One of the best ways to escape to a tropical paradise if you live in the United States is to take a flight down to Puerto Rico, a Latin American gem. As a U.S. Territory, entry requirements are nearly the same as visiting one of the contiguous states, making it a location that should certainly be on your vacation bucket list.
Now, when you think of this Caribbean island, the first thing that comes to mind is likely the beautiful beaches. We’ll certainly cover those, but there are many other natural and historical sites that you should explore while you visit this lovely island as well.
Keep reading for the ultimate 4 Day Puerto Rico Itinerary, and get all the information you need to have the best long weekend getaway to this Caribbean gem.
Brief Island History | Puerto Rico
The island now known as Puerto Rico was originally inhabited by the Ortoiroid peoples as far back as several thousand years. Subsequently, the Saladoids came and displaced the original inhabitants around 400 – 250 BC. The Arawak are then thought to have settled in the island, bringing their Taíno culture with them. They called the island Borikén, which means “the great land of the valiant and noble Lord”. The Spanish (with Columbus) arrived in 1493, at a time when the Taíno were in conflict with the Carib peoples as well.
The Spanish came and began to subjicate the native islanders, using them for slave labor. Despite rules known as repartimento, enacted to stop exploitation of the natives, within 50 years of the arrival of the Spanish, most of them had died from disease, violence, or suicide. Some of their numbers do survive today in their descendants, the current Puerto Rican inhabitants.
Over the centuries that followed, many European powers of the time fought for control of Puerto Rico because of its strategic position in the Caribbean. The English, French, and Dutch all tried to take the island from Spain but were not successful. Change came towards the end of the 1800s, when the Puerto Rican people began to revolt against Spain and seek independence, primarily due to the poor care that Spain gave the island. The fight took several years, but finally in July 1898, Puerto Rico began to operate autonomously, but this did not last.
In that same month, the US launched the Spanish-American War, taking the fight to Spain in Puerto Rico and Cuba. By the end of the war that September, Puerto Rico became a US territory. The fight for both independence and/or full statehood have been under discussion since this time, but there have been no major changes to-date.
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The 4 Day Puerto Rico Itinerary | All the Details
Day 1 | Old San Juan
As you will most likely start your trip by landing in San Juan, you should plan to start your trip here. There are a lot of interesting historical sites, great restaurants, and beautiful architecture, so it’s a great way to start a short trip to the island.
I recommend you start your first day with breakfast at Caficultura. They have nice outdoor seating and delicious affogatos. On my first trip to Puerto Rico, we stopped for breakfast here twice to enjoy their delicious food. Another break spot I’d recommend is Chocobar Cortés, where chocolate is used in every dish in some way. While there, try the classic puerto rican hot chocolate – they add in cheddar cheese for a savory touch.
There are a few sites you must absolutely see while you are in Old San Juan:
Castillo San Felipe del Morro
This fortress citadel is a UNESCO World Heritage Site and is also known simply as El Morro. Strategically perched on a rocky promontory, El Morro overlooks the Atlantic Ocean, a vantage point that once protected the island from maritime invaders.
El Morro’s history began in 1539 when King Charles V of Spain authorized its construction to safeguard the harbor of San Juan. The fortification was initially a simple tower known as ‘El Torreón’ but later expanded into an imposing fortress under the guidance of various architects over centuries.
This fortress citadel is also known simply as El Morro. As mentioned above, Puerto Rico had the eye of many European states during the colonial period, so El Morro was built as a way to protect the island from would-be conquerors. It witnessed numerous attacks, notably from the English in 1595 and 1598 and from the Dutch in 1625.
Each assault led to further fortification, transforming El Morro into a formidable citadel. It remained under Spanish control until the Spanish-American War in 1898, when Puerto Rico was ceded to the United States. During World War II, El Morro even served as a military base for the U.S. Army, showcasing the fort’s enduring strategic relevance.
As you explore El Morro you can get beautiful views of the ocean, and inside many details are provided on what it was like to live there for the soldiers who guarded the island.
A stone’s throw away from El Morro lies another historical gem of Old San Juan: Casa Blanca. Constructed between 1521 and 1523, Casa Blanca, or “White House,” was initially intended to serve as a residence for Juan Ponce de León, the first governor of Puerto Rico. However, de León never occupied the house as he passed away during an expedition to Florida while it was still under construction. Instead, Casa Blanca became home to his descendants for over 250 years, making it the oldest continuously inhabited residence in the Western Hemisphere.
