Want to plan a solo getaway to the Caribbean for 5 days in Puerto Rico? You’ve come to the right blog! Considered one of the most beautiful of the Caribbean islands, Puerto Rico offers stunning landscapes, rich history, and delicious cuisine that make it a great destination for a quick yet unforgettable first trip.
If you’re a first-time visitor or solo female traveler to the island (like I was!), Puerto Rico presents an exciting opportunity to get to know the island’s beauty, culture, and spirited Puerto Ricans that call it home.
Below, you’ll get a comprehensive guide that shares recommendations on where to eat, where to stay, and places to explore across the island. As a heads up, this itinerary is packed. I barely slept while I was in Puerto Rico as I wanted to make the most of my visit. However, you can take from this 5 day itinerary what you wish and what you’re most comfortable with.
I hope my personal suggestions below help you make the most out of your 5 days in Puerto Rico to experience ultimate Caribbean vacation!
How to Get to Puerto Rico?
Getting to Puerto Rico from the mainland United States is pretty straightforward. Flying is the best way to get there, and there are many direct flights offered by major airlines from major airports across the U.S. If you’re coming from East Coast cities like New York, Miami, or Atlanta, it’s extremely easy to find good routes to the island’s capital city, San Juan. For a direct flight, travel time is usually under 4 hours from these destinations.
You can find discounted flights on websites like Expedia, Google Flights, and Skyscanner to customize your search based on your budget and travel preferences.
Major airlines that offer routes include American Airlines, Delta Air Lines, JetBlue Airways, and United Airlines. Because of this alone, Puerto Rico’s vibrant culture, stunning beaches, and beautiful architecture are at traveler’s fingertips. I flew with American Airlines from Nashville, Tennessee with a short layover in Atlanta.
Renting a Car in Puerto Rico
Once you’re in Puerto Rico, renting a car is the go-to move for exploring the island. The roads are smooth and well-maintained, giving you the freedom to venture beyond the tourist hubs and uncover hidden gems. Plus, with rental car companies all over the place, especially at the airport and in major cities like San Juan, it’s super easy to grab a set of keys and hit the road.
Now, let me tell you about the sights you’ll see! Cruising through Puerto Rico by car is like flipping through a travel magazine. You’ll see the lush greenery of El Yunque National Forest on one side of the island, and cobblestone streets and colorful buildings of Old San Juan on the other. If you want to have the ultimate road trip, this is the place to do it.
The best part, is that U.S. citizens don’t need a passport to enjoy this Caribbean paradise!
When is the Best Time to Visit Puerto Rico?
The peak tourist season typically occurs during the winter months, from December to April. During this period, the weather is typically more dry and cooler, making it an ideal time for beach activities, sightseeing, and outdoor adventures. You’re more likely to enjoy temperatures between the mid-70s to low 80s Fahrenheit (around 24-28 degrees Celsius). There’s also fewer chances of heavy rainfall and hurricanes, providing optimal conditions for exploring the island.
However, don’t overlook visiting during the shoulder seasons of May and June or September and October. While you will have to keep an eye out for the possibility of hurricanes, you’ll also score great deals on hotel and resort accommodations while also skipping the massive crowds of high season. If you’re into experiencing the “real” Puerto Rican vibe without all the touristy chaos, this could be your ticket! I visited during the high season in mid June and still experienced some rain. However, it is an island after all, so some rain is expected!
Whether you’re all about experiencing the best weather, saving cash, or have no budget at all, booking a trip to Puerto Rico is always a good idea.
Continue reading below for a suggested 5 day Puerto Rico itinerary, highlighting recommendations of how to spend each day of your stay on the island!
Where to Stay During 5 Days in Puerto Rico
Luxury Option: Condado Vanderbilt Hotel
In order to maximize my time, I used San Juan as my base for the entirety of my trip, and did most day trips and half day trips from the city using local guides and tour companies since I don’t feel comfortable driving. For my first three nights, I stayed at the Condado Vanderbilt Hotel which is a luxury oceanfront hotel in the heart of the Condado neighborhood. Built in 1919, it’s a top pick for hotel accommodations in San Juan. The property offers one and two bedroom suites, as well as two different guest room layouts: Heritage and Tower. Tower guest rooms are slightly larger. The property also includes a stunning infinity pool, a pool bar, a jacuzzi, a beachfront wading pool with lounge chairs, a fine-dining restaurant, a fitness center, and a full service spa.
