4 Day Puerto Rico Itinerary For First Time Visitors
Planning a long weekend in Puerto Rico? Embarking on a Caribbean cruise? This 4 day Puerto Rico itinerary is for you.
I have visited San Juan on many Caribbean cruises, but recently had the opportunity to spend 4 whole days there.
Although Puerto Rico is smaller than most US states, there is a ton to do. During your 4 day trip to San Juan, you can explore the Caribbean, beach, Old San Juan, a rainforest and more.
A long weekend in San Juan is a great amount of time to experience the culture of the island before returning to the Eastern US or continuing along to another Caribbean destination.
Keep reading this guide for a complete 4 day Puerto Rico itinerary, where to stay, a complete list of what to do in San Juan, and other great travel tips.
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4 Day Puerto Rico Itinerary Overview
The key to an easy Puerto Rico itinerary is balancing your time between Old San Juan and the rest of the island. Although the island is relatively small, it can take a couple hours to drive across. To maximize your time, don’t waste time commuting back and forth.
The first two days, I recommend staying close to San Juan while you get acclimated. Plan for one relaxing beach day and one day exploring old San Juan.
For next two days of this itinerary, I recommend taking two day trips.
For the first day trip, you cannot go wrong with a combo tour to the El Yunque forest and Bioluminescent Bay. This will be a long but very exciting day.
For your final day in Puerto Rico, take a catamaran day trip. You cannot leave Puerto Rico without spending time on the beautiful Caribbean waters.
Day 1: Arrival, Beach Time, and Rum Tasting
Morning: Check in to your hotel and relax at the beach
Many flights into Puerto Rico are red eyes, so you will likely arrive early in the morning. To recover from your travels, spend the first part of the day relaxing at the beach.
The beaches in Puerto Rico are beautiful white sand, with warm water for swimming.
Afternoon: Head to the Bacardi factory for a rum tasting
One of my favorite things to do in Puerto Rico was a rum tasting at the Bacardi rum factory. The tours sell out, so be sure to book in advance.
During the tour, you will learn about the rum making process, tour the facilities, then be guided through a tasting of Bacardi’s most popular rums.
Day 2: Old San Juan
Morning: Take a self-guided walking tour of Old San Juan
Old San Juan is the historic center of the island. The best way to see the most popular sights is on foot.
While you can book a guided your, I recommend visiting on your own to explore at your own pace. Here’s an easy route to follow for a walking tour of San Juan:
1. Plaza Colón: Begin your tour at Plaza Colón, a lively square with a statue of Christopher Columbus.
2. Calle Fortaleza: Head southeast on Calle Fortaleza, one of the oldest streets in San Juan. Admire the colorful colonial buildings, shops, and cafes along the way. This is a great photo backdrop.
3. La Fortaleza: Visit La Fortaleza, the official residence of the Governor of Puerto Rico. While you can’t go inside without a reservation, the exterior and surrounding gardens are worth exploring.
4. Catedral de San Juan Bautista: Continue to the Cathedral of San Juan Bautista, one of the oldest churches in the Americas. Explore the interior and the adjacent Plaza de la Catedral.
5. El Convento: Walk to Hotel El Convento, a former convent turned luxury hotel. Take a moment to appreciate the Spanish colonial architecture and the beautiful courtyard.
6. Plaza de Armas: Head to Plaza de Armas, the main square of Old San Juan. It’s a great place to rest, people-watch, and enjoy the surrounding historic buildings.
7. San Juan Gate: Walk towards the San Juan Gate, a historic city gate that once protected the entrance to the city. Take in the views of the city walls and the sea.
8. Paseo de la Princesa: Stroll along Paseo de la Princesa, a walking path along the city walls. Enjoy views of the bay, sculptures, and the famous Raíces Fountain.
Afternoon: Take a Food Tour for a Late Lunch
After your self-guided walking tour, I’m sure you’ll have worked up an appetite. Instead of a restaurant, I recommend booking a food tour for lunch.
This is a great way to taste the most popular authentic Puerto Rican dishes. Some of the best things you’ll try are local coffee, traditional pastries, empanadas, and a Pina Colada.
In addition, the guided food tour is a great opportunity to ask your local guide about any of the sights you visited in the morning.
Check prices and availability of this food tour
Day 3: Adventure Day Tour
For day three your 4 days in San Juan, I recommend taking a day trip away from the city. Two of the most unique parts of the island are the El Yunque national forest and the bioluminescent bay.
Morning: El Yunque Forest
Get an early start with this half day rainforest tour. Travel from San Juan to the forest with a local guide.
Once at the El Yunque rainforest, you will embark on a guided hike and have the opportunity to swim in a natural waterfall with a natural rock slide into the water.
