By Zuzana Prochazka

Never chartered? No problem. Here’s how to plan, execute and enjoy a vacation on a charter yacht where life is easy and the sunsets can’t be beat.

Decide on a crewed or bareboat charter

A crewed charter means you have a captain who manages the boat and maybe a chef or mate as well. Crewed charters ensure a safe and comfortable vacation with most everything done for you. The chefs are usually outstanding so if you’re a foodie, you’ll be in heaven and you may be able to pick up new recipes too. Larger crewed yachts may also have a mate who works with the captain and will do things like getting toys (kayaks, SUPs, snorkel gear, etc.) ready for you to use so you do very little work.

Crewed charters mean you don’t need to know how to sail, how to operate and land the dinghy, how to dock the big boat, or how to manage water and power usage aboard. You don’t need to know much about the prevailing winds, incoming weather, shoal areas or how to read electronic charts or troubleshoot the engines. That’s the captain’s job.

It's key to get all the details of how to use your onboard electronics.

The more professional personnel, the easier the charter will be, but also the less private and more expensive. Some captains may teach you, so you walk away with the sense of being able to do a charter on your own next time. Otherwise, you can just relax and let the boat be someone else’s concern. 

A bareboat means you’ll be doing a self-drive for which you must have at least some experience. It’s less expensive than a crewed charter but you’ll need basic boating knowledge and it’s best to start with a smaller boat. Some charter companies will provide a partial captain who will stay aboard for 1-3 days until you get the hang of things and then will leave the vessel.

Choose a charter company and island group

There are many charter companies from which to choose and lots of places to go. Most people start with the Caribbean which offers warm waters, short distances, predictable breezes and lots of companies that cater to new charterers. The British Virgin Islands (BVI) are the most popular for beginners due to fairly calm waters and lots of shoreside activities including hundreds of restaurants and bars.

Spectacular sunrises in the islands will make you glad you're first up.

In the BVI, you have a choice of large tier-one companies such as The Moorings, Sunsail, Dream Yacht and Navigare. But there are also excellent regional companies such as Horizon Yacht Charters, Voyage, CYOA and TMM. Most of these companies will provide a captain for a part or all of the charter.

Consider timing

Most companies offer seven and 14-day outings. Don’t over-plan your itinerary. Plan to be flexible even with a crewed charter. You may find a hidden gem of an anchorage where you will want to spend extra time snorkelling or exploring.

Itinerary planning with the crew will ensure everyone has input.

Some charter companies offer extra days (like 10 days for the price of seven) so you can sail longer during low or shoulder seasons. Others like Sunsail and The Moorings offer shorter charters for quick getaways (perhaps only four nights), so you’re not locked into a full week.

Shoulder season is less busy, so prices are a little lower, restaurants are easier to book and there are more available moorings in anchorages. Shoulder season in the Caribbean is May/June and early November.

Choose a boat type

Although most yacht charters are done on sailboats, there’s a growing number of powercats in fleets around the world so you can opt for faster, power-only boats. Also, most crewed charters are run on catamarans that are preferred for their stability and extra space. If you want a captain for a monohull, be sure to specify ahead of time.

Power and sail charters can be done in many tropical locations these days.

Set expectations

A crewed yacht charter takes care of many details but that doesn’t mean you don’t have a say in what happens on your vacation. If you’d like to know the itinerary, ask the charter company where their captains usually take guests or have a discussion with your captain when you arrive. For example, if you’d like to go diving and need air tanks and equipment, the captain can arrange to spend more time in a particular location. Some dive companies will come to your boat to pick you up or ask the captain to run you to the dive shop on the dinghy.

If hiking is your focus, ask about the best spots and have the captain prioritize nearby anchorages. And speaking of anchorages, professional captains often have an inside track on anchorages where other charterers may be too nervous to venture or will be able to reserve moorings in crowded coves ahead of time.

Cruising with a captain means you can relax and leave the work to others. 

The more information you can give your captain or crew, the more personalized your vacation will be. If you have people in your group who are prone to seasickness, your captain may be able to find calmer water. If you have people who need extra time due to mobility issues or a fear of water, your crew can work with them so everyone enjoys themselves. That said, set expectations for your group. This is still a vacation on a boat where time and resources are limited and the captain’s decisions trump all else for a safe outing. Unless you’re chartering a superyacht, don’t expect the crew to clean your cabin for you and be respectful of common areas.

Don’t expect miracles. Professional captains have their hands full running the boat and can only change itineraries if distances and weather allow, so be reasonable.

For the best meals, participate in the provisioning

Provisioning means stocking the boat with food. Most charter companies will provide a list from which to choose and then deliver the groceries to the boat. A crewed charter with a chef will have you completing a menu with preferences and allergies. Again, be reasonable and work within your own budget. If you want steak every night but have a hot dog budget, you can’t expect the crew to make up for that. You can ask your chef to put out cocktail hour food so you spend less on drinks and appetizers at a restaurant later.

Happy hour not only saves money at restaurants, it's often the best meal of the day.

Get ready for paperwork & regulations

Nobody escapes paperwork. Crewed charters will take care of most of it for you, but you’ll still need to provide passport and arrival information as well as completing any health visas and COVID testing. If you’re not sure about requirements for a certain country, check online or with the charter company. You’ll need to provide a crew list with the names and ages of all guests. You’ll also need to complete insurance waivers.

Take the plunge

Swaying palm trees, tropical breezes and sandy beaches where you only see your own footprints are closer than you think. If you’re completely new to boating, check out a crewed charter – it may get you hooked. If you’re unsure of your abilities, ask for a captain for a few days. There’s no vacation like a boating vacation and it will open up new options for you around the world.

Lone footprints are your reward for going off the beaten path.