Your First Charter Sailing Vacation

By: Charter, Destinations, Learn To Sail

When ASA started over 35-years ago our primary goal was to get people sailing safely and competently so they could reach the goal of buying their own boat and living happily ever. At that point, charter companies were few and far between, however, as time went on, the bareboat charter industry became more and more substantial and omnipresent. Now sailors can rent all different kinds of boats, in nearly any location in the whole world.

Today ASA has over 400 affiliated schools, has taught over half a million students and has a team of over 7000 certified instructors. As ASA has grown so has the charter industry. When Ginny and Charlie Cary founded Moorings Bareboat Charters in 1969 could they have imagined an industry where you can charter a boat almost anywhere in the world?

ASA believes a great charter experience is truly the reward of a superior sailing education.

In those early days of chartering a boat you needed to prove your competency and have the money to pay for the boat; these days things have changed. You still need a credit card to sail away on a million dollar yacht but to some extent you have to show you know a bit more about sailing. In Europe, the International Proficiency Certificate (IPC) allows you to charter a boat and in the Caribbean Charter Boat Companies utilize your ASA certifications and logbook as proof of your ability to safely operate a charter boat.

Today bareboat chartering is the culmination of your sailing education. When you walk across the deck and get your sailing diploma you step on to the metaphorical boat of your future and you can sail it anywhere you want! That is the goal, to set you off confidently on your own. We know we have done our job when you are in a breathtaking anchorage with your feet up enjoying the sunset.

Our goal is simply to get you sailing, safely and confidently in all conditions.

How Do You Get Started?

You have taken a sailing course now what?

Ask yourself a few questions to make sure that you are ready to go out on your own. Keep your answers in mind as you read through our suggestions and tips for embarking on your first charter.

Are you qualified to sail a boat in unfamiliar waters?

  • Does a course alone qualify you to charter a boat?

How is your sailing resume?

  • Have you logged enough hours to give yourself the confidence you need?

Can your ego handle it?

  • Would it hurt to sail with a captain for a day or two?

Don’t answer just yet. Keep your answers in mind as you go through our tips for a first time sailing charter vacation.

First Charter Tips and Suggestions

Setting off on a sailing Charter Vacation is not unlike planning any other vacation except for the little detail of where your accommodations will be. With a sailing charter vacation, your hotel is your boat so you have to factor in the sailing conditions within your planning.

If this is your first charter vacation there is a good chance you’ll want predictable wind, easy navigation and a destination that is charter-friendly. With that in mind, the British Virgin Islands are as an ideal location as you can get. Essentially, the BVI are a giant pond surrounded by lovely islands full of onshore diversions and excursions.

Navigation in the British Virgin Islands is virtually line of sight. You see where you want to go and you find the heading to get you there.

Why BVI?

  • Year round warm weather and warm water
  • Caribbean Culture
  • Predictable wind
  • Plenty of resources from other sailors to charter company bases

Other destinations in the Caribbean: St. Martin, Grenadines,  Bahamas

Looking for something more from your first charter vacation?

However, if you want to head off the beaten path you can find plenty of charter destinations that can cater to the first time charter vacation sailor.

A few questions to consider when deciding on the right destination for your first-time charter vacation.

What type of sailing do you want to do?

What onshore excursions and distractions are you hoping for?

Looking for a rustic beach bar in the tropics or a fine dining experience in St. Tropez?

A Few More Options For Your First-time Charter Vacation

Why the Mediterranean? The allure of European culture has long been the draw to chartering  a boat in Europe with a historical component as well as a multitude of onshore attractions. You’ll need an International Proficiency Certificate if you plan to charter a bareboat in Europe.  Also, familiarize yourself with the med moor as it is quite common in European ports.

Take a Look at a Few More Ideas for Your Sailing Destination


Who Are You Sailing With?

You will be spending a week with friends and family in a small space with very little privacy; choose your companions well.

When selecting a crew you will need at least another person who can handle the boat and the various duties required. As captain, you’ll need a first mate and deckhands.

Questions to consider:

  • Do you have someone with sailing experience as part of your crew?
  • Do you have someone who will plan your proposed itinerary with you?
  • Are you willing to spend a week with these people in close quarters?