Mid-Range Option: La Terraza de San Juan
For my final two nights, I decided to save some money and stay at La Terraza de San Juan. If you want to spend less but still want to experience a great stay, I highly recommend this property. It has a great location within walking distance to San Cristobal, and features a beautiful rooftop with a pool and dining area. I stayed in a Kind Deluxe Room which offers a very large attached bathroom, mountain views, a refrigerator, flat screen with Netflix, and free wifi. This may sound silly, but it also has great air conditioning, which you might need especially if you visit Puerto Rico during the hotter months!
Day 1: Savor Traditional Puerto Rican Cuisines
Puerto Rican cuisine is a delicious fusion of Spanish, African, and Taino flavors, resulting in unique and flavorful dishes. To sample the best of the local cuisine, consider booking a food tour on the first full day of your trip. I absolutely loved the Flavors of San Juan Food Tour, which allowed me to indulge in delicious Puerto Rican delicacies and connect with other solo travelers. It’s the perfect way to maximize your time and savor the essence of Puerto Rican cuisine while making lasting memories.
Below are my personal recommendations for things to eat and where to eat them!
1. Mofongo
Your first stop no doubt has to be for mofongo. A beloved Puerto Rican dish made from mashed fried plantains, garlic, and pork cracklings, mofongo offers a delightful blend of salty flavors and hearty texture. A great place to savor this iconic Puerto Rican dish is the local restaurant of Triana Tapas & Flamenco in Old San Juan. Here, you can take a mofongo making class while listening to authentic renditions of flamenco and other live music.
2. Alcapurrias
These deep-fried fritters are made from a dough of green bananas and taro root. They are stuffed with savory fillings such as ground meat or seafood. Alcapurrias are a popular street food snack in Puerto Rico, offering a crispy exterior and a flavorful, savory interior that’s a perfect snack to curb hunger while exploring the island’s vibrant streets. At $4.75USD, they are also a very affordable snack as well!
3. Paletas
Beat the Caribbean heat with refreshing paletas — delicious fruit popsicles made with fresh tropical fruits like mango, pineapple, and coconut. The best place to get paletas is from either Señor Paleta or Zippops Gourmet paletas, where you can choose from a variety of flavors and enjoy a sweet and refreshing treat. I recommend grabbing a paleta to enjoy while strolling around Old San Juan. I chose the Toasted Coconut & Strawberry Cheesecake with chocolate drizzle, and then went back for a Mango and Passionfruit paleta the next day!
4. Hot Chocolate with Cheese
One of the most popular spots in Old San Juan that offers both traditional and innovative sweet treats, is Chocobar Cortez. This Caribbean chocolate bar has an iconic menu that features some truly unique menu items. One of the most iconic menu items to order is the grilled cheese hot chocolate. It’s exactly as it sounds, too! Rich and creamy 80 percent Puerto Rican chocolate is melted with cream, with a block of cheddar cheese dropped in. It sounds weird but it’s absolutely delectable. If you’re feeling something savory, I recommend the turkey and ham sandwich on chocolate mallorca bread. It comes with a side of seasoned curly fries and chocolate ketchup — yes, I said chocolate ketchup!
5. Puerto Rican coffee
There’s nothing like the rich and aromatic flavor of Puerto Rican coffee. In fact, I would argue that a cup of Hacienda San Pedro is simply the best. Sourced from a historic coffee plantation in the mountains of Jayuya, this coffee offers a smooth and robust taste that’s sure to delight coffee enthusiasts. The best way to explore the coffee scene in San Juan is a book a craft coffee tour.
If you want to keep it simple, tell your barista that you want “un cafe con leche” — a simple cup of coffee with milk. In many places you can get hot (caliente) or cold (frío). I found the best coffee shop to visit is Cuatro Sombras in San Juan. I paired my coffee with a fresh ham, cheese, and guava croissant for the perfect morning pick-me-up before a day of exploring!
6. Empanadillas
These savory turnovers are a popular snack in Puerto Rico, featuring a crispy pastry shell with fillings such as seasoned ground beef, chicken, cheese, or seafood. Empanadillas are perfect for on-the-go snacking or as a hearty appetizer during your culinary adventures on the island. During my time in San Juan, I loved walking to a small beachfront stall in next to my hotel every afternoon for a quick empanadilla snack. Personally, I think the best place to enjoy them is on Condado Beach paired with a freshly cracked coconut or smoothie! You can get both of these at many of the empanadilla stands as well.
