This series of articles aims to describe some of the inside hints for chartering a catamaran in a tropical destination such at the Caribbean or the Bahamas. It is directed toward 6-12 person boats and aims to fill in some of the gaps left by the rosy, simple, and optimistic “What to Bring” checklists provided by most of the charter companies. Planning a bareboat adventure requires that the captain and crew make the best of any and all changes to the original plan. Trip plans are organic and ever changing throughout the planning phase to the moment the boat is returned to the charter company. Attempts to over specify the details of the trip will likely be thwarted by airlines, ferries, nature, or physics! Keeping expectations in line with reality can really help make the trip as enjoyable as possible.

Charter Catamaran Sailboats at Anchor in Great Harbour, Jost van Dyke, British Virgin Islands BVI

A variety of charter yachts moored in Great Harbour, Jost Van Dyke

The charter organizer/ skipper will have already considered a monohull sailboat and decided that the amenities of a cruising catamaran are worth the responsibilities and fun that a larger crew can provide. While this document will hopefully be helpful to those planning a bareboat trip on a smaller monohull, it is intended to help manage the increased complexity associated with a larger crew and more complicated vessel. 

The key amenities/benefits of a cruising catamaran are:

Dinghy Stowage. Almost all charter catamarans allow for the dinghy to be hoisted out of the water and slung under davits or carried on the aft deck. Being able to lift the dinghy out of the water helps the boat sail as fast as possible, especially to windward. It also allows for keeping the dinghy more secure overnight from theft or just having the dinghy painter knot coming undone. 

Air Conditioning. While newer monohulls are becoming more likely to be configured with generators and air conditioning, the space requirements of these systems mean that only the largest monohulls have functioning air conditions while at anchor. Almost all cruising catamarans in charter in tropical climates will be equipped with these items, however. 

Space to spread out and no heeling. True sailors scoff at the elimination of heeling, but on a weeklong charter with crew members of varying experience, eliminating heeling facilitates meal preparation, reduces fatigue and seasickness, and reduces the opportunities for damage to items (and people) below and on deck. Catamarans have a lot more space to spread out, and the cabins at the end of each hull have more privacy.

The key disadvantage of catamarans is the increased cost of these vessels, which can be mitigated by spreading the costs of the charter across a larger crew.

Crew Recruiting

This section is intended for considering a crew of social acquaintances; for a family charter, the participants will already be known. However, this section may help a family considering a charter to determine whether they would realistically enjoy chartering a bareboat together. 

This process begins with the skipper initially considering potential crew members. Time and money are the two obvious requirements for participation in a charter trip. Just as importantly, the recruiter has to consider each individual’s ability to be in the close company of others during the week. Ben Franklin's “Fish and visitors begin to smell after three days” should to be kept in mind! Not only do people need to have a history of being tolerable to others for a significant length of time, they need also to have the constitution for dealing with the discomforts that will inevitably be encountered along the trip. How would this person react to being sprayed with cold water and smacked with a stick for a few hours? If the answer is that they’d laugh it off, then you may have a good crewmate. Can this person keep a smile on after the third straight day of rain? If so, it’s probably a desirable recruit.

The skipper must manage crew expectations, and the easiest way to do this is to start right from the initial discussion of the trip. The skipper should have a fairly good idea of the various costs that will be encountered by the participants and be able to summarize them during the initial conversation. Recruits should be made aware of any potential weather factors for the time of year that the trip is being planned. People should be aware that, while most of the charter boats are very nice and even may appear luxurious in pictures, there are aspects of the trip that are much closer to camping than visiting an all-inclusive resort. The boat takes effort to be kept clean, and water and electricity can be limited depending on the habits that the skipper instills on the crew. It should be considered a “working vacation.”

As the crew becomes assembled, the skipper needs to begin deciding if the crew lends itself to a group that wants to rush around and see every sight, or whether it would be best to miss a number of tourist destinations in order to have more time relaxing in certain places. In a place like the British Virgin Islands (BVIs), there is plenty to see even on a 14 day trip, and a balance must be struck between being on the go constantly and more time for relaxing or exploring specific places by land. 

The crew of a bareboat charter catamaran on the bow trampoline entering Sopers Hole, Tortola, British Virgin Islands BVI
A bareboat charter crew relaxing on the foredeck entering Soper's Hole, Tortola. When the crew is getting along and each individual contributes in their own way, a large crew can be very enjoyable. 


