Chartering a Sailboat

Chartering a Sailboat


Chartering in the British Virgin Islands
Chartering in the British Virgin Islands

Chartering a sailboat, bareboat or crewed makes for a wonderful holiday.

There are many sailboat charter companies available, some great and some not so great.

This is where a sailboat charter brokerage company can be of great assistance. Charter brokers are paid by the sailboat charter company – not by you. An experienced charter broker will be familiar with the area you want to sail in and offer you some great suggestions as to the type of sailboat you need to suit your sailing needs and budget.

In the British Virgin Islands (BVI), as an example, there are numerous sailboat charter companies – where do you start? You could pick a well known charter company like the Moorings or SunSail, but you may not be getting the biggest bang for your buck. A charter broker will give you choices, find last minute sell offs and will generally get you the best deal.

We are not yacht charter brokers but having chartered sailboats in different parts of Canada, U.S. and the Caribbean we have learned a few things over the years.


Sailboat Charter Companies

There is a hierarchy of charter companies. At the top, larger chartering companies offer sailboats that are generally less than 5 years old. Most of the sailboats in charter are owned by private individuals who place their boats into charter as a way of off-setting the cost of maintaining and storing the boat.

At the end of five years service the boat is removed from the charter fleet and replaced with a newer boat, also privately owned.

The next level of chartering companies, like Footloose Charters, will pick up boats released from the upper echelon chartering companies. This allows the boat owner to continue to have his boat placed in charter for a further period of time. Boats in this class of chartering are somewhat older but still have lots of life left in them and are more affordable to charter.

Eventually a boat in companies like Footloose will have served their purpose and will be released from the charter fleet. The boat owner may choose to sell his boat at this stage or keep it for personal use only.

Smaller charter companies are more prone to owing their won boats but will still happily place a new boat owners boat into their charter service. This means that a charter fleet may consist of relatively new boats or relatively old boats and everything in between. Chartering prices will vary based on boat size and boat age. We have had some great charters on older more affordable boats through smaller charter companies.

Yacht charter brokers are not always available for all charter areas so do your due diligence before chartering.


How much are you really paying?

The charter rate for the sailboat is only part of the cost involved with chartering.

All charter companies will charge you an overnight fee if you arrive late in the day and need to overnight in the boat before your check-out the next day. The same applies if you need to overnight before catching your flight the next day.

You must also consider the cost of hull waiver insurance. This is typically a daily rate or it could be a flat rate. Never charter a boat without taking out hull waiver insurance.

In some areas, like the British Virgin Islands, there is a cruising tax and a national water park tax.

Some smaller charter companies will charge you extra for bedding and towels. Others will charge you for slip usage if you spend any of your charter days in the boat’s own slip.

Add to all or some of the above, the cost of provisioning.


When to Go?

Chartering has high, mid and low seasons following changes in weather and customer demand.

A good time to charter is early in the chartering season just before rates start to increase. Although you may be able to get the same rate later in the season, you must also factor in that the charter fleet has been well used for the majority of the season with little time for maintenance between charters. If you charter late in the season expect to find worn lines, latches that won’t catch, lights that won’t work and other small annoyances.



This is one area where you can save a considerable amount of money.

In areas like the British Virgin Islands, U.S. Virgin Islands, Bahamas you can pre-order online and have your provisions delivered to your boat on your arrival. This is certainly better than using up your holiday time trying to find a provisioning outlet that will provide you with all your essentials and then lugging it back to the boat yourself – not to mention the taxi fare you will have to pay.

If you are chartering in the U.S. or Canada then stopping in at the local grocery store in not a big deal and more affordable.

When we charter, we take most of our provisions with us. Toilet paper, canned goods etc., even frozen meals already prepared. We will use a provisioning company, if we are in the Caribbean,  for fresh fruit, vegetables and beverages. If we are in the U.S. or Canada, we will still take some pre-made frozen meals (hamburgers, chili, stew etc.) and buy the rest at a grocery store nearby.

Foreign Customs have no problem with you taking food provided it is for personal use, canned or processed (including dairy products) or cooked. We have taken cooked frozen meat to the BVI and different parts of the U.S. and Mexico on numerous occasions.


Picking the right Sailboat

Know your cruising ground before you select a sailboat. The Florida Keys and parts of the Bahamas and Belize are very shallow. Sailing in a monohull with a 6′ draft would severely limit your cruise area – the better choice would be a catamaran.

Catamaran’s are roomy, have a shallow draft, are difficult to tack and are more expensive to charter.

If you are going to be sailing in open water we suggest that you not charter anything smaller than a 35 foot sailboat monohull. This is going to be your home for the duration of your charter, you don’t want to be too cramped. More importantly, if the seas pick up, a boat smaller than 35′ can get knocked around quite a bit.

If you are two couples sailing, it is nice to have a third cabin for storage space.


Prepare in Advance

We always buy large scale charts for our charter area and a good cruising guide, well in advance of our departure. This allows us to plan a well thought out itinerary with a Plan B & C in the event the weather does not co-operate.

We always take a small handheld GPS and we will enter our waypoints (check and triple check) before we go.

This will save you a lot of time and help avoid errors (such as entering waypoints). This will also make you more knowledgeable of the area during the checkout chart orientation so that you can ask important questions about hazards,  weather or navigation.

To speed the checkout process, we take our own checklist. Sometimes the checkout person is in a rush and will over look certain aspects of the checkout – like is there a “Y” valve or how do you use the emergency steering mechanism.



Sailboat chartering is a great way to spend a holiday and to see different parts of the world from a different aspect that most people do not get to enjoy.

Take your time, do your research but go – life is too short to miss such a wonderful experience.