One Day in Old San Juan: A Step-By-Step Walking Tour
During my recent visit to Puerto Rico, I came up empty when trying to research a great walking route around Old San Juan. The same landmarks were mentioned in everything I read, but there was no mention of how to navigate between them.
Old San Juan really isn’t that big, and we found ourselves wandering around in circles. Based on that experience, I’ve put together what I think is the perfect walking tour of Old San Juan.
If you have all day, this will fill the whole thing nicely. However, you can easily cut one of the forts out or forgo the last part of the itinerary if you have only half a day to spend.
1) Grab breakfast in Old San Juan
I recommend Waffle-Era. Their waffles are to die for, and it’s a great location to start your day. After breakfast, walk a few steps down to the small park at the end of the street for some spectacular views!
2) Walk down to Paseo de Princesa
Turn left on Calle Tetuan and turn right as soon as you can. You’ll see cruise ships and find steps that will take you down to Paseo de la Princesa. There are often little vendors along here selling various knick knacks. Eventually you’ll reach a beautiful fountain and some great views of the water. The path is also a prime spot to view the cruise ships coming in and out.
3) Enter through the Old San Juan Gate
Keep going along the path and you’ll reach the Puerta de San Juan. This is the only remaining of the historic entrances to the city. Once reserved for ambassadors and other people of importance, walk through with your head held high!
4) Visit Castillo de San Felipe del Morro
Once you’re through the gate, turn left and follow the road all the way to Castillo de San Felipe del Morro. You’ll likely see people flying kites on its huge lawn. It’s $5 to get in, but well worth it. Take your time exploring the old fort, enjoying its spectacular views, and taking advantage of all the great photo-ops!
If you’re up for it, you can also visit the beautiful cemetery, Cementerio Santa María Magdalena de Pazzi, right next the fort.
When you’re finished exploring, make your way up Calle Norzagaray until you reach Plaza del Quinto Centenario (you can’t miss the giant totem pole and sheep statues), and walk up through the plaza.
5) Wander along Calle del Cristo
This is Old San Juan! Take pictures of the beautiful buildings. Browse through the shops. Grab a coffee, beer or snack.
You’ll pass Hotel El Convento, an old convent that is now a hotel. Just past that is Catedral de San Juan Bautista, the second-oldest cathedral in the Americas, and home to Ponce de Leon’s tomb.
6) View La Fortaleza
Turn right onto Calle Fortaleza to see “The Fortress” where the Governor of Puerto Rico lives. During the holidays, they go all out with decorations, which we enjoyed. Either way, it is a very picturesque street.
7) Optional (brief) detour: See the birds at Parque las Palomas
You can continue further along Calle del Cristo if you wish to visit Parque las Palomas, a park with nice views and a ton of pigeons that live in holes in the wall.
8) Grab lunch along Calle Fortaleza
Keep going along Calle Fortaleza (the opposite direction of the Governor’s mansion) to see more of Old San Juan. Be warned, this is a central but touristy street. You’ll see tons of souvenir shops. Feel free to wander and snake your way around Old San Juan.
This is also a good time and area to grab lunch. Many people rave about Chocobar. We enjoyed drinks at a rooftop restaurant called Punto de Vista (in the Hotel Milano). The rooftop has a nice atmosphere, and they have Puerto Rican food as well.
9) Visit Castillo de San Cristóbal
Continue along Calle Fortaleza and you’ll reach Plaza Colón. A little further and you’ll find yourself at Castillo de San Cristóbal, the largest Spanish fort in the Americas.
If you have time, consider taking a tour, as there is a lot of fascinating history here. While I have not had the fortune of taking it myself, I have spoken to Karen at Archtours about her tour of this fort and it sounds incredible. (All of her tours do! She is a professional architect who has worked on many of Puerto Rico’s heritage sites, so she really knows her stuff.)
10) Take a breather
After your tour of San Cristóbal, take a little time to relax. This may be a good time to go back to grab a drink, or head back to your hotel to unwind and change.
11) Enjoy dinner in Condado or a night on the town at La Placita
Feeling up for an evening of fun with the locals? Head to La Placita (especially on a Thursday or Friday). There are plenty of food options, so if you want nourishment but not a late, crazy night, go earlier in the evening or during other days of the week.
If the day has left you exhausted, enjoy a more low-key evening in Condado. There are plenty of places to eat, but we really enjoyed Di Parma Trattoria. It has a great ambience (and great for people-watching) right on Parque La Ventana al Mar (which, as its name implies, is right on the ocean). If oceanfront views are especially important to you, there are plenty of other options.
Follow me to Fiji!
Today I’m getting back to my travelin’ and work abroad ways. I’m spending the summer in Fiji working as a Global Communications Coordinator for Rustic Pathways.
I’m not sure how much updating I’ll be able to do while I’m on the ground, but you can follow along with my adventures creating future global citizens on Instagram at @rusticrachael!
An African safari is a dream for most travelers, a bucket list item almost everyone hopes to do some day. I’ve had safari dreams for as long as I can remember, but I always imagined it would be something I wouldn’t get to do until much later in life.
