Sail Puerto Rico – Drop a hook or pass it by?

When sailing northeast along the Caribbean island chain it’s possible to skip Puerto Rico. Many cruisers sail from the Virgin Islands, over the top of Puerto Rico, and up to Turks and Caicos or the Bahamas. They choose not to sail Puerto Rico.

Skipping Puerto Rico on the way down, however, is not as easy.

From the Dominican Republic through to Antigua the sailing route takes you directly into the trade winds (refer to map below). Diehard sailors attempt to sail but it can take a substantial amount of time to make very little easterly progress. And some passages you want to get out of the way rather than prolong them! Many cruisers motor for a substantial part of the time.

Bypassing Puerto Rico on the way down is not easy. Often, sailing across the Mona Passage (waterway between the Dominican Republic and Puerto Rico) can be quite messy, and seeing Puerto Rico is a sight for sore eyes.

But why would cruisers want to skip Puerto Rico in the first place?

Many non-American cruisers skip Puerto Rico because it’s an America island. If you’re not American or don’t hold a B1/B2 Visa you can’t enter. There are no exceptions. If you do enter, you run the risk of having your boat impounded, being deported, and/or a very hefty fine.


Or, you might be forced to leave your boat in Puerto Rico, fly out of America to the closest American Embassy (perhaps in the British Virgin Islands) to get an emergency B1/B2, and then fly back into Puerto Rico.

Time and time again I hear of people entering an American port with an ESTA Visa – the one that you fill out online to fly into America. That doesn’t work. And the American’s don’t mess around. Saying ‘sorry’ doesn’t work and fines are in the $1000’s. You’ll also get banned from entering America for a while too!

So non-American’s have been known to skip Puerto Rico. But why else would anyone want to skip the island?

Well…the island has been working hard to recover from hurricane Irma and Maria. The rumors are worse than reality, however. Some marinas are not fully functional but they’re fine. And not once did we see any half-sunken boats.

But let me back up to the point of my whole article…Sailing Puerto Rico – Drop a hook or pass it by?

When we left the US Virgin Islands heading for Turks and Caicos our plan was to skip Puerto Rico.

Our reasoning was total ignorance. We didn’t know anything about the island. Simon had his B1/B2 Visa and the rest of us are American so there was no issue entering.

Just before pulling up anchor in the US Virgin Islands a cruiser friend sent me a message saying, ‘We decided to stop in San Juan, Puerto Rico. The old town is beautiful and it’s well worth a stop. I wouldn’t pass it up.’

Thankful for our friend’s message, we decided to stop in San Juan for a few days.

Our stopover made us realize that Puerto Rico had a lot to offer. The old city of San Juan was magical. With an old fort high on a cliff overlooking the port entrance, the blue brick cobblestone styled roads, and the alleys of beautiful restaurants and shops our eyes were spoiled from the beauty of it all. We spent two days in San Juan and vowed we’d one day return. Read about our passage and watch our first Puerto Rico video here.

Fast forward two years later…

While making our way from the east coast of America down to the southern Caribbean island of Grenada we attempted to sail from Turks and Caicos straight to Puerto Rico.

Once we rounded the top northeast corner of the Dominican Republic, however, the seas became huge and motoring across the Mona Passage became untenable. We diverted to Samana, Dominica Republic.

The Mona Passage is the waterway between the Dominican Republic and Puerto Rico. It’s not an easy passage!

Little did we realize that the Mona Passage was notorious for being turbulent. During our previous experience with sailing around Puerto Rico, we were making our way northwest. Not only was sailing easy, as we were pushed by the constant trade winds, but we avoided the Mona Passage altogether by traveling above Puerto Rico rather than below.

After waiting for an appropriate weather window, we managed to motor across the Mona Passage and arrive safely in Marina Pescaderia. And let me tell you that I was happy to see the land. When crossing the Mona it’s best to leave the DR after the sun sets and sail overnight when the trade winds are at their calmest. Even with calm-ish winds, it was quite a bumpy passage.

And making your way along the south coast of Puerto Rico isn’t a quick passage.

Many boaters wake at first light or before and get to the next anchorage before noon when the seas start to get unruly.

On our more recent trip to mainland Puerto Rico, we spent several weeks visiting six locations by boat including two marinas and four anchorages along the south coast. And by car, we traveled the east coast, west coast and a bit of the north to visit the capital city, San Juan.