For potential crew that have never been on a bareboat charter or in a small boat at sea, the skipper should provide plenty of warning about the potential for seasickness and suggest to the crew to make some preparation for this. If seasickness potential is a big concern, getting a prescription for a set of scopolamine patches ahead of time is probably the most powerful option (they often work well with just a ½ patch applied). Otherwise, an over-the-counter medicine such as Bonine is an easier and good alternative. The skipper should recommend that, whatever method is chosen, the crew try a dose prior to the trip to make sure there are no negative side effects ahead of time. It may be wise to bring a reserve supply of an OTC medicine to have on hand in the case of a crew member who is unprepared for seasickness, which can otherwise negatively impact the crew’s enjoyment of the trip and potentially reduce the morale of the whole crew somewhat. 

Finally, there will often be a lot of informal interest in crew joining the trip. However, they should only really be considered as officially committed once they have paid up their share of the charter cost!

Crew assignments

During the planning phase, it makes sense to make some crew assignments. The following four assignments work well for a large charter catamaran, but the skipper should also ensure that the other crew members who do not have an assignment feel that they are still an important part of the crew and have ways to contribute (especially with cooking, handyman-type skills, and/or medical and first aid knowledge). 

1 - Captain (Skipper)– generally the organizer of the trip, the one who signs the charter paperwork, and the one in charge of the operation of the vessel throughout the charter
2 - 1st Mate – the skipper’s right hand, generally the second most (if not the most, depending on who organizes the charter) knowledgeable boater aboard. The person to ask the skipper, “are you sure you want to do this?” or “I noticed the battery state of charge is getting a little low” etc. 
3 - Social Director – This optional position can reduce the social and crew organization needs of the skipper. This person can be the organizer and sheepdog for shore excursions and the one to make decisions regarding all aspects of the trip that aren’t related to the boat or its operation. The “people person!”
4 - Galley Boss – The galley boss is the lead provisioner, the one who most knows where all provisions are stored, when or what needs to be restocked, and the one to organize which crew member is preparing any given meal. This is not to be confused with having to wash all dishes or do all cooking, but this person needs to ensure that all galley-related tasks get delegated effectively as the skipper should not need to do this in addition to the other duties related to the operation of the boat. 

The following responsibilities can be applied to the four different positions. 

  • Choosing specific anchorages and moorings – Skipper
  • Ensuring the boat is being operated appropriately/safely - Skipper
  • Timing arrivals and departures for each destination – Skipper and 1st Mate
  • Developing schedule of activities at each destination based on crew’s interests (within times provided by skipper) – Social Director  
  • Running and maintaining the engineering systems of the boat – Skipper and 1st Mate
  • Making sure that boat is anchored/moored properly and deck equipment is secured – 1st Mate
  • Dealing with any other moorage requirements - Skipper and 1st Mate
  • Making sure the skipper doesn’t do anything dumb or miss something important due to oversight – 1st Mate
  • Ensuring the crew is entertained and comfortable – Skipper and Social Director
  • Guiding the ashore tour groups and keeping track of time – Social Director
  • Determining the proportion of time spent during cocktail hours on shore vs aboard – Social Director 
  • Sheepdogging the crew to stay on schedule (the crew usually wants to stay put wherever they are if they’re having fun) – Social Director
  • Galley management (ie keeping track of needed resupplying, deciding who cooks when, being able to inform whoever is cooking on any given day where a missing ingredient may be – Galley Boss

Alternatively, if the skipper is particularly extroverted, he or she may enjoy taking on the social director role instead of delegating it. In this case it may make sense to assign a ship's engineer position to take care of the vessel maintenance activities such as monitoring the batteries' charge level, doing the engine room checks, monitoring the water tank levels, etc., so that the skipper doesn't need to also do all these tasks. 

Choosing a Boat and Charter Company

As the rough size of the crew comes into focus, the skipper must choose an appropriate boat and charter company. This decision involves a number of factors stemming from the company and the boat types available. The following sections summarize these factors.