Lucky for me, the opportunity came much earlier (basically because I have an awesome dad!). The park, Zulu Nyala Safari Park, and even the region of South Africa (near Hluhluwe in KwaZulu-Natal) doesn’t have the largest wealth of information about it on the internet, so I was apprehensive that the animals would be very hard to spot or far away. Thankfully, this was not the case at all.
Our safari was, in a word, incredible! We enjoyed five days of pure safari bliss, and every single day was amazing. Without further ado, here are some of our safari highlights. Read more…
Celebrate Valentine’s Day With Some Snuggly South African Animals
When I was in South Africa I witnessed a lot of animal lovin’. Some if it was not quite appropriate to share here… but some of it was cute!
So whether you’re spending your Valentine’s Day cuddling up with a backpack, a book, or another human being you care about… enjoy some cute and cuddly African wildlife!
The first thing we saw on our first day on safari at Zulu Nyala… nuzzling zebras!
Young zebra cuddling up to mama….
A cozy hippo pileup at iSimangaliso Wetlands Park.
Awww.
I conveniently cropped out the jealous ex-lover so it would seem sweeter 😉
But I guess we should live in reality….. He’s there! ————–>
HAPPY VALENTINE’S DAY!
The Best Way to Spend Three Days in Cape Town
Sawubona!
So you’ve got three days to spend in South Africa and you’re at a loss of what to do. My first and most important secret tip: spend more than three days! If there is any possible way to do that, do it.
Planning to have an extra day in Jo’burg or Durban? I may get flack for it, but cut that day and add it to Cape Town! There is SO much to do in this incredible town, three days just isn’t enough.
That being said, I get it, sometimes three days is all you have… And it’s better than two! I myself was guilty of allocating only a trio of days to the lovely Cape Town, and while I left feeling I had just scratched the surface, I certainly didn’t leave disappointed so I dare say my itinerary is one worth following if you are looking to build a three-day itinerary. Read more…
How to Have A Perfect Day Exploring South Africa’s Cape Peninsula
Cape Peninsula is a must do if you have more than a day or two to spend in Cape Town.
During my three-day visit to Cape Town, we felt it would be easier to hop on a day tour since we were strapped for time and hadn’t had as much time to plan ahead as we’d have liked. The day tour — which we took with Cape to Addo — was fine, but we felt rushed and wished we could have spent more time in certain places than we were able. We also would have liked to have been able to stop off at different places and maybe not stop off at others. We wished we could have had more flexibility. Read more…
Wine Flies: The Ultimate Wine Tasting Around Cape Town
Excuse me while I gush, but South African wine is to die for! I wish America would figure this out and stock more if it in regular stores. If you’re looking for a classic South African wine to try, the Pinotage (a red) is a great place to start.
There are three main wine regions around Cape Town: Stellensbosch, Paarl, and Franschhoek. Given the nature of wine tasting, it’s probably best to join a wine tour rather than try to drive yourself to full enjoy the experience. I highly recommend the tour company Wine Flies. 
We had a fun mixed group of couples, friends, students and solo travelers from the UK, US, Japan and Brazil. By the end of the day the group had become close (admittedly in large part due to our shared making fun of, and later annoyance at, one group member, who proceeded to get drunk at the first winery and remain so all day), we even met up later that evening for drinks. On the one-day tour, we visited five wineries, which represented a wide range of styles and sizes. Read more…
Adventure in South Africa: Abseiling Down Table Mountain
No trip is complete without at least one adventure activity. Whether you’re a thrill seeker or a worry wart, abseiling down Cape Town’s Table Mountain is one of the best choices you can make!
Abseil Africa runs abseils at the top of Table Mountain every day, weather permitting. If you’ve never been abseiling or rappelling before, the idea of doing so off the top of a 3,500-foot mountain may seem terrifying, but there is really nothing else like it. Truth be told, I can’t think of a better place in the world to do it. Talk about spectacular views!
Tips for a Fantastic Fall Getaway in New England
Believe it or not, until last October I had never been anywhere in New England before. Yes, I am one of those ridiculous people who has been to more countries than states. I also had not seen a typical all-American fall in very long time, having lived in Florida and Australia for the past few years.
So I was very excited to do a road trip through one of the world’s premier “fall foliage” destinations.
In one week I drove through 11 states — six of which I had never been to before! When I go, I go big. As a New England newbie, I learned a lot from my experience and gathered a few tips on how to make sure you have a perfect fall getaway in New England. Read more…
Why Gutsy Women Travel
The first time I traveled alone, I spent part of my time on a backpacker bus in New Zealand. As far as solo travel, that’s about as easy as it gets — a) it’s New Zealand, and b) you’re “alone” on a bus full of other travelers, that takes you from point A to point B to point C, so you really don’t have to worry about much.
And yet, time and again I met other women who were shocked that I was traveling alone.
“I could never do that,” they would say. “You’re so brave.”
At the same time, those women were gutsier than they even realized, because there are plenty of women back home who would say the same thing about traveling abroad at all, whether with another woman, or even a man or group. In short, it takes a gutsy woman to travel abroad, alone or otherwise, and we think more courageous women out there should take the leap! Travel. Take a gap year. Volunteer. Teach. Get out there.
Girl, Unmapped 
