Puerto Rico promises days under the sun and nights on the dance floor. It’s nicknamed la isla de encanto, which means the island of enchantment. The hum of tree frogs, the turquoise blue waters, and colorful cobbled streets cast a spell on you that whispers, “Come back to Puerto Rico” in your ear long after you’ve left the island.
So, pack your bags and grab your friends because we’re going to San Juan, Puerto Rico, again and again. Puerto Rico should prepare to be sick of you and your crew.
San Juan, Puerto Rico, is perfectly poised for a girls’ trip. It’s the heartbeat of the island with great places to dine and dance while still being within driving distance to the jungle and beaches. Every day in San Juan is a chance to chase the euphoric feeling of getting ready with the girls for a fun night out after the sun has kissed your cheeks. The blueprint to your daily itinerary is to spend time outdoors, whether it’s the beach or the jungle, and then go out at night for dinner and dancing.
San Juan v. Viejo San Juan
When you picture San Juan in your mind, what do you see? Colorful colonial facades and cobbled stone streets. The postcard of San Juan you’re imagining is Viejo San Juan (Old San Juan). Viejo San Juan is the oldest city in the United States and its territories (Puerto Rico is a U.S. territory!). Viejo San Juan lives in its own bubble at the tip of the larger capital city of San Juan. It’s very walkable, and you’ll spend a lot of time here exploring, going to dinner, and dancing til 2 a.m.
While Viejo San Juan is the main tourist destination of the island, it isn’t the only part of San Juan. The greater San Juan area includes places like Condado, Santurce, and Isla Verde. This is the real city where most locals live. There are plenty of spots to explore in greater San Juan; you just need to know where to go, so let’s get into it.
The Hit List
Wander the streets of Viejo San Juan
Viejo San Juan is the #1 tourist attraction in Puerto Rico. A walk around the town will take you past colorful colonial buildings, fortified castles, and Spanish-style plazas. The streets are lined with plenty of stores, cafes, and bars to pop into to escape the heat with a blast of AC. You can walk every street in Viejo San Juan within an hour or two, but you’ll likely spend more time here while taking photos and stopping for a drink.
Marvel at the Castillo San Felipe del Morro
A 16th-century Spanish fortress sits at the tip of Viejo San Juan. While its formal name is the Castillo San Felipe del Morro, everyone just calls it “El Morro.” It costs $10 to enter the actual castle, but you don’t need to go inside to see its prowess. You can see it from the exterior and walk its perimeter on the Paseo del Morro, which is a trail that takes you around the castle and past historic areas of Viejo San Juan. From the outside, you’ll still be able to take photos in the Spanish colonial towers known as garitas that are an iconic symbol of Puerto Rico.
The best day to visit the castle is on Sunday afternoon, when locals and tourists fly kites in the field leading up to the fort. You can pack a picnic and lie on the lawn to enjoy a sunny day.
ThatPlannerFriend Tip: The sun at El Morro is unforgiving, with minimal places to hide in the shade. If you’re visiting during the summer, plan to go during the morning or late afternoon.
If you do buy a ticket to the Castillo San Felipe del Morro, you can use the same ticket to enter the San Cristóbal Castle on the other side of town.
Explore El Yunque
El Yunque is a lush, green tropical rainforest amidst mountains. The rainforest sings with the sounds of coquis (tiny Puerto Rican tree frogs) and rushing waterfalls.
The best way to see El Yunque is on a guided tour that will take you to areas hidden away from tourists. You can book a tour through HighSoClub, a travel company that organizes events for visitors across the island. Most El Yunque tours will take you to natural pools that you can slide into that you wouldn’t be able to access on your own.
If you rented a car and feel comfortable driving in the mountains, you can do a self-guided tour by driving to the top of the mountain road of El Yunque and working your way down, stopping at sights along the way.
Spend the day at the beach
The best beaches near San Juan are Isla Verde, Balneario de Carolina, and Piñones. Isla Verde and Carolina have more of a resort vibe with white sand and amenities catered to tourists. At Piñones, you’ll find more of a local vibe with a rockier shoreline and families playing in tide pools. Piñones is more fun because you can hop from chinchorros (small beach bars) for drinks and food.