During the hike, you will also learn about the local ecology, flora, and fauna.
Evening: Bioluminescent Bay
Once it gets dark out, embark on a kayak tour through the bioluminescent bay.
The bioluminescent bay is where a natural phenomenon occurs where organisms in the water cause a florescent blue color that can only been seen at night.
The tour includes a guided tour of the bay and roundtrip transportation back to San Juan.
Day 4: Catamaran Day Trip
The final day of this Puerto Rico 4 day itinerary is all about relaxation. Plus, you can’t visit Puerto Rico without spending some time on the beautiful blue water.
Full Day: Catamaran Tour
This six hour tour starts and ends in San Juan, traveling to nearby islands and along the coast of Puerto Rico.
During the tour, you’ll have the opportunity to swim in the water, visit some small islands, and enjoy a local lunch onboard.
From the boat cruise, you will also see unique views of the El Yunque rainforest, Old San Juan, and other parts of the island.
Check prices and availability of this Puerto Rico catamaran tour
What to Do in San Juan Puerto Rico
There are so many great things to do in San Juan Puerto Rico. Some activities are based in and around San Juan and others are easy day trips to other parts of the island or the area.
If you prefer to plan your own 4 days in Puerto Rico, below are the top things to fit into your itinerary.
1. Explore Old San Juan
As mentioned above, Old San Juan is the historical and cultural center of Puerto Rico. You can see a lot of the city by simply walking around and visiting the sites.
While exploring Old San Juan, start with a walk along the oceanfront path to the San Felipe del Morro Castle. You can pay for entrance or view the grounds from the outside.
Near the castle, there are also many stray cats that are super cute.
Next, visit Fortaleza Street, a fun, colorful street that is often decorated with hanging umbrellas. On Fortaleza Street, be sure to grab a pina colada from Barrachina, where they were invented.
2. Old San Juan Food and Walking Tour
For a more in-depth experience in Old San Juan, I highly recommend this food and walking tour.
Puerto Rican food is amazing, and this food tour is a great way to try a lot of it in a short amount of time. In addition, you will learn about the city from a local guide.
3. Casa Bacardi Rum Tasting
Casa Bacardi in San Juan is where over 90% of Bacardi is made today. Their rum tasting tour is one of the best tours I’ve taken ever.
The tour includes a visit of the grounds to learn about the history of the brand and the rum making process.
After seeing the grounds, you will enjoy an immersive tasting of 4 varieties of their best rums. The guides at Casa Bacardi are what make the tour so incredible.
Honestly, I don’t usually love rum unless it’s mixed into a Mojito or Mai Tai. However, after learning about the process I gained a huge appreciation for rum and even enjoyed the tasting!
They are fun, personable, and extremely knowledgeable. This tour is expensive, but worth the money in my opinion.
4. El Yunque Forest and Walking Tour
If you are looking for adventure, this half day El Yunque tour is for you. Although I recommend staying near San Juan, I also highly recommend exploring the rest of the island on day tours.
This El Yunque national forest tour includes a tour of the forest and surrounding area and a swim at a waterfall.
5. Bioluminescence Bay Tour
This Bioluminescent Bay tour explores an incredible phenomenon. Set out on a glass bottom kayak at night to see the unique activity of glow in the dark plankton that light up the lagoon around you.
This phenomenon only occurs in a few places around the world, so don’t miss it during your Puerto Rico vacation.
6. Catamaran Day Trip
One of the biggest draws of Puerto Rico is the beautiful, blue, Caribbean Ocean. Spend a day on the water with this catamaran day trip.
The tour includes a cruise along the scenic coast, a couple hours on a nearby island, lunch, and a swim. This tour is a great way to see the Caribbean, and spend time relaxing.
7. Condado Beach
Condado Beach, nestled in the heart of the vibrant Condado district in San Juan, is the most popular beach near the city. It’s known for its golden sands and clear blue waters.
You can simply soak in the tropical sun and take a refreshing dip in the calm waters, or try various water sports such as paddle boarding and jet skiing.
There are also many beachfront restaurants and bars, so Condado is an ideal spot to try local cuisine with a breathtaking ocean view.
8. Castillo San Felipe del Morro
Castillo San Felipe del Morro, known as El Morro, is a historic fortress on the northwestern tip of the city.
Part of the San Juan National Historic Site, El Morro is a great place to explore the city’s rich history dating back to the 16th century.
Marvel at panoramic views of the Atlantic Ocean and San Juan from its elevated vantage points, potentially even witness the a cannon firing demonstration.
9. Museo de Arte de Puerto Rico
For art or museum lovers, the Museo de Arte de Puerto Rico (MAPR) in Santurce is a must-visit destination.
