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Puerto Rico Sailing — Best Places to Sail, Sailing Charters & Lessons

See which tour in Puerto Rico was ranked “Top Sailing Tours – World”

Puerto Rico is an archipelago consisting of the main island by the same name, two inhabited islands of Vieques & Culebra, Desecheo, Mona Island, Caja de Muertos, and hundreds of cays, keys and islets protected as nature reserves.  A gorgeous coastline, marinas, offshore treasures to explore, and plenty of interesting places and attractions to visit inland, make Puerto Rico a popular destination for sailors.  Sailing is great all year round in Puerto Rico with warm weather and winds averaging 10-15 knots.

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If you’re vacationing in Puerto Rico you may book a sailing charter, typically including food, drinks, music, and of course friendly and professional hospitality.  Stops typically include coral reefs for snorkeling, and pristine beaches, most of the charters are on the east coast of the island.   The most attractive destinations in Puerto Rico for visiting wishing to go sailing are the east coast, most charters leave from marinas in Fajardo, the capital city of San Juan.  On the west coast, the towns of Cabo Rojo and La Parguera in Lajas are sailing favorite spots.   There are many marinas in Puerto Rico, including the famous Marina Puerto del Rey in Fajardo, the biggest marina in the Caribbean.  There are three marinas in San Juan (see locations and names on the map at the end of this page).

 Following we go into more detail about the most popular sailing destinations and stops around the island.

San Juan Bay

For visitors vacationing in the Capital City of San Juan, will have easy access to one of the best experiences in Puerto Rico… sailing in the San Juan Bay, one of the most scenic waters and most significan in the history of Puerto Rico and the Caribbean.  San Juan is home to various UNESCO sites and the best vantage point to admire them is from the San Juan Bay.

Featured Sailing Charter

Return home with travel bragging rights for experiencing a sunset sailing tour by Sail PR, which proudly earned the #7 spot on the coveted Traveler’s Choice Best of the Best 2021 for Best Sailing in the World.

Top Rated San Juan Bay Sailing Charters

Piñeros Island

Cayo Piñeros, best known in English as Piñeros Island is one of the less known offshore islands of Puerto Rico.  While most of the sailing and boat charters head to Icacos, Janise Sailing Charters offers travelers a more intimate experience of Piñeros.  On the cay, you can swim in crystal waters, snorkel, and admire the coastline and views of neighboring islands.

Top Rated Sailing Charters to Piñeros Island — Puerto Rico

Sunset Sailing along the East Coast

Add the sunset to the fantastic experience of sailing the coastline and offshore keys of Puerto Rico… and you have magic.   Surprise your loved one with this special experience, propose to the glow of the golden and firey tones of the sunset… whatever the reason for your stay in Puerto Rico,  you deserve to treat yourself to this special time for memories that will last a lifetime.  Following you’ll find sunset sailing tours for small groups and private charters.

Sunset Sailing Charters in Puerto Rico

Cayos de la Cordillera Nature Reserve – Puerto Rico

Off the east coast of Puerto Rico is the perfect place to go island hopping, from the marinas of Fajardo you can sail off to Cayos de la Cordillera Nature Reserve (Cordillera Cays Nature Reserve), Cayo Piñero and the islands of Culebra, and  Vieques.  The most popular boat and sailing charters head to the cays of Cordillera, Palomino, Icacos & Lobos are the most visited islands for their spectacular clear turquoise waters, snorkeling sites, and proximity to Fajardo.

Top Rated Island Hopping Sailing Charters in Puerto Rico

Top Rated Private Sailing Charters to Palomino Island

Jobos Bay Reserve

For those staying on the south coast of Puerto Rico or wishing to sail to a more intimate location without any crowds will enjoy a charter along the southern coast.   Sailing charters take guests to Jobos Bay Reserve & Cayos Caribe, a line of 15 mangrove islands with an extensive reef system where you can swim and go snorkeling to explore marine life.

Sailing Charters — South Coast of Puerto Rico

If you’ve ever sailed, you know it is one of the purest and most romantic ways to experience the coastline of a beautiful place.  You can book a sailing lesson  charter to enjoy the pleasures along the coastline of Puerto Rico while learning the principles of sailing or refining your skills.

Private Sailing Lessons in Puerto Rico

Tours Visitors Love in Puerto Rico

Why You Should Go to Puerto Rico Post Hurricane Fiona 2022

Contrary to what you may think, the best thing you can do for Puerto Rico right now is not to cancel your trip.


ive years ago, Puerto Rico gained international acclaim when the hit song “Despacito” reached the top of the Billboard charts. For the first time, it seemed like all eyes were on this small island in the Caribbean, approximately 100 miles long by 35 miles wide. Suddenly, there was a surge in visitors like never before. Even neighborhoods like La Perla, previously considered off-limits to tourists, were receiving renewed interest. Then Hurricanes Irma and Maria hit, and the island was devastated. Lives were lost, relief funds were mismanaged, and hundreds of thousands of Puerto Ricans emigrated to the mainland United States.

Still, those who remained promised to build back stronger. And build back they did. New entrepreneurial ventures were born. Macro-mural projects by the nonprofit Pintalto revitalized residential neighborhoods with colors of hope, igniting a sense of community and driving tourism beyond Old San Juan.

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In January 2020, earthquakes struck the southwest corner of the island. Images of collapsed houses filled the news, and tourists hoping for a winter getaway were once again deterred from visiting, despite the damage being largely limited to one specific area. In March 2020, the pandemic hit, and the island adopted strict restrictions compared to the states.

