Catherine - Savvy Family TravelIf you’re the kind of traveler who wants to pack a little bit of everything into your trip—beaches, rainforest hikes, hidden waterfalls, and vibrant city life—this 5 day Puerto Rico itinerary is for you.
With only five days, you’ve got to make the most of this beautiful island! From snorkeling in secluded coves to exploring historic forts and even kayaking through glowing waters, this itinerary is all about diverse experiences, adventure, and a taste of local culture.
5 Day Puerto Rico Itinerary
Day 1: Arrival & Beachside Relaxation in San Juan
Afternoon: Arrival and Beach Time
Arrive in San Juan and check into your hotel—whether it’s a beachfront resort in Condado, a boutique stay in Old San Juan, or a budget-friendly Airbnb, we will share our suggestions below.
Note: We highly recommend renting your own car for this 5 day Puerto Rico Itinerary. Be sure to plan extra time for car pickup. The last 3 car pickups we’ve done in Puerto Rico have been an ordeal, whether we used in terminal providers or offsite companies. They just didn’t seem to have enough vehicles ready to go.
Kick off your 5 day Puerto Rico Itinerary with sun and surf at Atlantic Beach or Isla Verde Beach. Both offer golden sand and clear waters, perfect for lounging or taking a dip. Isla Verde has somewhat calmer waves, making it better for families.
Get settled and soak in the island vibes and libations.
Evening: A Taste of Puerto Rico
Dine at a local Puerto Rican restaurant and try mofongo—a classic dish made of mashed plantains, garlic, and savory toppings like shrimp or pork. Some Old San Juan favorites include La Casita Blanca or Deaverdura. If you want to enjoy a Pina Colada in it’s birthplace, have dinner at Barrachina.
Near Condado Beach, the Jose Enrique Puerto Rican restaurant is a great dinner option.
Nightlife: Dance & Music
Adult only trip? Enjoy craft cocktails at Scryer Rum Barrelhouse & Rooftop in Old San Juan or head east of San Juan to La Placita de Santurce for a mix of bars, live music, and street parties, or enjoy salsa dancing at La Factoria, one of the most famous bars in Old San Juan.
Day 2: Old San Juan’s History & Culture
Morning: Explore Historic Old San Juan
Stroll through Old San Juan’s cobblestone streets and colorful colonial buildings. Visit:
- Castillo San Felipe del Morro – A historic fortress with breathtaking ocean views. It’s a site run by the National Park Service. Ours kids enjoyed earning their Junior Badge by completing the activity book. Here’s a link if you want to print it in advance to start working on it.
- Castillo San Cristóbal – Another impressive fort with rich history.
- Paseo de la Princesa – A scenic walkway lined with shops and cafes.
Mid Day: Shopping & Local Eats
Head to Calle Fortaleza for souvenirs, artisan crafts, and local boutiques. Then get lost in the cobblestone streets while enjoying the colorful facades.
Make sure to pass by the Catedral de San Juan Bautista – a breathtaking church where Ponce de Leon’s tomb rests.
Grab a tasty Puerto Rican lunch—perhaps alcapurrias (stuffed fritters) or arroz con gandules (seasoned rice with pigeon peas).
Evening: Dinner with Ocean Views
Soak in the great weather with a rooftop dinner at a spot like Punto de Vista or Eter Rooftop & Lounge, soaking in the island’s last sunset before departure.
Day 3: Waterfalls & Snorkeling Mini Road Trip
Morning: Chase Waterfalls at Gozalandia
Drive two hours from San Juan to experience the Gozalandia Waterfall, a hidden gem with cascading falls and natural pools.
Parking costs $10. Adjacent to the parking lot are modern bathrooms and a restaurant.
Wear sturdy hiking shoes for the often-slippery downhill path and bring water shoes for rocky waters. If you’re traveling with kids, pack life vests for safety. Swim, jump from the falls, explore the stream, and finish with lunch at the onsite restaurant.
If you chose not to rent a car, there are several companies that offer excursions out to Gozalandia.
Afternoon: Snorkeling at Mar Chiquita Beach
Head to Mar Chiquita Beach before returning to San Juan. This beautiful beach sits along a crescent-shaped cove known for its calm waters and snorkeling spots.
Relax on the soft sand and explore the underwater world.
Several vendors are setup offering snacks and tropical drinks. There are only portable toilets onsite.
You’ll want water shoes here for exploring the tide pools.
Grab dinner and head to bed early tonight, tomorrow’s an early morning!
Day 4: Island Escape to Vieques or Culebra
Morning: Flight or Ferry
Grab your coffee and take the earliest ferry or short flight to either Vieques or Culebra for a day of secluded beaches and crystal-clear waters.
Whichever transportation option you choose, it is important to book well in advance! If the ferry sells out online, they reserve some “day of” tickets but that would mean arriving extra early without any guarantee you’ll get onboard.
Mid Day: Beach Hopping
- If in Culebra, relax at Flamenco Beach, one of the most beautiful beaches in the world.
- If in Vieques, rent a golf cart and explore hidden beaches like Playa Negra or Caracas Beach. Keep your eyes open for the famous horses that roam the island.
Note: If you’re traveling with kids, check the age minimums for the Golf Cart rentals. You may need to opt for a Jeep rental if your kids are too young.
