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puerto rico

Old building in San Juan

For the love of













Our small group trip to Puerto Rico caters to travelers in their 20s and 30s looking for cobblestone magic in Old San Juan, rainforest thrills in El Yunque, and sun kissed Caribbean paradise as far as the eye can see.

Meet up with a crew of new friends to explore Puerto Rico's capital as you find a rare American escape from the ordinary. We'll dive into the rich history and culture of the island, getting up close and personal with centuries-old fortresses by day and vibing to the pulsating beats of bomba music by night. Then, you'll meet up with the Caribbean sun on pristine beaches, explore the lush, untouched beauty of El Yunque National Forest, and dance the night away in the colorful streets. And let’s not forget the mouth-watering local cuisine - mofongo, anyone?

This trip is about more than just sightseeing—it's about making unforgettable memories, forging new friendships, and embarking on an adventure that will ignite your wanderlust. So pack your bags, it's time for Puerto Rico living.

5 days/4 nights

starting at $2,099 USD

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Limited single room upgrades starting from $480 are available and can be added during booking, subject to availability.


Payment can be broken down into a $500 deposit + 3 additional installments.


  • 4 nights in a hotel in Old San Juan

  • 4 breakfasts, 1 lunch, 2 dinners (welcome and farewell dinners)

  • Guided historical food walking tour of Old San Juan, the capital's most atmospheric neighborhood

  • Sunset salsa class in San Juan

  • Day trip to El Yunque Rainforest (the only tropical rainforest in the U.S National Forest System), including entrance fee and guide

  • Excursion to the secluded pools and waterfalls of Rio La Tinajas

  • Cliff jumping (not required!) in the Puerto Rican jungle

  • Traditional street food lunch experience

  • FTLO Trip Leader

*All activities are weather dependent; in the unlikely event that we are unable to run an activity, we will have a suitable alternative in place.

not included

  • Flights to & from Puerto Rico

  • Mandatory trip insurance 

  • Meals not mentioned (budget around $200)

  • Incidental expenses

more details

day by day

*Itinerary is subject to change

Day by day
Day 1 - San Juan
Welcome to
San Juan

Congrats, you've made it to one of the natural wonders of the United States! Drop your bags, and get ready to dive into San Juan.

After a welcome rendezvous with the group, we'll kick things off with a welcome drink. Get to know your new travel mates over fruity cocktails or try a local rum; with a massive sugarcane crop, the island’s home to more than a few distilleries (hello, Bacardi!).

Now that we’ve said hello the right way, it’s time to get to know the fusion flavors of the island's cuisine at one of our favorite San Juan restaurants. With a menu that focuses on local dishes dating back to the 1800s, it is a historic, tasty welcome to Puerto Rico. Salud!

Puertorican flag on a balcony


Day 2 - San Juan
Cuisine and Culture

Today, we'll continue to discover Puerto Rican culture through its history, people, and food on a walking tour of Old San Juan. In a city filled with historical sites, it's only fitting that you step back in time for a few hours and discover the island's blend of Spanish, African, and Taíno influences.


Savor some of the region's exceptional food like pan de agua and quesitos. Try street food favorites like alcapurrias and bacalaítos from vendors with generations of culinary expertise. Quench your thirst with a refreshing piragua, then discover the stories and traditions that shaped the island's culinary landscape.

That night, we'll be hitting up a salsa class in oceanfront Condado to check out the pulsating Afro-Caribbean beats and learn some Puerto Rican moves of our own. After dancing the night away, grab a late night bite to eat with the crew.

Man dancing bomba


Day 3 - El Yunque National Forest
Rainforest Adventuring

Today we're exploring Puerto Rico's tropical El Yunque National Forest. Picture towering ancient trees, a chorus of coqui frogs, and the mist of hidden waterfalls. Our local guides will lead the way, sharing all the inside info you need on El Yunque's unique flora and fauna.

We'll head to the rainforest's secluded natural pools where you can cliff jump, float in tranquility, and marvel at paradise. We’ll no doubt work up an appetite, so after the rainforest, we'll head over to Luquillo Kiosks' 60 family-run stalls for the best to connect with the local community as you feast on tostones, pinchos, and delicious seafood along a laid-back beachfront.

The afternoon and evening are yours; siesta in hammocks or head toward local artisan shops for more Puerto Rican charm.

Rainforest road


Day 4 - San Juan
Sun and Sea

The next 24 hours are yours for exploring in the picturesque Old San Juan area. Head to San Juan Bay and check out the beautiful beaches, grab a recliner at Condado Beach, or see how the high class live over in Isla Verde. For more adventure, check out the water sports and rent a jet ski for an hour or two.

If you're after a more local vibe, Old San Juan's narrow streets are lined with historic buildings. Hunt for souvenirs, savor the island's famous tropical ice cream, or immerse yourself in the rich culture and history. If you're up for it, head to the Santurce neighborhood to check out the city's acclaimed art scene. 


That evening, meet up with the crew at our farewell dinner. Here's to unforgettable adventures, laughter, and living life on the wild side, in true Puerto Rican style!

sand and ocean


Day 5 - San Juan
Until Next Time!

Rise and shine, it's time to sip on that last cup of rich Puerto Rican coffee and reminisce about the epic rainforest hikes, the soul-stirring rhythms of local music, and the mouthwatering flavors of street food.

So here's to the memories, the friendships, one beautiful island, and to countless adventures that lie ahead. Until the next time, hasta la vista, adventurers!

If you're wanting to expend your time, consider checking out Cabo Rojo on Puerto Rico's west coast, heading east to Luquillo Beach, cruising to spectacular Flamenco Beach (skip the beach resort and explore on your own), or joining one of the many tours to check out the world's brightest bioluminescent bay in Vieques.

Fast facts

“Nothing is better for your soul than to visit Puerto Rico.”
-Lin-Manuel Miranda

People dancing on the street


Just for fun

Puerto Rico is home to Bacardi's rum factory. Also known as the cathedral of rum, it's the world's largest.

Puerto Rico's Catedral de San Juan Bautista was first constructed in 1521 and is the oldest in the US.

Puerto Rico is the birthplace of the Piña Colada (we see a trend).

Trip notes

  • While we can’t guarantee private rooms, you should book your trip earlier if you prefer one, as they usually fill up.

  • Puerto Rico is a U.S territory, so there’s no need for a passport if you are a U.S citizen.

  • All activities are weather dependent; in the unlikely event that we are unable to run an activity, we will have a suitable alternative in place.

  • More information for all other nationalities and Covid restrictions can be found here.

about puerto rico

Located in the heart of the Caribbean, Puerto Rico offers a unique blend of natural beauty, rich history, and vibrant culture. The island is known for its lush rainforests, home to a diverse range of flora and fauna, including the emblematic Coqui frog. La Fortaleza, a UNESCO World Heritage Site, and landmarks such as the Catedral de San Juan Bautista, the oldest cathedral in the U.S., stand testament to the island's rich past. As for gastronomy, the island boasts an array of flavors, including the world-famous Piña Colada, a refreshing cocktail invented here.

Good to Know

  • Puerto Rico uses the U.S. dollar as its official currency.

  • Puerto Rico has a tropical climate with pleasant temperatures year-round. Occasional showers are brief and followed by sunny skies.

  • Tipping is customary in Puerto Rico, similar to the mainland U.S.

  • Spanish is the predominant language in Puerto Rico, but English is widely spoken.

Palm trees sand and ocean


Fly into San Juan (SJU)

Arrive by 4pm on day 1 and grab a cab to our hotel in San Juan. We do recommend flying in earlier to have some time to explore the city on your own!

Fly out of San Juan (SJU)

We recommend flying out of SJU or extending your trip and enjoying a few more days in San Juan.


Want to check out flights for your trip?

Feel free to also set up flight alerts so you can grab the best deal!

*FTLO is not responsible for any fees or costs related to flights. We strongly suggest that all travelers wait until they receive the official FTLO Greenlight Email to book flights. This will be sent 3-4 months prior to the start date of your trip.

Learn More
Colorful alley in Puerto Rico


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