Top 10 Mistakes to Avoid on a Yacht Charter Trip

mooring mistake with a single line through the pennant eye

Photo: catamaran with one line to secure to the mooring ball. This method can easily break the line and cast the yacht adrift. 📸 Sean O’Leary

We all make mistakes.

That’s part of becoming a seasoned yacht charter skipper.

But, want to get a head start? Read these and you’ll be ahead of 75% of other skippers.

I also suggest you pick up a copy of the Smarter Charter – lots of good practical chartering advice. I usually give it a scan through as a review before my next trip.

These are my top 10 mistakes to avoid on your yacht charter trip, some of which I’ve had to learn the hard way.

  1. Arriving to your anchorage too late
  2. Entering off-limits, red lined areas
  3. Running a single line through the mooring ball
  4. Not conserving water
  5. Forgetting to pull the dinghy line in when mooring
  6. Ignoring weather reports
  7. Sticking to a planned itinerary
  8. Leaving your fenders out
  9. Letting your engines run unattended
  10. Racing through a mooring field
Cane Garden Bay | Read about an incident below that happened here as the result of arriving too late

Arriving to your anchorage too late

Don’t be that crew that pulls into the mooring field while everyone else is relaxing over a sundowner, or worse, after dark.

Most yacht charter trip contracts require you to be anchored or moored at least 1 hour before sunset.

There is good reason for this.

Arriving before daylight begins to fade allows you to safely navigate through the approach. This matters if you have to pass through a channel and identify the markers (such as Cane Garden Bay or North Sound). Or, you want to be able to see where you are dropping the hook – pick the sandy patch, not the coral.

Additionally it gives you time and the visibility necessary to inspect your mooring ball condition or to dive on the anchor.

What can happen if you arrive to your anchorage too late

Here’s a real world example of what can go wrong from an incident that happened at Cane Garden Bay in 2020:

  • The crew of a Helia 44 arrived after dark, tied off to a mooring ball, and then went ashore for dinner or drinks
  • The mooring ball they tied off to? A private, ill-maintained ball not designed for a 44 foot catamaran. If they had arrived with more daylight, they likely would have noticed it was not a regular ball
  • When they returned on their dinghy, the boat was missing 😮 The yacht had broken loose and went adrift. Somehow no one noticed and it drifted past the reef
  • Luckily, it was later recovered off the north shore of St. Thomas, USVI
  • The crew learned an expensive lesson and had to pay a hefty fee for the recovery

Having a backup plan

Another reason to arrive early? What if your Plan A falls through? What if there are no mooring balls available?

You need enough time to be able to execute your backup, Plan B.

This yacht entered the red lined area between Beef Island and Little Camanoe in the BVIs
Off-limits passage between Little Camanoe and Beef Island
This red lined areas has claimed more charter yachts than anywhere else

Entering off-limits, red lined areas

Red lined, off limits areas present serious hazards to yacht charters.

Reefs, shallow water, and exposure to weather conditions such as north swells, to name a few.

Don’t believe me? Check out Groundings of BVI for some examples of the severe consequences that can result.

It’s simple.

Pay attention during your charter briefing and stay out of areas that are red lined. You can read about the more notorious BVI red lined areas here.

Running a single line through the mooring ball

I see this happen often with beginners.

When tying off to mooring balls, they run one line, through the pennant eye, and then tie it off to the cleat on the other side of the vessel..

This is bad practice.

As the yacht swings on wind and tide, the pennant eye acts like a saw on the line. Eventually it can break it loose, setting your yacht adrift.

Better idea? Run two independent lines, one from each side or pontoon. Secure the lines back to the same cleat on either side.

Check out my charter beginners guide where I posted a video about how to properly pick up a mooring ball.

The consequences of your yacht going adrift? Find out what happened to the Sunsail catamaran Panema.

Not conserving water

Ever heard of a navy shower? 

Or better yet?

We like to bring reef-safe shampoo and take a sea shower off the back of the catamaran. Do your final rinse with fresh water.

Many yachts have water makers these days, but not all of them. Relying on a water maker to work for your whole trip is, well, playing with fire.

It’s no fun needing to pull into a marina to fill up your water tanks when you could be offshore catching fish or lazing on a beach.

Brief the crew: use water sparingly. Don’t take long showers. Do dish washing heavy lifting with sea water if you can.

If your water maker is working and you have just a couple days left with full tanks? Go wild! You are water rich.

Forgetting to pull in the dinghy line when mooring

Yup. I’ve done it.

I’ve wrapped the dinghy line around a prop. You can read about my experience in this article about the top 3 mistakes I’ve made personally while chartering.

It wasn’t a big deal for me, but I did have to spend 30 minutes diving on the prop to cut loose the line. If this happens you should also inform the charter company since there could be unseen damage to the saildrive.

Just make this one part of your crew’s anchor/mooring routine. 

