Four Days in Puerto Rico

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Advisor - Brittany Heyward
Curated By

Brittany Heyward

  • Nature Escapes

  • Beaches

  • Adventure Travel

  • Group Travel

  • Puerto Rico

  • Local Culture

  • Local Food

  • Shopping

Red kite pennants on street photo
Curator’s statement

As a travel advisor, it probably comes as no surprise that one of my bucket list dreams was to have a destination wedding. After my first trip to Puerto Rico in 2020, I told my boyfriend (now husband!) that this was the destination and the rest is history. We got married earlier this year in San Juan with 60 of our closest family and friends. With multiple trips to Puerto Rico for wedding planning, I’ve got the perfect four-day itinerary to introduce you to la Isla del Encanto (“The Island of Enchantment”).

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Day 1: Welcome to Puerto Rico


Puerto Rico has two main airports, but if you only have four days in Puerto Rico, I’d recommend flying into SJU. This airport is right near Isla Verde and San Juan, and also just a 40-minute drive to Dorado, where you’ll find some of the island’s best golf and luxury resorts.

After a day of plane travel, I love to get a lay of the land at my resort and the surrounding areas. If you stay on the popular Condado strip in San Juan, you’ll have your choice of beachfront resorts, shops and restaurants to choose from. Some of my top picks for accommodations include the Condado Vanderbilt Hotel, O:live Boutique Hotel & O:LV Fifty Five and La Concha Renaissance San Juan.

After getting checked in, rested and recharged, head to Cayo Blanco, Mario Pagán or Kumo Rooftop for dinner. There are several rooftop bars for an after dinner drink as well. Settle in for the night or hit up a hotspot for dancing and cocktails.

Day 2: Explore the Island


Get into some Puerto Rico history by visiting Old San Juan, the oldest city in America. In addition, you’ll find restaurants, bars and shopping.

Fun fact: During one of my pre-wedding visits, we picked up my wedding band from a duty-free jewelry store in Old San Juan. Want a more guided experience? There are several tours, from history-themed to food tastings. Yummy Puerto Rican food and walking around the city? Sign me up!

Maybe you want something cool and refreshing after walking around Old San Juan. How about a mojito? Head over to Casa Bacardi for a tour of Bacardi’s distillery and a tasting of one of the world’s most famous rum brands.

Day 3: Adventure day


By day three, you should be feeling a bit adventurous. Good, I’ve got a few options for you — day and night!

Daytime: El Yunque National Forest is the only tropical rainforest in the United States. From waterfalls and hiking trails to ziplining and ATVs - there’s so much to do and in the most beautiful, natural setting. If a water adventure is more your speed, the nearby islands of Culebra and Vieques offer several diving and snorkeling options and are accessible by boat ride.

Want a unique, nighttime adventure option? Take a guided night kayak tour in a clear bottom kayak and enjoy the sights of the lagoon below you.

Day 4: It’s so hard to say goodbye


You’ve spent four days in Puerto Rico and now it’s time to head home. Maybe you need to pick up souvenirs or just want to grab something to remember your amazing trip. San Juan has plenty of shopping options, including Plaza Las Americas, the largest shopping mall in the Caribbean.

If you want to hang with the locals and get one last touch of Puerto Riccan culture head to Loíza, the town right outside of Isla Verde. You’ll ride right through Piñones, where the streets are lined with food vendors stocked with delicious and inexpensive eats that are fresh and made-to-order.

Need to Know

For more travel tips, check out Fora Advisor Arina Polyaeva’s guide, San Juan, Puerto Rico Getaway.

Advisor - Brittany Heyward

Travel Advisor

Brittany Heyward

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This guide is part of our ongoing series on travel to Puerto Rico.