Throughout the centuries, the house underwent several modifications, its architectural style evolving from medieval to Renaissance, reflecting the changing aesthetic trends of the time. The house was later appropriated as a military barracks during the Spanish-American War in 1898, and it again served the military during World War II, much like its neighbor, El Morro.
Today, Casa Blanca is a museum open to the public, housing artifacts that provide a glimpse into 16th-century domestic life. The house, set in lush gardens overlooking San Juan Bay, is styled with colonial furniture and is another site that offers impressive ocean views.
Catedral de San Juan
In the heart of Old San Juan, the Catedral de San Juan Bautista, or the Cathedral of Saint John the Baptist stands as another historical landmark. Built in 1521, it is the second oldest cathedral in the Western Hemisphere. The cathedral, despite suffering damage from numerous earthquakes and storms over the centuries, is still used as an active place of worship today.
The Cathedral’s architecture is a splendid blend of Gothic and neoclassical styles. Inside, you will find a calm, inspiring space adorned with ornate stained glass windows and beautiful religious artwork. The cathedral also houses the tomb of Ponce de León, adding to its historical significance.
Stepping away from the cathedral, one comes across La Fortaleza, or The Fortress, another significant landmark gracing Old San Juan’s skyline. Serving as the official residence of the Governor of Puerto Rico, it is the oldest executive mansion still in use in the Western Hemisphere. Built between 1533 and 1540, La Fortaleza was initially constructed as a defensive fortress against the Carib Indian raids. However, its military inadequacy led to its transformation into the governor’s residence in the early 16th century.
La Fortaleza boasts an interesting blend of architectural styles, reflecting the various periods of Puerto Rico’s history. Its initial medieval-style structure, made evident by its towering walls and guard towers, later evolved into a more palatial design during the 18th century.
The building’s exterior, adorned with a distinctive blue hue, offers a delightful contrast to the vibrant cobblestone streets of Old San Juan. Inside, the mansion showcases a vast collection of historic artifacts and exquisite furnishings, reflecting the island’s rich cultural heritage.
In front of the building you’ll find the Calle de la Fortaleza (Fortaleza Street), which displays umbrellas in different colors / themes depending on current events, holidays, etc. At Calle de la Fortaleza, there is a delicious gelato place called Anita. If you love ice cream, you have to make a stop here.
For the best experience in getting to know the history of the island while you explore, I recommend that you take a guided tour with a local guide. This San Juan Walking Tour is a great way to learn more about the sites listed above and others like La Casa Estrescha, one of the narrowest houses in the Northern Hemisphere.
If you’re looking for a magical experience, I recommend that you take a San Juan Sunset Cruise. On this two hour experience you’ll sail around the historical city center and watch the sunset on the water. The experience also comes with provided beverages and the music selection of your choice. My friends and I did this on our last trip to Puerto Rico, and had a great time.
For your first night, head to Barrachina for delicious standard Puerto Rican fare. This restaurant is very close to La Fortaleza, and is most famously known for originating the Piña Colada. You may also want to look for a place to watch live music, such as Mono Stereo Bar.
For more tips on things to do in the city, see my post on the Best Things to Do in Old San Juan.
Day 2 | El Yunque National Forest
On your second day in Puerto Rico, I recommend keeping your Old San Juan stay as your home base, as you venture out to explore El Yunque National Forest and more of the island. Established in 1903, El Yunque is the only tropical rainforest within the U.S. Nationals Park system. Named after the benevolent Taino god, Yuquiyu, which stands for “Forest of Clouds”, the lush expanse of El Yunque is a paradise for nature enthusiasts and adventure seekers alike.
Covering approximately 29,000 acres, El Yunque National Forest is home to a unique ecosystem of endemic species of flora and fauna. It features over 240 species of trees, a rich variety of ferns, as well as an array of unique wildlife, such as the Puerto Rican parrot and the Coquí frog. The forest’s vibrant biodiversity is accentuated by its stunning geography, which encompasses cascading waterfalls, crystal clear rivers, and the majestic peaks of El Toro and El Yunque.
The park offers an abundance of recreational activities, allowing visitors to immerse themselves in its pristine natural beauty. Popular activities include hiking along the numerous marked trails that criss-cross the forest, swimming in the natural pools beneath the waterfalls, and bird-watching. For the more adventurous, El Yunque National Forest also provides opportunities for zip-lining and rappelling.
There are two ways to get to El Yunque: (1) drive yourself or (2) take a tour. I recommend taking the tour, unless you truly enjoy driving.
The tour that I’d recommend is the San Juan Scenic Puerto Rico Instagram Tour. This tour will take you to the following locations:
- Old San Juan Historical Sites (Highlights)
- El Yunque National Forest
- Secret Locals-Only Beach
- Dinner at the Beach
Once you get back from exploring El Yunque, I recommend heading to bed early to get ready for an early day.