The museum is in a neoclassical building surrounded by lush gardens. This art museum showcases a diverse collection of Puerto Rican art spanning centuries. From paintings and sculptures to photographs, the museum offers a comprehensive overview of the island’s artistic heritage.
Explore the various exhibits featuring works by prominent Puerto Rican artists, and check for any temporary exhibitions or special events during your visit.
There are also guided tours if you want an explanation of the exhibits.
Where to Stay in San Juan
Puerto Rico is a small island, around the same size as Connecticut. Within the island, most resorts, hotels, and activities center around the capital city of San Juan.
I recommend staying in the San Juan area in any of the three neighborhoods listed below. These neighborhoods each have their own benefits, but all have great luxury hotel options.
Old San Juan
Old San Juan is the historic and cultural center of Puerto Rico. Stay in Old San Juan if you want to visit the historical sites, experience nightlife, or are looking for a city feel.
The best hotel in Old San Juan is the Hotel El Convento, a luxury boutique hotel in the heart of Old Town.
The hotel is historic, centrally located, and has an onsite pool and restaurant. If you are looking for a luxury hotel in Old San Juan, El Convento is the best option.
Condado Beach
Condado beach is the most popular beach area near Old San Juan. Stay here for larger resorts, a more laid back vibe, and easy beach access.
If you plan to have beach or pool days in addition to exploring the island, Condado is a great option. The best resort in Condado beach is the Condado Vanderbilt Hotel.
This resort has a beautiful pool area, easy beach access, and luxurious rooms and amenities.
Carolina
Carolina is a beach neighborhood near the San Juan airport and is known for having luxury properties. If you value a high end resort such as the Royal Sonesta or Fairmont, this area is the best option.
Its also a quick drive to Old Town, so you can easily explore. My favorite hotel in Carolina is the Royal Sonesta. This large property has a stunning pool area, renovated rooms, multiple restaurants, and a beautiful beach.
Traveling to Puerto Rico
To get to Puerto Rico, you can fly into San Juan’s Luis Muñoz Marín International Airport (SJU). There are many direction flights from the continental US on airlines such as American, United, and Jet Blue.
Fun Facts about Puerto Rico
- Puerto Rico became a US territory in 1917
- There are 270 miles of beaches in San Juan
- Puerto Rico is considered the world’s oldest colony
Frequently Asked Questions about San Juan Puerto Rico
When is the best time to visit Puerto Rico?
Puerto Rico is a beautiful destination year-round with temperatures often around 80 degrees and blue skies most days.
However, Puerto Rico experiences hurricane season from June through November, so I recommend planning your visit around that.
What is the currency in San Juan?
Since Puerto Rico is a US territory, the official currency is the US dollar.
What is the official language of Puerto Rico?
Puerto Rico has two official languages – English and Spanish. Nearly all locals will be fluent in both.
Is San Juan safe?
Yes, San Juan Puerto Rico is safe. As with any city, be aware of your surroundings and travel in a group at night.
Potential Trip Extensions from Puerto Rico
Puerto Rico can be a great standalone vacation or starting point for a bigger Caribbean vacation. After completing this 4 day Puerto Rico itinerary, some trip extensions are a Southern Caribbean cruise or a trip to a Caribbean island.
During my recent trip to San Juan, it was the embarkation port for a 7-day Royal Caribbean Southern Caribbean cruise. On the cruise, we visited 6 Caribbean islands.
From San Juan, I highly recommend boarding a cruise or simply visiting one of the ports on your own. This guide to a Southern Caribbean cruise explains what to expect and how to plan your trip.
Summary of this Puerto Rico Travel Itinerary
Puerto Rico is such an amazing destination for a vacation or as starting point for a cruise. In fact, I get to return in a year and I literally cannot wait!
Since there are so many great things to do, it can be hard to squeeze it all into a four day itinerary. However, it’s doable.
Day 1 of this Puerto Rico itinerary begins with a relaxing morning at the beach to recover from your travels. In the afternoon, head to the Bacardi factory for a rum tasting experience.
On Day 2, take a self-guided walking tour of Old San Juan, visiting popular sights such as Plaza Colón, Catedral de San Juan Bautista, and the San Juan Gate. In the afternoon, indulge in a food tour for a delicious late lunch.
The next day, take a trip to the El Yunque rainforest for a guided hike and a swim in a natural waterfall. In the evening, embark on a kayak tour through the bioluminescent bay.
Finally, on Day 4, enjoy a full-day catamaran tour, exploring nearby islands and coastline while swimming and enjoying a local lunch onboard.
Throughout your vacation in Puerto Rico, be sure to soak in the local culture and natural beauty of the island. If you’re continuing on to a Caribbean cruise, check out my guide to the top Southern Caribbean cruise ports.
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