So, you want to charter a boat, but have no idea how to go about it? Maybe you have angst about the steps of securing the right boat in the right location, or maybe you’re apprehensive about managing a large powerboat or cat? Chartering is easier than you think, so in our three-part series we’ll explore how to 1) find and secure your dream vacation, 2) manage a model of boat that you’re likely to encounter out there, and 3) approach your first day of charter to elevate your time on the water. Let’s start with what seems like the intimidating process of swimming through the paperwork.

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The Caribbean has lots of bases and charter companies to choose from. Photo by PropTalk

Where to go

Your destination of choice will depend on a few factors including who’s in your party and what you want to experience. Are you looking for beaches and bars? The British Virgin Islands (BVI) are a good choice. Do you seek history and culture? Greece and Croatia fill the bill. How about a somewhat remote and exotic bucket list location? Tahiti is your answer. Or maybe you want to charter a fishing boat for a day or an overnight excursion? Florida is a go-to.

Get a good sense of what you want to see and do and take into consideration who’ll be with you. If you’re bringing kids, make sure there are shoreside distractions, and if you boat with those who are prone to seasickness, choose calmer waters with shorter hops between islands or towns. 

When to go

You’ll want to dodge cold weather and hurricane season when planning your getaway. The Caribbean and Florida are great from November to June, while the Mediterranean is good during the summer but can be chilly in the spring and fall. Ask the charter company about “shoulder seasons” at your targeted destination. The rates are usually cheaper, and the crowds are smaller. I’d stay away from Europe in August due to tourist madness and out of the Caribbean from July to October due to the chances of large storms. 

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The BVI is a destination where most charterers gain confidence on their first few outings. Photo by PropTalk

Start simple and close to home

The last thing you want to do is haul your party halfway across the globe and then embark on a complicated itinerary in a country where you don’t speak the language. You can fish or cruise the Chesapeake without a big travel budget. Or, for North Americans, the Caribbean is an easy flight, English is widely spoken, and there are lots of bases and charter companies to choose from. 

For example, the BVI is a destination where most charterers gain confidence on their first few outings with line-of-sight navigation, moderate weather, and easy provisioning. You can choose to stay strictly in the BVI, so there’s no need for the bureaucracy of checking in and out between countries (like the USVI), and the distances between islands are short, so your crew isn’t exhausted. Also, if something goes wrong with the boat, assistance from the base is just a phone call away. 

Get your crew organized and include them in the planning

Decide who’ll come with you and choose your “first mate.” This is the person whom you will depend on for the safe operation of the boat. But don’t forget the rest of the tribe, including kids. Get everyone involved early so that they feel they have a stake in the outcome. A few boat outings close to home with the group will help them learn to work together, and you’ll identify who’s best at which function. Hold periodic calls or meetings during the charter leadup to keep everyone excited. Charter companies often have guidelines for packing to share with your crew. 

Start with the ‘majors’ for lots of options

There are a lot of excellent charter companies of all sizes so you can specialize in a small fishing charter or go big with a cruise in a distant location. In the latter case, the largest companies have the most choices of destinations. The Moorings, Sunsail, Navigare, and Dream Yacht Charter have bases in dozens of places around the world. 

A deciding factor may be choosing a company that offers powerboats rather than sailboats. MarineMax Vacations in the BVI is all power all the time. The Moorings offers power charters in 14 locations including the BVI, Croatia, Greece, and more. Dream Yacht has six bases with power charters including the Abacos and Australia. 

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The largest companies generally have more choices as far as destinations. Photo by Zuzana Prochazka

Lean on the charter company’s expertise

The paperwork may seem daunting, but it’s not hard to navigate. Let the company guide you. They’ll walk you through what they need and how to submit your experience and resume, how to choose a boat including amenities and size, and how to sift through the contract, insurance payment, and crew list. Start with the company website and pick up the phone because a conversation is always better and faster. 

Most companies will post sample itineraries on their websites. These are invaluable for planning purposes. Don’t try to pack too much into one vacation, or you’ll be constantly running, and your crew will be unhappy.

Some destinations are straightforward while others get tricky. The BVI and USVI are simple, but if you want to charter in certain European countries like Greece and Croatia, you’ll need specific qualifications. Chartering in Belize necessitates a Certificate of Competency from the government, but the charter company will be able to ease you through the process. 

Let the charter company do the heavy lifting

Once the charter reps walk you through the requirements, ask them about other issues. Let the company help you with provisioning. Some locations outsource the provisioning function and will refer you to a local outfit that will purchase and deliver the food right to your boat on the day of departure. 

It’s best not to take the “full” provisioning option. Choose instead the “partial” option because you’ll want to explore local restaurants and supplement with goodies you purchase along the way. In most locations, you won’t need to plan for every meal but having your drinking water brought aboard will save your back when someone else does the heavy lifting. 

If in doubt, go beyond bareboat

If the whole process of bareboating (where you do everything including drive the boat yourself) is too much or if you’re uncertain of your boat management skills, consider crewed options. 

You can choose to join another group if you’re solo or with just a partner. Most larger companies offer by-the-cabin charters where you’ll be aboard with others and a professional captain. Fully crewed options include a captain, a chef, and possibly a mate, so you’ll hardly have to lift a finger all week long. And finally, there’s a partial captain option at certain destinations where a local will stay with you for a day or two until you get the hang of it. You’ll need to provide them with a cabin and food, but their local knowledge and skills will help build your confidence before you are set free for the latter part of your vacation. 

Take the first step

There are lots of steps in getting ready for charter, but the most important is the first one. You’ll soon see it’s not that mysterious. There are lots of people along the way to help. Good luck and have fun out there.  

By Zuzana Prochazka


Stay tuned for part two: Tips for Managing a Charter Powercat and visit proptalk.com/category/chartering for more charter how-tos and destination features.