For a day trip to a beach, drive about two hours to Isabela on the northwest side of the island. Isabela is home to some of the island’s prettiest beaches and the Pozo de Jacinto, an open sea cave carved into rock by the ocean, featured in Bad Bunny’s song Weltita. Go to Playa Jobos to see the cave or Montones Beach to swim in an ocean lagoon sheltered by rocks.
Go island hopping
If you think the water at the beach is pretty, wait til you go to the islands offshore. From Fajardo, you can charter a boat to take you island hopping to Icacos and Palomino. Icacos is an uninhabited cay or sandbar with white sand and crystal clear water, while Palomino is a larger island with a resort.
If you want to charter a private boat, drop a message in the comments, and I can share with you my captain’s contact. Otherwise, there are plenty of options on Airbnb Experiences or Get Your Guide. The marina to hop on the boat in Fajardo is about an hour’s drive from San Juan. If you’re looking to save money, you can also take a water taxi to and from Icacos or Palomino instead of booking a full-day experience.
Other larger islands to visit are Vieques and Culebra. Vieques is known for its wild horse population that roams free. Ferries run between both of these islands, but be warned that the waters can be rough, so if you’re prone to motion sickness, you should take Dramamine.
Taste the local flavors
Puerto Rico is home to so many flavors you can only get on the island, like chillo (local red snapper), tostones de pana (crispy fried breadfruit), and Medalla (a local light beer). And, a trip to Puerto Rico is your chance to try them all.
Puerto Rican food is similar to many cuisines in Latin America, centering around rice, beans, and protein. A few must-order items are mofongo, queso frito, and any fried food dipped in mayo-ketchup.
As for drinks, anything with rum and parcha (passion fruit) is a must, and you can’t leave the island without having a piña colada (it originated here!). At the grocery store, you can buy Gasolina pouches of parcha and Sangriiia (yes, sangria with three Is), which are great for taking on the boat. You’ll also find Gasolina drinks sold in pouches at bars for cheap or in slushy form.
Take a mixology class at a rum distillery
Rum originated in the Caribbean, and Puerto Rico is a hub for rum-soaked history. Take a tour of a rum distillery and put your bartending skills to the test at a mixology class. Casa Bacardi is the most famous rum tour because of its international popularity. For a more local taste, take a tour of Ron del Barrilito. Both distilleries offer mixology classes you can take in addition to a tour of the grounds.
See the street art of Calle Cerra by day
The Santurce Art Walk is an outdoor gallery of murals on Calle Cerra in Santurce. Grab a coffee or cocktail at Café con Cé and walk around admiring the art.
Bar crawl on Calle Cerra by night
By night, the streets of Calle Cerra fill up with partygoers. This is where the locals go out. You can start your bar crawl at Esquina Watusi where people spill out into the street with beers in hand. Across the street, you can dance to reggaeton at Patria en la Cerra or El Patio de la Cerra. Down the block, you’ll find cooler, lounge-ier bars like Machete or La Disquera for cocktails.
Hang out at La Placita de Santurce
La Placita de Santurce transforms itself from a daytime market into a going-out destination. The area is lined with bars catered toward tourists. The later into the night it gets, the more popping it is. On a Sunday evening, you’ll find locals dancing salsa and singing karaoke al fresco. It’s a great place to people-watch as night falls.
Party on Calle San Sebastián in Viejo San Juan
For a good time, go dancing on Calle San Sebastián in Viejo San Juan. This street is famous for its many lively bars. La Factoría is a must for salsa dancing. It’s one of those rare places where you can dance and have a craft cocktail at the same time. You can pop into any bar and have a good time on Calle San Sebastián, but another favorite is El Quinqué de Douglas’ Pub.
Bars in Viejo San Juan close at 2 a.m., but if you want to keep the party going, you can go to the clubs in San Juan. Club Brava in the Fairmont Hotel in Isla Verde is open until 5 a.m., and Fifty Eight in Condado is open til 4 a.m.
How many days to spend in San Juan and Puerto Rico
You can spend 10 days or 3 days in Puerto Rico. To explore San Juan, you need at least three days, but four days is ideal. If you want to explore the rest of the island to visit places like Rincon and Ponce, you’ll need a week to 10 days.
