San Juan Cruising Travel Guide
A little History of San Juan
San Juan is not only the capital but one of the most touristed areas of Puerto Rico. Also known as “the walled city”, San Juan was founded in 154 and holds the title of the oldest European-founded city in the Americas under US sovereignty. Not a history lover? There’s plenty more things to do! With art museums, shopping centers, the variety of nightlife and of course tropical beaches; a visit to this charming city will leave you enchanted.
Our original sailing itinerary did not include San Juan, but through our travels we’ve met some wonderful people who couldn’t recommend this city enough. So once we had our fill of Culebrita, we continued our way West. Another beautiful downwind sail, the 55nm sail was easily completed in one day with us anchoring at sundown.
Table of Contents
Pocket Guide for Sailors
While the Southern coast or Puerto Rico offers a great deal of anchorage options, the Northern coast is definitely lacking. San Juan harbor is the only anchorage on the Northern coast that is well protected.
Navigating the mouth of San Juan bay is relatively easy but high northerly winds can cause waves to stack at the entrance. The channel is very wide and very deep at 42ft/13m. Not surprising, as the San Juan port is the principal port of Puerto Rico. In addition to the commercial traffic, San Juan is a favorite port for many cruise lines.
Land Access/Dinghy Docks
San Juan Bay Marina
Land access is relatively easy with both Club Náutico de San Juan and San Juan Bay Marina found right next to the anchorage. We can’t speak for Club Náutico, but San Juan Bay Marina charges $10/day for dinghy access. But with that $10/day you’ll also gain access to their coin operated laundry, wi-fi, and gated car parking. Many just tie up to the sea wall to avoid these charges, but the sea wall is covered in barnacles so you have been warned!
Provisioning (Grocery Stores)
Supermercado Pueblo/Costco
Provisioning is also on the forefront of every cruiser’s mind once arriving at a new location. If anchored in the San Juan Bay, there is Supermercado Pueblo within walking distance at 0.75mi/1.2km away from the dinghy dock. If you decide to rent a car, the world is your oyster! The best part? San Juan has a Costco! Only 11mi/18km away from the dinghy dock, we were over the moon to go costcoing! While we are not members, we ran into some friends we met in Cabo Rojo who ARE and they were kind enough to let us tag along! In addition, there’s also a Sam’s Club if you have a membership there!
Chandlery
West Marine
One of the best things about San Juan is that located just 3.5mi/5.7km away from the dinghy dock is the largest West Marine in Puerto Rico! If you drive, parking is fantastic and they won’t charge you as a patron of the store. An absolute WONDERLAND, this store has everything you could possibly need! It was definitely one of the largest chandleries we’ve ever been to!
Looking at a map, it seems like we could dinghy over to the store. We decided to try and found that it is absolutely dinghy-able! Through the San Juan Bay you’ll enter the Puerto Nuevo River and if you stay left you’ll enter the Martín Peña Channel which ends adjacent to West Marine. It does get VERY shallow, so watch your depths and go slow. We tied off at what looks like an abandoned ferry terminal and steps away is West Marine!
Anchoring
San Antonio Channel
The main anchorage is found at the end of the San Antonio Channel. Depths around 32ft/10m and good holding in mud, but pay attention to your charts! Many boats inadvertently stray too close to where cruise lines and other large vessels tie off. You don’t want to be woken up by spotlights and angry boat captains trying to dock!
What is the best way to get around San Juan?
Unlike the majority of Puerto Rico, San Juan has both Uber and Lyft available! So it’s not necessary to rent a car to get around. That being said, if you plan to do any exploring outside of San Juan (which we highly recommend!) a car rental is the way to go. We decided to rent a car for a few days so we chose our old standby, Enterprise. We chose the location at the Luis Muñoz Marin Intl. Airport but there is a closer location at the Condado Plaza Hotel. LOL, oversight in my research there! As we were paying for dinghy dock access at San Juan Bay Marina, the gated access to their parking lot was already included! So, win win!
Best Places to Eat and Drink in San Juan
The largest city of Puerto Rico, San Juan has become a foodie destination! A choice of all different types of food from world class restaurants to little hole the walls, there’s something for everyone! We really explored the food scene in San Juan, primarily because we hadn’t eaten out for awhile annnnnd we couldn’t resist with all the fantastic options available!
