The most romantic month of the year is upon us, and what better way to celebrate your love than with a dreamy retreat to Puerto Rico? The Island of Enchantment is home to stunning beaches, nature-filled adventures, delectable cuisine, and countless awe-inspiring locations to soak up with your special someone.
To help you plan your perfect getaway, we've put together three outing options, each designed to highlight Puerto Rico's unique offerings. Whether you're craving fine dining on the beach at sunset or a heart-pumping zipline through the rainforest, there's something for every pair here.
Make your Valentine's vacation as smooth as possible with Tradewind Aviation's private charters to and from Luis Muñoz Marín International Airport (SJU) in San Juan. Our fleet of Citation CJ3 light jets offer the latest in comfort and performance, including seating for up to seven passengers and ample luggage space, making them ideal for private charter trips from the East Coast to Puerto Rico.
In addition, when you book your stay at Tradewind partner Condado Ocean Club, you'll enjoy a room upgrade (depending on availability at check-in), complimentary welcome drinks for two, a $25 food and beverage credit, and complimentary 1pm late check-out. Featuring an infinity pool that stretches out toward the ocean, private cabanas, and rooms designed with the sophisticated traveler in mind, this adults-only hotel is designed with maximum relaxation in mind, and is an ideal jumping-off point for the many adventures that await.
To prepare for your trip, please note that travelers entering Puerto Rico are required to fill out a Travel Declaration Form through the Puerto Rico Health Department’s online portal, get a molecular COVID-19 test no more than 72 hours prior to visiting the island, and show proof of a negative result or they must quarantine. Because Puerto Rico is a U.S. territory, you are not required to provide a negative COVID-19 test result to return to the mainland United States.
A Walking Tour of Historic Old San Juan
The best way to get to know a city is by strolling through its streets and taking in its personality one step at a time. Old San Juan is particularly charming to explore on foot. Its colorful buildings, cobblestone avenues, and vibrant atmosphere treat visitors to countless photo-worthy vistas and interesting historical insights — the perfect outing for history and architecture buffs.
Begin your self-guided tour at the Plaza de la Dársena. Here, grab a map from La Casita Tourism Information Center and then head toward your first stop: Castillo de San Cristóbal.
Named after the patron saint of land travelers, Saint Christopher, the fortress is the largest in all of the Americas and took over 150 years to complete. Finished in 1783, its three stories, extensive series of outer defenses, and inner courtyard contain countless stories and gripping moments, many of which are explained by plaques throughout. While there, be sure to check out the two observation posts, each offering incredible views of the coastline.
From here, make your way to El Morro, arguably the most popular landmark in Puerto Rico. Designated a UNESCO World Heritage Site in 1983, El Morro is as picturesque as it is significant. The Spanish began construction of the fortress in 1539, and it took more than 200 years to complete. Over the centuries, El Morro has succeeded in blocking several naval attacks, and continued to prove useful into the 20th century, when the U.S. military used it to track the movements of German submarines. Today, El Morro is a haven of relaxation; on any given afternoon, you'll find locals flying kites, enjoying a picnic, or simply soaking up some rays. Join in the fun and purchase a kite (called a chiringa) of your own from one of the many vendors.
Continue your tour of Puerto Rican history at La Casa Blanca. The home (literally: The White House), built by Puerto Rico’s first governor Juan Ponce de León in 1521, is one of the oldest remaining monuments in San Juan. While Ponce de León himself never lived there, his family inhabited the house for more than 200 years. Made of stone, La Casa Blanca also served as the first military structure on the island.
Next, follow San Sebastián Street to Cristo Street, turn right, and take in one of Old San Juan's busiest and most picturesque streets. Dozens of landmarks dot this stretch, including the lovely El Convento Hotel, La Catedral de San Juan Bautista, and La Capilla del Santo Cristo de la Salud. When you get to Fortaleza Street, turn right and enjoy the beauty of La Fortaleza, the oldest governor’s mansion in the western hemisphere, completed in 1540.
