I’ve always maintained that the best way to see a city is on a bicycle. And in the past few years I’ve had the good fortune to be able to tour Ottawa, Edinburgh, Moscow, St. Petersburg, Montreal, San Francisco, Helsinki and a few other great cities on two wheels.
But, listen, one of the best city bike tours you can take is right here in Florida. Try this 26-mile self-guided Ancient City Ramble to experience the best that historic St. Augustine has to offer (sorry, New Mexico, Virginia and Mass, but we’re still No. 1 on the oldest city list).
Leave from the Ocean Pier on St. Augustine Beach. Why? Because it’s a great spot for a start-of-ride photo.
0.9 miles: Where the white crosswalk crosses Beach Blvd. look for a short unpaved footpath. Turn right there to get off A1A and into a lovely tree covered old Florida neighborhood.
2.2 miles: That’s the St. Augustine Amphitheater on your right. There’s probably a concert there tonight. We’ve seen Willy Nelson, Steely Dan and a few other oldies but goodies there.
2.9 miles: Stop and take the walk to the top of the St. Augustine Lighthouse. Best views in the city.
3.9 miles: The Conch House is one of the better known restaurants in St. Aug. Think a fish house on steroids.
5.1 miles: Cross the historic Bridge of Lions. Take your lane, the cars behind you will wait.
5.9 miles: If you haven’t seen the honkin’ big Castillo de San Marcos, now’s your chance. Bristling with cannon and history.
6.6 miles: That’s the Great Cross on your right. Mariners can see it from miles out at sea. Great photo opportunity. Beautiful grounds.
7.0 miles: The Fountain of Youth is not nearly as tourist hokey as it sounds. In fact, it’s a beautiful stroll along the Matanzas River and an informative walk through early Florida history.
6.6 miles: Yeah, you’re gonna cross that really tall bridge. It’s the only way to get to the quaint seaside community of Vilano Beach.
8.8 miles: Well, you did the hard work of getting over that ginormous bridge. Might as well take a quick spin through Vilano before you have to ride back over it.
12.5 miles: That lovely campus on your right is the Florida School For The Deaf and Blind.
13.8 miles: You are at Ft. Mose Park, site of the first free African settlement in North America. The fort is gone but there’s a museum there preserves its history and a really beautiful boardwalk stroll will lead you out into the marsh to the original site.
14-14.3 miles: Exercise CAUTION on this left turn onto U.S. 1 quickly followed by another left to get off of it. It’s a four-lane divided highway so take your time and execute these turns carefully and safely.
16.1: You’ve reached the Old City Gates and all of the Ancient City attractions on the pedestrian-only Spanish Street. Park your bike and take a stroll through history.
16.6: Flagler College is another excellent place to stop and walk. I recommend the guided tour, which will take you to the roof for great views.
17 miles: St. Augustine Distillery. You know what to do.
18.1 miles: That compound to your right is where the horses live when they are not pulling carriages up and down Ancient City streets.
18.1: You have arrived at one of St. Augustine’s best kept secrets, Freedom Park. Its circular bike-ped path gives you great views of the San Sebastián and Matanzas rivers, and there are great sculptures depicting the city’s African American heritage.
19 miles: You are in the heart of St. Augustine’s historic African American neighborhood. Martin Luther King Jr. was arrested near here. Check out the Civil Rights House.
19.4: The coolest neighborhood in St. Aug. is the quaint waterside neighborhood of Lake Maria Sanchez.
19.9: Lightner Museum on your left. The restored San Marco Hotel (great bar) on your right.
20.2: Why did the cyclist cross the Bridge of Lions twice? To finish the ride of course.
22.2: St. Augustine Alligator Farm and Zoological Park. In addition to a swampload of reptiles this place boasts a world class rookery (birds like it here because the gators protect them from predators that can climb trees).
22.8: Can’t visit St. Augustine without seeing Anastasia State Park. You can rent kayaks and paddle boards on the salt run. Or walk for miles on its car-free beach.
25.4: Thousands of motorists pass the St. Augustine Beach Sculpture Garden every day and don’t give it a second thought. But that’s their loss. This quirky collection of statuary clustered on the edge of a small lake is very cool.
26.2: You’re on Beach Blvd. Tons of great restaurants in case your hungry.
26.4: Back at the Ocean Pier. You took a beginning-of-ride photo, might as well end the same way to commemorate a memorable urban ride.