One Week in Puerto Rico Itinerary: History, Nature & Food (Teen Approved)
Escaping Winter, Finding Sunshine
As The Baby’s graduation nears and our escape from the frozen north grows closer, winters feel more unbearable by the day. So, when February break rolled around, we did what we always do - fled toward salt, sun, and sea breezes.
This year’s destination: Puerto Rico.
For a week, we traded icy driveways for coconut palms, snow boots for sandals, and casseroles for mofongo. We hiked through cloud forests, wandered the cobblestoned streets of a 16th-century walled city, and ate our way through smoky barbecue, spit-roasted pork, and just enough cocktails to keep The Hubs in vacation mode. Even our moody teen gave it her stamp of approval (between eye rolls).
Where We Stayed
When we plan to stay put in one location, we like a rental house or condo - more space to spread out, coffee in pajamas, and room for everyone to do their thing. For this trip, we booked a condo in Ocean Villas at Río Grande, tucked beside the Grand Wyndham Río Mar Resort.
From our balcony: a postcard view of palm trees, pools, and the sea. Not far from our front door: a hot tub, multiple pools, and a short walk to the beach. Location-wise, it was central to everything we wanted; close enough to El Yunque, Old San Juan, and the marinas, but with a quiet, kick-off-your-sandals pace that let us actually relax.
Day 1: Pools, Plans & Puerto Rican BBQ
I had lined up a mini-boat adventure for our first afternoon - snorkeling, reef-hopping, and sunbathing on the white sands of Icacos. Instead: clear skies, rough seas, canceled trip. Welcome to island life.
We shrugged it off, retreated to the pool, and saved our appetite for La Estación, an old gas station turned BBQ temple that’s equal parts roadside shack and foodie pilgrimage.
We started with cocktails, a guanabana mojito for The Hubs, a Fajardo Sunrise for me, and ceviche with crispy tostones. Then came the grilled whole red snapper, smoky and tender, absolute chef’s kiss. The Baby tucked into a brisket empanada, mostly to prove she wasn’t starving. Tip: Go early. By 6:30 they were already out of half the menu, and the line was wrapping around the parking lot.
Day 2: Hiking, Sliding & Bruising in El Yunque
The next morning we traded flip-flops for trekking shoes and headed into El Yunque National Forest. The Spanish once called this area “El Yunque,” after the word for anvil, because of the mountain’s shape. Today, it’s the only tropical rainforest in the U.S. National Forest system; a lush, misty world of waterfalls, orchids, and tree frogs that sound like chirping birds.
We tackled the Mount Britton Tower trail, a one-mile climb through cloud forest that felt like walking into a green cathedral - narrow trail, mossy rocks, dripping leaves. At the top, a 1930s Civilian Conservation Corps tower offered sweeping views of both the Atlantic and Caribbean. Standing above the canopy, I could almost imagine Spanish lookouts scanning the horizon for sails.
On the way down, we stopped at Yokahú Tower, a quick walk from the lot with panoramic views (if you can snag parking). The stone lookout, built in the 1960s, feels almost medieval, though its purpose is more practical, a reminder that for centuries, the highest ground meant safety.
Then, Las Pailas natural waterslide. Imagine a river smoothed by centuries of rushing water, forming slick chutes wThen came Las Pailas natural waterslide. Imagine a river polished by centuries of rushing water, smoothed into chutes where locals (and plenty of tourists) shoot down into deep pools. It was exhilarating until I stepped on moss, slipped, and bruised my tailbone. The Hubs and The Baby happily slid away while I sat glumly on the bank, reconsidering my life choices.
Dinner that night was Dos Panza, a cheerful Mexican spot near our rental. Tamarind margarita for me, strawberry-kiwi for him, queso fundido for the table. For a bruised mom with a sulking mood, it was perfect.
Day 3: Pork Highway & Hurricane Scars
Puerto Rico has an entire road dedicated to spit-roasted pig, and yes, it’s as glorious as it sounds. The Pork Highway winds into the mountains, lined with rustic lechoneras where whole pigs roast over open coals, basted until the skin snaps like glass.
We ended up at El Rancho Original, a cavernous hall clearly designed for weekend crowds. At 11 a.m. on a Tuesday, we had the place to ourselves. Ordering was part cafeteria line, part leap of faith. The English menu helped, though no prices were listed - I had a fleeting Soup Nazi panic. But it was easy enough: pork with macaroni salad, chicken with arroz con gandules (rice with pigeon peas), and stewed beans. The pork skin was shatteringly crisp, salty, perfect.
The Baby, true to form, declared she didn’t like pork and pouted. Some vacations are just uphill battles.
