How to Charter a Boat

This time of year, it’s an inevitable thought: Life would be that much better out on the water. Specifically, on a boat.

Even if you have neither a boat nor boating experience, it’s never been easier to make your nautical dreams come true — whether you want a day trip on your local lake or a fully staffed multiday voyage in a far-flung locale. Here are the initial questions that will help you plan an adventure on the water.

Whom are you traveling with?

Thinking about the size and dynamic of your group is an important first step, even if you are simply going on a day trip. Will children be on board? How old? What about elderly parents?

Dan Lockyer, the chief commercial officer of Dream Yacht Worldwide, strongly encourages travelers to determine group size — and, ideally, get people committed — before booking.

“The location that you want to go to, the time of year that you want to go, the type of boat that you want will entirely depend on the makeup of the group that you’re sailing with,” Mr. Lockyer said.

Do you want to captain, or do you want a captain?

Different charter companies specialize in certain locations, types of boats, itineraries and services. Some companies offer the opportunity for a “bareboat” charter, in which you rent the boat and take on the navigation and provisioning yourself, while others exclusively offer fully staffed options, including a captain and a cook.