See it all! A Long Weekend in San Juan

See it all! A Long Weekend in San Juan

Looking for an itinerary for your weekend in San Juan? Look no further! We’ve squeezed a bit of everything into our plan for a long weekend visiting Puerto Rico. Below you’ll find ideas of what to do for your long weekend. We’ve laid it out for a Friday – Monday long weekend, take a look at our blog for ideas for longer stays!

Book your stay with us at Casa Santurce and experience the island of enchantment from San Juan.

Day 1 – Friday

Arrive on Friday and kick start your weekend!

Day 1 Afternoon

Firstly, head to Condado Beach for a dip in the ocean. If you’re early enough, be sure to take your towel so you can sunbathe on the white sands. Look out for a local selling traditional tropical sorbet for $2!

Take in the sunset from the beach, or rent a SUP on Condado Lagoon.

Stand up paddle boarding on Condado Lagoon at sunset

Day 1 Evening

Stroll back to the hostel and head to El Crucerito, the “bar across the road.” Grab a Medalla, the local beer, for $1.50.

If you’re looking for somewhere to try some local cuisine, we’d recommend trying the Mofongo at El Camaron. A Puerto Rican dish, Mofongo is deep-fried green plantains mashed together with garlic and sometimes a little pork. Normally served in a bowl shape it’ll often contain meat served in a generous sauce. You can also add it as a side to many meat dishes!

Mofongo at El Camaron

For great nightlife, you have to check out La Placita! Basically a ‘Block Party,’ La Placita is an area full of bars playing every type of music you can imagine! Normally busy from 11pm, it’s a great place to dance the night away!

Day 2- Saturday

Get a real feeling for Puerto Rico with a mixture of activities today. Great coffee, great food, nice beaches, local life and some popular nightlife!

Day 2 Morning

Start the day with a delicious breakfast and coffee at Gustos Miramar – try the pastries or menu items, everything there is tasty!

Take a slight detour on your way back to the hostel to check out Calle Cerra. They say it has the ‘highest concentration of street art in the Caribbean.’ Meander around the streets and be blown away by the amazing murals that line almost all of the walls and buildings in the area.

Take in the street art around Calle Cerra

Day 2 Afternoon

For a local experience, take in the sights, sounds (and flavors!) at Piñones. With a mixture of restaurants, lean-tos ad roadside stalls, this is the home of Puerto Rican street food. Grab some fried snacks and set up on the sand. 

To get there you can Uber for around $10 each way. To bus there, take the T3 outside Marshalls. Get off at Estacion Sagrado Corazon and hop on the D45. You’ll know when to get off – you’ll start seeing a bunch of food stalls everywhere! Bus stop: Carretera PR-187! Find it on Google Maps before leaving wifi so you know where you are.

You might also like to rent a bike in San Juan and ride there along the cycle way and board walk. 

Try an empanada, bacalaito or alcapurria while your here!


Day 2 Evening

Take in the sunset at New Reef Bar in Piñones. It’s a great place to watch the sunset over San Juan. Or, just sit on the beach below! If you’re hungry, there are some great pinchos on a grill outside a near by eatery – look for the smoke and lines of people!

Take in the sunset looking back toward San Juan

For a Saturday night hot spot, check out La Factoria in Old San Juan. Featured in the top 50 bars in the world, you might recognize it from the Despacito video. They’re known for their cocktails, or you might like to bar hop in the area before heading in.

Day 3 – Sunday

Day 3 Morning

Take the T5 bus into Old San Juan and grab breakfast from the famous La MallorcaTry a classic Mallorca – sweet bread with ham and cheese sprinkled with a little extra icing sugar. Don’t forget a cafe con leche! Open from 7am you can get an early start to the day here.


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After fueling up on breakfast, walk to El Morro. Designed to protect the Spanish and their entrance to the San Juan bay, construction on the fort began in the early 1500s. You’ll recognize it from many iconic tourism photos of the area! Take your time to explore and learn more about the local history. Most people spend an hour or two here. Your $7 entrance ticket will also get you in to Castillo San Cristobel.

Explore the forts in Old San Juan

There are a lot of lunch options in San Juan. For a fresh salad, soup or Sandwich try St Germain. Another popular spot is the Stuffed Avocado . Or try El Meson Sandwiches, a Puerto Rican fast food sandwich chain.

Day 3 Afternoon

Walk down towards the cruise ships and stroll along the waterfront towards Puerta de San Juan. Stroll along the beautiful Pasea de la Princesa. The coast is beautiful and there’s a few seats along the way so you can watch the boats go by. Walk through to Caleta de San Juan and head up the beautiful tree lined street – at the top you’ll see the Cathedral, pop your head inside!  

Take a walk around Old San Juan

Described by google as a ‘great spot for bird watching’ there’s a nice view from Parque las Palomas. If you’re in to pigeons you can buy seed from a local vendor, otherwise dodge past them to see the bronze shoe statues and admire the scenery.

Home to the Pina Colada, enjoy the tropical cocktail in the peaceful courtyard of Barrachina – where the popular drink was invented!

Barrachina – where the Pina Colada was invented!


Day 3 Evening

Watch a sunset from the large grassy field outside El Morro. You can purchase kites from street side vendors if you want to run around with the local kids!

On Sunday evenings there’s live music at La Verguenza. Have a drink while enjoying the sea breeze and island vibe. A popular hang out for tourists, there’s always a lively atmosphere here when music is playing! Take a seat on a balcony upstairs to watch from above, or join in some dancing in the lane way!

Day 4 – Monday

Day 4 Morning

Try a ‘Desayuno’ for $3 from Don Juan‘s restaurant, just at the top of our street. It’s typical Puerto Rican fare that you can order off a menu, or by selecting items in the warmer. He can also make you a special ham, egg and cheese ‘Breakfast Empanada’ to order. Coffee is strong and hot and only $1.50!

Day 4 Afternoon

Grab a mask and snorkel from the office and head to Escambron. A relaxing spot for a swim, there are a couple of areas where you can often spot sea turtles. The rock wall not only makes a nice area for swimming but it can also be home to some sea life too!

Escambron beach San Juan

Day 4 Evening

After an action packed weekend, take an Uber back to the airport. For around $8, they’re super reliable and the best option for getting around.


Other blogs you might like:

Best BeachesIf you’re just looking for a beach vacation, take a look at our post about our favorite beaches in San Juan!

Nightlife for every night of the week. Read our top picks of the best places to experience great music, dancing and nightlife every night of the week in San Juan!

Best Transport around San Juan. For a little info on how to get from A to B while you’re here!


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