Charter Company

A very significant make-or-break moment of the charter is the moment the skipper steps aboard the boat for the first time. The boat must be present, available, and clean, and the systems must be functioning adequately so that the boat is safe and reasonably comfortable for everyone aboard. The choice of the charter company depends on maximizing the likelihood of these four conditions being met. It is likely that one or more of the boat’s systems will not be perfectly functional and this is to be expected; the question is whether or not they are able to function adequately to ensure a safe and enjoyable charter. 

When choosing a company, the likelihood of satisfying the four items above must be considered a very high priority. Does the company have a large enough inventory of boats so that if something unpleasant happens to a reserved boat the day before its skipper will arrive, a spare boat can be substituted? Do the boats have a group of mechanics and caretakers that can solve inevitable problems quickly? Are the boats generally kept in a good state of repair, and small problems repaired before they become big problems? The cleanliness of the boat is probably the least important item, as boats can be cleaned rather quickly, but any event that originates in an unpleasant beginning is probably more likely to stay unpleasant. Diligence with internet searches is the most likely way to sort through the likelihood of success with these factors. One must remember, though, that the internet tends to concentrate problems and make unlikely and unusual issues seem commonplace. Obviously, discussing these issues with someone with specific experience with one of the charter companies would be ideal, but that is not always an option.

There are a few criteria for the choice of charter company that are secondary to the above. 

Types of boat available – Different companies have different approaches to their choice of fleets. Some choose to have as wide a variety of boats as possible; some only have one brand. The company’s inventory must match skipper and crew preferences. Some company’s boats look as though they are all individually owned while some look to be slab sided barges that are obviously charter boats. One’s reception in an anchorage or marina may be affected by this; do you appear to be a “credit card captain” or a salty and knowledgeable mariner? Some companies will also allow upgrades to larger boats between the time of the initial reservation and the start of the charter. If the crew is not exactly nailed down, or its size may swell as time progresses (as often happens when discussing trips like these in social situations), this can be a real selling point. 

Location of charter base – This may not be a critical determining factor, but it is important to keep in mind how easy it is to get to the charter base during travels. Also, if sleeping aboard the boat the first night (which almost always makes for a more relaxed first day aboard), the charter base should be an enjoyable place to spend an evening as relaxing after a long day of traveling is an important part of the trip. Proximity to provisioning options or stores with items for last minute purchases before departure can also make a particular location more preferable. 

Relative cost – The charter companies are in very direct competition with each other so it is reasonable to expect that the pricing market is fairly efficient and the same money will buy the same level of desirability among the various companies. However, each skipper and crew may not value exactly the same characteristics. It may be possible to find boats that seem underpriced because they have features that a particular skipper's crew desire and lack features that are of no concern to that crew. Vessel age range is a large determinant of price, but some crews may not be as concerned with how new their vessel is. Also, different companies have different dates of seasonal price adjustments. If the time of the trip is known, it may be beneficial to research whether one company considers that period of time to be a ‘lower’ season than another company. 

Individual Boat Selection

Some skippers will find the choice of individual boat to be paramount, and others won't have much concern about the design or style of boat that they charter; they'll be more interested in time spent with their crew and destinations visited. The latter will obviously find the boat choice to be easier. The following characteristics should all be considered when choosing the actual style of boat to be chartered. And, in as much as certain companies only inventory certain types of boat, the considerations below also will affect the choice of charter company. 

Head/shower layout – Does the layout of the heads and showers make sense for the crew that is participating in the trip? In many boats, the head has a drain in the floor and the sink faucet is extendable and this serves as the shower. The user closes the toilet, slides the cover down over the toilet paper, and goes to work making a soaking mess of the small space. In some respects, this is simply the yachting experience – and typically results in the crew often using stern or transom showers (assuming tropical locales) to clean off because showering inside makes a mess that doesn't dry quickly. Only the largest charter boats will have space for separate shower stalls, but this can be a welcome addition at the expense of a fair amount of space. Often, charter boats seem to be extremely over- or under-showered. Moderately-sized or even large cruising catamarans could benefit from just two nice stall showers as opposed to 4 or 5 in-head showers for all cabins. 