Types of Questions to Ask Your Potential Crew:

  • Do you get seasick?
  • What is your sailing experience?
  • Can you swim?
  • Do you have a passport?
  • How much are you willing to spend?
  • Do you need a rigid itinerary or are you flexible?
  • How much do you drink? Light, heavy or medium alcohol use.
  • Are you an early riser or night owl?
  • Do you have any dietary restrictions?

What Type of Charter?

What type of charter is the next question to ponder. Do you head out alone on a bareboat charter or do you sit back and enjoy the ride on a crewed boat?


This type of charter gets you a captain and possibly some crew. You could even have a personal chef if you so choose.  Be prepared to give up a berth for the captain and crew.

Pro: You get to go on a sail vacation without having to stress about much. The captain will set the course and you will be along for the ride. You are paying for an experience and you can be sure that with the proper communication you will have a great sail. You’ll get to sail as much or as little as you’d like.  With the right captain and crew you can get anything you want. Also, the size of the boat matters here as you will be sharing living space with the crew.

Con: Someone else is calling the shots so you might not get that extra few hours at the beach bar or be able to spontaneously change the itinerary. You get what you pay for so prepare to pay more for what you really want.

Captain for a Few Days

The idea behind having someone come aboard for the beginning of your charter is to help you gain confidence with the boat, the destination and to give you a good idea of what is to occur during the portion of the charter where you take over.  This is a good idea if you are just getting your feet wet driving a twin screw catamaran or in a destination that has so many options that local knowledge is extremely helpful.


When you embark on a bareboat charter you are on your own. While the charter company might help you with some maps, tips, and emergency support, you are basically on your own to set your itinerary and your provisions. You essentially rent the boat and agree to bring it back by a set date. No crew, no schedule, no timetable other than a start and end date.

This option saves you the most money and affords you the most amount of flexibility. You are responsible and in charge of everything. If you feel like you have the training and confidence this could be the best way to experience your first sailing charter vacation.

Take a look at a few tips on planning that first sailing vacation.


Choosing a Charter Company

These are the questions to consider when looking for the company that will rent you a boat for your first sailing charter vacation.

  • How do you find a charter company that is right for you?
  • Charter company operates in your chosen cruising grounds
  • How much do you want to spend?
  • What type of boats are in their fleet? Catamaran or monohull? Small or large?

When you took your first ASA 101 course this is the moment you were dreaming of. The sailing vacation where you are the captain and the entire family is your crew. You could see it happening as you first picked up your Sailing Made Easy textbook. When you took ASA 103 it became all too clear that no matter what happened for the rest of your life, your excursion would not be complete until you chartered your own boat. After ASA 104 all the confidence you had gained led you to this moment when you began your search for a charter boat.

Well, it’s time for you to set off on your own and explore endless shorelines and secluded coves. You have mapped out your plan and you have reserved your vacation time now all you need is a boat.

How do you choose a charter company to rent a boat for a week?
Before you start your research for a company pick up a  Cruising World Magazine and look at their charter company advertisements. They also have an online directory: see it here

First Question: How much do you want to spend?

What kind of vacation do you want? Is this a luxury cruise or a budget sailing adventure? Charter companies offer varying amenities from 5-Star,  First Class crewed to barebones bare boats.

If you decide on deluxe, you should probably consider one of the large, full-service companies. Look at what “extras” are offered—some base locations, for instance, are mini-resorts unto themselves. Some have full-service hotels at the base, with a pool, grocery/liquor stores, and shops. Decide how important these before-and-after-charter amenities are to you. If your budget is limited to one of the lesser expensive companies, you’ll likely still have a grand time, but it’s important to alter your expectations accordingly.

One way to know what you can expect is to look at the age of a company’s fleet at the base where you intend to charter.

Chartering Rule: Older boats are usually less expensive.

However, many companies offer impeccably maintained boats that are 5 years old or more. Older boats that are well taken care of can provide an excellent charter experience, but go into the charter knowing what you’re getting so you won’t be disappointed on arrival.

