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Historic San Juan in a day Walking Tour

Whether you have an extended stay in Puerto Rico, or less than a day from a cruise stop over, here’s my walkable itinerary for seeing the best of San Juan.Puerto Rico in one day! Experience history, art, shopping, and admire tons of cool city architecture.

Start

The San Juan Port in the historic area. Grab some bottles of water from the shops around the port as you’ll head up the hill on Calle Marina street to Castillo San Cristobal, the largest fort built by the Spanish in the New world.

Distance ~0.5 miles

Along the way you’ll pass some squares with little shop tents if you’re a fan of the blown glass, one of the tents that is along the way makes little blown glass animals right there for figurines or jewelry. You’ll also see lots of brightly colored buildings and as you finish the uphill trek, you get an awesome view of the port looking down on the big ships docked there.

Peak down all the colorful alleyways as you trek up the short hill

Vising Castillo San Cristobal

Hours: 9:00-6:00 PM everyday

Cost: (16+): $7.00

*If you have a National Parks Pass, you can get 4 adults entry for free.

This fort as mentioned is the largest Spanish fort in the Americas, spanning 27 acres. It took 150 years to build with construction beginning in 1634. It covers the Eastern gate of San Juan Island and its walls extend in either direction of the coast. There are 3 levels to explore: cannon embrasures, sentry boxes, tunnels to explore, and exhibits to learn about the former military quarters. All in all, it’s a great stop and won’t take longer than an hour for self-guided tours.

**You can also get married here.. *swoon*

After San Cristobal, follow the sea coast along Calle Norzagaray where you can explore old parts of the wall that made up San Cristobal’s defenses with multiple garitas (guard towers) and historical markers. Learn about the La Perla area of San Juan where another fort used to be as you make your way to Castillo San Felipe del Morro. Here walk across the great lawn taking in all the kite flyers and the size of this incredible fort perched on the bay.

Distance ~ 1 mile

Vising Castillo San Felipe del Morro

Hours: 9:00-6:00 PM everyday

Cost: (16+): $7.00

*If you have a National Parks Pass, you can get 4 adults entry for free.

If you have to choose between visiting the 2 forts, this would be the one to go with. While overall containing less “acres” than San Cristobal, this fort has 6 levels and unparallel’d views of the bay and San Juan Isle. While San Cristobal was built to defend against land invasions primarily, this fort was built to defend the bay. And defend it did as there is only one instance where the fort was penetrated by enemy invaders making it the most successful of all the Spanish forts built at that time. Construction began in the 1500s when the battery and tower were built to protect the harbor. In 1632, the governor of San Juan began construction on San Cristobal and the city walls. It was also the center of Spanish life at the time so the structures contained within the fort have a lot more complexity making the tour a bit more interesting.

After a visit to the fort, walk down the stairs on the right/ East side to the start of multiple trails. If you follow the same trail to the right/ East it will take you to the cemetery you pass as you approached the fort from the street. Heading left/ West the path wraps around the bottom of the fort and connects to the Paseo del Moro trail.

Views looking East along the Paseo del Moro trail

Paseo del Moro

This trail was my favorite part of San Juan. (shocker right.. I do love trails) It follows the old wall almost around the entire western side of Old San Juan with nothing else along the way besides the ocean and cats. The old wall has been wonderfully maintained dating all the way back to 1630! Between the wall and the ocean, it’s like walking into Pirates of the Caribbean scene. Along the trail you can also watch the big ships leave from port back to the open ocean easily catch wildlife (other than cats) out in the water. The area directly under the fort has multiple tide pools that can be peaked into, but be careful not to slip on the wet rocks or get soaked by a sneaky wave.

Watching a large ship sail out of San Juan Bay

The area which is maintained by the NPS like the forts, is also serving as a cat sanctuary with little cat boxes, food, and water to help the strays out. There were so many adorable cats, most of which won’t let you get too close but will play with a bit of string if you have some. (My dad led a cat by the string quite a ways down the path as it follow and continually pounced on it)

After following the trail a ways (approx. 0.75 miles) you’ll have two options to make you way back into town and then back to the port. The first option is to turn in at the Puerta De San Juan The Iconic red gate that served as the doorway for dignitaries and bishops to enter into San Juan back when there were only 5 gates into the city.