After the world’s involuntary slumber, it seemed like 2022 would finally be the year tourism rebounded in full force. Huge conferences were being held on the island. Major Hollywood projects, from Black Panther to Transformers, had chosen Puerto Rico as their filming location. Places that had been closed since the 2017 hurricanes, including El Portal, the visitor’s center in El Yunque rainforest, and El Conquistador, an iconic hotel with one of the island’s only water parks, reopened after years of renovation and anticipation. Hispanic Heritage Month arrived, and a mere two days later, the celebration turned to devastation once again when Hurricane Fiona made landfall.

Post-Fiona, Puerto Rico made headlines for being the disaster’s epicenter. However, this was not the same Puerto Rico from five years prior, and the response was rapid.

They say Hurricane Maria used wind as its weapon of choice, while Hurricane Fiona used water. Flooding, and the subsequent effect on an already tenuous electrical grid, were the biggest issues. Once again, Puerto Rico made headlines for being the disaster’s epicenter. However, this was not the same Puerto Rico from five years prior, and the response was rapid. Crews were out in full force the very next day, working on restoring power. Within a week, 60% of the island had electricity back. Locals pooled their resources and organized, ensuring essential supplies were delivered to remote areas and offering help to anyone who needed them. The hurricane hit on the weekend, and by Monday, the San Juan airport was fully operational. Hotels and tour operators alike took to social media to reassure guests they were open for business and encourage them to keep their travel plans. Still, the narrative remained one of trauma instead of resiliency and triumph.

On my flight into San Juan on September 24, 2022, 47 out of 162 seats on the plane were empty. I couldn’t remember the last time I had a row to myself, especially in the current travel climate of high-priced flights and limited routes. When I left, every seat was full. As a Puerto Rican, full-time resident of the island, and travel writer, this grim reality hit me most of all. Puerto Rico was back to square one when it came to tourism, fighting an uphill battle in how it is perceived, and once again needing to convince tourists that it is safe to visit.

Hurricane season is from July to November, but the fear perpetuated by hurricane coverage remains for years after the fact.

I live in the southeast corner of the island. When I returned from a work assignment, I returned to a house with water, power, and internet. This is not the case for everyone on the island, but it is in most tourist zones. For better or worse, San Juan is the gateway to Puerto Rico and is fully operational. Beyond that, many neighborhoods and small businesses are returning to business as usual and urging tourists to frequent them once more.

Now more than ever, it is critical you visit Puerto Rico. It may take a few weeks for the entire island to resume functioning as per usual, but sites are generally open and eager to welcome you. If you’re wondering whether to cancel your trip, don’t. Instead, keep your travel plans and make it a goal to support and promote local businesses and initiatives. Here are a few of my favorites.


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A post shared by Frutos Del Guacabo (@guacabo674)

This sustainable farm was featured in Down to Earth With Zac Efron and is revitalizing nutrition on the island. An estimated 85% of the food in Puerto Rico is imported, making it difficult to find fresh produce. I was thrilled to see Frutos del Guacabo announce they were reopening with minimal damage. Guests can tour the farm to learn about endemic plants and ingredients, have a farm-to-table meal (reservations required), and support an initiative that’s reimagining Puerto Rico’s food supply chain.» data-instgrm-version=»14″>


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A post shared by Sheila Osorio (@taller_nzambi)

Bomba music is culturally significant in Puerto Rico. It is a form of dance that originated on slave plantations as a way for workers to express themselves freely through movement. At Taller N’Zambi, renowned instructor Sheila Osorio leads locals and tourists alike in an hour-long dance lesson, learning classic bomba moves to the beat of live drums. Classes take place on the beach, in an outdoor theater Osorio has built over the years. Check out the Grand Drum of Loiza while you’re there, a seven-foot-tall work of art and the largest drum on the island, erected in July 2022.


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A post shared by Montadero Chocolate 🍫 (@montaderochocolate)

Puerto Rico’s gourmet cacao industry has been flourishing over the last couple of years, winning international awards. Montadero Chocolate is a local chocolatier that opened a brick-and-mortar store in March 2021. They use 100% locally sourced cacao beans and transform them into decadent treats, from truffles to cookies.

At the shop, guests can take a chocolate-making lesson, learn about the harvesting and roasting process, and make three bars of their own. Everything about the Montadero brand exudes Puerto Rican pride, from the mural featuring the owner’s grandmother to the design of the chocolate molds shaped like the mountains in the family’s hometown.


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A post shared by DISTRITO T-Mobile (@distritotmobile)

Puerto Rico’s newest entertainment district is a tribute to Puerto Rican achievement. Featuring 11 dining concepts highlighting Puerto Rican culture and sports heroes, this destination is not only open but serves as a point to drop off and collect donations for hurricane relief. Distrito T-Mobile is home to one of the largest 4K horizontal screens in the Americas and the only ScreenX theater in the Caribbean. While there, you can experience urban ziplining at Toroverde Urban Park. Note, if you want to fly on the original Toroverde line reaching speeds of 90mph+ in the mountains of Orocovis, they are also reopening as of the 29th of September.


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A post shared by Puerto Rico Cultural Tours (@islacaribepr)

Melina Aguilar Colón is a historian, guide, and owner of Isla Caribe tours. When not searching through microfiches and archives, she shares her extensive knowledge of the island through social media. Located in Ponce, she provides historic walking tours of the area, covering everything from art to music to architecture. Tours are available in both English and Spanish, and private bookings can be made with advanced notice. Excursions to nearby towns like Jayuya and Utuado are also available, along with themed tours covering topics like coffee and Carnaval, the annual celebration held in February.

Puerto Rico is a place unlike any other. Hurricanes come and go, but the soul of the island remains. Don’t let fear or negative coverage keep you from experiencing it for yourself.

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