Where to stay in San Juan, Puerto Rico
For a girls’ group trip, an Airbnb is your best option, especially if you’re more than four people. When looking for an Airbnb, try to book stays with locals to support the people from the island rather than foreigners trying to make a quick buck. Many Airbnb hosts are proud to be Puerto Rican and include it in their host bios.
Viejo San Juan
Viejo San Juan is best for first-time visitors who don’t want to rent a car. The area is very walkable and picturesque. We rented this colonial home on Airbnb for six girls. If you’re renting an older, historic home, make sure to check that it has AC before booking.
Isla Verde
Isla Verde is a great place to stay if you want to be beachfront. It’s right by the beach, airport, and main highway, making it super easy to get everywhere you need to go. There’s a mix of fancy hotels and rental apartments here.
Condado
For more of a hotel and resort vibe, stay in Condado, just east of Viejo San Juan. There are a lot of national hotel chains here. We like to stay at the Hilton Garden Inn. Although it’s not technically in Condado, the nearby Caribe Hilton is an iconic resort to stay at. This is where the piña colada was supposedly originally invented, and it has its own secluded beach.
Carolina
Carolina is the best place to stay if you’re renting a car and looking to explore other parts of the island on your own. Carolina covers a large region, but the area close to the highway and airport (just east of Isla Verde) is the best place to stay. When looking for a place in Carolina, book a spot within a gated community. It’s very common for housing communities to be gated in Puerto Rico. Don’t worry, extra security doesn’t signal an unsafe area, but it’s always good to have.
Getting Around
In Viejo San Juan, the best way to get around is by walking. Everything is less than a 20-30 minute walk away within the old city walls. While there are other walkable areas in the San Juan metro area, you’ll likely need to drive to them and then walk around. Calle Cerra and the area around La Placita in Santurce are walkable, as is Condado. The beachfront in Isla Verde and Piñones is also walkable once you’ve been dropped off or parked your car.
The best way to get around the San Juan metro area is via Uber or other ride-sharing services. As long as there are no big events or festivals, Ubers are generally affordable. There is a metro rail called the Tren Urbano, but driving is much more convenient.
A private van is great for bigger groups going to events or to the marina in Fajardo. If you’re looking to book a van, comment, and I can connect you with the phone number of a driver.
Rent a car if you want to explore other parts of the island, like El Yunque or the beaches of Isabela, on your own.
When to go
Puerto Rico benefits from warm weather year-round because of its proximity to the equator. High season is December to April, during the dry season, when there is less rain. Many US tourists visit during this time to escape the cold. You can find better deals during the low season from May to November, but this coincides with hurricane season. The highest risk for hurricanes is August and September.
I’ve visited in the midst of hurricane season, and it was totally fine. When it rains on the island, it’s typically quick with fast-moving clouds.
For more of a party, visit Puerto Rico during Martin Luther King Day Weekend for Las Fiestas de la Calle de San Sebastián, a free cultural music festival on the streets of Viejo San Juan. At Sanse (as the festival is affectionately called), some of Latin music’s biggest acts perform like Jowell y Yandy and Juanes. It’s like a Mardi Gras but centered around music instead of parades.
Language + Currency
Puerto Rico is a U.S. territory, which is why you don’t need a passport to visit. Spanish is the primary language in Puerto Rico, but almost everyone speaks English. Puerto Rico also uses the US dollar. It’s good to keep cash on you for visiting stands on the beach, but most places accept credit cards.
Safety
Puerto Rico is safe as long as you don’t venture into the wrong neighborhoods or areas. In Viejo San Juan, avoid La Perla, a community along the water on the other side of the city walls. Tourists have been killed for disrespecting the locals in La Perla because of the current political tensions between the US and Puerto Rico.
If you’re staying outside of Viejo San Juan in areas like Carolina or Santurce, make sure where you’re staying has security. In Santurce, stay on the Calle Cerra streets and near La Placita. There are a few blocks near the projects that you don’t want to find yourself wandering into. Like any major city, the buddy system is key to staying safe when going out with friends.
Reply