Planning a trip to the Island of Enchantment but unsure of where to start? We’ve got you covered. Here’s a know-before-you-go guide to Puerto Rico, perfect for creating your itinerary. 

Check out our Instagrammer’s Itinerary to Puerto Rico, as well as our scoop on the island’s coffee culture


  • Official Title: The Commonwealth of Puerto Rico (Estado Libre Asociado de Puerto Rico)
  • Capital: San Juan
  • Population: 3.7 million (2018)
  • Official Languages: Spanish and English
  • Currency: USD ($)
  • Annexed: 1898, after the Spanish-American War
  • Time Zone: Atlantic Standard (UTC -4)
  • Drive on the: Right


Puerto Rico is an archipelago in the Greater Antilles that lies at the confluence of the Caribbean Sea and the North Atlantic Ocean. Located east of the Dominican Republic and Haiti and west of the British and U.S. Virgin Islands, the U.S. territory maintains a tropical marine climate with temperatures that rarely spike above 80°F (26°C) or drop below 70°F (21°C). The 100-mile-long by 35-mile-wide island is the smallest island of the Greater Antilles, and consists of the main island of Puerto Rico as well as Vieques, Culebra, Mona, and numerous other islets.

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Although many consider Christopher Columbus’ fateful landing on September 24, 1493, the beginning of Puerto Rico’s fraught history, the island’s origins stretch back much further. The Ortoiroid people settled the archipelago between 3,000 and 2,000 B.C., though the Saladoid, Arawak, and Tainos peoples, who weathered many of the offenses by Columbus and his crew (including, but not limited to, infectious diseases, exploitative behavior, and violent warfare), populated it in later years.

These tribes subsisted off of the archipelago’s fertile land, fishing in its waters and foraging cassava root and tropical fruit. However, all of this changed with the arrival of the Spaniards in 1493, which marked the beginning of nearly 400 years of colonial rule. During this time, conquerors founded a European colony (Caparra), chose a governor (Ponce de León), enslaved a race of indigenous people, and discovered a continent (thanks to Florida’s jutting tip).

By then, many other Western nations had taken note of the potential profitability of the small island. From the 16th to the 18th century, France, Britain, and the Netherlands contested Spain’s chokehold on the thriving archipelago with little success. It wasn’t until September 23, 1868, that the occupants of the small town of Lares revolted against Spanish rule with the goal of establishing Puerto Rican independence. Though not initially successful (the Spanish quashed the protest almost immediately), the revolt spurred political and social reforms into the 19th century, culminating in an autonomous Puerto Rican government in 1898. That year, the Spanish-American war broke out, the result of which was the ceding of the island to the United States.

Today, Puerto Rico remains a territory of the U.S., though it is unincorporated and still lacks statehood.


The island is easily accessed from the continental U.S. by plane, although ferries from the Dominican Republic and the Virgin Islands are also time-efficient and modestly priced.

There are non-stop flights from many U.S. cities (and even major European hubs) to San Juan International Airport (SJU), which is also known as Luis Muñoz Marín International. Another popular route to Puerto Rico is via cruise ship, which is a slower — but more scenic — method of accessing the island paradise. Cruise ships depart regularly from Florida and the southeastern coast of the United States. Though Puerto Rico may feel like a world away, it’s really only a hop, skip, and a jump away.


Regardless of how you choose to get to the island, a number of transportation options await to connect you to its cities, ports, and popular destinations.

Flights between various regional airports connect well-known spots like Culebra and Vieques, and a regular (and rather inexpensive) ferry service runs between San Juan, Fajardo, Vieques, and Culebra.

For more local travel, Taxi Turístico is the way to go, which you’ll be able to identify by the garita (sentry tower) logo. For a cheaper option, take one of the many public buses — known on the island as guaguas — the A5 line runs conveniently from Old San Juan to Isla Verde, while the B21 line links Old San Juan, Condado, and the Plaza Las Américas Mall.

If you’re on a budget and want to travel a longer distance to a destination, consider catching a público, a privately operated shuttle that takes passengers all over the island. 

Interested in driving the island yourself? You’ll have no shortage of options as most big names in the car rental industry (Hertz, Avis, and Charlie Car) have a hub in Puerto Rico.


While Puerto Rico remains a U.S. territory, there are still communities that don’t necessarily speak English, though large cities on Vieques and Culebra are the exception. With this in mind, taking a refresher course on Spanish — or even using a daily language app — before you depart is a great idea. At the very least, you should know simple phrases like “hello” (hola), “good day, how are you?” (¿Buenos días cómo estás?), “how much?” (cuánto cuesta), and “thank you” (gracias), as well as short, directional phrases.

The good news for American travelers is that they can leave their passports at home! When flying to Puerto Rico, they’ll only need a driver’s license or other (valid) form of photo ID. Because PR lies within the boundaries of the United States, American cell phone plans will likely work without any overages or roaming fees, though it’s best to check with your particular carrier before you take off.

Puerto Rico is a lovely island destination, but that doesn’t mean it isn’t affected by pickpocketing and theft. These things occur, specifically in high-volume, tourist areas. A word of advice: leave your valuables in a hotel safe when you’re out and about, avoid areas that locals advise against, and take a cab if you’re going out at night.

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If this guide has convinced you to plan a vacation to the island paradise, note that most travelers aim to arrive during Puerto Rico’s peak season, from December to April, when the weather is beautiful, but the prices are not. Travelers on a budget may want to consider visiting between May and November when they can get a better deal — but plan carefully, because hurricane season falls between June and the end of November!

Hasta luego!

Header image by Ricardo Dominguez