If you’re looking for a Caribbean trip that has a little bit of everything—culture, adventure, beaches, and great food—Puerto Rico should definitely be on your list.
For our latest GoHabesha group trip, Puerto Rico gave us everything we wanted. We explored colorful streets, learned about the history, hiked in the rainforest, relaxed on beautiful beaches, enjoyed good food, and made unforgettable memories together. One of the best parts for U.S. travelers is that you do not need a passport to visit Puerto Rico since it is a U.S. territory.
Over five days, we visited Old San Juan, hiked through El Yunque National Forest, spent the day at Flamenco Beach, went snorkeling, and ended the trip with great food in the city.
If you’re planning your own trip—or thinking about joining a future GoHabesha trip—here’s exactly what we did.
Why Puerto Rico Is a Great Group Trip
Puerto Rico is one of those places where everyone can find something they enjoy. Whether you like relaxing, exploring, eating, or trying new activities, it all works well here.
Puerto Rico is especially great because:
- It’s easy to get to from the U.S.
- No passport is required for U.S. citizens
- You can mix relaxing and adventure in the same trip
- It works well for solo travelers, couples, and groups
- San Juan is a great base for day trips
Our GoHabesha trip had the perfect balance of fun, connection, and new experiences.
Day 1: Arrival in San Juan and Exploring Old San Juan
We started our trip by flying into Luis Muñoz Marín International Airport, the main airport in Puerto Rico. From there, it was a short drive to Old San Juan.
This time, instead of staying in a hotel, we booked an Airbnb because we wanted something that felt more like home. After checking in and getting ready, we headed straight to Castillo San Felipe del Morro.
Watching the sunset there was one of the best moments of the trip. The views were beautiful, and it was a great way to start our time in Puerto Rico.
Best Photo Spots in Old San Juan
We walked around the city taking photos at some of the most iconic spots. Some of our favorites were:
- La Puerta de la Bandera
- The flag murals along Calle San Sebastián and Calle Fortaleza
- The “I Love PR” signs near Paseo de la Princesa
- The colorful streets and balconies throughout the city
Everything is walkable, and honestly, every corner is picture-worthy.
That evening, we had dinner at:
Triana Tapas & Flamenco
The flamenco performance was amazing, but the guitarist was the star of the show—he was outstanding.
Pro tip: Staying in Old San Juan makes it easy to walk to restaurants, shops, and historic sites.
Day 2: Visiting El Yunque National Forest
The next day was all about nature and adventure. We booked a guided tour to explore El Yunque National Forest, the only tropical rainforest in the U.S. National Forest System.
Our guide took us through hidden trails, waterfalls, and natural pools.
We:
- Hiked through the rainforest
- Learned about local plants and wildlife
- Visited waterfalls
- Swam in natural pools
- Enjoyed beautiful views
The hike was challenging but fun. We even jumped off cliffs and slid down natural rock slides—definitely one of the most exciting parts of the trip.
If you have extra time, consider adding a bioluminescent bay tour, since there are only a few in the world, and Puerto Rico has some of the best.
Pro tip:
Book your tour in advance, wear comfortable shoes, and bring your swimsuit.
Day 3: Day Trip to Flamenco Beach
One of the highlights of our trip was visiting Flamenco Beach. The water is clear, the sand is soft, and the atmosphere is very peaceful. It’s a great place to relax and enjoy the day.
There are two main ways to get there.
Option 1: Drive and Take the Ferry (Most Affordable)
The most budget-friendly way to reach Flamenco Beach is to drive to the Ceiba Ferry Terminal, which is about 1 to 1.5 hours from San Juan.
Here are the steps:
- Drive to the Ceiba Ferry Terminal
- Take the ferry to Culebra
- Ferry ride takes about 45 to 60 minutes
- When you arrive, take a taxi or rent a golf cart
- It’s about 10 minutes to Flamenco Beach
This option saves money, but you need to plan ahead and arrive early.
Option 2: Book a Guided Tour (Easier Option)
If you don’t want to worry about transportation, you can book a guided tour from San Juan.
Most tours include:
- Hotel pickup
- Boat transportation
- Snorkeling gear
- Time at Flamenco Beach
- Lunch or drinks
This option costs more, but it’s simple and stress-free.
Day 4: Snorkeling and Enjoying the Ocean
On day four, we stayed closer to the city with a morning snorkeling trip.
Seeing the fish and clear water was fun, relaxing, and something everyone enjoyed.
Later, we explored Condado, a popular area known for its hotels, restaurants, and beach views. It’s a great place to walk around, grab food, and enjoy the atmosphere.
We had dinner at:
Condal Tapas Restaurant & Rooftop Lounge
The food and vibe were great.
Pro tip:
Some beaches in Condado have strong currents, so always swim in safe areas.
Day 5: Food and Exploring Old San Juan
Our final day was relaxed and simple.
We enjoyed a slow brunch, walked around Old San Juan one last time, and soaked in the views before heading home. It was the perfect way to end the trip.
Before leaving, we stopped at:
Barrachina Restaurant
This is known as the birthplace of the Piña Colada, so of course we had to stop and try the original version before ending our trip. It felt like the perfect final Puerto Rico moment.
We ended the day with great food, good conversations, and a lot of gratitude for the memories we made over the past five days.
Where to Stay in San Juan
Choosing where to stay depends on the type of experience you want.
Old San Juan — History & Walkability
Great if you want culture, history, and a walkable area.
Top picks:
- Hotel El Convento
- The Decanter Hotel
- CasaBlanca Hotel
Condado — Beach & Lively Atmosphere
Great if you want beach access and a lively atmosphere.
Top picks:
- Condado Ocean Club
- Condado Vanderbilt Hotel
- La Concha Renaissance San Juan Resort
- Caribe Hilton
Travel tip:
Consider splitting your stay between Old San Juan and Condado for the best experience.
Where to Eat in Old San Juan
Here are a few places we recommend:
- Café El Punto — great local food
- Barrachina — known as the birthplace of the Piña Colada
- Restaurante Raíces — traditional Puerto Rican dishes
- Marmalade Restaurant & Wine Bar — nice option for a special dinner
You really can’t go wrong with food in Old San Juan.
Best Time to Visit Puerto Rico
Puerto Rico is beautiful all year, but the best time to visit is usually:
December to April — warm weather and less rain
Other good times:
- April to June — fewer crowds
- May or November — good prices
July to November is hurricane season, so just keep that in mind when planning.
Travel Tips for Puerto Rico
- Wear comfortable shoes for walking
- Bring sunscreen and stay hydrated
- Book ferry tickets in advance
- Arrive early for tours and activities
- Take your time and enjoy the trip
Ready to Travel with GoHabesha?
If this Puerto Rico trip inspired you, stay connected for future GoHabesha group trips. We’re always planning trips that bring people together to explore new places, build friendships, and create lasting memories.
Whether you’re traveling solo or with friends, you’re welcome to join us.