7. Piña Coladas
It’s not a trip to Puerto Rico without sipping a sweet and refreshing piña colada. After all, Puerto Rico is the birthplace of one of the world’s favorite mixed drinks! This classic Puerto Rican cocktail is made with rum, coconut cream, and pineapple juice. It’s usually topped with a fresh slice of pineapple, orange, and a cordial cherry. A must-visit place to get piña coladas is at Barrachina Restaurant, the literal spot where they were first made. Here, you can enjoy this iconic drink in a charming garden courtyard setting, surrounded by lush greenery and tropical vibes. The food at Barrachina isn’t bad either if you’re looking for lunch or dinner!
8. Arepas de Coco
This sweet Puerto Rican fry bread is a favorite street food among locals and tourists alike. It combines the tropical flavors of creamy coconut with the warmth of freshly baked and slightly fried bread. You can find a number of street food stalls that sell them, or you can check out La Prena.
9. Tostones
Crispy on the outside and tender on the inside, tostones are a beloved Puerto Rican side dish made from green plantains that are twice-fried until golden brown. The best place to get them is at Patio de Sam, where you can enjoy these delicious plantain bites served alongside flavorful dipping sauces for the ultimate snack experience.
Day 2: Take in Puerto Rico’s Natural Beauty
On day two, jump right into the awe-inspiring natural wonders of Puerto Rico! From the towering rainforests to the shimmering bioluminescent bays, day two promises adventures filled with breathtaking landscapes and unforgettable experiences.
1. El Yunque National Forest
You can’t visit Puerto Rico and not explore El Yunque rainforest. It is the only tropical rainforest in the North American national forest system, after all! Bring your hiking boots and lace em’ up to prepare to explore more than 29,000 acres of lush trails adorned with cascading waterfalls and vibrant flora.
You can also book a tour of El Yunque rainforest with a local guide, which usually includes pick-up and drop-off from San Juan hotels, a hiking guide, and occasionally lunch depending on the tour operator. If you have a rental car, you can drive to El Yunque to enter the park for free, although parking spots are limited. When you arrive, stop by the El Portal Visitor Center first for information about the hiking trails or sections of the park that might be closed to visitors. When I went, the island had just re-opened up during Covid, and very few trails and sections of the park were open to visitors. Weather and ongoing construction can also impact what is available to explore. Regardless, it’s a great way to take in Puerto Rico’s natural beauty and get some exercise in at the same time.
Popular Hiking Trails in El Yunque
Some of the most popular trails include the Mount Britton Trail & Tower for a cloud forest, the El Yunque Trail, and the El Toro Wilderness Trail. While all of the main trails in El Yunque are relatively short, they range in difficulty. For easier trails, choose the Angelito Trail (0.2 miles rated as easy), and the Caimitillo Trail (0.4 miles rated as easy). Whatever you choose to enjoy, you’ll quickly realize that El Yunque is one of the most beautiful places on the island, and a day trip there is absolutely necessary!
2. Bioluminescent Bay
After spending the first half of the day at El Yunque, you can experience a bio bay either in Condado Lagoon, or in Vieques. To save time, I chose to do a nighttime tour of Laguna Grande in Fajardo after visiting El Yunque. I was still able to see the bioluminescent organisms light the water up like blue electricity!
If you decide to venture further for a tour of Mosquito Bay in Vieques, you will have to drive to Ceiba in East Puerto Rico. In Ceiba, you will board the ferry to Vieques. You can hop aboard a guided kayak tour or an electric boat excursion to slowly glide through the dark waters illuminated by the shimmering glow of millions of bioluminescent organisms. Bio bay is truly mesmerizing as the water comes alive with ethereal blue-green light for an enchanting glow. It’s a unique experience that is hard to forget.
If you want to take photos and videos during your tour, you can bring camera equipment. However, it’s best to bring a camera that has manual settings to adjust the shutter speed, aperture, and ISO for dark lighting if you want the best shot at capturing the “glow”. If you decide to take a kayak, you’ll want to put your belongings in a waterproof bag that is usually provided to protect against unexpected splashing or tip-overs.
Day 3: Discover the Vibrant Landmarks of Old San Juan
You might be a bit tired from the busy day before, but try to get an early start. Begin day three of your 5 days in Puerto Rico with a guided walking tour of Old San Juan’s vibrant landmarks! With its cobblestone streets and colorful colonial architecture, this UNESCO World Heritage Site is incredibly walkable, allowing first time visitors and solo female travelers to explore its iconic landmarks in a single day (if you start early that is). Exploring the city by foot is absolutely one of the best things you can do to immerse yourself in the city.
