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5 Day Itinerary Exploring Puerto Rico

5 Day Itinerary Exploring Puerto Rico

What vacation destination provides a fun, affordable getaway with beaches, nightlife, plenty of restaurants to delight foodies, off the beaten path spots, and has history to explore?  If that wasn’t enough, what about an island paradise that doesn’t even require a passport if you’re a U.S. citizen?  With Spring Break around the corner, Puerto Rico provides the best balance of everything you want in a vacation to destress, adventure and party up.  Here’s a comprehensive five day itinerary that lets you live your own 5-star vacation story in Puerto Rico and takes you to places that most tourists never get to go to.

Day 1 – Get Your Beach On

Image via Flickr by denizdurmus

You’re going to want to maximize your time out here so I’d recommend catching the earliest flight you can find to San Juan which is where the international airport is located in.  Check into your hotel and once you’re settled in, grab a rum drink, hit the beach, and kick back.  There’s no better way to start off your vacation.

For dinner, check out Oceano for an amazing modern culinary experience.  Your tastebuds will thank you.

Day 2 – Old San Juan

Old San Juan


After a hearty breakfast, it’s time to head out and explore Old San Juan.  I recommend that you start your trip at El Morro National Monument which is an impressive 16th century Spanish fort that costs less than $5 per person.  The views from up here are awesome.  From here, make use of the free white tram and hop off and hop back on along the way to take advantage of the numerous quirky boutiques.  It’s in the old city where you’ll want to freely roam around and admire all the old-world colorful buildings that surround you.  Along the way, you’ll end up grabbing a rum drink or a fresh fruit frappe at one of the many watering holes.

For lunch, consider a local favorite, Restaurante Raices, which serves up delicious mofongo and chimichurri and where the waitresses dress in traditional Puerto Rican outfits.

The afternoon is free for you to either explore further or head back to your hotel and take advantage of the beach or pool.

San Juan is one of the nightlife capitals of the Caribbean and to not take advantage would be a shame!   Soak up the energy and show off your best dance moves at a spot like La Placita.  Salsa, hip hop, bachata, reggaeton, this place has it all.  Best part is that locals come here too so you know it’s authentic.

Day 3 – El Yunque

El Yunque

It’s time to hit the road on the third day and head to one of Puerto Rico’s best attractions, El Yunque National Forest.  This tropical rainforest is filled with incredible waterfalls, hike-able dense forests, and a ton of wildlife to spot.  You’ll want to start off at the El Portal Tropical Forest Center where oyu’ll be able to learn more about the area’s wildlife, grab a few maps and ask for advice on hikes.  One hike I’d recommend is the one that takes you out to La Mina Falls which is only 30 minutes.  If you’re up for a challenge there are also a number of 3-4 hour hikes.  At a minimum make sure you make sure you stop by La Coca Falls and climb up to the Yokahu Lookout Tower for spectacular views from the top.  If you’re lucky, you’ll be able to spot the Coquí frog and the Puerto Rican parrot during your time here.

Tip:  Make sure you bring a poncho because you never know when it’ll rain.  It is the rainforest after all.

For lunch, I recommend the many kioskos of nearby Luquillo.  These row of humble restaurants along Route 3 are a great place to sample Puerto Rican favorites like arepas and plantains.

In Luquillo is a natural water rock slide called Las Paylas where there are smooth rock downhill rivers make for a thrilling ride.  There’s no cost to this since it’s just part of the local river but you can pay $5 to park at a local’s house where he’s sectioned off an area as a parking lot and provides easy access straight down to the river.  As always, be careful of the slippery rocks and chat with the people there first to find out what where the easiest access to the start of the slides are.

Once you’re done, head over to the Fajardo ferry terminal (25 minutes from Las Paylas).  Here, you’ll catch a 1 hour ferry to Isla de Vieques.  It will only cost $2.  Keep in mind that the two late departure ferries leave at 4:45 PM and 8:15PM.

When you reach Vieques, get a cab to one of the many hotels nearby such as Hacienda Tamarindo and Casa de Amistad.

Logistically, you can either do a one-way car rental from San Juan for the day or you can coordinate with a tour company like Natural Wonders and negotiate a drop off in Fajardo.

