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.
Sailing in San JuanCapital City of Puerto Rico
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
Sailing on the East CoastPuerto Rico
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
Sailing the South CoastPuerto Rico
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
Sailing LessonsPuerto 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.