Filtrado
Found in Old San Juan, Filtrado is just steps away from La Fortaleza. This coffee shop is an absolute gem! Hidden amongst the pastel hues distinctive of San Juan, you can easily miss this haven for coffee lovers. The coffee beans are locally sourced from Hacienda Juanita and the area of Ciales. This café is famous for their specialty pour-overs, but they also offer espressos, and specialty drinks both hot and iced. Hungry? Try one of their sweet treats, if they aren’t sold out! Make sure to grab a seat on their patio and enjoy the quiet, shaded sanctuary under the pothos vines. Only open after noon, Filtrado’s main focus is not a caffeine fix, but to unwind and savor the complex flavors of each cup.
Café Cuatro Sombras
This popular café provided the perfect place to sit and relax after hours on our feet. Located near the cruise port, this stylish café provides an exquisite cup of joe. Café Cuatro Sombras prides itself on their farm to cup philosophy. Their single origin beans are harvested at the historical Hacienda Santa Clara in Yauco. Founded by Domingo Mariani in 1846, Hacienda Santa Clara stopped producing coffee in the 20th century. Pablo Muñoz, a descendant of Marianis, and his wife Mariana Suarez reopened the farm and in 2011 opened this café where they roast the beans on site! You will not regret a visit to this family run café!
La Tortuga Bistro Bar
Surrounded by popular late night bars, you may think this bistro is a little out of place. Location aside, La Tortuga is one of the few locations in Old San Juan to find delicious fresh bread. They also serve breakfast, lunch and dinner options. During our visit to this bistro we enjoyed some Medallas of course and pizza. But, we must mention their staff was incredible! If you find yourself in the area, stop in for a quick bite or buy some bread for later!
Pirilo
Just steps away from Café Cuatro Sombras, Pirilo is one of the best places in the area to grab a slice of pizza. Believe it or not, the crust uses a starter that’s 300 years old! Everything here is not only made from scratch, but you’ll also find pizzas ranging from unique to traditional! It has 2 locations, one in the neighborhood of Ocean Park called Pirilo Pizza Rustica and one in Old San Juan. We visited the location in Old San Juan. This restaurant also has a focus on artisanal beers to accompany your tasty pie. Believe me, you’ll want to try this pizza for yourself!
Denko Asian Eatery
Find yourself in the mood for Asian cuisine? The Distrito T-Mobile houses Denko Asian Eatery which serves up Chinese, Japanese, Filipino, Vietnamese and Thai dishes. With that many options, there’s something for everyone! We found ourselves craving some sushi and Denko Asian Eatery hit the spot!
In addition to delicious meals, Denko Asian Eatery incorporates shabu shabu style cooking with griddles built into tables. The food delivery is another unique feature as the food comes whizzing out of the kitchen in a spaceship on top of a conveyor belt. How cool is that!
La Vergüenza Puertorrican Chinchorro
This rooftop bar and restaurant has unequaled vistas of La Perla and the Atlantic Ocean. More than phenomenal views, La Vergüenza Puertorrican Chinchorro has Puerto Rican cuisine and some pretty tasty mojitos! Even if you’re not hungry, swing by for a drink and enjoy the view!
Ocean Lab Brewing
If you find yourself craving an exceptional craft beer, Ocean Lab Brewing Company is the place for you! Did you know that a city in Michigan, Grand Rapids, has been voted Beery City USA for the past 10 years? Well, as Michiganders, we’re always on the lookout for new microbreweries to try. Jon, our resident beer aficionado, was certainly impressed! We highly recommend the B.O.B or Blood Orange Blonde as the ideal accompaniment for a Caribbean day on the water. Unfortunately, they cannot ship beers to the US and as a result our coffers were considerably lighter! 😃
Located INSIDE the Vivo Beach Club, off the pristine Isla Verde Beach, this brewery not only offers beers but small plates to munch on and even a raw bar! *Something important to note is that it is FREE to visit the Taphouse, but parking is a $5 CASH charge.* The beer menu frequently rotates with fan favorites and new additions, there’s no doubt you’ll find something for everyone! Something to note, we did have to pay a small fee in order to park. But, believe me it was worth it!