Air Conditioning – The ability to stay cool at night is more valuable to some crew than others. In addition to controlling the temperature in the boat, air conditioning systems have other benefits to consider. For one, the very humid salt air causes the boat to become quite humid and damp. Towels, bedsheets, and clothing gradually become damp throughout the charter. Air conditioning reduces the humidity of the conditioned air, and this dehumidification can be just as beneficial as the cooling effect. If the weather during the charter period has a lot of rain, this effect is even further magnified as the boat may gradually begin to resemble a steam room during warm rainy conditions with crewmembers inside and hatches shut. Another consideration, depending on the crew involved, is the auditory privacy that comes with the white noise of the circulation fans, generator, and air conditioning compressors. This can help prevent crew from disturbing or waking each other at night. 
To run A/C systems away from the dock, the boat must be equipped with a generator. This is the more significant cost to the air-conditioning-equipped boat. Some yachts have air conditioning and no generator. These can only run at the dock while on shore power. It is true that, while at anchor, the boat will probably be pointed straight into the wind resulting in the hatches easily encouraging flow through the boat. At docks, the boat may be more sheltered or oriented in such a way that airflow is minimal. For these reasons, shoreside-only air conditioning can be useful and is worth considering. However, for the cost, it may not be much more expensive to go the whole way and have a generator and air conditioning, which also allows for increased flexibility in terms of keeping the batteries charged. 

Bleeding the air conditioning cooling pumps aboard a bareboat charter catamaran in the British Virgin Islands BVI

One of the most common A/C failures that will occur during a charter is air pockets being drawn into the A/C cooling pump intake due to wave action while underway. Here, the author is bleeding the A/C cooling line by loosening the hose clamp at the pump and easing the hose from the pump to let the air escape and allow the hose to fill with seawater.

Dinghy storage – In general, charter dinghies can be transported in one of three ways: hanging from davits, on deck in chocks, or by towing. Towing a dinghy is relatively easy in reasonable or calm weather, but it does add significant drag to the boat, especially when sailing upwind. Depending on the distance that needs to be traveled and the type of sailing that the skipper prefers, this may or may not be a problem. Davits and deck chocks eliminate the drag and risk of swamping associated with towing the dinghy, but are usually only available on relatively large boats. Davits and deck chocks are usually more secure as well. It is far more difficult to quietly steal a dinghy that is stored out of the water than one left in the water. 

Towing the dinghy and storing it aboard in deck chocks on a charter catamaran cruising the British Virgin Islands BVI
Storing a dinghy in davits on the back deck vs. towing. Sailing downwind, the wind and waves help carry the dinghy along with minimal drag, but upwind these forces are reversed and a boat may not be able to make much headway under sail. 

Style of the boat – Every aspect of chartering is prone to subjectivity, but none is more subject than the aesthetic of the boat. A boat is inescapably an aesthetic thing, and the chartered boat should evoke at least some bit of pride on the part of the captain and crew. Different crews will prioritize this particular part of boat choice differently, but selecting an aesthetically pleasing boat will facilitate the recruiting of crew as well as enhance the experience and perhaps even crew morale while on charter.  

Bigger boats tend to have the advantage in almost every category, providing the skipper can get enough crew members to keep the per-person costs affordable. The economy of scale of a large boat mean that, in-terms of per person costs, luxuries such as air conditioning, stall showers, and large galleys can be much more affordable. The only downside becomes the potential increased chaotic effect of the greater number of crew and their differing desires, expectations, habits, etc. 

In summary, the choice of a charter will be a compromise of all of the above factors and the cost of the charter. During the decision of the specific boat, the skipper should keep in mind that the cost of the charter may only be about 1/3 of the entire cost of the vacation when airfare, provisioning, and entertainment are included. A few hundred extra dollars may be well spent to get the right boat, and this additional cost should be considered on top of the whole trip, not necessarily just the cost of the boat. Many charter companies give repeat-customer discounts. Often, these can make the company of choice irresistible in future charters. Even first-time charterers should note whether their company gives repeat customer discounts; the next charter is probably sooner than one thinks when planning the first trip.

Time of Year of Trip

Almost all destinations will have seasonal price fluctuations due to varying demand throughout the year. Typically, companies will have between two and four seasonal price levels. Those with little concern for budget can schedule based only on anticipated weather and their own availability. The more budget conscious skippers will want to game the seasons as much as possible. Shifting a few days into a lower-cost season can save some money without necessarily involving a significant change in anticipated weather conditions. The group needs to remember that the charter cost generally represents less than half of the cost of the adventure, and that it isn't worth spending a week staring at rain clouds in order to save a few hundred dollars on a few thousand dollar vacation, however. 