After lunch, we drove into Carite Forest, where the scars of Hurricane Maria (2017) are still raw - collapsed pavilions, downed trees, trails washed away. We tried to find Survivor Falls (yes, as in the reality show), rumored to have rope swings and swimming holes, but between unclear signage and trespassing worries, we turned back. A sobering reminder that Puerto Rico’s lush beauty still carries wounds from storms past.
Day 4: Old San Juan — Forts & Flavors
Old San Juan is like stepping into a history book colored in tropical pastels. Founded by the Spanish in 1521, the walled city became a keystone of Spain’s colonial empire; its deep harbor guarded the shipping routes loaded with gold and silver bound for Europe. For centuries, its massive stone forts held off British, Dutch, and pirate attacks. Today, it’s a UNESCO World Heritage Site, still buzzing with music, plazas, and popsicle stands.
We fueled up at Café Cuatro Sombras; strong coffee that bit back, egg sandwiches buttery and warm, yogurt bowls with just enough fruit to feel virtuous. Then off we went to Castillo San Cristóbal and El Morro (Castillo San Felipe del Morro).
San Cristóbal, begun in 1634, is the largest fort Spain ever built in the New World. Its defenses stretch over 27 acres; layered walls, dry moats, hidden tunnels, and cisterns big enough to hold millions of gallons of rainwater to survive a siege. In 1797, British General Abercromby’s troops tried to take San Juan from the east. They failed, in large part because San Cristóbal’s defenses forced them back.
El Morro, built a century earlier, faces the sea. Its six levels of defenses were designed to blast any ship foolish enough to approach the bay. The garitas, those small, round sentry boxes clinging to the edges of the walls, have become symbols of Puerto Rico itself, their stone “eyes” forever watching the horizon.
Walking between the two forts, you feel history underfoot: Spanish engineers’ fingerprints in every stone, centuries of pirate raids, Dutch cannonballs, and eventually the shift of flags from Spain to the U.S. after 1898. Shoulders stiffen in the wind as you imagine cannon smoke curling, drums echoing, soldiers on high alert.
We cut through the María Magdalena de Pazzis Cemetery, its white marble tombs perched dramatically over the Atlantic. Haunting and beautiful, it felt like the kind of place where even in death, you’d never miss the sea.
From there, we strolled the Paseo del Morro, once the path where colonists and supplies unloaded from Spanish galleons. Today it’s a breezy walkway lined with bougainvillea (a vibrant, climbing plant). Locals swam in the calm turquoise cove; we were tempted to join them fully clothed.
For a break, we popped into Señor Paleta for gourmet popsicles, lemonade for The Baby, guanabana for The Hubs, strawberry mojito for me, and ate them in Pigeon Park, where exactly two pigeons eyed us like they were running security detail. Not quite Hitchcock, but enough of an audience to make us laugh.
DiDinner at Raíces was touristy but fun: mofongo piled high with seafood, washed down with (of course) mojitos.
Day 5: Sailing with Sea Turtles
Still craving our canceled boat day, we booked a catamaran out of Puerto Del Rey Marina. It was exactly what we needed. After a lazy sail, we dropped anchor in aquamarine water where sea turtles glided beneath us. With just six passengers, it felt like a private charter. Drinks and snacks flowed, the sun dipped low, and for a few hours, everything was perfect.
Dinner was at La Cueva del Mar, a lively seafood spot where we somehow ate an entire lobster tempura after already polishing off ahi nachos, calamari, and seafood rice. Vacation appetite is real.
Day 6: Beach & Farewell
Our last day was low-key - beach walks, one last swim, and sushi at W Sushi Bar. For dessert, we stumbled into Pal Patio de Lola, an open-air food court with ice cream and live music. I wish we had found it earlier in the week.
Final Reflections
Heading home is always bittersweet. I never want to leave warm sand and salt air, but I do miss my two-legged and four-legged family. Puerto Rico gave us exactly what we needed: sun, history, food, and just enough adventure to keep our moody teen somewhat entertained.
I hope this inspires you to travel, to eat, and to join me as I continue sharing my journey through seven continents and infinite foods.
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If You Go – Quick Itinerary
Day 1:
Panaderia Monte Brisas
La Estacion (takes reservations 2 weeks)
Day 2:
Las Pailas natural waterslide
Day 3:
Pork Highway - El Rancho Original
Charco Azul Recreation Area
Survivor falls
Rio Siete Chorros
Day 4:
Old San Juan
María Magdalena de Pazzis Cemetery
Paseo del Morro to San Juan Gate to Roots Fountain
Pigeon Park
Day 5:
Day 6:
**I would highly recommend that you make reservations in advance when available. I always book scheduled activities and typically make dinner reservations in advance. I’ve indicated with a parenthetical any restaurants that take reservations.