Or another 5 minutes down the path, the trail ends at a beautiful fountain on the Paseo de la Princesa which is lined with shops, galleries, and also includes for those of you who skipped out on bathrooms at the forts, a public toilet.

Watching a cruise ship sail past the old San Juan walls out into open ocean

Both gates are great options and worth seeing if you have to backtrack as the path between the two has beautiful trees overhanging the path and the fountain is really cool. The old gate takes you down Caleta de San Juan straight to the San Juan Bautista Cathedral. From either location, make sure to head over to Fortaleza street to see the fun umbrella covered walkway and explore more little shops and restaurants. And from there with whatever time you have remaining, head back to your hotel or cruise ship.

Distance ~ 0.75 miles depending on the road you take

Walking Distance for entire loop ~ 3 miles/ 5 km

Colorful buildings of San Juan visible over the old wall

The Paseo del Moro is also a wonderful walk to do at sunset

Other Points of Interest around San Juan to check out in a day:

Museum of Arts of Puerto Rico

Condado Beach

El Yungue National Forest and waterfalls

Tour of the Bacardi Distillery

OK Time for the ULTIMATE CONNECTICUT HISTORY SITE TOUR! First stop: The Nautilus Submarine Museum in Groton, Connecticut.

I kid you not, this is one of the coolest museums out there. (AND IT IS FREE!!!!)
Hours of operation: everyday 9-5, closed Tuesdays.
They WILL kick you off the property by 5:15. haha

As the sub part of the museum closes a bit earlier than the museum, we hit that up first.

They have a 20-30 minute audio tour that guides you around the sub. We didn’t have to ask “Permission to come aboard”

Tight quarters, steep ladders, and tight spacers. Do NOT recommend wearing a dress or flipflops. (My dad taught me well so you know I was in my closed toed shoes)

Back on top with the “Don’t tread on me” flag.

The entrance to the museum. I LOVE the contrast of the smallest sub vs. the largest marking the gateway to the museum.

Overall AMAZING museum for history on the Nautilus as well as Navy Submarine uses. They have family friendly activities including being able to look through a periscope to see real time “outside the museum” as you turn in different directions.
Left: a crazy “bomb” planter that people would literally pedal to power and would use to put explosives on the ocean floor.

Nautilus cool history: One of the first subs to be powered by Nuclear energy (as opposed to Diesel fuel) which allowed her to travel far greater distances submerged under water and at faster speeds. She broke quite a few records in her day, most notably as being the first sub to make a submerged transit of the North Pole in 1958.

For those not cool with the confined spaces on the sub, there is a lovely model in the museum with explanations of the various sub compartments. You can get a pretty good idea of what life was like on the Nautilus without having to step foot on it.

From Groton we headed across the water to Fort Trumbull in New London. Looking back across you can see General Dynamics (manufactures submarines!)

Fort Trumbull was a HUGE fort that I bet would be SUPER cool to explore, but alas we were there before it opened for the year.
Hours of operation: Wednesday through Sunday from 9:00 am to 5:00 pm from May 21 through Labor Day. For entrance to the visitor center museum and for fort tours, there is a fee.

The fort is considered a state park however and you are still able to walk around and enjoy the beautiful outside walls and ocean views FOR FREE! The park itself is open daily from 9-8. So bummed we didn’t get to tour around the fort, but hey free is free and the outside was QUITE impressive.

History of the fort: The original fortification (nothing like the current fort) was completed in 1777 and was attacked/ surrendered to the British in the Groton Heights Raid in 1781. (Much more on that later) There is only one small building from that time period left which housed the battery. The current fortress was built from 1839-1852 and served many a purpose throughout the years including a Union headquarters for recruiting and training during the Civil War, as a headquarters for the many other forts in the area in the time after the Civil War, as a Merchant Marine officers Training school until WWII where lastly it was used as a Division of War Research that developed Sonar systems. It opened as a State park in 2000.