Click here to book the San Juan Scenic Puerto Rico Instagram Tour!
Day 3 | Day Trip to Vieques
Vieques is a lovely little island off the coast of Puerto Rico that is well known for having some of the best beaches in the whole of the Caribbean. There are white and black sand beaches there and plenty of opportunities for excellent snorkeling. Some of the beaches worth exploring include Playa Negrita (the black sand beach) and La Chiva Beach, which is most known for great snorkeling opportunities. There are also historical sites to check out here as well.
Getting to Vieques from San Juan
Option 1 : Drive to Vieques
On the morning of your 3rd day in Puerto Rico, rent a car and head for a drive to Vieques. The trip to Vieques has a few layers. First, you’ll need to drive to Ceiba (~a 2 hour drive) where you’ll then buy your ticket for the ferry for the trip over to the tiny island of Vieques.
Departures from Ceiba to Vieques can be as early as 4:30AM, so you’ll need to think through how long you’d like to stay at the island before you head there. Note that the last ferry back to Ceiba from Vieques leaves before sunset. For the most current travel schedule, visit the Puerto Rico Ferry website.
Costs: It is roughly $8/day to park at the Ferry station, and the tickets are $4 round trip.
When to Book: Know that there are online tickets available, but they run out quickly. You’ll need to book at least several weeks out. The good news is that there are tickets they hold for in-person booking. But note, you’ll need to stand in line to obtain these tickets. This is something you’ll have to factor in when driving over to Ceiba.
Option 2: Take a Tour to Vieques
This From San Juan: Vieques Snorkeling Tour includes pickup from your hotel in San Juan and all the coordination needed to get to the island. It is certainly a pricier island, but can be helpful for those who like “easy travel”.
After spending the Day at Vieques, head back to San Juan for your last night staying in your hotel by the beach.
Day 4 | Beach Day in San Juan
On your last day in Puerto Rico, stay in a hotel by one of the local beaches. I recommend staying in either Condado or Isla Verde as there are many amenities in both areas. Relax by the beach, shop, or eat during your last hours of vacation.
Condado Beach offers a perfect blend of city sophistication and beachfront bliss. This trendy neighborhood is renowned for its sparkling turquoise waters, golden sandy shores, and its lively strip of high-end shops, eclectic restaurants, and vibrant nightlife. While here you can relax under the swaying palm trees, engage in water sports, or simply soak in the stunning views of the Atlantic Ocean. My friends and I spent a day here on my last trip to San Juan and we loved it. While here, you may want to check out the Condado Vanderbilt Hotel, as it offers fine dining options and several options for nightlife.
This area also offers unspoiled sandy beaches and clear turquoise waters that are ideal for sunbathing and swimming. Water sports enthusiasts will find opportunities for jet-skiing and paddleboarding as well. The area is also home to a diverse range of dining options, from luxurious fine dining restaurants to casual food trucks serving traditional Puerto Rican fare. Boasting glamorous resorts and casinos, Isla Verde comes alive at night, offering a taste of Puerto Rico’s lively nightlife.
For your last evening in Old San Juan, I recommend eating dinner or lunch at Mario Pagán. It’s a more high-end restaurant, but has delicious food options, and is a great way to top off the trip. Note: This is a pretty popular restaurant, so you should plan on making reservations at least a week early.
What to Do if You Have More Time
If your 4 day Puerto Rico itinerary gets (happily) extended, I recommend exploring in Vieques for more time, and doing a Bioluminescent Bay Tour while there.
In addition, you should also consider traveling to the west coast of the island, and stopping at wonderful sites like Gozalandia (local waterfall hangout) and Rincon, which is known for some of the best surfing beaches. If you prefer to travel areas where there are fewer tourists, this is the best part of the island for you.
Old San Juan City Map
For your reference, here is a map of key locations in Old San Juan. The city is quite walkable, but do plan to have water on hand for a few hours of strolling around.
- San Juan National Historic Site
- San Felipe del Morro Castle
- Casa Blanca
- La Fortaleza
- Catedral Bascilica Menor de San Juan Bautista
- Calle de la Fortaleza
- Castillo de San Cristobal
Getting to Puerto Rico
When traveling to Puerto Rico you are most likely to fly into San Juan, which is serviced by the Luis Muñoz Marín International Airport. This airport is relatively easy to navigate, but when flying home, I recommend that you get to the airport at least 2 hours early – especially if you are checking luggage. There are always deals to fly to Puerto Rico cheaply, at least from the US, so I’d just keep my eyes on tickets for at least 2-3 months before you plan to make the trip.
