Matt and Britney Weidert

Matt Weidert

Bareboat Charter Guide for Beginners: First Sailing Vacation

Photo: anchored in front of the Soggy Dollar Bar at White Bay, Jost Van Dyke on one of our recent trips.

Why go on a bareboat yacht charter trip?

To me, there is no better vacation than a bareboat charter on your own sailing yacht. It has everything I'm looking for - sailing, saltwater, unbelievable surroundings, a new adventure each day, deep sea fishing, good food, fun with friends/family, and epic sunsets.

It's not for everyone, but if this appeals to you, once you try it you will never want to go back to your old vacation ways. As soon as we finish a bareboat charter trip, I'm already starting to think about the next one.

Forget those touristy excursions. Get away from the crowds and access amazing places other people can't reach. Learn to sail, understand what it takes to go on yacht charter trip, and create your own memories and adventures to last a lifetime. If you haven't been before, it's not as hard as it may seem.

Look forward to other sailing destinations such as the British Virgin Islands, Exumas Bahamas, Spanish Virgin Islands, Dry Tortugas, Greece, and French Polynesia.

In this bareboat charter guide for beginners, I'm going to tell you everything you need to know to give you the confidence to start planning your first trip. Let's get started, there is not a moment to lose!
On our bareboat charter yacht in Anegada, BVI back in 2018

Four ways to go on a yacht charter trip

A bareboat charter isn't the only way to go on a yacht sailing vacation.

Bareboat charter

This is what my article focuses on - you serve as the captain, supply the crew, make provisioning arrangements, and decide where you want to go. The charter company will qualify your sailing experience to make sure you have a safe and fun trip.

Crewed charter

This is a great option if you want to decide if these types of trips are for you. You choose a yacht that comes with a dedicated captain and chef/hostess.

It's the "all-inclusive" option. They will cook gourmet meals for you, mix you drinks, and tailor a sailing itinerary to your preferences. The yachts usually come with a wide variety of water toys.

Keep in mind, as you might expect, this is the most expensive option.
At the helm of a Bali 5.4 in the Exuma Bahamas

Captained charter

You book this type of trip with one of the charter companies, and they help to provide you with a skipper. Choose also to add on a chef.

While this sounds similar to a crewed charter, you don't know exactly who will be assigned to your trip. The experience you have will be less predictable and the customer service is perhaps not quite as top notch.

By the cabin charter

This type of shared charter let's you book one or two cabins. You'll have strangers aboard that you share the charter trip with. It may be offered by the charter companies or by one of the many crewed options available.

What is a bareboat charter?

A bareboat charter simply means that you rent a boat from a charter company for a defined period of time. Most importantly, the arrangement does not come with a captain, crew, or provisions - it is up to you to provide those things.

On your charter, you have the freedom to do whatever you'd like (within reason or course) during your trip - sailing, snorkeling, fishing, etc. These are more of my favorite boat trip activities.
Lunch snorkel spot in the Exumas on our 2021 yacht charter trip

Skills that you need for a bareboat charter

You do not need to be sailing certified to charter a sailboat. If you have substantial sailing experience on similarly sized yachts, you can provide a sailing resume to qualify with the various charter companies.

We'd recommend going to sailing school and getting certified anyway. We took three courses through the American Sailing Association:

ASA 101: Basic Keelboat Sailing - This is the introductory course for sailing. We had no sailing experience and wanted to learn when we were living in San Diego.  We also joined a local sailing club to practice our skills once or twice a month in San Diego Bay. The course is two days and usually completed over a weekend.
ASA 103: Basic Coastal Cruising - Builds on the basics you learned in 101 and further develops your seamanship.
ASA 104: Bareboat Cruising - Teaches you more about a boat's systems and other skills such as anchoring, docking, provisioning, and advanced sail trim.
It's worth nothing that ASA 103 and 104 are often offered as a combo course. We suggest taking 101, getting some practice in, and then if you decide sailing is for you, go take the 103/104 combo course. The 103/104 combo can also be done over a weekend.

If you have some sailing experience and just want the resource, you can purchase ASA's book for the bareboat course.

The SmarterCharter book is also a great practical guide for skills specific to bareboating. There is also a monohull version.
Easy downwind sailing in 10 knots


Do you need to know how to sail? No! You can always hire a skipper or take a crewed charter for your first time if you want to test the waters first with this type of trip. The skipper can take you places that you might not have the confidence to go as a beginner.

Another option is to charter a motor yacht. Marine Max specializes in power catamarans.

You do not need to sail the whole time. One trip we had very light winds on several days, so we just motored. You will have plenty of fuel, even if you motor the majority of the time. You shouldn't need to worry about stopping at a marina to refuel.