La Factoría
Beer not your drink of choice? At La Factoría, the choices are endless! This speakeasy brought the art of mixology in San Juan to the center stage. Named one of North America’s 50 Best Bars for the past 5 years, there’s more than just fancy drinks here! Found in a nondescript building in the heart of Old San Juan, La Factoría is actually six bars connected by secret passageways!
- La Facto- Historically known as Café Hijos de Borinquen, this space belonged to the artists and revolutionaries of the 1950s and 60s. A visit here is like stepping back in time as the interior reflects its storied past. Make sure to order a Lavender Mule or Hijos de Borinquen!
- Vino- As the name implies, this bar is centered around (you guessed it) WINE! If you are a wine lover, with their variety of choices there is something for everyone!
- Shing A’Ling- If you find yourself in the area on Sunday or Monday, make sure to stop in. As it is their main dance hall, they offer LIVE salsa music and it turns into quite the party!
- El Final- With a wider choice of music, El Final is aptly named as it ends the line of bars.
- El Desvío- Not into big crowds? Perfect for quiet conversation, this candlelit space is the bar for you!
- La Cubanita- Serving up Cuban inspired cocktails, this space was once one of Old San Juan’s corner stores.
Best Things to do in San Juan
Below we have listed our favorite activities to do in San Juan. By no means an exhaustive list, we have have covered the main attractions if you only have a few days in San Juan. If you’re anything like us, a second visit is mandatory!
Castillo San Felipe del Morro
This citadel is a favorite attraction and one of the most visited in Puerto Rico. Named a San Juan National Historic Site and a UNESCO World Heritage Site, it is a must see while in Puerto Rico. Built between the 16th and 18th centuries, Castillo San Felipe del Morro or colloquially known as El Morro is a stalwart reminder of Puerto Rico’s colonial past. One of the largest Spanish built fortifications in the Caribbean, El Morro is definitely a testament to military strategy.
After 1598, El Morro was never taken again. But after the Spanish-American War, Puerto Rico was ceded to the US. Now named Fort Brooke, the US occupied the fortress through both WWI and WWII. Come 1961, El Morro or Fort Brooke transferred hands one more time into the National Park Service.
El Morro is the most successful defensive citadel in the Caribbean. Withstanding several attacks, it has NEVER fallen by attack from sea. But, in 1598 the English changed strategies and attacked over land. After an extended siege, the Spanish governor agreed to the surrender. Shortly thereafter, the English had to abandon El Morro. Dysentery ripped through the army and with barely enough men to crew the ships, there was not enough to hold their prize. Afterwards, the Spanish reestablished their occupation of El Morro and rebuilt.
Tickets to El Morro are $10 per person and will gain you access to Castillo San Cristóbal as well! You’ll be able to visit BOTH locations for 24 hours. We absolutely loved our visit here! Be prepared for walking, with 6 levels there’s plenty to explore and learn! Not only that, but the views of San Juan Bay are fantastic! Make sure to wear sunscreen and bring a water bottle because it’ll get hot!
Castillo San Cristóbal
Included in the San Juan National Historic Site and UNESCO Heritage Site, Castillo San Cristóbal is actually the largest Spanish built citadel in the Caribbean. Covering approximately 27 acres and partially encircling the city, Castillo San Cristóbal was completed in 1783.
After the English attack in 1598 and the Dutch attack of 1625 the Spanish learned their lesson. They started construction on San Cristóbal to defend against land-based attacks. Built with a very deep, dry moat and tunnels throughout to allow for the soldiers to move safely throughout the fort.
Make sure to see the dungeons while visiting. An anonymous captive passed their time by drawing on the walls of the prison. These drawings have been preserved and dated to the late 18th century. It is easy to see how extended time in this dank, miserable cave would be torture.
Another interesting component of both El Morro and San Cristóbal are the garitas or “sentry box”. One of the most recognizable symbols of Puerto Rico, it’s here where soldiers would stand guard protected from the beating sun or tropical rainstorms. These eye-catching garitas are undeniably popular and with the views they have, it’s not surprising!
Distrito T-Mobile
Located about 0.5mi/0.8km away from the San Juan Marina dinghy dock is Distrito T-Mobile, an entertainment complex that is hard to miss. There’s plenty to do here for everyone! Taking up 5 acres, there is a concert venue, 10 restaurants, a cinema, arcade, hotel, and even an obstacle course with ziplines!