Tip: Always take a video walkaround of your car rentals during your 5 day Puerto Rico itinerary. It will come in handy if there’s any dispute as to the original condition of the vehicle you picked up.
Evening: Bioluminescent Bay (Vieques Only)
If you’re in Vieques, consider visiting Mosquito Bay, the world’s brightest bioluminescent bay. However, this experience is best during peak months (April–June) and on nights with little to no moonlight. If you’re there during that sweet spot, be sure to book an overnight accommodation on the island as there are no late night ferries/planes back to the mainland.
If conditions aren’t ideal, skip it and catch the last ferry back to the main island for the rest of your 5 day Puerto Rico itinerary.
Here’s everything you need to know about Puerto Rico’s Bio Bays.
Day 5: Adventure in El Yunque
Morning: Rainforest Hike
If you stayed overnight in Vieques, take the morning ferry back to the main island.
Today’s highlight attraction is El Yunque National Rainforest.
On your way to the entrance of the National Rainforest, stop for a thrill at Las Paylas Natural Water Slide. There are some locals who live along this beautiful natural area, they charge a fee to monitor the vehicles parked and to cut through their property to access the natural slides. It was $5 when we visited, per vehicle.
Top Sites within El Yunque:
- Hike to La Mina Waterfall
- Hike to Juan Diego Waterfalls for a short trek and a refreshing dip.
- Visit Yokahu Lookout Tower for stunning panoramic views.
- Angelito Trail and Swimming Hole
- Check out the Visitor Center: El Portal de El Yunque ($8 adults, kids 15 and under are free.)
Tips for Visiting
- We suggest packing a picnic. All trash you carry in must be packed out with you.
- The cell service here is minimal to none.
- Pack water shoes that also have grip.
- Bathroom facilities are limited.
- Check trail closures and alerts before you go.
- Reservations are no longer required to visit El Yunque.
Afternoon: Beachside Lunch & Relaxation
If you still have leftover sunlight after your El Yunque excursion, grab a meal or snack at the Luquillo Kiosks, a row of beachfront food stalls offering delicious local eats. Afterward, unwind at Luquillo Beach, famous for its golden sand and calm waters.
If you want a quieter beach spot, head a little further southeast for Playa Costa Azúl.
Evening: 2 Options
Here are two great options to be your 5 day Puerto Rico Itinerary’s finale.
Bioluminescent Bay in Fajardo
If you skipped Vieques’ bioluminescent Mosquito Bay, take a kayak tour in Fajardo instead. The bay here is the second best in Puerto Rico for bioluminescent activity. Just remember to make sure you’ll have ideal viewing conditions before booking a tour.
Luquillo After Dark
As an alternative check out the nightlife in Luquillo, starting with live music at the C Note Jazz Club.
Day 6
Departure
That’s it for our 5 Day Puerto Rico Itinerary! Depart Puerto Rico by flight or cruise.
Where to Stay for this 5 Day Puerto Rico Itinerary
Night 1-3: In or Around Old San Juan (We’ve stayed as far as Luquillo to be centralized and we enjoyed it as a base.)
Night 4: Vieques if you’re doing Mosquito Bay, otherwise return to your original accommodations.
Night 5: Near the airport, especially if you have an early morning flight. We like to return our rental the night before and choose an airport hotel with a shuttle.
Additional Travel Tips & Essentials
Know Before You Go
- Best time to visit: November to April for great weather.
- Packing essentials: Sunscreen, bug spray, water shoes, and lightweight clothing.
- Safety & etiquette: Puerto Rico is generally safe, but be mindful of your belongings and respectful of local customs.
- Cruise embarkation and debarkation: If you’re starting or ending a cruise in Puerto Rico I’m glad you’ve chosen to extend your trip to explore this beautiful island. There are two main cruise ports in San Juan – make sure you double check which one your cruise line uses before booking a convenient accommodation.
Cruising with kids? Don’t miss our favorite cruise hacks for families.
Transportation in Puerto Rico
- Best ways to get around: Rental cars offer the most flexibility, but taxis, Uber, and public transportation are also available.
- Tips for efficiency: Traffic in San Juan can be heavy, so plan accordingly.
Adjusting Your 5 Day Puerto Rico Itinerary
If you have extra time, consider extending your stay with a two-night trip to Rincón for surf, sunsets, and more waterfalls.
We have a suggested route and top attractions for you in this Rincon article. It would fit well in this itinerary after Day 3.
If you want to condense your time, check out our 4 Day Puerto Rico Itinerary.
Save Our 5 Day Puerto Rico Itinerary for Later
This 5-day Puerto Rico itinerary ensures you experience the best of the island, from adventure-packed excursions to serene beach days. Save this guide for future trip planning and get ready for an unforgettable Caribbean escape!
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Catherine – Savvy Family Travel
My favorite pastime is finding fun, interesting experiences to share with family and friends.
I’m a mom of two energetic and curious boys who have endless patience with my tendency to over plan activities on our family vacations. My tireless husband, Troy, provides comic relief, is our favorite photographer, and expert navigator.
I’m a firm believer that travel with kids doesn’t have to be intimidating or expensive. It can be affordable, epic, and, dare I say, even relaxing!
Are you a travel loving parent too? I’d love to meet you, please reach out via Messenger and say “hi!”