A complete yacht charter guide that has everything you need to know about your next sailing holidays in Puerto Rico. Let’s get started.
The prime sailing season in Puerto Rico runs from December to April, overlapping with the island’s driest months and more predictable easterly trade winds. These steady 15–20 knot winds offer a comfortable passage around key cruising grounds near Fajardo and the offshore islands, including Culebra and Vieques. Although hurricane season (June–November) may provide quieter anchorages and potential off-peak rates, the increased risk of storms and heavier rainfall can complicate trip plans. Consequently, visiting during late winter to spring ensures milder weather, clearer skies, and fewer disruptions.
What are the sailing qualification and license requirements to charter a yacht or catamaran in Puerto Rico? Most Puerto Rican charter companies do not strictly require a formal certificate, but a recognized qualification such as ASA 104, RYA Day Skipper, or ICC can expedite the bareboat approval process. The key factor is whether you can prove sufficient sailing experience through a detailed resume outlining your coastal cruising history and navigational competence. Given Puerto Rico’s diverse conditions—from gentle seas near Fajardo to more challenging routes around Culebra or Vieques—demonstrating familiarity with anchoring techniques and reef avoidance will boost confidence with local operators. If you lack the needed credentials or desire a relaxed holiday, a skippered charter remains a popular choice for exploring this vibrant Caribbean locale.
Puerto Rico’s Spanish colonial heritage emerges in the historic streets of Old San Juan, where pastel-toned facades and fortress walls offer a charismatic backdrop. Docking nearby, try authentic mofongo (mashed plantains with garlicky sauce), arroz con gandules (rice with pigeon peas), and fresh seafood. The island also claims a proud coffee tradition—sampling locally grown beans is a must. Across Puerto Rico, live salsa music and bomba y plena rhythms animate local festivals, showcasing Afro-Puerto Rican cultural roots. This lively fusion of gastronomic and musical delights adds zest to any Puerto Rico sailing holiday.
Although Puerto Rico follows U.S. maritime guidelines, local port regulations can differ slightly from mainland rules, especially regarding anchoring and marine reserves. If you arrive from foreign ports (e.g., the British Virgin Islands), you must clear U.S. Customs at one of Puerto Rico’s official entry points. Certain nature reserves—such as Caja de Muertos—require mooring buoy use to protect underwater habitats. Keep valid registration and insurance onboard for inspection, ensuring a seamless experience while touring Puerto Rico’s vibrant coasts.
Puerto Rico perfectly combines solid jungles with unspoiled beaches and will give you the sense of discovering new lands. With 480 kilometers of coastline and nearly 300 beaches, sailing Puerto Rico is an ocean lover’s dream.
You can spend your sailing holiday becoming one with nature by hiking in El Yunque Forest, swimming through the Bioluminescent Bay of Vieques, or exploring caves at Parque de las Cavernas del Rio Camuy. Then the next day, explore the charming and colorful city of San Juan, where you can ride the hop-on, hop-off trolley through Old town and see the Museo de Arte de Puerto Rico, where you will find the Caribbean’s best and most extensive art collection.
Temperatures in Puerto Rico are classed as tropical and sit between 70-80ºF year-round. It is cooler inland, particularly in the forests and easterly trade winds provide huge relief when temperatures are high. The dry season is between January and April and the rainy season is between April and November, with more rain falling in northern Puerto Rico. The hurricane season is from August to October. The best sailing conditions for a boat rental Puerto Rico would be between November and January, when you will benefit from north-east trade winds between 15-20 knots, even reaching 30 knots during the X-mas winds.
Winds then move easterly from February and to the south-east by summer. The swell is between three and four feet.
The best way to start your boat rental Puerto Rico is to fly in to the Luis Muñoz Marín International Airport / San Juan Airport (SJU). You will land in San Juan airport and set sail starting from Fajardo. Luckily, getting to San Juan is easy enough - as SJU is a very large regional hub in the Caribbean. Despite being small, Puerto Rico has many major airlines, like United, American, Delta, JetBlue, Virgin, Southwest, and even Spirit, with cheap, daily flights to the island. The most frequent departures from the US are from Miami and New York.
For any UK and European travelers trying to kick off their bareboat charter Puerto Rico, the trip might be a little longer as there are no direct flights.
However, it will be well worth it! The best way to get to PR is to fly somewhere in North America (you can find direct flights from NYC, Miami, and Toronto) and then down to Puerto Rico. Also - worth looking into - British Airways and Virgin Atlantic are now operating seasonal direct flights to San Juan via Antigua.
Transfer time from the airport to base: 40 mins by car.
For entry requirements on your yacht charter Puerto Rico, you will not need a passport if you are a US citizen - since Puerto Rico is a US territory, traveling there is just like any other state. All other nationalities need a visa to enter Puerto Rico. As a tourist, the standard 90-day non-immigrant visa is likely what you will need. Be sure to check with your charter broker for more detailed visa requirements.
As mentioned, Puerto Rico is a US territory, so they use USD for their currency.
Alternatively, if you’d like - Yacht4Less can arrange your provisioning for you! Then you can arrive at the marina with a fully stocked boat.
Enquire with your charter broker for more details and pricing.
Day 1. Puerto Del Rey Marina (check-in)
Day 2. Puerto Del Rey Marina - Culebra (Ensenada)
Day 3. Ensenada - Culebrita - Las Pelas
Day 4. Las Pelas - Cayo Luis Pena - back to Las Pelas
Day 5. Las Pelas - Dakiti
Day 6. Dakiti - Palomino / Icacos Islands
Day 7. Palomino and sail back to Puerto Del Rey Marina
It depends. For example, the most important ones are the type of boat you will choose and whether you require a professional crew on board (e.g. skipper, hostess or cook). So, as you can see, there are many factors that can shape a price for a boat rental.
Check our full guide about yacht charter cost and how you can save much money in your next sailing holidays.
Puerto Rico’s varied coastline—from the bustling marina in San Juan to the quiet bays of Vieques—caters to bareboat, skippered, and crewed charters alike. Skilled sailors can opt for a bareboat charter to navigate on their own, island-hopping between Culebra’s idyllic Flamenco Beach and the bioluminescent bay at Fajardo. Want a leisurely escape? A skippered sailing holiday comes with an experienced local captain who knows the best snorkeling spots and shore restaurants. And for a truly indulgent vacation, Puerto Rico’s fully crewed yacht charters combine a private yacht cruise with on-board chefs and attentive crew, so you can unwind in style under Caribbean skies.
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