San Juan, San Two, San Three!

San Juan, Puerto Rico is like a fun beach cocktail created with a splash of Spanish charm, a shot of smooth Caribbean culture and topped off with an American fruity twist. Puerto Rico is a joyous  destination that sets the tone for its much deserved nickname, the “Island of Enchantment”.

San Juan has a rich history, a vibrant current culture and a bright future. One of the oldest European-founded cities in the Americas, its brush with Europeans began with the indigenous Taíno clans, governed by their chief Agüeybaná, met with the European explorers. Christopher Columbus landed in Puerto Rico in 1493 and renamed the island San Juan Bautista, after St. John the Baptist.

historic places in san juan puerto ricoWishing you were here!
The Spanish explorer and conquistador Juan Ponce de León (who hunted for the Fountain of Youth) arrived in 1508 and established the settlement that would become the San Juan we know today. One year later this settlement was relocated and renamed the City of Puerto Rico (Ciudad de Puerto Rico) which means ‘rich port.’ It wasn’t until 1521 that this newer settlement received its formal name, Puerto Rico de San Juan Bautista, which later evolved into simply, San Juan.

In the centuries that followed, Puerto Rico was established as an important military outpost for Spain. Forts were constructed to protect the island against attacks from the Dutch, French and English. The island experienced a brief period of autonomy during the late 19th century until 1898 when Puerto Rico was decreed an unincorporated territory of the United States as part of the Treaty of Paris that ended the Spanish-American War.

To this day it is subject to the jurisdiction and sovereignty of the United States. To quote the song “America” from West Side Story, “… nobody knows in America, Puerto Rico’s in America!”

Here’s a Pro-tip: the piña colada was created by bartender Ramón “Monchito” Marrero at the Caribe Hilton in San Juan in 1954. As the official drink of Puerto Rico and it is only polite that you indulge in quite a few while you’re there!

1 piña colada, 2 piña colada, 3 piña colada, floor!

Located in Carolina, 13 km (8 miles) from Old San Juan, Luis Muñoz Marín International Airport is the gateway to the city. Upon arrival you can take a taxi which will take around 20 minutes to transfer to the old town and cost around $20 (£14.50). For public transport, you take the AMA Buses (Autoridad Metropolitana de Autobuses). Buses depart from the second level of the Main Terminal (Departures). Note that large luggage is not permitted onboard the buses so this is only an option for those travelling light.

There is so much to do in San Juan that the most difficult thing is how to fit it all in. My advice is to bump the following attractions to the top of your list:

  • Old San Juan –Viejo San Juan is an islet that connects to the main island via three bridges. Wander the cobblestone streets on foot admiring the ornate and vibrant 16th century architecture or hop on the free trolley to preserve your energy.
  • Paseo del Morro – Take a stroll along this seaside broad walk and enjoy breath-taking views of San Juan Bay.
  • Castillo San Felipe del Morro – Construction began on this UNESCO World Heritage Site during the 16th-century and work continued for 250 years. Originally built to protect the city from invaders the fort is now one of the best places to dive into its history.
  • Santa Maria Magdalena de Pazzis Cemetery – It may seem strange that I’m suggesting you visit a cemetery but it’s truly a beautiful addition to your itinerary. Established in 1863 this is the final resting place for notable residents of Puerto Rico, including famous poets and artists. It also affords bountiful ocean views.
  • Castillo San Cristobal – Another significant landmark on the eastern side of Old Town, this fort was erected to protect the city from an attack by land. You can soak up the ocean and city views right across to Castillo San Felipe del Morro from the largest Spanish fortification built in the New World.

San Juan is primarily beautiful!

  • Casa Bacardi Puerto Rico – Stepping out of Old San Juan and across the bay, this is a worthy pilgrimage for any rum aficionado. Book an interactive distillery tour that will teach you all you want to know about the rum making process while at the same time providing an opportunity to taste vintage rum that isn’t available anywhere else. If like me, you enjoy an even more hands-on experience, you can book a mixology class to learn how to make delicious cocktails.
  • Casino Hopping – When Castro took over Cuba, the large hotel groups moved their gaming to San Juan. The old-style cool of Havana was recreated in San Juan and thrives to this day.
  • Seize the opportunity to take a sunset cruise aboard a historic topsail schooner, enjoy some nibbles and the colourful city from a different angle. Alternatively you can book a snorkelling or diving excursion from San Juan.
  • Beach hop – Whilst you’re in the Caribbean, you should spend at least every other day lazing by the beach. San Juan is blessed by wonderful stretches of sand and Isla Verde, Pine Grove and Ocean Park beaches.

