Sailboat Chartering 101

Interested in taking a sailing vacation? Start here! We’ve put together a guide on charter types, locations, qualifications and more.

If you’ve thought about chartering a boat for a sailing vacation, your list of questions is probably long — especially if it’s your first time. Where should we go? Am I even qualified to charter a sailboat? What’s included in a bareboat charter?

Not to worry — read on for information on what types of charters are available, from bareboat, which is basically renting a sailboat, to fully crewed options, and even learn-to-sail adventures; certifications and licenses, locations, what to bring and how to find a great deal.

Once the anchor is down, it’s time to jump in and explore. Courtesy of Sunsail

Charter Sailboat Directory Whether your destination is Belize or Baja, the Caribbean or California, the Mediterranean or Maine, consult the Cruising World directory of sailboat charter companies and sailboat charter brokers to help you get there.


Choosing the Best Charter Option Not quite ready to skipper but still want to charter? Don’t worry, there are plenty of other options to get you out there.

Types of Sailboat Charters Charters fall into two distinct categories: fully crewed—the boat you charter comes complete with a captain and a crew, and bareboat—you’re the captain, and your family and friends make up the crew. Both styles offer distinct advantages.

The Moorings crewed charter
With a captain to worry about running the boat, and a chef to handle all the cooking, a crewed charter offers a luxurious vacation indeed. Courtesy of The Moorings

How to Choose a Charter Company Check out our tips on what to consider when choosing a company for your sailing vacation.


Sailboat Charter Qualifications Are you ready to charter a sailboat on your vacation? Cruising World’s charter guru Elaine Lembo breaks down the qualifications you’ll need.

Sailboat Charter Destinations and Itineraries Not sure where to go on your sailing vacation? Check out Cruising World’s tips on how to pick the best sailing destination and itinerary.

When to Charter: Seasons, Sailing Conditions Cruising World* breaks down how to choose the best time for a sailboat charter vacation.

The Moorings
Bring the kids! A sailing vacation is perfect for families. Courtesy of The Moorings

Why You Should Charter The notion of sailing an unfamiliar boat outside of home waters can provoke lots of questions.

How to Plan a Sailboat Charter Cruising World explains how to plan a charter vacation, including boat type, cost, getting there, provisioning, contracts, paperwork, and what to pack.

Planning a Charter Itinerary Use these practical planning tips to make your next yacht charter the best sailing vacation of your life.

Be sure to try out some water toys on your charter vacation. Courtesy of MarineMax

The Web, E-Deals and Last-Minute Offers Visiting company websites is a great way to educate yourself about fleets, boat availability, destinations, rates, and special deals before you make your decision about which company to use.

Owning a Charter Sailboat Charter skipper David Kilmer shares insider tips on how to be a good charter boat owner, and how to decide whether it’s the right decision for you.

Put a Boat in a Sailboat Charter Fleet How do you pick a sailboat to put into the charter trade? Here are some suggestions.

Role of a Charter Broker Steve McCrea, president of Ed Hamilton & Co., shares the role of a charter broker with these tips for finding the best crewed charter vacation.

The Moorings charter
Tropics not your thing? Try a charter in the Med. Courtesy of The Moorings

Read more about charter sailing vacations: