Puerto Rico
Yacht Charter & Sailing Vacations

Puerto Rico • Where to go • When to go • What you should know • How to Book

The Passage Islands of Puerto Rico are known locally as the Spanish Virgin Islands and are one of the Caribbean’s best-kept secrets.  Vieques, Culebra and Culebra’s little sister island, Culebrita, as well as numerous other smaller islands and cays lie just a few miles to the east of Puerto Rico.  In keeping with naming traditions of the British and US Virgin Islands, these islands are thus the Spanish Virgin Islands (SVI). Due to the long-standing US military history in Puerto Rico and the SVI, most of the SVI charter area remains untouched by development (many compare it to how the BVI was about 20 years ago).   This makes for a charter abundant in natural beauty and wonder, crystal clear waters, marine life aplenty, remote anchorages, stunning white sand beaches, unique bio-luminescence, and a laid-back atmosphere.  Although Hurricane Maria took a significant toll on Puerto Rico and its islands, the unspoiled islands and cays, and vibrant Spanish culture and community remain. And, that’s what makes a charter in the SVI pure paradise.

What is a sailing vacation, yacht charter, etc..? Learn more here ›

Puerto Rico yacht charter and sailing vacation - beautiful beaches


We’ve been there!

We did a Thanksgiving trip to Puerto Rico and the SVI with a group of friends on three catamarans a few years back. We wrote up an extensive blog (see the link below) on the area. We had so much fun and the sailing area was fantastic. We felt like this area was like the BVI would have been 20 years ago. It was completely safe – people were friendly – we found remote anchorages and beaches to ourselves – we enjoyed the Dinghy Dock Restaurant and bar in Ensenada Hondo – the scuba diving was delightful – and afterward we visited the awesome and historic city of Old San Juan.  Good times were had and we are definitely going back.

When to go?

Anytime.  The Spanish Virgin Islands, like the BVI and USVI, are year-round destinations for yacht chartering.  But with very limited charter companies in the SVI, anytime you can find an available boat is a great time to charter!

December is very popular due to the holiday season. Boats tend to get booked way-way in advance. If you’re thinking about Puerto Rico for December, book 10 months in advance.

Sailing Requirements

Puerto Rico Bareboat charter requirements:

Sailing Resume



Learn more at Yacht Charter Resources ›

Sailing Skill Level

Knowledge – Skills – Experience:

✔ Intermediate Plus

The Spanish Virgin islands of Puerto Rico are a perfect destination for families and confident charterers.  Though a bit more complicated than the BVI or USVI, the SVI has relatively calm seas, line-of-sight islands, and minimal crowds.  However, there are quite a few reefs to navigate. And so coastal navigation and electronic navigation skills are paramount.

The tide ranges between 12 and 18 inches.

Winds during the later part of December and January can be quite strong reaching 25-30 knots. For much of the rest of the year, the wind speeds are 10-20 knots.

Sailing Skill Levels ›


Puerto Rico and the SVI have a tropical marine climate.  Temperatures are warm all year round with the hottest month being June and the coolest month being January.  The dry season occurs between January and April while the wet season occurs between April and November.  During the summer months, the water temperature averages around 84 F.  August through October is hurricane season (the last hurricane was Hurricane Maria at the end of September 2017).

Did you Know?

Puerto Rico and the SVI have a long military history.  In 1493, Christopher Columbus claimed Puerto Rico for Spain.  It was ceded to the US at the end of the Spanish-American war in 1783.  Puerto Ricans were granted US citizenship in 197 and in 1952, the island became a US commonwealth.

The US Navy and Marine Corp used the island of Vieques for bombing target practice; after a series of protests, the US military departed in 2003. Following WWII, the US Navy also used Culebra for military exercises including bombings.  Cleanup of remnants from the US military’s time on Vieques and Culebra (including remnants of bombs, tanks, rockets) as well as related underwater contamination is estimated to not be complete until at least 2032.

Must See & Do

  • Vieques: Vieques is the second largest island in all of the (BVI, USVI, SVI) Virgin Islands (yet one of the most uninhabited). It has stunning beaches and anchorages (alongside wild goats and horses).  The highlight though is Mosquito Bay where you can see the bioluminescence in the waters at night.  Also check out the quaint town of Esperanza whose promenade is lined with charming bars, restaurants, and boutiques.
  • San Juan:  Although not part of an SVI yacht charter itinerary, exploring San Juan for a day or more makes for a wonderful end-cap to a vacation.  Wandering Old San Juan and its Spanish colonial buildings, delicious restaurants, art galleries, souvenir shops, and old-town atmosphere make it like you stepped back in time.
  • Cuisine: If you’re in Puerto Rico and the SVI, you must try the Mofongo (a fried plantain-based dish from Puerto Rico) alongside a Medalla, the local beer.  A favorite restaurant is The Dinghy Dock on Culebra where the large surrounding tarpon will be sure there are no leftovers to take away.  Other popular charter restaurants include Duffy’s on the boardwalk in Esperanza, Vieques.  Don’t skip any chance to have a Pina Colada—this infamous tropical drink was actually invented in Puerto Rico.
  • FlamencoBeachPR

    Flamenco Beach Culebra Puerto Rico

    Culebra:  The wildlife refuge of Culebra is home to sea turtles, birds, and under-the-water marine life.  Snorkel, fish, or dive and enjoy the wildlife and natural beauty of this isolated island known as the fishiest place in Puerto Rico. Visit Playa Flamenco which is listed as one of the world’s top beaches due to its white fine sand. If you’re up to more history, check out the relics of M4 Sharman tanks left behind by the US Navy when it stopped testing weapons on Flamenco Beach in the mid 1970’s.

  • Culebrita: Hike to the lighthouse on this wildlife refuge island (but beware of the goats).  Enjoy beaches and coral reefs perfect for snorkeling.

How to get there?

Fly into Luis Muñoz Marín International Airport (commonly known as the San Juan Airport (SJU)) in San Juan, Puerto Rico direct from US mainland.  There is no passport requirement or customs for US citizens.  The charter base is located in Fajardo out of Puerto del Ray Marina (this is the largest marina in the Caribbean). Fajardo is about an hour drive from the airport.

The marina has golf carts, a small store, and a restaurant/bar, but no accommodations for yacht charter guests.

For provisioning, the charter company recommends stopping on the way to base at one of several grocery stores including Costco. They can arrange transfer from the airport to the market to the base which makes for an easy way to get your charter started especially with a noon embark time.

Sample Itinerary:

Here above we show the itinerary which captures the highlights. Don’t miss Ensenada on Vieques, the beach on Culebrita, the walk to Flamenco beach, and the Dinghy Dock at Ensendada Honda on Culebra Island (there is a good size grocery store there also).

NauticEd Puerto Rico Customer Experiences

Culebra Puerto Rico

Tamarindo Grande – Culebra

There couldn’t be a better sailing destination than the Spanish Virgin Islands.  Winds were perfect out of the east at 10 to 20kt with no rain until the day we returned the boat.  The charter company you connected us to was very helpful with all of charter needs and the boat was in immaculate shape. Thanks NauticEd for all your help.
Rudy Y.

Spanish Virgin Islands Sunset

Awesome sunset as we head for our anchorage

I recently moved to live in Puerto Rico and so I chartered a catamaran for a week with a great group of friends out of Puerto Del Rey Marina and went to Vieques, Culebrita, and Culebra. All I can say is that this is a wow sailing location. Not crowded at all – almost a step back in time and amazing sunsets. I will keep sailing this area for as long as we live here and never get bored of it.

Edward O.

Puerto Rico Sailing Vacation Related Blog Posts


NauticEd are expert Puerto Rico yacht charter agents. We don’t charge you a fee and can more than likely save you money on all your sailing vacations. We search the world’s databases for over 8,000 yachts in 55 destinations. We give expert advice on where and when to go – likely, we’ve been there. Make an inquiry and book your sailing vacations through NauticEd Sailing Vacations.

Puerto Rico Yacht Charter and Sailing Vacations

Additional Notes

Sailing Skill Levels

Local Knowledge + Education: as Sailing Vacation Experts, NauticEd’s team has chartered and sailed in almost all these locations – providing you with the “local knowledge” you need when planning a sailing vacation. And, as the leader in sailing education, NauticEd assigns different skill levels based on the knowledge-theory and practical/experience needed for chartering in different sailing locations.

Recommended Knowledge-Theory Courses for chartering: Bareboat Charter Master Bundle (six bareboat and near coastal courses), Catamaran Sailing Confidence (if chartering a Cat), Yacht Charter Crew Course (for your crew).

Skill Levels notably emphasize the overall practical experience and competency that is required to sail in certain areas. Of course, the “devil’s in the details” on specifics, and we recommend you contact us when planning a sailing vacation. We’ll save you money on your vacation – which is great – but being prepared to have safe fun experiences that will last a lifetime is priceless!

• Intermediate = Near Coastal <5nm within sight of land, some navigation hazards (always be aware), and generally mild weather conditions. Good seapersonship (i.e., “seamanship”) skills, knowledge, and experience apply.

• Intermediate +Plus = Near Coastal <15nm, within sight of land in clear atmospheric conditions, moderate navigation hazards, and/or challenging weather. Good seapersonship skills, knowledge, and experience apply.

• Advanced = Near Coastal <20nm, within sight of land in clear atmospheric conditions, many navigation hazards, and/or potentially difficult weather. Expert seapersonship skills, knowledge, and experience apply.

*Atmospheric conditions: from the deck of a sailboat, your “visible horizon” is about 12nm on a clear day (considering typical freeboard + your height). Visibility is decreased by haze, fog, rain, smoke, and similar atmospheric considerations. Navigating by line of sight is obviously greater if your destination has features such as mountains, lighthouses, tall buildings, etc…

*Navigational hazards may include features such as rocks, shoals, rough inlets or anchorages, challenging tides and currents, lee shores, commercial traffic, etc…

*Weather: examples of challenging or difficult weather include thunder/lightning storms, areas prone to high winds, or even seasonal risks such as excessive heat.


My vision for NauticEd is to provide the highest quality sailing and boating education available - and deliver competence wherever sailors live and go.
Grant Headifen
Last updated on October 9th, 2023