If you’re currently on the mainland USA daydreaming of white sand beaches, crystal clear waters, and a frozen piña colada, San Juan, Puerto Rico may be the perfect place for a weekend getaway. A 2.5 hour flight from Miami with no passport requirements, Puerto Rico offers unbeatable ease of access. You’ll find the historic architecture of Old San Juan adjacent to new resorts and picturesque Caribbean beaches of Condado. Our guide to 72 hours in San Juan offers a bit of everything and will leave you planning your next trip on the flight home.
Friday
Check into hotel
We love arriving Friday evening to enjoy a sound rest and make the most of the following day. If sipping coffee on the beach in the morning before a day of exploration sounds sublime, Condado is the neighborhood for you. Located on prime Condado beachfront, La Concha Renaissance offers sweeping ocean views, a beach-side pool, and brightly decorated rooms. Quite a few Airbnbs in the Condado neighborhood also offer modern amenities and easy beach access. If you’d prefer to awake in a venerable convent-turned-hotel that boasts 400 year old architecture at the center of Old San Juan, turn to Hotel El Convento. Plus, maybe you’ll snag the same room Beyonce slept in!
Saturday
Morning
Explore Old San Juan
Old San Juan can be crowded during the day, so if you’re interested in great shots of the architecture and happen to be a morning person, I recommend heading out early to snap away. Pick up a cafe con leche and a Pan de Mallorca or Quesito pastry from a local street vendor or bakery for an authentic Boricua breakfast. After devouring these tasty delights, head to El Morro, the city’s 16th century fortification built to protect San Juan from potential attack. The fort sits at the protruding edge of Old San Juan, and includes multiple levels of towers, ramps, staircases, hiding places, and complex pathways. After exploring the history of El Morro, meander along Paseo Del Morro, which leads from the citadel and wraps around the old city.
Lunch
No first trip to Puerto Rico is complete without trying Mofongo. A dish of mashed plantains served with meat, Mofongo was brought to Puerto Rico by enslaved Africans and is now ubiquitous. You can find the dish in swanky eateries and at street carts, but some of Old San Juan’s best Mofongo can be found at El Campeon and Cafe Manolin. Wander to either of these restaurants for a classic dish and a rest for your weary feet.
Afternoon
With a sated belly, roam the streets of Old San Juan, appreciating the colorful architecture and cobblestone streets preserved from its Spanish-colonial era. After an afternoon stroll, return to the hotel for a nap before a festive evening.
Dinner and Dancing
1919 Restaurant is an eatery by Michelin Star chef Juan José Cuevas. An exquisite dining experience, 1919 features locally sourced ingredients in an upscale atmosphere. Classic Puerto Rican dishes are reinvented in mouthwatering plates. With an extensive wine list and servers who can assist with any pairing, expect to fully indulge every sensation. 1919 is a worthwhile splurge. After dinner, grab a cab and make your way to La Placita de Santurce, a square surrounded by bars where locals and tourists mingle, musicians play live tunes, and dancers elate into the wee hours.
Sunday
After an eventful Saturday night, enjoy a relaxing Sunday at the beach. Start at Wicked Lily, where brunch classics are served up alongside (yes, you guessed it!) piña coladas. When busy, the service can be on the slower side, but with a breathtaking ocean view, waiting feels more like a treasure than a chore. The beach awaits, where chairs and umbrellas are available for rental. Bring a water bottle, a frisbee, and a good book for all-day fun. Right off the beach, you’ll find plenty of small street vendors and to-go restaurants with empanadas, tostones, alcapurrias, and other Puerto Rican classics. These are a perfect mid-day beach snack. Whether you’d like to rinse off or prefer to stay sandy, La Marqueta is perfect for casual Sunday night dining. La Marqueta is a beachfront food hall with options from top Puerto Rican chefs and a stand-out bar. The vibe is relaxed and once you’ve landed a table, feel free to enjoy the music, drinks and atmosphere until closing.
Monday
On your last day in Puerto Rico, take a day trip to the world famous beaches of Culebra Island. After a short car ride down the coast to Fajardo, you’ll set sail on a catamaran to the sparsely populated island. Snorkel off the boat, kayak, relax on the famous Flamenco Beach, or explore the island’s forests. Most boating companies include light food and beverages throughout the day, but be sure to book the trip focused on the activities you prefer.
Dinner
After a long day of sun and sea, you’ll likely be hungry and a little tired. SOCIAL is our pick for an elevated but relaxed dining experience with a spectacular view. Request a patio table before sunset, and let the sounds of the waves and colors of the sea relax you while you sip a superb cocktail. With fresh seafood and hearty meat options, SOCIAL will delight. Save room for the decadent desserts.
What To Pack
I am a strong believer in laying out every outfit before any garment finagles its way into my suitcase. I’ve been caught one too many times with tops and bottoms that don’t match because I just threw anything cute into my bag. Instead, I’ve learned first hand that the best way to go is to think about each day’s activity and to plan full outfits accordingly. Another sound tip is to pack neutrals or garments that can be mixed and matched to the max. Adventurous patterns can be très chic, but try to think realistically about how you’d wear them before committing. Remember, your carry on is prime real estate. Every outfit must earn its place! With that in mind, here are some of my must-haves for three days in Puerto Rico:
Comfortable white sneakers • Strappy sandals • Rubber Birkenstocks
One-piece • Bikini • White linen shorts • Denim shorts • Breton striped t-shirt • Long linen beach cover up • Two dresses – relaxed and fancier • Sweats/leggings for plane ride home
Small cross-body purse • Leather belt • Sunglasses
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