Walking the Streets of Old San Juan

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San Juan was our sixth and final stop on our Southern Caribbean cruise. Since neither of us had spent any time to speak of in San Juan, we made a point to spend an extra night in San Juan following the end of the cruise.

We throughly enjoyed the history of Old San Juan, not to mention the great food. It did not take long to get to Old Town from the docks, requiring only a brief cab ride.

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Disembarking in San Juan

As anyone who has cruised can tell you, cruise lines are experts in moving large numbers of people quickly.

Our disembarkation off the Adventure of the Seas was fairly painless and the folks on the ship did a good job of metering people so as not to back up the immigration and customs lines.

Pro Tip: while you can purchase airport or hotel transfers through the cruise line, the taxi service in Puerto Rico is both straight-forward and price-fixed. We saved a good bit of money by just getting a taxi.

We took a taxi to our hotel, the Condado Plaza Hilton. The drive from the docks was a bit less than a mile, but I wouldn’t try to walk it, especially with wheeled luggage. There aren’t a lot in the way of sidewalks getting there.

We were upgraded to a suite at the Hilton Condado Plaza, affording us a sitting room and a balcony.
We were upgraded to a suite at the Hilton Condado Plaza, affording us a sitting room and a balcony.

We found the hotel fantastic. The location is great. We were able to check in early, despite Citi SNAFUs. They did not have Puerto Rico has a country we were traveling to, despite the fact it is actually a territory of the United States. It took a couple of calls to get squared away.

Read TripAdvisor reviews and book the hotel.

Pro Tip: Be prepared to call Citi if you are traveling to more than five countries. Yet another great reason to have more than one card with you when you travel.

Our upgrade got us a balcony with a pretty good view.
Our upgrade got us a balcony with a pretty good view.

We met our spend on the Citi Hilton Honors Reserve Visa and Hilton upgraded us to Diamond status. The Condado Plaza Hilton upgraded us to a balcony room with a pretty good view.

Walking the Streets

The streets of old town San Juan were fairly pedestrian-friendly and we had no difficulties walking from our hotel to Old Town.
The streets of old town San Juan were fairly pedestrian-friendly and we had no difficulties walking from our hotel to Old Town.

We settled in at the hotel and grabbed our daypacks and walked into the Old Town San Juan for lunch. It was only 2.5 miles away, so nice little stretch of the legs.

The walk was really quite pleasant. It was Saturday following Thanksgiving and there was not a lot of traffic on the roads. We strolled along the Avienda de la Constitucion, walked by the capital of Puerto Rico, the Spanish House, past the Plaza Colon and into Old San Juan.

Old San Juan is a jumble of narrow streets amidst shops and restaurants.
Old San Juan is a jumble of narrow streets amidst shops and restaurants.

The best way I can explain Old San Juan is a bit of the Old World in the New World. There are narrow one-way cobblestone streets, shops, restaurants and just a lot of charm.

Cafe Manolin in Old San Juan has a great lunch service and serves authentic Puerto Rican food.
Cafe Manolin in Old San Juan has a great lunch service and serves authentic Puerto Rican food.

For lunch, we stopped at Cafe Manolin Old San Juan. A staple of the town for 70 years, the diner served authentic Puerto Rican food. We had onion steak and grouper fillets, both very hearty and tasty, for easily about $30 for the two of us. The restaurant really impressed us and we would recommend it to anyone looking for a good lunch in Old San Juan.

The food a Cafe Manolin was outstanding and quite afffordable as well. This grouper dish was quite tasty and less than $15.
The food a Cafe Manolin was outstanding and quite affordable as well. This grouper dish was quite tasty and less than $15.

San Juan National Historic Site

Our primary destination for this day trip was San Juan National Historic Site. We are Park People, so whenever we have the chance to visit a National Parks site, we make a point to do it.

We visited the Castillo San Cristobal. one of two Spanish colonial forts on Old San Juan. The Spanish spent 150 years building Castillo San Cristobal. It was the largest European fortification in the New World. The fortification overlooks the north coast of San Juan and provides protection for Castillo San Felipe del Morro, another fortification and unit of the San Juan NHS.

The Castillio San Cristobal provided impressive fortifications for Old San Juan when it was a Spanish Colony.
The Castillio San Cristobal provided impressive fortifications for Old San Juan when it was a Spanish Colony.

We have visited a lot of forts since we started visiting National Parks sites. We have seen the evolution of fortifications from the Revolutionary War to World War II coastal artillery gun emplacements. While the castillo had a lot of similarities, it still had a very distinct, Spanish feel to it.

We walked the battlements of the old fort. We walked out to the garitas, the distinctive sentry boxes along walls. The views of the city, both old and new, were great from the walls.

A view of Old San Juan from the Castillio
A view of Old San Juan from the Castillio

We dodged rainstorms through the afternoon and took a break in the weather to walk back to the hotel. The past week aboard the boat wore us out. We grabbed dinner at the hotel and went to sleep early.

The short amount of time you get at each stop is not nearly enough. San Juan is no exception. There is so much more to see just in the city alone. We must go back to Puerto Rico.

For more from our 2016 southern Caribbean cruise, be sure to read our overviewtips on staying healthy on a cruisepros and cons of staying in an aft cabin, as well as our port reports from Saint MartinSaint KittsAntigua,  Saint Lucia and Barbados.

Travel Resources
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What do you use to find a hotel?

We typically stay at Hilton properties, so we use the Hilton website. We can find good Hilton Honors discounts or AAA discounts for a hotel there. We make great use of our free night certificates from our Hilton Honors American Express.
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If there are no Hilton properties available, we use TripAdvisor to read reviews and book the hotel. We find we can get the best price that way.
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What if I need more space than I can get at a hotel?

We use Vrbo for the times when we have rented a cabin for a weekend getaway, like this cabin in Townsend, TN, or needed to rent a house for a large family vacation. We had a great experience with them in terms of refunding deposits when COVID hit and will continue to use them.
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Who do you use for rental cars?

As a general rule, we book with Hertz for rental cars. We have had nothing but good experiences with them. Plus, we really like unlimited mileage and not worrying about crossing state lines. We have even rented from Hertz overseas in both Slovenia and Croatia.
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How about booking a cruise?

We have found some amazing prices booking a cruise through Cruise Direct. We have saved a lot of money on our cruises compared to what we found elsewhere, making a last-minute Bahamas cruise even cheaper.
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What if I want to rent an RV?

We highly recommend Outdoorsy for RV rentals. We rented a camper van for a week to visit Rocky Mountain National Park for the elk rut and Custer State Park for the Buffalo Round-Up and had a blast. The program was easy to use and we really enjoyed the freedom of having a camper van for that trip.
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What do you use for booking tours?

We don’t often book tours. Typically, we like to do stuff on our own. That said, there are some experiences you just can’t have any other way. So, when we do want to book a tour, we always check Viatour first.
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Do you use anything to get discounts on the road?

We make extensive use of both Good Sam and AAA on the road. Good Sam is normally regarded as a discount card for RVers at campgrounds and Camping World but anyone can use the 5 cents off a gallon at the pump at both Pilot and Flying J.
Click here to get a Good Sam membership.

We have had AAA as long as we have been married and it has more than paid for itself in discounts at hotels, aside from the peace of mind of having roadside assistance. Add in paper maps and the ability to get an international driver’s license and it is more than worth it for any traveler out there.

Walking the streets of Old San Juan, our final stop of our southern Caribbean cruise, and seeing the San Juan National Historic Site.
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