Anchoring and mooring

Do you need to know how to anchor? Yes! This is a skill that you should be comfortable with. Even if you only plan to tie off to mooring balls, consider a situation where all of the mooring balls are taken. In this case you may be forced to anchor.

We'd recommend picking a first destination such as the BVI where you can pick up a mooring ball at most popular anchorages. Familiarize yourself with how to reserve Boaty Ball moorings in the BVI, if necessary. This will keep the stress down for your first trip - you shouldn't need to anchor overnight. Practice anchoring at a day lunch stop, such as Sandy Spit near Little Jost Van Dyke in the BVI.

On our first trip we did just this - we used mooring balls. Now that we have plenty of experience, we seek out secluded anchorages and enjoy anchoring overnight.

This video from Sailing La Vagabonde provides a good overview about how mooring balls work.
Getting ready to deal with an isolated squall in the Florida Keys


For a complete guide to BVI weather and marine forecasting, check out my post here.

Plan to take your first trip during periods when settled weather can be expected. For the Bahamas and the Caribbean this means April-May and late November. Tropical systems are unlikely. The trade winds blow consistently out of the east at 10-15 knots - perfect conditions to practice your seamanship.

Plan to monitor weather conditions for the week leading up to your trip. This will help you to notice patterns that could affect your trip. Marine weather forecasts are available online from resources such as the National Weather Service. Your charter company will provide more detail on how to monitor weather during your charter.

If sailing in the Virgin Islands, know if a ground swell is forecasted. They are common between November and April. Make sure you are check the forecast since it could have an impact on your itinerary. Any anchorage exposed to the north will be unusable if a ground swell is running. The NWS Marine Forecast will include information about ground swells. They are very well forecasted.

You should also be familiar with how local conditions such as tides and island geography can affect your boat - such as being backwinded (this is more important if you plan to anchor).


ASA 104 should prepare you well to manage the boats systems. The most important part is making sure you are monitoring fuel, water, and battery levels. Ask lots of questions during your boat briefing and make sure you are comfortable working the electrical system by yourself. For example, they will explain how to charge the batteries and turn on the AC system.


You'll want to understand how to read the water color, read charts, and plan a route. Pick a destination like BVI that has easy point and shoot navigation.


Docking can be stressful and intimidating. You can read all about it, but unfortunately the only way you get better is by practicing.

Here's the solution - for your first trip, request assistance from the charter company when leaving the marina. They can help with the dock lines and also pilot the boat out for you. Use them! It will keep the stress down. At the end of the trip, reach them on the radio and they will send someone out in a dinghy to pilot the sailboat back in.

Practice docking on your own terms under ideal conditions.
Aboard a 33 foot monohull in North Sound, BVI - the trip that started it all for the Yacht Warriors

What to consider when choosing a yacht charter boat

On our first boat trip, the one that started it all, we went out on a 37 foot, 2 cabin monohull. Every trip we've taken since has been on a ~45 foot 4 cabin, 4 head catamaran.

But, pick what you like! There is no right answer here. A couple things to consider:

Catamaran vs. Monohull

This can be a fiercely debated topic amongst seasoned sailors. For a sailing vacation, I believe a catamaran is the way to go. I write about it in more detail here. And if you want a complete review of a catamaran with lots of pictures, check out my thoughts on the Bali 5.4.

We enjoy having more space, a salon above the waterline, and the stability two hulls provide. I also find that I can maneuver a catamaran more easily because it has twin engines.

We also tend to go vacation with a crew of 8, and this works well with the space cats provide.

As far as sailing performance goes, monohulls tend to sail closer to the wind and can be faster than the catamarans that you'll find in bareboat fleets. They will also keel over, which some people enjoy.


After you've picked a type of boat, I recommend that you choose the newest one that you can afford. Older yachts tend to have a greater chance of a breakdown. Your charter company will do their best to fix any issue, but it can definitely disrupt your plans (speaking from experience here!).

Spending a bit more on a newer sailboat is a good insurance policy.


Sometimes it will just come down to what's available. Don't sweat it. We've sailed on Lagoons, Leopards, and Balis. You'll have a great time on any of them.

One feature we love is a fly bridge - essentially a common area up top that includes the helm station where everyone can hang out while cruising. We find that this is more fun than a separate area where the skipper operates the boat.
Plenty of room for the whole crew on this Bali catamaran

Charter Company

We've used many different charter companies over the years. In the British Virgin Islands, you have many to choose from. In other sailing destinations, you may only have one or two options.

Each of them has different bases or marinas they operate from - some will have specific amenities that might appeal to you.

