Making the Most of Your Cruise Day in San Juan

By on January 1, 2013
San Juan Island

By Vicki Boster –

A Fairly Leisurely 6 Hour Itinerary

The tropical island of Puerto Rico is only a short flight from the mainland of the United States, but it’s worlds away from the winter weather that most of us are experiencing right now. Here you can find warm and sultry breezes blowing every day of the year. You’ll enjoy summertime temperatures while exploring one of the greatest historical cities of the world. And best of all–you’ll be enjoying the convenience of traveling in a US territory where the language and currency are the same as at home— and- most importantly– your cell phones work without roaming fees! It’s the perfect wintertime escape–

natural sunscreen with zinc oxide

The famous red door on San Juan IslandOLD San Juan is one of the great “walled” cities of the world. If you are arriving via cruise ship- you will want to be on deck with your camera ready when you approach the island as the views are nothing short of spectacular. From the cruise deck you’ll view turquoise waters, a crashing white surf, the ancient El Morro fortress, the San Juan lighthouse and that famous red door– the towering impressive structure dating back to the 16th century that once served as the onlyentryway to this great city.

Once inside the city — as you begin your tour, you will immediately notice that the streets are — blue. The blue cobblestone streets of old San Juan are part of the unique heritage of this city. The streets are made from blue ballast stones that came to the island as weights in the bottom of the sailing ships that once crossed the oceans. The great history that is the very essence of OLD San Juan only begins with the cobblestone streets. This city – a UNESCO World Heritage site– is steeped in historic and religious traditions that date back hundreds and hundreds of years.

For many people– their only exposure to this city of historical treasures is by way of a cruise ship. Most ships that dock in San Juan Harbor have only limited time here– usually 6 -8 hours. (That is not really enough time to get to any of the beaches but– don’t worry, BE HAPPY because Old San Juan is one of the most historic and beautiful colonial cities in the world and it is only a few steps from the pier.)

In order to make the most of your cruise day here you’ll need to make a plan AND be ready to hustle as soon as the ship is cleared for your exit. Lucky for you (!!) we’ve been there and done that– so here is our 6 hour itinerary to help you get the most of your day in historic Old San Juan–

Vicki Boster on San Juan IslandHour 1
Exit the ship as early as possible! Walk toward the hill and bear to your left along the bay beside the water— you will be walking towards the harbor entrance along a wide, paved sidewalk that will lead you to the famous Red Door. But first, just a short distance from the pier (under a group of shade trees) you will pass a small artisan market. Local artists set up shop here to sell their locally handmade items. Take a few minutes to shop if you want– if you see something you want- buy it now– it won’t be there on your return later today. (My pick of the artisan crafts– locally made sea glass earrings. I buy bunches to give as souvenirs and Christmas gifts.)

Have your cameras ready because the entire stroll along this path is a huge photo op! When you get close to the door watch for kitties who live in and amongst the large rocks that line the coastline. They are protected and cared for by the local humane society (Actually the organization is ‘Save a Gatto. it is not THE humane society). Hundreds of kitties live here– if you love cats– (and we do!)– you will love this section of your walk. You can see them sunning along the banks near the water and on the hillside. Some are friendly and love to be petted, while others are more timid and will watch you from afar. Please don’t feed the kitties– they are well cared for as evidenced by the little food and water bowls that you will see tucked in amongst the rocks. Want to help? Give a small donation to the society volunteers if you see them along the path– your donation will be so greatly appreciated.

San Juan Island CathedralHour 2
Pass through the massive red door (stopping to take photos of course!)–and walk up the hill until you see the majestic 16th century San Juan cathedral. The Cathedral of San Juan de Bautista dates back to 1521. It is one of the oldest buildings in Puerto Rico and is considered to be the second oldest cathedral in the Western Hemisphere. Take about 30 minutes to explore the cathedral- perhaps even visit the grave site of the famed spanish explorer, and first governor of Puerto Rico,Ponce de Leon.

Hotel El ConventoHour 3
Just across the street from the cathedral you will fine one of San Juan’s most beloved treasures– the Hotel El Convento. This hotel (which is on the National Historic Register) originally began as a nunnery. Founded in 1651- this historic building has now been converted into a 5 star prestigious hotel. Noted for its old world charm and decor, this is the perfect place to take a little break. Walk inside the hotel lobby and marvel at the stunning black and white tiled floor– be sure to notice the intricate woodwork on the walls and doors. Inside the beautiful atrium you will find both a bar and a restaurant. This itinerary allows time for you to grab a quick lunch or drink. ( I recommend the house salad with fried cheese garnish!). If you don’t stop for lunch- you can use your extra time to explore the plaza and area right around the cathedral and hotel– it’s one of the most beautiful plazas in the city.