After walking in, the first thing you’ll notice is the 14,500 square feet of LED screens in the central courtyard. You’ll find yourself surrounded by artistic videos, beautiful locations on the island, and scenes from nature. We ended up grabbing some drinks from Arena Medalla and enjoyed the atmosphere.
The primary reason we visited was to go to the cinema! With the pandemic and traveling throughout the Caribbean for 3 months we hadn’t had the opportunity to see a film in theaters in a very long time. One of my favorite things to snack on ever is movie theater popcorn with, of course, an unhealthy amount of butter! Unfortunately, we found that in Puerto Rico they do not offer butter to add to their popcorn. 
Talk about a let down!
We wandered over to Toroverde Urban Park to check out the arcade and we were not disappointed! They have everything from classic games like Galaga (Jon’s favorite), to new VR games. We are always up for a little competition! If you look up, you’ll see a hanging obstacle course for kids to test their courage! They also have indoor rock climbing, and 2 zip lines that run completely across the Distrito T-Mobile!
Explore Old San Juan
Old San Juan is one of the most picturesque areas of the city. With its cobblestone streets and architecture, it’s representative of San Juan’s colonial past. Put the map down and admire the wrought iron balconies, and brightly or pastel hued housing. This city is a photographer’s dream!
Paseo del Morro
This lovely path splits the edge of Old San Juan on one side and San Juan Bay on the other. Approximately 0.8mi/1.4km in length and circling the base of El Morro, the view over the bay is magnificent. It is completely paved and relatively flat. But it doesn’t offer much shade, so bring some water and wear your sunscreen! Along the path you’ll find lazy iguanas and LOTS of sweet kitty cats! The Cats of El Morro have been around for quite some time! With their booming population, Save A Gato was formed which traps, neuters, and vaccinates the stray cats. They continue to monitor them after returning them to their colony. You’ll find information about this organization posted along the path.
Catedral Basilica Menor de San Juan Bautista
This cathedral is hard to miss and is the seat of the archdiocese of Puerto Rico. The Catedral Basilica Menor de San Juan Bautista is the oldest church not only in Puerto Rico but on US soil! The original church was built in 1521 but sadly was demolished by a hurricane. The current church dates back to 1540 with additions and renovations throughout history with the most recent in 1917. Surviving its fair share of hardship ranging from robberies and pillaging to hurricanes and severe storms, this church also houses the famous explorer Ponce de Leon’s tomb.
La Puerta de San Juan
At one point the historic city of San Juan was completely surrounded by walls to restrict and control access to the city for protection. Of the 6 gates, La Puerta de San Juan or “the Red Gate” is the last standing. It was guarded and the doors to the gate were closed each night. Built in 1635, this gate is 16ft/4.8m tall and 20ft/6m thick and was the formal or symbolic entrance to the city. The top of the gate an inscription reads, “Benedictus Qui Venit In Nomine Domini” or “Blessed is the one that comes in the name of God ” which reminds us that the city’s foundation is based in Catholicism. Finally, closest to La Fortaleza and the Cathedral, this iconic gate was used to welcome esteemed visitors like bishops and governors to the island. Thankfully, in 1897 when many of the walls and gates were demolished to ease traffic in and out of the city, La Puerta de San Juan was spared. Found at the beginning of Paseo del Morro, you can walk the same weathered, tree lined path to the Cathedral that so many others have.
Go Sailing!
While we can’t offer reviews, getting out of the beautiful water of San Juan Bay is something we will always recommend! Club Náutico de San Juan has a sailing academy called CNSJ Sailing Academy that offers sailing lessons for both children AND adults. You have a plethora of options from one class to multiple with a range of experience from beginner to advanced! Anchored right off of Club Náutico de San Juan, we were able to see plenty of their regattas from the comfort of our cockpit! We saw Optis, Lasers, and 420s. Want to get out on the water but don’t want to learn how to sail? There are plenty of choices to charter a boat with a licensed captain! Sail Old San Juan is just one chartering option located right at San Juan Bay Marina.
*Sail Old San Juan*
*CNSJ Sailing Academy*
With everything we were able to see in San Juan, we BARELY scratched the surface of things to do! This by no means is a complete guide. We LOVED our visit and wish we were able to spend more time seeing this romantic and captivating city! Don’t believe us? You’ll have to visit and see for yourself!