Have someone responsible for pulling in the dinghy so there is minimal slack in the line, every time.

Virgin Islands NOAA Forecast Zones
NOAA marine forecast zones for the Virgin Islands and Puerto Rico

Ignoring weather reports

On my first trip to the BVIs, I didn’t pay attention to the weather reports at all during the trip.

That was a big mistake.

Luckily, we had the consistent, beautiful BVI trade wind weather that is often present.

But what if a north swell was running? I could have been caught off guard.

Take it a step further beyond the marine forecast printout you’ll receive (sometimes) at your charter briefing. Check the forecast resources everyday. In most charter destinations, cell phone coverage or wifi should be available most days.

If you are sailing during hurricane season, be even more vigilant.

I talk about which resources I use for by bareboat charter trips in my BVI marine weather post.

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Dodging squalls on the way to the Dry Tortugas on a bareboat charter trip
A squally day on a recent trip to the Dry Tortugas, the least of the challenges we encountered

Sticking to a planned itinerary

Be. Flexible.

The boat is going to have a maintenance issue.

Someone of the crew might be seasick.

A day or two of thunderstorms and squalls might interrupt your plans.

On my recent yacht charter trip to Key West to the Dry Tortugas, we had a lot of issues to deal with, but we adjusted. That’s part of the territory with yacht charter trips.

  • We had to swap boats after our first day
  • The AC didn’t work in August in South Florida ☀️☀️☀️, so we moved the boat to a better slip for a breeze
  • We added an extra day to the trip so we could make it all the way to the Dry Tortugas
  • Lost a day of exploring in the Dry Tortugas, but it was better than not going at all
  • Lastly, we grabbed a hotel room the last night, well, because of ☀️☀️☀️

One of your jobs as skipper is to create a happy ship. Shake off the disruption, whatever it is, and adjust the trip as needed. Even if it means you have to cut out a favorite stop or destination.

Another good piece of advice? Don’t try to do too much on your first day. Have a short and easy passage. Let the crew get adjusted to the yacht. We also rarely get out of the marina as early as we’d like to.

Leaving your fenders out

Ok. This really isn’t that big of a deal.


There is no better way to identify yourself as a beginner to other yachts 😎. Don’t be that skipper!

Letting your engines run unattended

It might be tempting to charge the batteries in idle while your ashore enjoying a specular meal.

No one likes to hear the engines running.

But seriously, don’t do that. We don’t run any systems – engines, generator, or water maker, when we are not on the yacht.

Here’s an example of what can happen if you don’t take my advice.

Anegada Setting Point anchorage and mooring field
The somewhat crowded mooring field at Setting Point, Anegada

Racing through a mooring field

Don’t try and race another yacht to try and pick up the last first come first serve mooring ball at Cooper Island.

It’s dangerous, and not worth it.

Lots of people, myself included enjoy swimming off the back of the boat and would love it if you don’t run us over 🤝.

Thanks for reading my post about the top 10 mistakes to avoid on a yacht charter trip and making it all the way to the end! If you enjoyed it, please subscribe or check out some of my other articles, like this one about my favorite BVI anchorages.

Top 5 Culebra Anchorages in the Spanish Virgin Islands

Lagoon 46 in the Spanish Virgin Islands, Culebra at sunset; culebra anchorage

Often overlooked by it’s more popular sisters to the east, the USVIs and British Virgin Islands, the Spanish Virgin Islands continue to be a well-kept secret for those in the know. Don’t miss out on these spectacular Culebra anchorages!

I love them because they are less crowded, stunningly beautiful, and offer great opportunities for snorkeling and fishing.

In this post, I’ll cover my top 5 favorite Culebra anchorages to check out the next time you visit the Spanish Virgin Islands on a yacht charter. You can also learn more about them in my cruising guide. I’ll cover Vieques in another post.

DNR mooring balls at Culebra anchorages

Before we dive in, be aware that the Department of Natural Resources (DNR) has several mooring balls throughout Culebra. This helps protect the seabed and the National Wildlife Refuge areas.

Make sure you inspect these balls after tying off! Last time we visited we found at least one ball that didn’t pass for us.

Most are also marked as day-use, but this doesn’t seem to be enforced. Stay on them overnight at your own risk!

Last time we visited (Dec-2020), we counted the number of balls we saw. Here’s what we found.

Number of Mooring Balls
Bahia de Almadovar
Ensenada Dakity
Cayo de Luis Pena
Playa Tamarindo
Playa Carlos Rosario
6 (and 3 additional to the north marked for diving)
View of Culebrita, one of the Culebra anchorages
Beautiful Culebrita, one the of the Spanish Virgin Islands' gems

Culebra anchorages

Culebrita anchorage (Bahia de Tortuga)

Hands down, this is my favorite Culebra anchorage. Tortuga Beach is a perfect crescent shaped, palm tree-lined piece of paradise.

There are several (DNR) mooring balls here, which are designated for day use and are free. You can also anchor.

