‘Twas the first night at anchor and all through the boat, not a creature was stirring not even a…

Oh baloney.

The skipper is wide awake.

Show me a new sailor the day after anchoring for the first time – or the first ten times – and I will show you a very tired sailor. Let’s face it, when you are new at sailing and put your boat to bed for the night, whether it is anchoring, mooring, or docking, you replay every step it took to get you there and second guess whether you did it right. Are you in a good spot? Is your holding secure? What could you have done better? You check and double check.

That is ok, that is what learning is about. And better to be extra vigilant than to accidentally drift out to sea or worse, onto shore. I remember every one of our “firsts”. Not a one of them was executed perfectly. Same can be said for the “seconds”. But the more you sail, the more you learn, the easier it gets.

One way that new sailors can help bolster their confidence is to have a daily plan that includes where they are going, the ideal route they will take, and perhaps most importantly, how they will secure their boat for the night. Knowing what to expect when you arrive at your destination can help every sailor best communicate plans and roles to the crew.  But if you are brand new to sailing, you might not know how to piece together the information you need.

The good news is there are many resources and recommendations available that can help sailors craft excellent, safe itineraries that are a match for their skills, conditions, and desired destinations.

Chart Briefing

Chart briefings are a gold mine of information, so don’t make the mistake of rushing through it and not asking questions, especially if you are new to sailing or new to the area.

When you charter your boat, there will be a boat check to familiarize you with the boat and a chart briefing to familiarize you with the area. Good chart briefings include itinerary recommendations often with tips for spots to stay for the night and what you can expect when you get there. I always take lots of notes during chart briefings because there is so much valuable information provided. More times than I can count, I have revisited the details of those notes when we were evaluating places to stay for the night.

If your charter company doesn’t volunteer itinerary information, ask. This is your opportunity to learn as much as possible about the area. You can gain valuable anchoring or mooring insight, find out how to contact specific marinas and if reservations are advised, and learn about potential hazards.

Navigation Charts and Books

Your boat should be equipped with navigation charts that, depending on how comprehensive and current the charts are, will identify anchoring areas, mooring fields, and marinas. They also indicate low-tide depth so you will know what to expect when you arrive and, if you plan to anchor, you can assess whether you have enough chain and rode ahead of time. Often other books and resources will be provided on board that offer additional information on how to approach popular areas and what amenities and features can be found.  You can also ask your charter company if they have itinerary details in advance as many put together excellent documentation for their guests.

Pre-trip Online Research

Before you head out for your charter, do some online research about the area you are visiting. There is so much written about sailing destinations around the world. Read about the experiences and recommendations of sailors who have been there before.  On this website, escapeundersail, we have a Destinations section with blogs about places we’ve sailed.

In addition to websites and blogs, you might also want to join a Facebook Group set up for sailors in the area you will be visiting. We joined a Bahamas sailing Facebook Group before our last trip and it was jam-packed with great information from local sailors who graciously answered our questions.

Know Your Limitations

It is smart to avoid options that you do not think are a good match for your current skill-set. Be smart! If you are not confident in docking between pillars at a very busy marina, you might not want to choose a bustling marina for your nightly stop until you have had a chance to complete the ASA 118 Docking Endorsement. If anchoring in shallow water makes you nervous, pick a location with more depth, if the coral situation in Belize is more than you are ready to take on (it probably is) go somewhere different. The safety of you, your boat, and your crew is paramount and there are always options. Plan ahead and make thoughtful choices.

Consider a Flotilla

If you are sailing somewhere new, particularly somewhere with something you have never tried such as Mediterranean Mooring, we recommend joining a flotilla for your first trip. Flotillas are great because the guess-work of where to go is taken care of, any language barrier issues are minimized, and the destination choices are typically excellent. You will always have a lead boat waiting for you when you arrive, and the skipper of that boat can assist you with tasks that you may not have tried before.

We joined a flotilla for our first sailing trip in Croatia and looking back, we can’t imagine doing it any other way. Having the help of our flotilla guides when we tried Mediterranean Mooring for the first time was priceless, and the wineries and restaurants we visited were incredible! I am not sure we would have found them if we’d been on our own. When we went back to Croatia a second time without the support of a flotilla we felt so much more confident. We explored new areas and visited some places we’d been before so we could share them with our new crew mates.

Wind and Weather

If you and your boat are playing the lead roles in your charter, the wind and weather are the best supporting actors. Often, charter companies will share the expected wind patterns for the week at the chart briefing, but we recommend you pay attention daily. There are online tools such as windguru.com that can help with the most up-to-date information.

Why is this important? If you are anchoring, you want to make sure you are staying on the Lee side of an island or in a protected inlet. For that you will need to understand wind direction. If the weather is going to be rough, you might opt for a marina, second anchor, or mooring ball for extra security.

In all cases, understanding wind direction during the day can help guide where you go so that you have a pleasant sail if possible and so that you end up in an optimal place for the night.

Have a Plan B

Our excellent ASA 101, 103, and 104 instructor, Matt Holt, gave us this valuable piece of advice which we take to heart on every charter sailing excursion: When selecting a location for the night, always have a Plan B.

When we visited British Columbia, we’d planned to stay at Gibson’s Marina. We sailed into the marina, called the appropriate VHF channel, and were told if we didn’t have a reservation, we’d need to leave. We ended up spending the night at anchor in the protected inlet of Port Graves instead. In Belize, there were times when we arrived too late and the handful of mooring balls were taken, so anchoring was our Plan B.

Having a good understanding of options available in case the first one doesn’t work out and making sure you leave yourself enough time to head to your Plan B is smart charter sailing.

As a new sailor, be prepared with as much information as you can so you can confidently make decisions and communicate with your crew. As a new sailor, you also need to give yourself a break. Not everything will go smoothly the first few times, so take it in stride, know that it gets easier, and be sure to enjoy every second of the journey. After all, you are on the water doing something amazing that most people only dream about.

Good for you for making it happen!

Lea Maxwell is the sailor and scribe behind Escape Under Sail, a web|blog project that connects new and future bareboat sailors with the resources, information, and motivation they need to competently and confidently sail beautiful destinations around the world.

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