The historic Caribe Hilton in San Juan, Puerto Rico, is a symbol of old-world charm meets modern comfort. Established in 1949 as the first Hilton outside the continental United States, this captivating mega-resort nestled on a private peninsula offers sweeping ocean vistas and access to a secluded beach. It’s a perfect blend of historical allure and modern amenities, featuring expansive oceanfront pools, diverse dining options, lush tropical gardens, a state-of-the-art fitness center, and a lively bar that resonates with live music. The majority of rooms come with private balconies overlooking the water. It’s also one of the locations, according to one boozy history, that lays claim to the home of the original piña colada.
Photo: Jeff Colhoun
Puerto Rico's Iconic Caribe Hilton Is the Perfect Home Base For an Adventure-Filled Trip
History, and drinks, are easy to find here. Yet it’s also the perfect jumping off point for seeing what’s below the surface, too. Its location makes it easy to explore the abundant nature on Puerto Rico, from the secluded beach to the waterfalls of El Yunque. The 632-room hotel has 10 dining concepts, a beachfront spa, tropical gardens (complete with peacocks), and a hammock garden.
Photo: Jeff Colhoun
One of the unforgettable experiences offered on-site is the Sea Trek Helmet Diving Tour. The moment I donned the helmet, I transformed into an underwater astronaut, preparing to explore a hidden universe beneath the azure waves. As I stepped off the shore and descended into the ocean depths, a sense of thrill washed over me. It’s a world that usually remains hidden from our eyes, a universe teeming with life and brimming with untold mysteries.
Photo: Jeff Colhoun
The beauty of Sea Trek is that it’s accessible to anyone over eight years old and weighing more than 80 pounds, making it an exceptional family-friendly activity. The sense of shared discovery and adventure is palpable surrounded by vibrant marine life, multicolored corals, and schools of curious fish. It’s not only an adventure but also an educational experience, offering insights into the aquatic world and its diverse inhabitants.
Photo: Jeff Colhoun
The adventure begins directly from the hotel’s beach, eliminating the need for a boat trip and providing a seamless transition from land to underwater exploration. Also included in the package are essential amenities like towels and a bottle of water. The use of the resort’s facilities, like showers and changing rooms, is also part of the deal, making it an all-inclusive, hassle-free adventure.
Photo: Jeff Colhoun
The sea and the sun easily works up an appetite. Following my aquatic adventure, I embarked on a culinary odyssey from the hotel with Flavors of San Juan Food Tours. My first stop was Café Cuatro Sombras, where I savored a cortadito, an intense espresso softened with a touch of milk. Its rich taste danced on my tongue and was superbly balanced by a croissant filled with Black Forest ham and Havarti cheese, sweetened with a dab of guava butter.
Photo: Jeff Colhoun
Next, at Señor Paleta, I refreshed my palate with a tropical parcha popsicle made with passion fruit. This icy indulgence provided a sweet relief from the Caribbean sun, setting the stage for more savory delights. Our journey then led us to the local delicacies at El Nido, where I relished a mini alcapurria, a fritter made from green banana, yuca, yautía, beef, and garlic, accompanied by a croquette filled with taro and longaniza (pork sausage). A bite into the bolitas de queso, balls filled with local cheese and mozzarella, was an unforgettable culinary delight.
Photo: Jeff Colhoun
At La Mallorquina, I was greeted with a refreshing mojito before diving into a plate of mofongo. This quintessential Puerto Rican dish is a comforting mix of garlicky fried and mashed plantains that’s served with rice, beans, and criollo chicken. Finally, the tour ended at Chocobar Cortés. Here, I indulged in a chocolate quesito, a decadent pastry filled with cream cheese and coated in rich chocolate.
Getting out in nature
Photo: Jeff Colhoun
No trip to Puerto Rico would be complete without venturing into El Yunque National Forest in the heart of the island. It’s the only tropical rainforest in the US National Forest System, and its sanctified grandeur revealed itself during a half-day exploration, putting on a magnificent show of nature’s splendor.
Photo: Jeff Colhoun
El Yunque is a treasure chest of natural marvels, from the vibrant quilt of flora and fauna to the mesmerizing waterfalls and towering mountain peaks. The verdant canopy seemed to pulsate with vitality, every leaf and branch brimming with a rich biodiversity. Exotic birds weaved their dance among the towering trees, while the undergrowth teemed with the rustling whisper of hidden creatures. Waterfalls emerged as jewels tucked amidst the dense greenery, their melodious gushing forming a symphony with the surrounding wilderness. From the rainforest’s highest vantage points, panoramic vistas unfolded — an endless sea of green kissing the crystalline blue sky.
Photo: Jeff Colhoun
Don’t forget your camera, as each moment in El Yunque deserves to be captured. The visual spectacle spanned from the shy bloom of orchids peeking from the undergrowth to the majestic vision of waterfalls tumbling down rugged cliffs. It was in this place that I was reminded of the boundless beauty nature bestows upon us.
Photo: Jeff Colhoun
As the sun set, San Juan’s nightlife came alive. I found my way to La Factoria, a treasure in the city’s nightlife landscape that’s been listed among the World’s 50 Best Bars. Famous for elevating Puerto Rican mixology, this underground speakeasy serves exceptional cocktails in a down-to-earth setting. The signature drink, the Lavender Mule, is a must-try.
Photo: Jeff Colhoun
Once the sun had set and the city was bathed in a gentle golden light, I ventured to my final stop for the day: Vianda. Situated in the heart of Santurce, this restaurant is the creation of a husband-and-wife duo, Francis Guzmán and Amelia Dill, who boast more than twenty years of hospitality experience and have earned recognition from the prestigious James Beard Foundation. Vianda is a tribute to Puerto Rico’s agricultural richness, boasting a small but continuously evolving menu based on farm-to-table principles.
Photo: Jeff Colhoun
Whether you’re an intrepid explorer ready to take on the underwater world, a food lover eager to taste the flavors of San Juan, or a nature enthusiast keen to immerse yourself in the verdant El Yunque National Forest, a stay at Puerto Rico’s Caribe Hilton provides an unforgettable travel experience.