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Puerto Rico, USA, Roadtrip, Itineraries Ashlee Wagner Puerto Rico, USA, Roadtrip, Itineraries Ashlee Wagner

5 Days in Puerto Rico with Friends: The Ultimate Multi-Family Adventure Guide

If you’ve ever dreamed of a vacation filled with tropical beaches, lush waterfalls, vibrant culture, and endless laughter, Puerto Rico is your place. After falling in love with the island on our first visit, we couldn’t wait to come back, but this time bringing another family along for an unforgettable 5-day Puerto Rico adventure. Traveling with friends and kids meant double the fun, double the memories, and yes, sometimes double the chaos. But that’s what made this trip so special. From hidden waterfalls to historic forts, here’s our day-by-day itinerary packed with Puerto Rico travel tips for families and friends.

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Puerto Rico, USA, Roadtrip, Travel Tips Ashlee Wagner Puerto Rico, USA, Roadtrip, Travel Tips Ashlee Wagner

Renting a Car in Puerto Rico: The Ultimate Guide to Self-Driving the Island

If you’re planning a trip to Puerto Rico and wondering whether you should rent a car, the short answer is: absolutely yes. While tours and taxis have their place, nothing beats the freedom of exploring the island at your own pace. From lush mountains and cascading waterfalls to colorful towns and hidden beaches, self-driving in Puerto Rico opens up a world of adventure you simply can’t get with public transportation or guided tours.

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Puerto Rico, Itineraries, Roadtrip, USA Ashlee Wagner Puerto Rico, Itineraries, Roadtrip, USA Ashlee Wagner

Family Adventures in Puerto Rico: The Perfect 6-Day Itinerary for Nature, Culture & Fun

If you’re searching for the perfect family vacation in Puerto Rico, this itinerary blends tropical beaches, lush mountain escapes, historic cities, and kid-friendly adventures, all in just six days. The best part? No passport is required for U.S. travelers. From relaxing in a treehouse in the mountains to exploring Old San Juan’s colorful streets, chasing waterfalls, and watching sunsets over the coast, this trip gave us the perfect mix of adventure and downtime. Here’s exactly how we spent our holiday break in Puerto Rico so you can plan yours too.

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Just Another Wagner Adventure | A woman with sunglasses holding a young girl in front of a beach with penguins and rocky dunes in the background. Boulder's Beach in South Africa.
Just Another Wagner Adventure | A man and woman taking a selfie in a dense, green forest with chimpanzee in background. Kibale National Park in Uganda.
Just Another Wagner Adventure | Two young girls and a woman sitting on a swing under a large tree, with colorful decorations and buildings in the background. Yauco in Puerto Rico.
Just Another Wagner Adventure | A woman with long hair, sitting and smiling at Machu Picchu, an ancient Incan citadel in the Andes Mountains with terraced fields and stone structures against a backdrop of green mountains and steep peaks.
Just Another Wagner Adventure | A man holding and kissing two young girls in princess dresses in front of Walt Disney World Magic Kingdom castle.
Just Another Wagner Adventure | A woman holding a baby on a bus, looking out the window at zebras in the safari. Bakubung Lodge in PIlanesberg National Park in South Africa.

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Just Another Wagner Adventure | A happy family of four smiling outdoors, with two adults holding two young girls, under a wooden trellis with green foliage, mountains and trees in the background at Airbnb in Furnas, Azores.