Below are personal recommendations for things to see on a walking tour of San Juan:
1. Castillo San Cristobal
You can literally step back in time decades when you visit the imposing Castillo San Cristobal, a historic fortification dating back to the 18th century. It’s considered the largest fortress built in the Americas. You can explore its sprawling grounds and intricate tunnels which once served as a defense against naval attacks. From its elevated vantage points, you can admire panoramic views of Old San Juan and the sparkling waters of the Atlantic Ocean below. The entrance fee is just $10USD, making it an affordable attraction to enjoy during your 5 days in Puerto Rico.
2. Castillo San Felipe del Morro
Also known as the “El Morro” fort, this national historic site is known as the most iconic fortification built by the Spanish in the Americas. It towers over the Bay of San Juan at 140 feet in height, and consists of 6 levels facing the ocean which were designed to protect San Juan with heavy artillery fire. Construction of the fort originally began in 1539, but was updated in the late 16th and 17th centuries. It’s the perfect spot for Insta photos, too, with stunning backdrops over the Atlantic and perfectly framed stone walls and windows. El Morro is about a 15 minute walk from San Cristobal, so you can easily see both in one day. The entrance fee for El Morro is also $10USD.
3. Bastión de las Palmas
Located within the city walls of Old San Juan, Bastión de las Palmas is a charming plaza surrounded by colonial-era buildings and lush greenery. Most walking tours of San Juan make a quick stop here to stroll through the square and admire its picturesque fountain and historic architecture. It’s a great spot for people-watching as it’s always buzzing!
4. Parque de las Palomas (Pigeon Park)
If you have a phobia of pigeons, this may not be the place for you. Otherwise, Parque de las Palomas is tranquil oasis nestled within the heart of Old San Juan. This charming park is home to hundreds of pigeons that you can feed and interact with if you wish. I enjoyed a peaceful moment on one of the park benches, surrounded by lush greenery and the soothing sounds of nature.
5. La Casa Estrecha
Even if it’s just a quick stop, make sure you appreciate the architectural marvel known as La Casa Estrecha, or the Narrowest House in the World. This colorful, slender building is just five feet wide, yet it manages to squeeze in two stories of living space. Snap a photo of this quirky landmark and imagine what life must have been like for its former inhabitants.
6. Catedral de San Juan Bautista
Explore Old San Juan with a visit to the majestic Catedral de San Juan Bautista. This stunning cathedral, dating back to the 16th century, is one of the oldest buildings in Puerto Rico and serves as the final resting place of the island’s first governor, Juan Ponce de León. Take a time to admire its beautiful Gothic architecture and ornate interior which features intricate stained glass windows and impressive works of art.
7. Santa Maria Magdalena de Pazzi
Discover the hidden gem of Santa Maria Magdalena de Pazzi, a historic church tucked away in the heart of Old San Juan. Dating back to the 18th century, this charming chapel boasts a stunning Baroque facade and a serene interior adorned with intricate wooden carvings and religious artwork. Take a moment to admire the peaceful ambiance of this sacred space, steeped in centuries of history and tradition.
Day 4: Adventure Beyond San Juan
If your base is San Juan during your 5 days in Puerto Rico (which I recommend), it’s extremely easy to book full-day or half-day tours for outdoor adventures. There are plenty of options for half-day or even full-day excursions just beyond the city or on the other side of the island. Whether you’re craving beach relaxation or cultural exploration, there’s something for everyone to enjoy outside the city limits.
1. Explore the town of Fajardo
Wake up early to explore the coastal town of Fajardo. Known for some of the best beaches and outdoor activities, it’s just a short drive from San Juan. First, head to Seven Seas Beach for sunbathing and swimming in crystal-clear turquoise waters.
For some adventure, hop aboard a two hour catamaran tour out to Icacos Island to snorkel, swim, or just enjoy the sunshine and sea. I went on a 3 hour catamaran tour to Icacos with Castillo Tours and had the absolute best time. Snorkel gear, flotation devices, cocktails, and snacks were provided on board which made the experience stress-free.
2. Take a Tour of Casa Bacardi
One you return to San Juan, head to Casa Bacardi to spend a late afternoon. Located in the town of Catano, Casa Bacardi is a great spot to dive into the world of rum. However, make sure you book your mixology tour or tasting tour at least a few weeks in advance as they sell out often! To get there, you can Uber to Catano, but I chose to hop on the Catano Ferry for a scenic journey across the Bay of San Juan for just $1.25USD. From the ferry port, I took a public bus to the distillery. This option is much cheaper (and quicker!) than taking an Uber.