We also dropped anchor in two spots in the Spanish Virgin Islands (owned by Puerto Rico) but the mainland and the islands seemed worlds apart. I’ll explain more below…

The destinations we visited included:

If you want to see we got to number 1 we Sailed Across The Mona Passage from the Dominican Republic.

1. Our first experiences in Puerto Rico were in Cabo Rojo.  Sailing Puerto Rico demonstrates what we got up to and Marina Pescaderia is a review of the wonderful marina we stayed in.
2. Gilligan Island can be checked out in the video, Sailing Puerto Rico – South Coast
3. Ponce & Isla De Cardona can be seen in the video, Sailing Puerto Rico – South Coast
4. Cayo Puerca can also be viewed in Sailing Puerto Rico – South Coast
5. Lastly, get an idea on what Puerto Patillas is like in this video – Sailing Puerto Rico – South Coast
6. Watch this for our tour of the marina and further afield – Palmas Del Mar
7. Culebra & Culebrita

E. San Juan (2016) – Check out our first visit to Puerto Rico on 2016.

If you’d like an overview of all the places we’ve visited in the Caribbean please read our destination overview: Caribbean

So, all that being said, why is Puerto Rico a worthwhile sailing destination?

It’s difficult to sail past it!

First and foremost, if you’re heading east it’s going to be a very very long sail or a very long motor to pass it by. Knowing what I know now if I was a foreigner I’d get my B1/B2 visa (read my ‘how to’ article here)  just in case I needed to stop. The seas state is very lump and the wind is almost always on your nose!

Good anchorages along the south coast

Every anchorage we stopped in provided a good degree of protection from the swell. The areas were relatively quiet and peaceful during the week. We enjoyed great snorkeling and refreshing swims. And the beaches we visited were all very nice.

For us, our anchor bit in at every anchorage with no holding issues. Our, buddy boat, Pura Vida, however, had several issues in Puerta Patillas. They have a Rocna and it just wouldn’t bite. There were loads of grass and it wasn’t easy to drop the anchor on a sand patch. (Side note, our Mantus Anchor is amazing – if you’re going to get an anchor, get a Mantus!)

Anchoring is an art!

If you’re not 100% sure about everything there is to know about anchoring, make sure to get my guide, ‘How To Anchor: A Checklist To Prevent Dragging.’ You’ll learn the tips and techniques to ensure your anchor is the right anchor, it’s set correctly and what to do when common issues arise (dragging, fouled anchor, windless failure, and more). Get the guide here: How To Anchor

The only downsides of Puerto Rico, if you want to get picky, is that on the weekends many of the anchorages get very loud with day boaters. Several boats meet up and anchor off an island such as Gilligan’s Island or Isla Cardona and blast their music as high as possible.

And not every anchorage has access to shops or stores so you have to plan ahead for provisions.

Otherwise, the only other thing to mention is the massive amount of seaweed in the sea but that’s all over the entire Caribbean. For some reason, it must be a high growth year. Some beaches are covered in the grass and it can make fishing impossible!

Top-notch affordable marina’s

Unlike the high priced marina’s that you’ll find in America, Turks and Caicos, and the Bahamas, those in Puerto Rico are only $50/night. We stayed in two marina’s and visited one other to get parts. All three of them provided excellent service, great facilities, and had a wide variety of shops, restaurants, and services.

Furthermore, all the marinas are very safe and secure (not that I ever felt unsafe in Puerto Rico).

Easy passages

For most of our passages, we didn’t sail more than three to four hours. Errr, I need to write motor rather than sail.

With the wind on our nose, we motored the whole time we were in Puerto Rico.

Following the advice of Bruce Van Sant, from the book The Gentleman’s Guide to Passages South: The Thornless Path to Windward, we woke up early, left the anchorage and found our next anchorage before 12 pm.

From time to time we had to dodge crab pots and fishing nets but overall the passages were easy.

The best island in the Caribbean for provisioning

Before we left Charleston, South Carolina we visited Costco (low-cost bulk food grocery store), West Marine (boat chandlery), Home Depot (DIY store), and Walmart (low-cost department store), to get food, boat parts, tools/cleaning supplies/etc and clothes.

100’s of miles and 3 months later we were happy to see those same stores again, all in Puerto Rico. And Sienna was excited the see the golden arches for a Happy Meal too.

Being in Puerto Rico is just like being in America.