Where to Stay in Puerto Rico
Where to stay will depend on what you prefer to do during your vacation. Here are a few options for a variety of interests:
Where to Stay in Old San Juan
I recommend staying in Old San Juan if you like being in very walkable places, and are a history buff. There are many old historical sites in Old San Juan, and the architecture in this central area is quite lovely.
Casa Blanca Hotel – This hotel is right in the heart of Old San Juan, but La Fortaleza, one of the most known locations in the city.
Hotel El Convento – Highly-rated hotel in Old San Juan with 2 restaurants, and walking distance to the cruise pier.
Where to Stay in Condado Beach or Isla Verde
If you are traveling primarily to get some beach time, but don’t want to be too far away from the city, I recommend considering Condado Beach or Isla Verde.
AC Hotel Marriott Condado – This hotel is a three minute walk to the beach, and is perfect for a few nice beach bum days.
TRYP by Wyndham Isla Verde – This is another hotel right on the beach, except this one is at Isla Verde.
Getting Around Puerto Rico
Walking: If you stay in Old San Juan, it’s very easy to get around the whole area by foot. It’s honestly the best way to travel in this area as the streets are narrow and the roads are quite bumpy.
Uber: For shorter trips, Uber is a very straightforward option. You’ll find the ubers are affordable and can take you around San Juan easily.
Car Rental: If you plan to travel to Vieques or Rincon, or anywhere else in the island, you should certainly rent a car. Some islands have a more “challenging” driving culture, but it is not that way in Puerto Rico. Book your car rental here!
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When to Go to Puerto Rico
The best time to visit Puerto Rico depends on what you’re looking for. If you’re keen on basking under the tropical sun, December to April is the dry season (and high season) and boasts warm, sunny days perfect for beach-side relaxation or exploring the natural wonders. However, for those interested in experiencing cultural events, the San Sebastián Street Festival in January and the Ponce Carnival in February offer vibrant displays of local traditions and festivities. Be aware that these peak tourist seasons also come with higher prices. If you’re looking for a balance between pleasant weather and fewer crowds, the shoulder seasons of late April to June, and September to November, offer a good compromise, though it’s wise to keep an eye on potential hurricane forecasts during the latter period.
Language in Puerto Rico
The official language of Puerto Rico is Spanish. You won’t have any trouble with English in the touristy areas (except in Ubers, perhaps), but you should learn some Spanish if you plan to venture out. Check out my post on Spanish for Travel to get all the phrases you need to survive!
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Spanish Phrases PDF
This free download includes all the key Spanish phrases that you will need for your travels throughout Spain, Mexico and any Spanish-speaking country. In addition, get details on the best resources to improve your speaking and listening skills as well.
Money in Puerto Rico
The currency used in Puerto Rico is the US Dollar, so if you live in the US, there is no need to change money.
Frequently Asked Questions About Puerto Rico
You can see some of Puerto Rico’s highlights in 4 days, but a longer stay would allow a more in-depth exploration of the island’s diverse attractions and culture.
A trip of 7 to 10 days is often recommended to experience Puerto Rico’s main sights, including its beaches, historical sites, and natural wonders, though the ideal length may vary depending on individual interests.
The best months to visit Puerto Rico are typically from mid-December to April, when the weather is warm and dry, avoiding the hurricane season.
Traveling around Puerto Rico is most convenient by renting a car, as this provides flexibility to explore various parts of the island, though public transportation and guided tours are also available.
Puerto Rico can be both affordable and expensive depending on travel preferences; budget accommodations and local eateries are available, but luxury resorts and dining can make it a more costly destination.
Final Tips | 4 Day Puerto Rico Itinerary
That wraps this 4 day Puerto Rico itinerary, which I think is perfect for first-time visitors. I love this beautiful island, and can’t wait to go back. Here is just a quick recap of tips to keep in mind when you visit the island:
- Don’t visit during Hurricane season to avoid rainy weather (and worse). Consider traveling between late November to April
- If staying in Old San Juan, don’t rent a car until you are planning to travel outside of the area, as parking in this area is very challenging
- See more of the island than just San Juan. San Juan is such a small part of the island – there is much more beauty to explore, even if you do not have a lot of time to travel there
- Book your ferry tickets early if you plan to Vieques (or Culebra); the online tickets go fast, and no one enjoys waiting in line for the in-person tickets
I hope you enjoy your Puerto Rico vacation! If you have already been there, let me know of any other places you’d recommend people check out in the comments below!