How to Charter a Boat: travel 101

"If you want to sail off into the sunset, at least temporarily, you need to understand how to get aboard first.

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.

If you want to captain the boat yourself, almost all outfits require some kind of proof of sailing or boating experience, often in line with local regulations.

Edward King, 45, an executive at a streaming company based in San Francisco, is experienced in sailing the city’s waterways. But on vacation, he said he would prefer to let a captain and crew take the lead.

Mr. King said he appreciates a captain who is familiar with both the local waters — “they’ll know how to avoid sailing into a certain sandbar,” he said, — as well as the local attractions.

In contrast, Matt Blake, 38, a software engineer based in Oakland, Calif., was eager to grow his sailing experience during a recent trip to La Paz, Mexico, with his fiancée. He hired a captain but made clear that the captain was there to help and teach.

Where do you want to go?

“Do you want something that’s more culturally oriented? Nature oriented? An adventure trip?” asked Mary Curry, the voyage product director of Adventure Life, which offers small group tours and private trips on land and on water around the world.

That answer can determine your destination. Popular cruising grounds include the Caribbean, Croatia, Alaska and French Polynesia, but the sky — or the sea — is really the limit. For help narrowing your focus, travel advisers often have relationships with charter companies or outfits around the world, and sailing publications offer recommendations.

Kyla Malkani, who has had experience with charters working as a destination wedding planner, recommends consulting the concierge of waterfront hotels, particularly for short-term or day rentals.

“A lot of times they will have either their own fleet or they will have some sort of connection at a dock,” said Ms. Malkani, 37, who is based in Washington, D.C., and is currently working as a content creator and freelance event planner.

What kind of boat?

Where you want to travel and for how long will likely determine the kinds of boats that are available to you. Crucial at this point, too, is an understanding of the boat’s layout and amenities.

“You definitely want to choose the right kind of boat,” said Ms. Malkani. “If you want more adventure, a sailboat is nice. If you’re looking for a luxury party environment, a yacht is best. And if you’re looking for something smooth, for older people or with kids, a catamaran is great.”

David Barclay is a luxury travel adviser who has also chartered boats for his own vacations.

“You want to match what the travelers want to what the boat offers,” he said.

Perhaps a group of friends might not mind a catamaran with functional but not luxurious marine bathrooms, but a multigenerational group might prefer more high-touch amenities.

When should I book?

Often, charter trips are once-in-a-lifetime experiences that require a great deal of advanced planning.

“You may have a specific place you want to go, or a specific time of year you want to travel,” said Mr. Barclay. “And some places just aren’t good at certain times of year.”

Naturally, you don’t want to be at sea in the Caribbean during hurricane season, or in the Mediterranean during winter storms. But you also might want to avoid peak cruising seasons, too.

The first three weeks of August are quite popular, said Mr. Lockyer. “If you have some flexibility and can travel in early July, you’ll get the same sort of great weather, a greater selection of boats and the anchorages won’t be as crowded.”

How much does it cost?

Charter costs are incredibly variable, dependent on all of the factors coming into play: your boat type and size, your destination, your group size, the amount of crew you’d like and the amenities on board.

That said, costs could range anywhere from $2,000 for a day on a sailboat to hundreds of thousands of dollars for a multiday mega-yacht charter.

Have a budget in mind when beginning your research process.

What if I didn’t plan far in advance?

While advanced planning is encouraged, and often necessary for bigger boat trips, it’s possible to book a boat last-minute.

Boatsetter, an Airbnb-like platform for boats, is a good resource for last-minute bookings, especially for day trips, and even has an Instant Book option for down-to-the-wire bookings.

“If it’s for a special event, or around major holidays, you may want to book a month or two in advance. But for general bookings, you can find options within a week or two,” said Kim Koditek, Boatsetter’s head of brand strategy and communications, of the company’s overnight offerings, which appear on their platform under the luxury yacht charters category.

Ms. Malkani has used Boatsetter for some of her charters, most of which have been booked with a specific goal in mind.

“I’m a sunset chaser,” she said. “My husband and I just really love being on the water, and we always try to squeeze in some sort of boat day activity when we’re traveling.”" [1]

 

1. How to Charter a Boat: travel 101. Sloss, Lauren.  New York Times (Online) New York Times Company. Jul 16, 2024.