Sailboat charter: 8 considerations before booking

Sailboat charter: the ultimate guide to considerations before booking

It’s a winter evening, you’re having dinner with a couple of friends, and you nostalgically reminisce about last summer’s vacations, dreaming of the sea, sunsets on the beach, and the salt in your hair.

Your friends share their wonderful sailboat experience with you—the sense of freedom and the unique way of experiencing the sea. Intrigued, you decide to plan a similar vacation for yourself…

That’s where we come in with this guide. We aim to help you truly understand whether a sailboat experience might be right for you and to encourage you to consider several key aspects before booking a sailboat charter. Our insights come from years of working together on our boat, Moby Dick, and living aboard with hundreds of different people.

1 – Sailboat Charter: who will you be going with?

The first consideration before booking a sailboat charter is undoubtedly who you will be traveling with. It’s important to choose companions with whom you already have a good rapport, as living together on a boat means being in close quarters 24/7, and you don’t want it to turn into a nightmare.

Consider whether you want the boat exclusively for yourselves or if you are open to sharing it with other, unknown guests. Sharing the boat comes with some risks and inevitably affects costs.

Next, you will choose your sailing area, which will determine the boat and the skipper you select.

2 – Choosing the skipper

Selecting the crew who will be taking care of you during your vacation is crucial. The success of a sailboat holiday largely depends on the experience and professionalism of the captain.

So, make sure to thoroughly research the crew before booking a sailboat charter. Find out who the skipper will be and ask for information about the sailor or chef who might also be on board.

This research is quite straightforward nowadays, thanks to social media. It’s easy to find and evaluate the experiences of previous guests. For example, on Moby Dick, we work as a team of two to pamper our guests, but this isn’t always the case.

3 – The itinerary is decided by the wind

You’ve chosen your sailing area, and the skipper has given you a general idea of the itinerary. However, surprise—the sailboat vacation is not a type of trip where you will decide each stop along the way.

If the weather is favorable, it will certainly be easier to accommodate all your requests, but this may not always be possible. So, forget about arriving with a day-by-day list of places to visit. If you want to decide where to go without considering the weather, a sailboat vacation may not be for you.

The precise itinerary is determined by the captain based on weather forecasts, which become reliable about three days before your arrival. During a sailboat charter, the direction and intensity of the wind are what dictate the route. The stops are decided day by day, based on these conditions.

Too often we hear complaints like, “The skipper didn’t take us to Corsica” or “We wanted to go there, but the skipper wouldn’t.” It’s important to understand why certain destinations might not be feasible. Ask the captain to explain why a specific place might not be reachable or why a particular route isn’t possible. Learn to check wind forecasts, wave conditions, and storm predictions to better understand how the itinerary is chosen in a sailboat charter.

4 – Sailboat charter: onboard rules and safety

If you’re relying on a professional, they will explain some essential rules upon your arrival. These are usually few but crucial, so always follow them and avoid contradicting the captain, who will certainly have extensive experience.

It’s common for someone on board, who might have had a previous sailing vacation or took a sailing course years ago, to say, “Oh, I already know how this works; I’ve been on a boat before.” This is a mistake, as every boat has its own rules, and every captain has their own way of navigating.

Sailing embodies the feeling of freedom, which is true, but it’s also a specialized environment where caution is necessary. More than once, we’ve had to stop people from touching the control panel or the sheets without asking first. Would you ever enter an airplane’s cockpit and start pressing buttons? It’s the same on a boat.

On Moby Dick, we’re always happy to explain how the equipment works to those interested in learning or who want to delve deeper. However, excessive initiative can often compromise onboard safety.

5 – Resource management on a sailboat charter

A boat, whether sail or motor, has limited water reserves and generates its own electricity. Therefore, it’s important to assess whether you’re prepared for a vacation where conserving these resources is necessary. If the boat doesn’t have a desalination unit, once the water runs out, you’ll need to dock to refill the tanks.

It’s clear that a charter boat is equipped to provide a certain level of comfort, so yes, you can shower daily without issue, but not to the extent you would at home. If you plan to anchor every night and take long showers or leave the tap running while brushing your teeth, a sailboat charter might not be the vacation for you.

Alternatively, you could choose to dock more frequently throughout the week to ensure a steady supply of water. However, this option should be discussed and agreed upon by all guests in advance with the skipper.

6 – Dietary needs

If you’ve chosen a sailboat charter with a chef on board, this person will handle your dietary needs. Special diets such as veganism or food allergies or intolerances can be accommodated without issue.

However, if you are particularly demanding with numerous specific requests, prefer customized meals, or only eat certain types of specialty foods like kamut pasta, this type of vacation may not be ideal for you.

The boat’s galley is small, and the chef will be preparing meals for seven or more people, so they can’t realistically make personalized meals for each individual guest with just two burners.

You will certainly enjoy breakfast with a sea view each morning, and savor lunches, appetizers, and delightful dinners at anchor in beautiful bays. But, you’ll need to be flexible and accommodate the needs of the other guests as well.

7 – Sailboat charter: respect for common spaces

As we’ve mentioned, a sailboat experience involves 24/7 close quarters living, and for the well-being of everyone on board, it’s important to respect others. Remember the famous quote from Martin Luther King, “My freedom ends where yours begins.” Use that as a starting point.

Do you like to spend 30 minutes in the bathroom each morning? Then choose a boat with a bathroom for each cabin to avoid inconveniencing others. Prefer to lounge in the cockpit, taking up all the space while others are squeezed in and the crew’s maneuvers are obstructed? Opt instead to relax in the bow, where you won’t disturb others.

Are you a bit messy? Try to be tidy for at least a week: if you leave your belongings scattered in a shared space like a boat, someone will have to clean up after you to maintain some order and cleanliness.

Respect is always crucial, but it’s even more important on a boat. It’s rare to live so closely with others, whether they are people you know or complete strangers, for an entire week. So, if you choose a sailboat charter vacation, keep in mind that it’s not just about your needs but also about adapting to those of others.

8 – Children on board

Is a sailboat vacation suitable for children? Absolutely, children aged 2-3 years and up can enjoy it with no problem. In fact, they often have the most fun. A whole new world full of stimuli, the sea always beneath them, plenty of fish to see, and knots to learn—there’s no chance of boredom. However, there is a “but”: if your children are unruly, temperamental, and prone to constant crying and screaming, this type of vacation might not be ideal for you.

These considerations are meant to help those approaching this type of vacation for the first time to understand the key aspects of such a wonderful but unique experience, where nothing is left to chance. We truly hope that after reading this article, you’ll be better prepared to consciously choose your next sailboat vacation!

Fair winds from the Moby Dick Sail team