Charter Company Examples:


Moorings have been in business for over 50 years and they boast 20+ destinations to charter a monohull or catamaran. Their operation handles everything down to the airport transfers if you need them. They are a one-stop travel agent for would-be charter customers.

Where They Sail

You’ll find Moorings charter bases in the Caribbean, Mediterranean, Tahiti, Tonga, Thailand, and Seychelles.

How Big Is Their Fleet

400+ Yachts. Their fleet is seemingly endless with options that vary from their “Exclusive Plus” boats that are less than a year old to “Club” boats that are 3+ years of age up to 10 years old.  All of the yachts are maintained to high standards and briefings from Moorings staff prior to your sail are thorough and designed to make you as comfortable as possible with your boat.

Horizon Yacht

Where They Sail

Grenada, British Virgin Islands, St. Vincent

How Big Is Their Fleet

Their fleet is made up of both monohulls and catamarans with a majority being late models and some in the range of 3 to 6 years old. Their fleet varies in age.

Choosing a Boat

Choosing the right boat for your sailing charter can be simple as you really only need to think about four basic questions :

  • How many people?
  • How big of a boat?  – Does size matter?
  • What type of boat?  Monohull or Catamaran
  • How much do you want to spend?  – Luxury or budget?

Take a look at some suggestions for choosing a boat for your first sailing charter

How Many People Will You Sail With?

If you decide to take a quaint sailing vacation with just you and your significant other you might find that a small monohull is more than adequate for your sailing vacation. If your crew consists of children, mother-in-laws and sailing newbies you may want to consider a large catamaran that boasts space enough for everyone’s needs and personalities.

When you are taking more than your immediate family ask questions about the number of berths and the number of heads. Also, is your group the type that will need more or less privacy? Will kids share a berth or sleep in the salon? Spending a week on the boat? The need for space and privacy will be magnified if the group does not normally live in the same household.

How big of a boat?   Does size matter?

The bigger the boat the more hands you will need to be active crew. Even though charter boats have all the required bells and whistles that make sailing easier, if a boat is much larger there will be a need for more experienced and willing crew members. You can expect most boats over 36 feet to have twin steering stations that allow for easy passage from the cockpit to a swim platform carved into the transom. Most handling will be done from the cockpit.

If this is your first charter consider a smaller boat and fewer people so that you have less crew with which to deal.

There are a few things to remember when dealing with the size of a boat. A larger and therefore heavier boat requires more skill to maneuver and takes practice. The crew will be required to work with larger anchors and dock lines and that requires more muscle power.

What type of boat?  Monohull or Catamaran

The choice is between a monohull and a catamaran. Simply put it is between the roomier accommodations and increased privacy of a catamaran and the generally smaller layout of a monohull. Two boats of the same length will vary significantly on the beam and will sail vastly differently.

Does your crew enjoy the feeling of heeling and cutting through the swells or is a condominium on the water what your group is going for? With two boats of the same 43-foot length, a catamaran will provide more generous living space – with four cabins, each with its own head – than a monohull. However, it is also a bigger boat to maneuver under power and sail.

  • How much do you want to spend?   Luxury or budget?

Cost is a factor in how you choose your boat for a sailing vacation. Catamarans on average will be more expensive relative to your sailing location. Size, quality, features, and amenities all play a role, as do location and season. Establish upfront how your group will share the charter and incidental expenses.

Things to Know

These are some of the details that you may want to be familiar with. If you are on a bareboat you’ll need more knowledge than if you are on a crewed charter.

  • Docking
  • Anchoring – Operating a windlass – bridle use and placement
  • Picking up a mooring ball
  • Handling a Bigger Boat
  • Roller furling mainsail
  • Understanding Lazy Jacks
  • Electric Winches
  • Generators
  • Dinghy Operation
  • The Watermaker
  • Can you discharge? Where do the pipes empty?
  • Battery power management

What to Bring


Consider the climate and personal preference but try to remember that you will be on a boat and oftentimes space is limited so if you feel like you really will not wear 6 pairs of shoes, you might want to leave the extras at home. Also, ask if there is a washing machine on board. If you are on a large boat you’ll be surprised as to what will be tucked away on board.  Will you be going out to a fancy dinner? What type of clothes will you need for that?

