Old San Juan – Anniversary Trip

It all started with the airfare. We had booked a cruise out of San Juan, Puerto Rico to celebrate our ten year anniversary, and all that was left was to find a way down there. Well Eric, being the travel guru that he is, found us an AMAZING price on airfare…the week BEFORE our cruise. So naturally, he asked if I’d be interested in renting an Air Bnb in Old San Juan and exploring the old city for a week. Well, it turned out to be the BEST decision ever. Outside our one-bedroom AirBnb penthouse apartment had phenomenal views from our private terrace. Inside it came equipped with a kitchen, dining area, living area, and even a washer dryer! Living like locals and exploring the all the hidden places around the city was an incredible experience (not to mention an incredible leg workout, those hills are no joke!!)

We have what feels like a million pictures from Old San Juan, plus our tips for staying in the city, AND a bonus list of our favorite sights, and our favorite places we ate. These are a mix of mine and Eric’s DSLR and camera phone pictures. ENJOY!!

Our kitchen and our private terrace!old-san-juan-tips_0064.jpg
old-san-juan-tips_0065.jpgOur view from the terrace!

old-san-juan-tips_0067.jpgThe cathedral from our kitchen!
old-san-juan-tips_0068.jpgPaseo de la Princesa
old-san-juan-tips_0079.jpgCasa Blanca
old-san-juan-tips_0083.jpgEl Morro
old-san-juan-tips_0091.jpgPaseo de la Princesa at night!
old-san-juan-tips_0093.jpgThe gardens at La Fortaleza
old-san-juan-tips_0097.jpgSo. Many. Pigeons.
old-san-juan-tips_0099.jpgThe San Juan Gate at night.
old-san-juan-tips_0101.jpgLOTS of well-behaved cats on the Western side of the city.

Our Tips for Staying in Old San Juan

– Don’t Rent a Car – Unless the beach is important to you won’t need one. Parking is a nightmare, and navigating the tourist laden one-way streets seems like a hassle. Plus, the city is roughly 8 by 7 blocks, getting everywhere by foot is easy. There’s also a great free trolley system that will take you around the city,

– Carry an Umbrella (or disposable ponchos) – Caribbean climates are known for short rainstorms, but it was especially rainy during our trip. It rained every day, and once ALL day.

– Rent an Apartment – Especially if it has laundry, a kitchen, and AC (because the humidity was REAL folks). Living like a local was our favorite part of our experience, especially since our Air Bnb was located so conveniently to everything we wanted. There’s even a grocery store located very centrally in Old San Juan where the prices and selection were surprisingly great.

– See the Local Attractions, Avoid the Tourist Traps. – Most of the major historical sites, gardens, and monuments in the city were either free or extremely cheap to see. Just walking the city was nice, especially in the early morning, or in the evening when there aren’t ships in port. The really touristy restaurants, shops, and tours aren’t worth your money if you have the time to wander on your own.

– Know when there will be Cruise Ships in Port – Old San Juan has a BIG port, and the city gets BUSY when there ships docked. It can mean the attractions are a little more crowded, but the hustle and bustle was a nice contrast to the sleepy more relaxing days. Use a website like http://ports.cruisett.com/ to get the info.

– Wear a good sunscreen and a good bug spray – Just because there’s plenty of shade on the narrow streets doesn’t mean you won’t burn. And speaking of those narrow streets, they are full of little uneven areas where mosquitos can breed. The city does a GREAT job trying to keep puddles from sitting too long, we rarely saw any insects, with the exception of a few restaurants and private residences that weren’t as vigilant. If Zika is a concern for you always put it on before you go out, and ensure you’re staying in a place that has glass windows and air conditioning.

– Wear Comfortable Shoes – In fact, bring several pairs of comfortable shoes. Your feet WILL get sore, because the city is much bigger and much steeper than it seems in pictures. The historic forts by themselves are each enormous complexes with multiple stories to explore.

Our FAVORITE sights in Old San Juan:
Paseo de la Princesa – Daytime, nighttime, anytime.
Castillo San Felipe del Morro – The iconic fort on the North Western tip of the island.
Castillo de San Cristobal – Another huge historic fort with amazing views!
Museo de Casa Blanca – Ponce de Leon’s House
La Fortaleza – The Governor’s Mansion for the current Governor of Puerto Rico, FREE tour!
The San Juan Gate – The last remaining gate into the city.
Parque de las Palomas – Endless entertainment for people and pigeon watching.
The Cobblestone Streets and the Colorful Buildings.
Our FAVORITE food in Old San Juan:
Pirilo Pizza Rustica – Legit Pizza, amazing flavors, great ambiance if you’re seated upstairs.
The Mezzanine at St. Germain – Tasty tapas, and delicious drinks. Their happy hour specials are amazing!
Deaverdura – Authentic Puerto Rican food. Hole-in-the-wall with no menu, ask for the Taste of Puerto Rico platter.
El Meson Sandwiches – Fast food, but on amazing soft fresh bread. The corn fritters were to die for, and the sandwiches were big enough to split.
Waffle Era Tea Room – Insanely good, ridiculous cheap waffles. Take me back!!
Case Cortes Chocobar – A family run and owned restaurant where they make their own chocolate, and it’s in every dish. Try the chocolate covered coffee beans!
Cafe Don Ruiz – Great ambiance for a little coffee shop so close to El Morro fort. Tasty mallorca sandwiches, and fantastic coffee (that they roast themselves!)
Cafe Cuatro Sombras – My favorite coffee in Old San Juan, my favorite coffee EVER. They roast their own beans and the result is perfection.

That’s all for now, but if you’ve got specific questions send us a message, we’re happy to help! Next up: a recap of our cruise!