You can get everything you want. We also found a replacement TV for the one that crashed and burned. We found Best Buy, an electronics store, and they had a very low-cost small TV that will play movies from our hard drive.

Knowing that provisions can get very high priced or completely unavailable on many of the Caribbean islands it’s a great island to fill the freezer and bilges.

Find out why it's worth sailing around Puerto Rico here!Click To Tweet

What about excursions?

I’d like to say that we spent a lot of time seeing the land part of Puerto Rico but we didn’t. We traveled to Rincon on the west coast of the island as we were passing through. We also drove from the southwest corner of the island to the northeast to visit San Juan but that was to catch a flight.

The interior of the island has massive mountains and low plains. It’s breathtakingly beautiful.

We tried to make more of an effort to see a forest or go for a hike but unfortunately quite a few of the excursion based things are still closed to the public due to hurricane damage.

Even while driving through San Juan a good portion of the traffic lights are not operational or missing completely. Most of the signs on the highways are crumpled up along the side of the road.

Cell or Mobile Phone coverage was great

If you’re like me and enjoy keeping in touch with the world, Puerto Rico is great for cell coverage. All our friends that had T-Mobile got 4g coverage and on my UK phone, I had the option of paying £4.99/day for unlimited 3g coverage. It worked very well. And every restaurant had great wifi – not something that you’ll often find once you head south from Puerto Rico.

The people are great and the towns are colorful

Jose, the manager at Marina Pescaderia, is the best marina manager/owner we’ve ever met. He’s genuine, kind and can’t do enough for his customers. They guys and girls at Palmas Del Mar were outstanding. And everyone we met at the shops and restaurants was super kind and helpful. There were very few times when we couldn’t communicate – most people in Puerto Rico can speak great English.

And any time we asked for directions while walking, the person telling us where to go said… ’hop in my car, I’ll just take you!’

The one thing that might be disconcerting for newcomers is that Puerto Rico is a rather poor island.

Most houses are concrete boxes with rod iron bars around the doors and windows. Although the homes are colorful the overall feel is very unpolished.

Cruisers that visit Puerto Rico after spending time in America, the Bahamas and Turks and Caicos…PR can appear, at first, as a bit of a mess. There’s pollution all over the place and with the hurricanes, it’s even messier. Saying that, however, it’s important to realize that many countries are similar.

Many countries don’t have the funds to pick up the trash or run campaigns to educate the community nor do they make enough money to fix things when they break. Puerto Rico still has a great majority of homes with a blue tarpaulin covering the roofs.

Those of us that grow up in the States or the UK or any first world country don’t realize how good we have it.

All I can say is that just because the cities and towns don’t look that appealing doesn’t mean that it’s a bad thing. It’s just the way it is. And after a while, you can see the beauty in all areas.

Culebra and Culebrita are nothing like mainland Puerto Rico

On Culebra, a Spanish Virgin Island 27km off the east coast of Puerto Rico you’ll find no fast-food chains, no traffic jams, no big hotels, and no stress. It’s a quiet island with long beautiful beaches, small quiet restaurants, and tourists driving around in golf carts.

And Culebritta doesn’t have anything on the island, bar a lighthouse, if I remember correctly!

The Spanish Virgin Islands are quiet, beautiful, and calm. They’re not touristy. They’re a place to go after you spend time on mainland Puerto Rico to decompress and watch the ebb and flow of the beautiful blue sea.

Do you have anything to add about Puerto Rico? If yes, please leave it in the comments below so we can all benefit.

Do you want to reduce the overwhelming feeling of being a new cruiser? Get my ready-made guide (and best selling guide too), ‘Checklists For Sailors: Passage Planning, Sailboat Maintenance, Cleaning, Medical and More.’ Hit the ground running rather than stumbling around to figure out what you’re missing. These checklists will help you know what you need to do and how to do it! Get the checklists here!

Some more pictures – sail Puerto Rico

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Other Videos & Articles That May Interest You…

• How about Sailing Across The Mona Passage
• Sail Puerto Rico – Cabo Rojo
• Marina Pescaderia Review – Cabo Rojo
• Sailing The Coast of Puerto Rico – Ponce, Isla de Cardona, Cayo Puerca & Puerto Patillas
• Sailing into Palms del Mar – Puerto Rico
• Anchoring in Culebra – The Spanish Virgin Islands
• Sailing The Spanish Virgin Islands