My next favorite history spot is actually back in Groton at the Fort Griswold battlefield which I explored one day while Katie worked so Olive accompanied me instead. (so yes Dogs are welcome here as well as long as they are leashed.) Fort Griswold is ALSO a state park and the battlefield is free to explore and open daily. The monument and museum onsite is also free and open from 9-6 but closed on Mondays and Tuesdays which means.. I didn’t get to go in them. 🙁 (also like Fort Trumbull is only operational in the summer from Memorial day to Labor day)

BONUS THOUGH: Fort Griswold has a CELLPHONE Audio tour. and it is AWESOME. You just call (860) 424-4005 and select which stop you are at. (Unfortunately you do have to call again at each stop but there are only 5… so not a big deal) It took me maybe 20 minutes to listen and explore all 5 stops. The main gate and cannons at stop 2 (with the monument/museum being stop 1)

It’s a bit small in this photo, but looking across the way you can actually see Fort Trumbull.

A summary of the battle here is that on September 6,1781 the infamous traitor Benedict Arnold led the British in a raid on the Groton area with troops of 1700 men to take down both Fort Trumbull and Griswold. The British forces were divided into 2 groups of around 800 men. Fort Trumbull fell first, after which the British were able to turn their full attention on Griswold. There were only 166 American volunteers defending Fort Griswold so to say they were the underdogs is an understatement for sure. This realization didn’t take long to sink in, however the British offered no quarter so the Colonel Ledyard led his men to continue in the battling in the fort’s defense. The fort did push the British back a time or two, however they still were able to overtake the Americans. When the British asked who was in command, Colonel Ledyard handed over his sword and said “You are now” and was reportedly then killed with his own sword. While some men were able to escape using the various dry moats around the fort, over 80 men were massacred as the fort was surrendered and another 60 men were “mortally” wounded according to General Arnold’s reports. The British losses were 45 men killed and another 145 men wounded causing General Arnold to complain of the high casualty rate on their side. As this battle occurred towards the end of the Revolutionary war, it was one of the last British Victories as only a few months later, General Washington led us to victory in Virginia.

This is the main gate into the fort. It was recorded that one British solider was able to successfuly scale the fort’s walls and opened the gate for everyone else to invade. The fort has sunk quite a bit in but still remains pretty tall, especially with the dry moat running around the outer edge.

On the other side of the fort is a smaller tunnel entrance.

I absolutely loved the audio tour (if you couldn’t tell) as I actually remembered all of that information (though I did fact check my memory when I typed it all up) so I definitely recommend the audio tour. There are a few informational plaques that have a summary of the day’s events at the entrance to the fort. There is also a memorial plaque dedicated to those volunteers who fought at Fort Griswold, and another plaque within the fort dedicated to Colonel Ledyard (where it is said he was killed with his own sword)

A view from one corner looking at the inner fort with the monument in the background. The monument is super interesting as well as it was the FIRST obelisk monument built within the United States and was constructed from 1826-1830. It stands at 135 feet tall and has 166 steps, 1 step for each volunteer that fought in the battle for Fort Griswold. (I really wished it was open but alas… I was there on my last day, a Tuesday.)

Sooo there you have it, a lengthy overview of the incredible historic sites/museums that were all within 30 minutes of Stonington Connecticut. I’m glad that I was able to glimpse a bit more of American history both Revolutionary time periods and modern while I was visiting out there. As I visited over Memorial day, it was so much easier to ponder these battlefields and the men who fought on them.
Again price recap: All of these places are FREE (with exception to tours in Fort Trumbull which I wasn’t able to do anyways) If you are in the Connecticut area, I highly recommend a visit to each of these places.

Walking Tour of old San Juan

Visiting the COOLEST Connecticut history sites