Suggested packing list:

  • 3 pairs of shorts
  • 2 swimsuits one wet one dry
  • 1 pair of long pants
  • 1 windbreaker
  • 3 t-shirts because you will inevitably buy 3 more
  • 2 buttoned up evening shirts (short sleeve)
  • 1 pair of flip flops
  • 1 pair of deck shoes
  • 1 pair of walking shoes
  • 1 cover up
  • 1 summer dress
  • 1 light sweater
  • 1 hat
  • underwear at your discretion


Plenty of boats will come with a welcome kit

  • Enough for the first few days but you can buy most things when you arrive.
  • Books
  • Charging devices
  • Sunglasses
  • Sunscreen (it’s cheaper at home than on vacation)


  • Is your camera on your phone all you need?
  • Do you need a waterproof camera like a GoPro for action shots?
  • Do you need high-quality video of your charter?

Diving Equipment

Should you rent your gear if you are only doing a couple of dives or is this a dive vacation?

Does the charter company provide snorkel equipment? If you are diving you could rent your gear at your destination so it is probably best to travel with your dive computer and mask, especially if it is prescription. When you factor in the cost of checking in your gear at the airport it may be more cost-effective to rent.

Water Toys

Charter companies will have plenty of options when it comes to kayaks, stand up paddleboards, snorkel equipment, etc. Leave them at home and let the charter company supply them.


Most charter companies supply towels for the boat but some do not supply beach towels. Once again this is all dependent on the size of the boat and the type of charter. If you spend more on your charter there is a good chance that everything is on the boat but if you go with a barebones company you may have to pack your own beach necessities.


Check with the charter company to make sure that they provide pillows, blankets, etc. (small independent charter companies might not provide these essentials)


Bring your own meds (keep in your carry-on, not in your checked luggage).  Also, ask the charter company if there is a pharmacy near the charter base?


Charter companies often include a starter pack for the boat. An example such as this might be found on your boat. Of course, this all depends on the type of boat and company you decide to charter with.

Example Starter Pack:

The pack includes: 1 bottle of rum, 2 limes, sugar, 1 pack of 6 Coke cans, 1 gallon water, 1 small bottle of dishwashing liquid, 1 dish cloth/sponge, garbage bags,1 roll of paper towels, 1 box of matches, 1 roll of toilet paper in each head.

Before You Go:

Are there items from home that you should take to your destination?

  • Snack items travel well, meats do not.
  • Most boats will have all the equipment for cooking meals but they might not have specialty items that you are familiar with. Coffee maker, yes, coffee grinder, no. Chef’s knife, yes, paring knife, no. Blender, maybe, food processor, no. You are still on a boat. It is best to ask your charter company about what to expect on the specific boat you will be on.
  • While most charter boats have freezers it is possible that the boat that you charter may not have a freezer/refrigerator combination that will accommodate all of your food for a week.  Ask about ice chests and the availability of ice.
  • You will need space for local foods. Conch, lobster, rockfish, etc.
  • Water. Water becomes very valuable on a boat so it is important to understand the limitations of its use. This is a valuable commodity so ask these questions of the charter company: Does the boat have a watermaker? Can you return to the base for water? Are there convenient locations to get water?

While the charter company can shop for your food for a week plan on eating on shore a few times..


Do opt for the damage waiver as you do not want to be saddled with a bill because something went wrong. The cost of the damage waiver is minimal compared to the potential bill when a nearby boat drifts into your bow while at anchor.

Trip Insurance, should you buy it? There are a lot of moving parts when deciding on a boat vacation so consider insurance that allows you to cancel in the case of bad weather or sickness.

DAN Boater – Evacuation insurance? If you are an ASA Member you get a great deal on evacuation insurance. While no one wants to be evacuated you also don’t want the bill if you need to be evacuated.

Tipping the Crew and Captain

Yes, if you are on a chartered boat with a crew you will be tipping the crew for their service. 15 to 20 percent of the cost of the charter is customary but it really depends on how well you think they took care of your needs.