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We enjoyed drinks at a rooftop restaurant called Punto de Vista (in the Hotel Milano). This is also a good time and area to grab lunch.
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Feel free to wander and snake your way around Old San Juan. Be warned, this is a central but touristy street. Keep going along Calle Fortaleza (the opposite direction of the Governor’s mansion) to see more of Old San Juan. 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. Either way, it is a very picturesque street.ħ) Optional (brief) detour: See the birds at Parque las Palomas During the holidays, they go all out with decorations, which we enjoyed. Turn right onto Calle Fortaleza to see “The Fortress” where the Governor of Puerto Rico lives. Just past that is Catedral de San Juan Bautista, the second-oldest cathedral in the Americas, and home to Ponce de Leon’s tomb. You’ll pass Hotel El Convento, an old convent that is now a hotel. This is Old San Juan! Take pictures of the beautiful buildings. 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. If you’re up for it, you can also visit the beautiful cemetery, Cementerio Santa María Magdalena de Pazzi, right next the fort. Take your time exploring the old fort, enjoying its spectacular views, and taking advantage of all the great photo-ops! You’ll likely see people flying kites on its huge lawn.
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Once you’re through the gate, turn left and follow the road all the way to Castillo de San Felipe del Morro. Once reserved for ambassadors and other people of importance, walk through with your head held high!Ĥ) Visit Castillo de San Felipe del Morro This is the only remaining of the historic entrances to the city. Keep going along the path and you’ll reach the Puerta de San Juan. The path is also a prime spot to view the cruise ships coming in and out. Eventually you’ll reach a beautiful fountain and some great views of the water. There are often little vendors along here selling various knick knacks. You’ll see cruise ships and find steps that will take you down to Paseo de la Princesa. Turn left on Calle Tetuan and turn right as soon as you can. After breakfast, walk a few steps down to the small park at the end of the street for some spectacular views! Their waffles are to die for, and it’s a great location to start your day. 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. Based on that experience, I’ve put together what I think is the perfect walking tour of Old San Juan. Old San Juan really isn’t that big, and we found ourselves wandering around in circles.
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The same landmarks were mentioned in everything I read, but there was no mention of how to navigate between them. During my recent visit to Puerto Rico, I came up empty when trying to research a great walking route around Old San Juan.