End your tour (preferably at sunset) at The Raíces Fountain. Considered one of the most romantic spots in Old San Juan, the terraced decks surrounding the fountain provide a lovely place to cuddle and enjoy the bronze masterpiece designed by architect Miguel Carlo to commemorate and celebrate the New World’s 500th anniversary. The statue honors Puerto Rico’s mixed African, Spanish, and Taino/Amerindian heritage, and is made all the more beautiful with San Juan Bay as its backdrop.
Fine Dining With a View
Photo courtesy The Eclipse Restaurant Facebook
When it comes time for a romantic dinner, there are several places sprinkled around the island that provide exquisite cuisine with equally phenomenal views. The menu at The Eclipse, part of Villa Montana Beach Resort (perched on the northwestern corner of the island), showcases the best local produce from this part of Puerto Rico. Each dish is designed to pair with one of the many bottles gracing the restaurant's award-winning wine list.
Photo courtesy Vistas Restaurant Facebook
Located in Ponce, on the south-central coastline of the island, Vistas Restaurant lives up to its name. The eatery is surrounded by several historic sites, features two dining terraces (one on the rooftop, where the views are particularly stunning), and sits in front of the historic Square of Ponce. The menu ranges from fresh seafood dishes to prime steak cuts, à la a classic supper club, as well as local specialties.
Photo courtesy Kikita Beach House Facebook
For breathtaking views of the coast, look no further than Kikita Beach House on the island's northern coast in Dorado. Words can't do the scenery justice; suffice to say, the soothing sounds and rhythms of the crashing waves, sparkling water, white-sand shoreline, and epic sunsets are all perfect pairings for the restaurant's innovative cuisine. The menu features several varieties of risotto, Puerto Rican classic mofongo, fresh fish, specialty lobster dishes, and every type of mojito, margarita, and mule cocktail you can imagine.
Eco-Friendly Natural Wonders
If being active is your love language, Puerto Rico is your perfect match. The island is home to three of the world’s five bioluminescent bays, rare ecosystems in which microscopic, single-celled organisms called dinoflagellates thrive in quantities large enough to produce a “glow-in-the-dark” effect when stimulated by movement. Mosquito Bay, in Vieques, was even recognized in 2006 by the Guinness World Records as the brightest bioluminescent bay in the world. Explore the other-worldly neon blues and greens of the bioluminescent bay in Fajardo's Laguna Grande Nature Reserve with a nighttime kayak tour. Each paddle leads to a new surge of illumination, creating a magical effect that's made even more spectacular when experienced in a kayak with your love. Learn more about booking a bioluminescent bay kayaking tour with Kayaking Puerto Rico.
For adventure on land, head to El Yunque National Rainforest. The only tropical rainforest in the U.S. National Forest Service, it has an average rainfall of 120 inches a year and a supremely diverse ecosystem, hosting hundreds of unique plant and animal species, including the island's famous coquí frog. Whether you opt to embark on an exhilarating hike, zoom through the trees with Yunque Ziplining, or spend a couple of hours on a Carabalí horseback ride, there are endless things to see and do in this unique swath of natural beauty.
One of beach town Cabo Rojo's most special tourist attractions (and favorite Instagram locales), the Pink Salt Flats boast beautiful pink and red tones that contrast with the turquoise color of the Playuela waters. They are one of the true treasures of the island's southwestern coast, and a delight to experience.
Finally, deep in Puerto Rico's mountainous region is the Tanamá river of Utuado. Over millions of years, its waters have carved a network of caverns, canyons, and tunnels into the surrounding limestone cliffs, creating Cañon de Tanamá. The area is a must-visit for adrenaline seekers, and a favorite of locals and visitors alike for caving, cave tubing, rappelling, hiking, and rock-climbing. Experience the area to the fullest on one of the six tours offered by Tanamá River Adventures.
To learn more about Tradewind's private charters to Puerto Rico and booking your vacation, please visit our website. To receive a private charter quote, please complete our charter request form or contact our specialists at charter@flytradewind.com or 1-800-376-7922. To learn more about Tradewind’s comprehensive safety plan, please visit our COVID-19 Response page. For the latest travel updates, please visit our Travel Advisory page.