Rainy squalls of a tropical wave aboard a bareboat charter catamaran in the Caribbean
Caribbean rain squalls are often a nice brief source of cooling breeze, shade, and fresh water. This three-day tropical wave with continuous showers in late October, however, was not nearly as welcome.

The group should also keep in mind the level of crowds present in various seasons and whether or not they are looking for a party scene or quiet private anchorages. Taking a gamble that there will be clear weather during hurricane season will yield reduced prices for almost everything (that actually remains available during that time of year), as well as quiet secluded anchorages that may be completely packed full during the peak season. When severe weather does coincide with scheduling a trip like this, however, the plan fails miserably. Trip insurance can help defray the cost of this, but purchasing that eats into the cost savings from scheduling during this time of year in the first place.

The goal should be to find the best season for the group for the least price. Scheduling at the very beginning or end of a lower season is probably the most logical way to do this, though these times may require more advanced booking in case others have the same idea. Finally, it can be gamed against the weather in the location where the group is coming from. It makes sense to schedule a trip when the weather isn't as nice in the location the group is coming from, especially if that results in scheduling during a lower season. 

Pulling the Trigger

As the choice of charter company, boat, and time of year comes into focus, the organizer will need to reach out to the charter companies of interest. The better charter outfits generally provide access to the availability calendar of their vessels- this greatly facilitates planning. If they don’t, the organizer will need to get in touch with the company and provide the date ranges and boats that are of interest. When the organizer lets the charter company know his or her selection of boat and date range, the charter company will hold that date for a couple of days while they prepare the charter contract. The organizer will need to make the first payment (typically 50% of the charter cost) and sign the contract during this hold time in order to lock in the reservation. The organizer should read the contract carefully and not hesitate to contact the charter company with questions or concerns. Typically, the remaining payment for the charter is due approximately two months before the charter start date. 


Provisioning, the stocking of the boat with food and beverage, is the aspect of the charter that requires the greatest effort and, after the charter cost, the greatest expense. Provisioning can be done by one or a combination of the following methods: in-person visits to stores; having the charter company provision the boat ahead of time, or placing orders with stores that offer delivery. All options require planning ahead of time; this can be generally done at a pre-trip social event in which the shopping list is developed. 

This is where a good galley boss can really shine. If the food is delivered, the better the galley boss knows the items in the order, the better they can find and address any mistakes or missing items while the delivery driver is still present. If possible, the galley boss should check items off of the printed order list and ensure everything makes it aboard as the rest of the crew brings it aboard. If the deliverer knows the orderer is serious, they will be more inclined to ensure they got everything correctly out of their van, which may contain provisions for multiple orders that are shifting around in the van on the road and easily getting mixed up. If planning to have the crew visit a grocery store, it may make sense to divide up the shopping list by category and have each crew member separately get the items in their category and checkout separately to minimize the time required. 

A bareboat charter crew loading pre-ordered provisions aboard in Soper's Hole, Tortola, British Virgin Islands BVI
Loading provisions aboard a bareboat catamaran. A good galley boss will check off items as the crew loads it all aboard, note any missing items, and keep track of where everything is stored.

In general, the simpler the meals are, the easier it will be on everyone. Changes to the original plan or itinerary generally result in less food consumed, not more, as often the crew will spot an unexpected restaurant that looks good, or they may have a “liquid lunch” that results in less appetite than might otherwise be planned. So, it makes sense to not over-order in the provisioning phase, especially in a charter location that has options to re-supply along the way. 

A bareboat charter catamaran anchored in Valley Trunk Bay, Virgin Gorda, British Virgin Islands BVI

All the work of organizing, provisioning, and traveling pays off – a charter catamaran anchored in the calm waters of Valley Trunk Bay, Virgin Gorda

This article is continued in Part 2: Arriving and Getting Underway. In the meantime, check out some of these boating and yachting blogs to help pass the time before your charter begins. They might help keep the Island Fever at bay!

The Swim and Sip Kickstarter prototype aboard a bareboat charter sailboat anchored in Antigua at sunset
The original Swim and Sip floating koozie prototype from Kickstarter aboard a charter catamaran in the mooring field at Great Bird Island, Antigua. The perfect companion for relaxation after a long day of big seas, hiking, and snorkeling aboard a bareboat charter yacht!

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