Day 4 – Isla de Vieques

Isla de Vieques

Isla de Vieques is a Caribbean island off to the east of the main island that typically stays under the radar but is a treat for anyone that knows about it.  This is an island that’s escaped major commercial developments and so you get a tropical paradise that is full of secluded beaches and wild horses that roam the countryside.

Spend the day lounging at your hotel beach or head out to some of those postcard perfect beaches that dot the island.  Blue Beach and Caracas Beach are easy to get to but just remember to bring your own food, drinks, and other beach gear because there are no shops out here.

You’re probably wondering why I didn’t include the Bioluminescent Bay in Fajardo.  The reason is because there’s an even better bay here since it’s been left largely undisturbed and unpolluted.  Under dim moonlight, you’re able to kayak into a body of water where every paddle stroke you make causes the water to glow around you.  It really is out of this world to see.  For this, I would recommend booking in advance as the tours do fill up quickly.  A company like Black Beard Sports ($65 a person) has nightly tours heading out to the Bio Bay.

If you’re close to Esperanza, end your night with drinks at Bananas and have dinner at El Quenepo (make sure you make reservations).

Day 4 – Culebra


Now if it were up to me, I’d keep this spot a secret but you really do have to check out the island of Culebra.  Think of this as the anti-tourist destination.  If you thought Vieques was quiet, this is another island where you won’t find any flashy hotels, tour buses, golf courses, casinos, fast-food chains, or rush-hour traffic.  Instead, you get long stretches of white sand beach and a sleepy and quaint town.

From Isla de Vieques, you’ll have an early wake up call so you can catch the 6AM ferry back to Fajardo and then link up with the 9AM ferry from Fajardo to Culebra.  Once you get here, check into your hotel.  Culebra Moon Villas or Casa Resaca would be good picks.

With Flamenco Beach, TripAdvisor’s Traveller’s Choice in 2015, it’s really a no brainer where you’ll end up spending the day.  As your last full day, this will be your chance to do everything you didn’t get to do on the trip or just a whole lot of nothing.  Go snorkelling.  Go diving.  Go sailing.  Rent a jetski.  Watch the sunset.  That’s a pretty good day right there.

For food recommendations, depending on where you find yourself, check out Zacco’s TacosDinghy Dock, or Vibra Verde.

Day 5 – Back to San Juan

For your final day in Puerto Rico, depending on your flight back home, you’ll either have extra time to explore or you’ll be focused on making it back to San Juan Luis Muñoz Marín International Airport.

Ferry wise, to get to Fajardo, catch the 6AM (only weekdays), 1PM or 5PM.  Once you get to Fajardo, to get to San Juan, you have the option of taking a cab (roughly $80) or you can do a one-way car rental once again.

The week will feel like a whirlwind but when you get back home you’ll reflect and think how epic of a Spring Break it really was.

Know Before You Go

Currency:  USD

Ferry Schedule:  Full details about the ferry to Vieques or Culebra

Cell Phone Service: If you have a US SIM card, this will work here.

Electrical Outlet:  Standard North American plug.

Best Time To Go:  The peak travel period is December to April and low season falls between May and November.  June 1 to November 30 is also hurricane season.  It’s safe to say that low season is the best time to go in terms of crowds and prices.

Numeric Confusion:  Puerto Ricans use both miles and kilometers: distances in kilometers, while speed limits are in miles. To add to the confusion, gas is sold in liters and not gallons.

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Puerto Rico Itinerary Pinterest

This post was sponsored by Puerto Rico Tourism but all thoughts and trip itineraries are my own.  Have fun out there!


About Will Tang

Will is a travel blogger writing for Going Awesome Places. Since quitting his consulting job in 2012 he's been travelling the world and along the way writing about his epic adventures and taking amazing photos. His true passion lies in telling stories, inspiring others to travel, writing detailed trip itineraries for others to follow and providing helpful tips and tricks to travel better. Also the founder behind Travel Blog Breakthrough and freelance writer for Hipmunk and currently working on the #‎HipmunkCityLove Project.


  1. Looks dreamy, especially that glow-in-the-dark bay! I don’t really understand the politics of Puerto Rico…how much of its policy does Washington D.C control?
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