Puerto Rico 4 Day Itinerary: Quick, Easy, FUN

Bali Swing

My grandmother is from Puerto Rico and yet somehow I had never been there until earlier this year. And now that I’ve been there I can barely believe it took me so many years, because it’s such a wonderful little country - easy to get to & navigate around, has lots to offer in terms of restaurants and nightlife, beautiful beaches, darling colonial architecture, and warm, fun locals.

I wanted to share a quick little itinerary that is doable in a long weekend. I did this itinerary over President’s Weekend - ONLY MISSING ONE DAY OF WORK. I left on Friday after work (red eye), Monday was off, returned home Tuesday night. Though short, it packed in a lot of sites & was immensely satisfying - combining a little bit of beach, rainforest/nature, culture, history and city life.

As always, make sure you are traveling safely with TRAVEL MEDICAL INSURANCE

Puerto Rico 4 Day Itinerary

Day 0 - Friday

Old Town San Juan

• Travel to Puerto Rico (after work if flight available)

Day 1 - Saturday

Sunset Walk & Taste Tour around Old San Juan

• 8AM-10:30AM:  Manatee Caretaker For a Day 

  • Fun, unique, off-the-beaten experience with incredible creatures!

• Afternoon:  Castillo San Felipe Del Morro & Castillo de San Cristobal; Stop for a Senor Paleta Popsicle

  • Fortresses - for beautiful architecture, history, and views of the ocean

  • Señor Paleta - popsicle chain that you’ll see all around San Juan - don’t miss out….they are DELICIOUS.

• 4PM-7PM: Sunset Walk & Taste Tour in Old Town

  • San Juan has very fun nightlife - so this tour is a great way to see Old Town, and and explore some of the best bars/clubs in the the area. Led by local guides who will share what it’s like to live (& party) in Puerto Rico - so you get a little bit of culture mixed with your cocktails!

• Late Night: La Factoria for drinks & dancing

  • This iconic bar/club (that was featured in Despacito music video) is a must while in San Juan. It features numerous bars/restaurants and dance floors for endless exploring! Including a secret underground passageway between the different bars.

Day 2 - Sunday

Beratan Lake

• 8AM-3:30PM:  Body Rafting, Caving & Hiking Tour 

  • Another unique, off-the-beaten path experience that you to Northwestern Puerto Rico in the tropical rainforest - great for adventure & nature!

• Early Evening: Unwind with a cocktail on Condado Beach at Oceano Beach Club

  • Tip: Get here around the end of lunch time hour (4PM) or right when they open for dinner (5PM) when they are less busy to avoid having to have a reservation!

• Evening: Dinner in Old Town at a rooftop restaurant and visit the Umbrella Installation on Fortaleza Street

  • Great rooftop dinner options: Punto de Vista, La Terraza de San Juan, The Mezzanine

  • The Umbrellas on Fortaleza Street are nice during the day too, but incredibly magical at night.

Mt Batur Sunrise Hike (dress warmly lol)

Day 3 - Monday

• Early Morning: Stroll along Condado Beach before the crowds arrive.

  • Optional 2nd visit, but a nice way to start the day if you are an early riser like myself

• 9:30AM-3:30PM:  Culebra Snorkeling Getaway 

  • No trip to Puerto Rico is complete without a visit to Culebra Island - it’s absolutely stunning and a day trip is an easy way to see it when you’re short on time. I felt a day trip was totally sufficient, but there ARE a couple accommodations ON Culebra if you wanted to extend your stay.

• Evening: Visit La Placita, a fresh-air market during the day, bursts with life at night. Here you can drink at one of the area’s many bars, and enjoy the site of locals dancing in the street (or join in yourself!).

Day 4 - Tuesday

• 8AM-12PM:  El Yunque Rainforest Waterslide & Hiking Tour 

  • El Yunque Rainforest is another staple when visiting Puerto Rico - it’s very close to the city and offers great hiking and scenic nature. It was heavily damaged by the hurricane but many of the paths and viewpoints are re-opening, so show it some support/love and go visit! You won’t regret it :)

  1. Evening: Return Home

I know there is a lot more to Puerto Rico than just San Juan and the activities mentioned above - but if you’re short on time, this will give you an awesome experience and is a great intro to PR. It will definitely leave you wanting more, like it did for me! I hope to get back and explore the western & southern side of the country at some point.

Have you been to Puerto Rico? Any experiences you absolutely loved? I plan to go back and would love any recommendations.

Fortaleza Street Umbrells at Night