San Juan IslandHour 4
Here we go- UP the hill! After leaving the hotel, bear to the left and walk up the hill towards the El Morro fortress. For over 400 years El Morro has guarded the San Juan Harbor. Visiting this ancient relic is one of Old San Juan’s must see attractions. (Since 1961 the forts in Old San Juan have been part of the US National Parks–so if you have a National Parks pass –you can use it here!) Have your cameras ready– the views from the top are going to be amazing! (If you are not up to the steady uphill climb- you can wait for the tourist trolly to take you to the top of the hill.)

Once you are at the fort– you will need to make some decisions. You can pay the entrance fee and tour the fort, or you can walk around the perimeter area outside and take LOTS of amazing photos. You could easily spend hours inside the fort- it’s an incredible structure and most definitely worth your time— but time is of the essence here– so if this is your first visit to old San Juan, my advice would be to spend almost an hour on the outside taking photos. You can take pictures of those ancient domed garitas- the iconic symbols of Puerto Rico– as well as stunning views of the harbor and areas surrounding the fort. Then we gotta go– we still have lots to see!

San Juan cemetaryHour 5
Just over the hill from El Morro- bordered against the crashing surf and turquoise waters of the Atlantic Ocean is MY most favorite place in old San Juan–the Santa Maria Magdalena Cemetery. Located just below El Morro on the cliffs overlooking the Atlantic- this final resting place is considered to be one of the most picturesque in the world.

This beloved colonial era cemetery dates back to the early 1800’s. Beautifully situated by the sea, on a sunny day the dazzling bleached white tombs and statues make for a stunning contrast against the turquoise waters and the deep blue sky. Famous for its religious figures and statues- this cemetery is one of my favorite places to photograph when visiting old San Juan. In the center of the cemetery is the red domed chapel dedicated to St. Mary.

You can take stunning photographs of the cemetery while standing on the hillside just below the fort. For those desiring a closer look– (like me!!)- a word of caution must be noted. The cemetery is located next to La Perla- one of old San Juan’s least desirable neighborhoods. During daylight hours you are perfectly safe to walk (Through the tunnel) and then go inside the cemetery and around the cemetery wall. ( a closer look will bring you to the Children’s tree. A memorial to the children who have died– the tree is hauntingly beautiful as it is filled with children’s toys and mementos). But from dusk to dark– Do not go there. The adjacent area is dimly lit and is known for unsafe activities. You should have plenty of time to take photographs from the hillside before it gets dark.

Hour 6
After leaving the fort /cemetery area–walk back down the hill towards the cruise ship pier– this should be about a 20 minute walk. When you get to the boutique lined streets in the historic area– it’s time for some shopping! (What? Did you think I wouldn’t allow time to shop?)

If you’ve stayed on task with this itinerary you should have about an hour to stroll the cobblestone streets taking in some of the unique and eclectic shops. This area is a shoppers haven with everything from outlet stores to high end designer merchandise.

Another note of caution–depending on the time of year you make your visit– it may be dark when you get to this part of your tour. Most cruise ships arrive in San Juan in the early afternoon and depart between 10 and 11 pm. The shops will stay open as long as ships are in port. When walking around town after dark– stay away from dimly lit side streets and alleys. Anywhere the shops and tourists are is perfectly safe– just avoid the side streets.

After a busy day– you will be able to get back on the ship and marvel at all the wonderful sights you’ve enjoyed in your tour of old San Juan. When someone asks “what did you do in the city today?” — you will have some amazing stories to tell!

Notes: If you are interested in touring inside either of the forts, the fees and hours of operation can be found on the National Park Service ( website but are generally from 9:00am until 6:00pm. The Cemetery closes at 4:00 weekdays and earlier on weekends. If you really love old forts then you might want to substitute a tour of Castillo San Cristóbal , the San Juan’s other famous fort, instead of the shopping portion of this tour.

With her bags always in a state of readiness, Vicki yearns to travel to places she has never been.   She and her husband have traveled around the world; her photo essays beautifully detailing the amazing places that she has visited.  When she is not on the go, you can find Vicki at her blog

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Making the Most of Your Cruise Day in San Juan