How to Plan a Sailing Charter

Jan 3, 2024

By Ian Pedersen

The yacht charter vacation product was pioneered in modern times by companies like The Moorings over 50 years ago, and for decades remained a best-kept secret of the boating industry. Back then, traditional sailboats comprised the majority of yachts available for many years, which required extensive sailing knowledge on the part of the customer in order to entertain the idea of enjoying a vacation like this.

In recent years, larger more comfortable yachts have been developed which cater to a wider boating audience, as well as different products and a wider array of crewed yachts now make charter vacations available to a much wider market than ever before.

If you’re considering a yacht charter for your next vacation, here is a step-by-step guide of everything to consider before confirming your home on the water.

Step 1: What Type of Boater are You?

The most important thing to consider when booking a yacht charter vacation is exactly what type of charter you want to experience. There are three main terms to know: “Bareboat”, “Skippered”, or “Crewed”. A Bareboat charter is one in which you are the captain of your own yacht. This is the most popular type of yacht charter vacation and requires varying levels of either boating or sailing experience, or official certification depending on the country in which you choose to set sail.

A Skippered charter is one in which you choose to hire a Captain to sail the yacht for you. It is still your vacation, on your own private yacht, but the Captain, in the case of The Moorings, is often an employee of the company who is experienced with the type of yacht and will assume all responsibilities of navigating and handling the yacht for the duration of your trip. You might even consider taking part in one of the Caribbean regattas.

Finally, a Crewed yacht refers to a charter managed by a full crew. At a minimum, this is a Captain and Chef team, but depending on the size of the yacht it may require additional crew to assist. The crew will then assume all responsibilities for the yacht – not just the navigation and handling, but the cooking and housekeeping duties as well.

Your first task on this journey is to decide which style of charter is right for you.

Step 2: Who Will You Be Traveling With?

Once you have decided what type of charter you are looking for, the next step is to decide who is going to enjoy this adventure with you! Is this a family vacation? A milestone birthday? Retirement celebration? Are there multiple couples traveling together? This is an important moment because these are your crewmates who will be aboard with you on this adventure every step of the way. In this author’s experience, who you bring along with you on a yacht charter vacation is the single biggest factor in whether the vacation is a success… or not. Look for family and friends who are game – people who are eager to explore that next snorkeling spot, or dance the night away at some remote beachside bar, or someone you can enjoy a meaningful late-night conversation with under the stars. Above all, a yacht charter vacation is what you make of it, so invite people who can make their own fun and get the most out of the trip, as opposed to people who wait for experiences to come to them.

Step 3: Choose Your Destination

The next few steps can come in any order, but my personal recommendation is to first establish where in the world your charter adventure will take place. With The Moorings, the entire world is open to you, from the white-sand beaches of the Caribbean to the historic seaside towns of the Mediterranean and the impossibly blue waters of the Indian Ocean, South Pacific, and beyond.

From the Virgin Islands to the Greek Isles or French Polynesia, each destination offers its own unique benefits and experiences. Are you looking for a laid-back beach adventure? Consider the remote cays of Belize, home to the second-largest barrier reef system in the world. Consider a charter in St. Martin, just a short sail away from the world-famous, celebrity-packed beaches of St. Barth. Looking for an immersive cultural experience? Consider a charter in Croatia or Italy and sail through centuries of history around each bend. You’ve decided who you’re chartering with, now just pick where you want to go!

Step 4: Choose Your Dates

This is an obvious step, but an important one nonetheless. The dates you choose can have a big impact on not only yacht availability, but also price, and the type of experience you have while on charter. Are you looking to charter in peak season? If so, prices will be higher, and you should consider booking your trip farther in advance to ensure you can reserve the yacht you want. Are you looking for an off-season charter? Here, you can usually find some savings on the cost of the yacht itself, but take into consideration things like the weather at that time of year, as well as whether many of the local venues are open. Peak season in the Mediterranean, for example, runs through the summer months from June-September. Conversely, the summer months are the slower period in the Caribbean as hurricane season approaches. All of these things need to be taken into consideration and are where a dedicated Vacation Planning Specialist can help guide you in the right direction.

Step 5: Choose Your Yacht

Some may choose to start with this step, but in this case, this is the last step once you’ve ironed out all the other details. By now, you know whether you are planning to captain the yacht yourself or hire a skipper to do the work for you. You know who in your group will be onboard with you, and how many total people there are. You know where in the world you plan to set sail and you have a window of dates to work with.

Now, you need to select your perfect yacht to act as your home away from home. This can be a traditional sailing monohull, ideal for experienced sailors looking for a more thrilling, hands-on sailing experience; a sailing catamaran, perfect for sailors who still want to get their hands on the lines but enjoy the added space and stability of a catamaran. Either way, one important factor to consider is the number of cabins on board, and ensuring there is sleeping accommodation for everyone in your party. Keep in mind, if you have a crew or a skipper, they will be on board with you for the duration of the charter and will need a place to sleep as well!

Step 6: How to Get There

Now that you have everything else in order, the last order of business is to confirm your travel to your chosen destination. It is strongly recommended that you confirm your flight and travel arrangements before confirming your yacht.

Step 7: Other things to Consider

Once you have determined everything above, you are ready to book your trip. Generally, a deposit is required, with the balance due as you get closer to your trip. In the intervening time, now is your chance to round out your vacation with charter “extras”, such as fun water toys like paddleboards, or kayaks, available electronics rentals, and organize your food and beverages. The Moorings offers an online provisioning site, allowing you to order all of your food and beverages, including alcohol, in advance, and everything is paid for and waiting for you on your yacht when you arrive!

Be sure to review all mandatory documentation, as each charter destination may have unique paperwork requirements that are required before you arrive.

We’ll see you on the water!