Once at Casa Bacardi, you can book the Legacy Bacardi Tour to learn about the history and production of Puerto Rico’s famous rum. On the tour, you will explore the interactive exhibits, shop at the gift store, sample delicious rum cocktails, and soak in the panoramic views of Old San Juan from the distillery’s rooftop terrace. If you don’t have time to do a tour, you can still visit the distillery grounds to enjoy a cocktail and an empanada on the outdoor patio. Be sure to take photos in front of the famous Bacardi barrel sign!
Day 5: Hit Up the Beach Town of Rincon
On the last day of your Puerto Rico adventure, wake up early and drive about three hours to the western coast of Puerto Rico to the laid-back beach town of Rincon. Here, you can enjoy some sun, snorkeling tours, surf, and relaxation. Nestled on the island’s west coast, Rincon is renowned for its pristine beaches, world-class surfing, and vibrant beach culture. Spend the day soaking up the tropical vibes, and then sample a few different dishes from the local food trucks!
Below are a few personal recommendations of things to do during a day trip to Rincon:
1. Tres Palmas Marine Reserve (Steps Beach)
Here you can enjoy the vibrant underwater world of the Tres Palmas Marine Reserve, home to colorful and protected coral reefs and diverse marine life. The marine reserve is home to a popular snorkeling and surfing spot known as Steps Beach. It’s a popular spot for outdoor enthusiasts to kayak, SUP board, or simply enjoy the sun and sand.
4. Domes Beach
Domes Beach is a favorite spot for both surfers and sunbathers, offering gentle waves and stunning views of the surrounding coastline. This beach is unique as it is located close by both the stunning Punta Higuero Lighthouse, and a former nuclear facility, the BONUS Reactor Facility.
3. Beachfront Dining
Rincon is a great place to enjoy fresh Caribbean seafood and traditional Puerto Rican dishes. Whether you’re enjoying a leisurely lunch or a romantic dinner, the beachfront restaurants of Rincon offer a memorable culinary experience. I dined at La Ana de Cofresi Restaurant and absolutely loved the Mashed Plantains Stuffed with Lobster! Rincon is also home to a number of popular food trucks at Gastropark that serve foods including fish tacos, tostones, fish and chips, smoothies, cocktails, barbecue, coffee, and ice cream.
5 Days in Puerto Rico: Safety Tips for Solo Female Travelers
Navigating Puerto Rico as a solo female traveler offers an enriching and memorable experience. While I didn’t experience any safety issues or dangerous situations during my time there, it is always important to remain vigilant and aware of your surroundings to prioritize safety no matter where you are in the world.
During your 5 days in Puerto Rico, always book accommodations in either Condado (where I stayed), or Old San Juan. Rincon Beach Resort, and St. Regis Bahia Beach Resort are some accommodation options you can consider outside of San Juan.
If you decide to venture out at night (San Juan has an amazing nightlife!), stick to well-populated and familiar areas. Many people tend to enjoy clubs and bars well into the late evening in Puerto Rico – especially in San Juan – so you likely won’t be alone when you decide to venture back to your hotel. You’ll find that many of the cultural norms in Puerto Rico are similar to that of the mainland U.S., although some are different.
Travel Tips for 5 Days in Puerto Rico
One of the most helpful things you can do before spending 5 days in Puerto Rico is to learn some basic Spanish words and phrases. Not only will this enrich your travel experience, but empower you to navigate situations more confidently. While Puerto Rico is a U.S. territory and many locals are bilingual, you can’t expect everyone to speak English. After all, the official language is Español!
Secondly, if you plan on exploring outside of San Juan during your 5 days in Puerto Rico, book reputable transportation in advance, or book a rental car that you can pick up and drop off from the San Juan airport. Make sure you have good rental car insurance if you choose the latter. Road conditions on this small island are generally good, and driving rules are the same as the mainland United States. However, locals tend to drive fast and recklessly, especially on highways. I wouldn’t recommend driving unless you are very experienced and can handle aggressive traffic.
Lastly, make sure you always travel will a fully charged phone, bring a portable charging block, and download any helpful safety or travel apps prior to your trip.
By following the above travel and safety tips, your 5 days in Puerto Rico will be both thrilling and secure, leaving you able to fully enjoy the island’s spectacular and diverse culture. Happy Travels!