Many consider this a day stop only, since the anchorage is exposed to northerly ground swells. Passing tropical waves or strong tradewinds can also make Culebrita uncomfortable. Nearby Bahia de Almodovar is a good nearby, overnight alternative.

On weekends, it also might be crowded since it is often visited by the ”Puerto Rican navy”.

One of the many residents that calls the abandoned lighthouse home

What do to at Culebrita

I wrote a bit about Culebrita in my Spanish Virgin Islands cruising guide and include a map of the trails.

Get out your hiking shoes and make the trip to the lighthouse – expect them to get wet and quite dirty! The 360 views at the top of the surrounding reefs and islands is worth the effort.

You can also visit the jacuzzis on the north end of the island. These are natural tide pools that heat up with the warm tropical sun.

Other things to do? Just enjoy the beautiful beach. Swim with the sea turtles. Snorkel the nearby reefs.

Ensenada Dakity anchorage
Aerial shot of Ensenada Dakity | You can also see Puerto Rico in the background

Ensenada Dakity anchorage

Just inside the reef after entering Ensenada Honda, you can find this Culebra anchorage, Ensenada Dakity. There are 20+ mooring balls you can use.

Be careful of the front row! It can get quite shallow at low tide. Monohulls should avoid those.

Despite being exposed to the trades, you won’t feel much swell at all thanks to the protection of the reef.

I prefer to use this anchorage rather than anchoring closer to the town of Dewey. Go get your provisions in Dewey, but re-locate to Dakity for the night. It’s also within dinghy range if you prefer to go out for a bite to eat, such as at the popular Dinghy Dock.

What to do at Ensenada Dakity

Activity-wise, there isn’t much to do. It is a very pretty area though and serves as a great jumping off spot for excursions out of Dewey.

Snorkel the nearby reef right from your yacht and enjoy the golden hour with a cold one.

Cayo Luis Pena
Cayo de Luis Pena bird sanctuary as seen from the north

Cayo de Luis Pena anchorage

As you continue to work your way clockwise around Culebra, you’ll find Cayo de Luis Pena – the larger cayo on the west side.

You have several options for anchoring or mooring. I like Lana’s Cove on the southwest corner. It is better protected and offers you easy access to the hiking trail which runs to the north end of the island.

Cayo de Luis Pena is part of the protected marine sanctuary. Last time we visited, there were two DNR day-use mooring balls here.

The anchorages here are notorious for not being, well, comfortable. Surge and swell seems to wrap in at all of them. So, consider this a day stop only.

What to do at Cayo de Luis Pena

More snorkeling and exploring! The hike is fun – you’ll especially enjoy it if you are a bird watcher – the island is a sanctuary.

The beaches are mostly rocky, but they do the trick if you have a dog aboard.

Carlos Rosario sunset in Culebra
Epic sunset over the cayos to the west from our mooring

Playa Carlos Rosario anchorage

There are several (~6) mooring balls here. Otherwise it is too deep to anchor. The shelf drops off quickly from shore. The bottom is also not good for anchoring.

The moorings, as with the other DNR balls, are marked as day use only, but that does not seem to be enforced.

Hiking to Flamenco Beach from Carlos Rosario
Hiking to Flamenco Beach on the trail from Carlos Rosario

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What to do at Cayo de Luis Pena

There is a super healthy reef here that is great for diving and snorkeling. Last time we were there on a catamaran we saw turtles, rays, and a few juvenile sharks. A school of yellowtail snapper hung around underneath our boat as well.

We also had to compete with some jellies, so take caution.

The hike over to world-famous Flamenco Beach is well worth the trip – the trail is quite easy to identify on Google Maps.

You will also experience amazing sunsets here. The cayos to west make for a perfect backdrop.

Tank at Flamenco Beach

Flamenco Beach anchorage

Use caution with this anchorage as it is very exposed to the north. This one only works in very settled conditions. I would definitely recommend this as day-use only.

You also might want to avoid if the wind direction has a northerly component.

If the wind is up, you might also have some difficulty landing the dinghy on the beach.

But you can’t miss Flamenco Beach. Other options are taking the hike from Carlos Rosarion or anchoring in Ensenada Honda and renting a street-legal golf cart.

Our catamaran at anchor at Playa Flamenco
Our Lagoon 46 cat at anchor at Playa Flamenco

What to do at Flamenco Beach

The main attraction here is the wonderful beach. It reminds me of the South Pacific with it’s reef, coconut palms, and mountainous terrain.

Make sure to go get your picture taken with the tanks that were previously used as target practice.

Park yourself, grab a beer and some lunch, and enjoy. There are several vendors that sell food and drink.

Thanks for reading my post about Culebra anchorages and making it all the way to the end! If you enjoyed it, please subscribe or check out some of my other articles, like this one about sailing to St Croix and visiting the Spanish Virgin Islands.