Puerto Rico’s fusion of Spanish and Caribbean culture means that you will find delectable cuisine while in San Juan! Here are places that should be stops on your culinary quest:

  • Lote 23 – This open-air gastronomic park with live music guarantees a magical evening and dining experience. Hop from kiosk to kiosk where you will find a variety of food from Puerto Rico and beyond.
  • El Jibarito – Make a date at this traditional restaurant and sample the signature dish, mofongo. This Puerto Rican staple comprises fried plantains that are mashed with garlic, salt and olive oil, then topped up with your choice of pork, chicken or seafood. It’s delicious!
It’s mo’ fun to go Mofongo!
  • Marmalade – You’ll find this upscale restaurant and wine bar in the very heart of Old San Juan. Take your pick from a four, five or six-course tasting menu which will give your tastebuds something to talk about long after the end of your holiday. Larger groups of over six guests can dine on a huge 15-course offering.

Here’s another pro-tip: Food trucks are popular in San Juan. Try a famous Puerto Rican ‘Tripleta’ sandwich which consists of marinated grilled steak, chicken and pork. Served on a loaf of sweet potato bread with pickles, chips, ketchup, and mayonnaise. This is a tasty treat!

San Juan knows how to party deep into the night. Here are my favourite places to enjoy nightlife:

  • La Factoria – This speakeasy-style bar is not your ordinary watering hole. A network of secret passages leads you to six individual bars each curated with its unique ambiance, music and speciality cocktail menu.
  • La Placita de Santurce – A farmer’s market by day, and the most happening corner in town by night, La Placita is a hub of restaurants, bars and clubs. From craft beers to salsa, you can sample everything Puerto Rican nightlife has to offer right here.
  • Casinos – Many of the large hotels have fabulous casinos where you can try your luck at the tables. Stellaris Casino in the Marriott Hotel is my favourite.

Accommodation in San Juan ranges from historic hotels in Old Town to world class resorts. Here’s where I recommend you stay:

  • Caribe Hilton – The home of the Piña Colada has to be at the top of my list. This oceanfront resort sits within 17 acres of resplendent gardens and is equipped with a multitude of facilities and a deluxe spa. With ten diverse dining options on site you’ll never go hungry.
visit san juan puerto ricoSan Juan’s balconies are beckoning!
  • Hotel El Convento – Old world charm meets luxury and elegance at this boutique hotel located in the old town. A beautiful example of colonial Spanish architecture, this former convent overlooks San Juan Bay.
  • CasaBlanca Hotel – This contemporary, Moroccan style hotel has scooped up awards and garnered international acclaim for its attention to detail. But why stay here? Where else can you luxuriate in a bathtub on a rooftop sundeck?

Here’s another pro-tip: San Juan has an amazing array of Paradores. These family-owned inns are dotted across the entire island and provide a cultural experience within cosy accommodation and excellent prices.

If there’s one place that will never lose its charm for me, that place is San Juan. The friendly islanders, unique culture and cool vibe will leave footprints on your heart for a lifetime!



Isabella’s Checklist

What to see: Castillos, Old San Juan, Barcardi Distillery, beaches (

Where to stay: Caribe Hilton, Hotel El Convento, CasaBlanca Hotel (,,

Night-time activities: LED Paddle Boarding, La Factoria, La Placita, Stellaris Casino (,

Where to eat: Lote 23, El Jibarito, Marmalade (,,

What to buy: excellent rum, traditional masks, spices

Enjoy Enchanting San Juan!
Isabella’s Checklist

What to see: Castillos, Old San Juan, Barcardi Distillery, beaches (

Where to stay: Caribe Hilton, Hotel El Convento, CasaBlanca Hotel (,,

Night-time activities: LED Paddle Boarding, La Factoria, La Placita, Stellaris Casino (,

Where to eat: Lote 23, El Jibarito, Marmalade (,,

What to buy: excellent rum, traditional masks, spices

Enjoy Enchanting San Juan!

4 Comments to “San Juan, San Two, San Three!”

  1. Pina Coladas, rum Distillery and casinos we are in sign us up

    Chalk and cheese travels at 10:02 pm
    1. Definitely a paradise for the rum lovers and salsa dancers, I am happy you enjoyed reading it. Will love to hear from you again soon.



      Sabrina Rivas at 3:42 pm
  2. Trying to go to P.R. in August . Flight cost so much . When is the price low?

    Sharon E Claudio at 11:41 pm
    1. Dear Sharon,

      The price can be high in August. It is a holiday month as well as a month when students return to university both within Puerto Rico and to the mainland US. For low prices, the best time to book is early September for a late September to mid-November trip. The weather can be variable (it’s the height of the hurricane season) but flights reduce significantly in price. That being said, latent demand for air travel is very high now because we appear to be at the end of the pandemic, so flight prices will be high for a little while longer. The next good window is booking February for a March – May trip. I hope you enjoy Puerto Rico. It is a wonderful place to visit!

      Warm regards,

      Shane on behalf of Isabella

      Shane Batt at 5:44 am

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