and when my best friend recommended this place we did not hesitate. We haven’t had tacos since my surgery, so I was weary but dying to have some. We ordered both beef and chicken tacos with the works, done kung-Fu style (which was a soft flour tortilla within a hard taco shell with cheese). It was absolutely delicious and not too heavy. They’re famous for their Mexican UFO, but we didn’t feel we could stomach it. My best friend had her tacos Baja style and spoke wonders of it too - I just don’t think you could go wrong here. It's in the heart of St. George street and seating can be hard to find, but they serve it food truck style and you can walk and eat.

Kilwins - Overrated

Kilwin’s is a chain ice cream shop that we saw in a couple of places. You can smell their goodies in all of historic St. Augustine, so we decided to give it a go. We ordered the St. Augustine mud, which was a vanilla based ice cream with nuts and caramel. It was good, but not as great as we thought it would be. Save yourself the calories and head to Whetstone instead.

Prohibition Kitchen - Not great, but I’d give it another chance

We came to this restaurant for the live music and supposed southern food. The service, music, and ambience was good but we weren’t big fans of the actual food. Adam ordered a “Madicola” which was basically just a rum and coke with vanilla coke, nothing out of this world for the price but he enjoyed it. We then ordered the chef’s special which was supposed to be a tender pork (similar to wild boar) with roasted potatoes and a mushroom cream made with three different types of mushrooms. Instead we got a practically raw pork chop, a spoonful of cold mashed potatoes that was more chives than potato (not roasted), and a small tin with cold sautéed mushrooms that tasted like canned mushroom cream. Disappointing, but hey - you can’t win them all. I think it may have been more about what we ordered so I’d still give them another shot, but not our best dining experience.

Tedi’s Ice Cream Shop - No thank you

I ordered a Kahlua ice cream here that was full of nutty goodness. It was yummy in the moment - but it was super heavy, not the greatest quality, and it did not sit well for either one of us. Again, save yourself the calories and head to Whetstone instead.

Ice Plant Bar - MUST DO

This was the best meal we had on our trip. The ice plant bar is located at the St. Augustine’s distillery and is a vintage style bar that makes crafted cocktails with hand carved ice. They only serve brunch on the weekends but it was amazing. Adam ordered the teenage dream cocktail which was like drinking a delicious ice cold strawberry juice. We shared the southern fried chicken that came with maple butter, hoecakes, and collard greens. It wasn’t too heavy and it was heaven on earth. We enjoyed this meal tremendously and the service was great, would absolutely recommend to make an afternoon of your time at the distillery and eat here.

Mojo’s Old City BBQ - Not the best, but that’s some good BBQ

We were craving some BBQ and Mojo’s was rated the best in St. Augustine. It wasn’t the best BBQ I had ever had, but it was delicious and the service was great. Also really economically priced for the amount of food we got. We ordered the ribs and chicken with mac & cheese and roasted corn. It’s all served on cafeteria style plates, nothing fancy - but it was pretty amazing. Their mojo sauce and sweet sauce were also pretty great - definitely recommend if you're in the mood for some BBQ.

Whetstone Chocolates - All things sweet it’s a must!

Oh, hey! Did I not mention Whetstone’s yet? Do yourself a favor and only stick to this place for dessert. They have about 2-3 locations in St. Augustine (one of them on St. George’s street), and they have everything from gelato to flavored coffee to pastries to chocolates. It was honestly all good (their salted caramel gelato is to die for).

All in all, St. Augustine is a small town with a lot of heart and plenty to see, do, and eat. If you’re planning a little trip there as well, we hope you enjoy your time taking in all the old charm the culture.

All my love,

Kristine