Reputation for quickly addressing any maintenance issues should also factor into your decision.

This is a complete list of the bareboat charter companies that we have relationships with, including destinations they operate.
Lady crew members lined up with painkillers at the Soggy Dollar Bar in BVI.

Picking your crew

Picking your crew members may be the most important decision of your entire trip. Who you decide to take with you matters. We have lots of friends, but we wouldn't want to spend 8 days on a boat with all of them (no offense friends!).

Choose wisely. Will they get along? Are they flexible if plans change? Would they be OK skipping a shower if the water runs low? Are they willing to help out (with cooking, cleaning, etc)?

How long should I plan the yacht charter trip for? 

We like to do trips that include 8 nights on the boat. The first night is usually a later check in and spent overnight in the marina after a day of travel. That makes for 7 full days of exploring and adventure on your sailing charter.

You can also consider staying in a hotel for your first night, but we like to stow away provisions and get familiar with the boat. It also allows for an earlier departure on your first full day - don't waste valuable cruising time in the marina! 


Most charter companies can provide a provisioning service. Coordinate with your crew for meal planning and make your selections. The food and beverages will be aboard your sailboat when you arrive, what joy!

Check out our post on how to get the crew organized to help with provisioning planning.

You can also do the shopping yourself depending on the destination - Key West and the Spanish Virgin Islands are good candidates.

For a first time bareboat charter, keep it easy and let one of the provisioning services handle it for you.

We always plan for big breakfasts - eggs, bacon, and hash browns. Start your day right!

Lunches we keep simple since we are usually on the move or exploring ashore - sandwiches and chips work great.

For dinners, consider how many meals you'll plan to eat ashore at beach restaurants. The other nights, simple is always better. Pasta, burgers, and tacos are some of our staples. Spend less time in the galley and more time soaking up that Caribbean sunset.

We also recently started preparing meals ahead of time, freezing them, and taking them with us. Read about my other top 10 bareboat charter travel hacks to help you have more fun and lessen the stress.
One of the marina bases that you might visit - this at Palm Cay, the gateway to the Exumas

What is the check-in and check-out process like? 


You will typically board your boat in the evening. Get comfortable, and in the morning, a representative from the charter company will meet you for the boat briefing. Here's what they'll cover - I talk more about what to expect for the boat briefing on this post. If you sign up for my free newsletter, I'll send you a pdf version of my Boat Briefing Checklist that you can print and take with you on your first trip.

  • Cruising grounds - they can give you advice on where to go and what areas may be off limits. 
  • Boat systems and operation - you'll do an inventory and cover all you need to know about the sailboat's systems and sailing equipment. Have a list of questions prepared in case they miss something.
  • Safety - such as where the life jackets, life raft, plugs, and emergency tiller are located. You should also cover radio procedures if you need a refresher.
  • Communications - how to get in touch with the charter company if you have a repair issue or what to do when you are ready to return to the marina.


Check out is usually mid morning on your last day. You can either return to the marina the night before, or stay in an anchorage nearby.

Sometimes they ask you to visit the fuel dock, but you can also pay the charter company to handle this service for you. They might do another inventory with you, but usually you just need to disclose if anything is broken or missing.
Spanish Virgin Islands' sunset on the west coast of Culebra

What does a bareboat charter cost?

Expect to pay anywhere from $5,000 to $20,000 for most bareboat charter trips. So what inflluences the pricing?
  • Type of yacht: monohulls are going to be more affordable than catamarans (all else equal)
  • Size of yacht: not surprisingly, the longer and bigger the boat, the more expensive it will be
  • Number of cabins: a 3-cabin catamaran with an owner’s cabin is going to be more affordable than a 4-cabin equivalent
  • Age: you’ll pay a premium for newer boats (but also might experience fewer maintenance issues)
  • Season: when you charter matters a lot. The high season holiday periods are always the most expensive, whereas, you can find great deals (and solitude) in the low season when tropical disturbances might threaten in the Caribbean
  • Discounts: charter companies offer various promotions, but you can usually expect to receive an early booking or a repeat charter discount (5 or 10% each). Last-minute discounts are another great way to save money if you are flexible (or work from home!)
Read more about bareboat charter pricing, the components of your quote, and what things you will need to budget for separately.

Popular snorkel spot: The Indians in the BVIs

Charter destination for your first trip: British Virgin Islands

There is no better sailing trip for beginners than the British Virgin Islands. Here's why:
  • Idyllic Caribbean surroundings - numerous tropical islands that rise sharply out of the ocean. Plenty of protected anchorages. Coconut palm lined white sandy beaches. Great snorkeling and fishing. What else do you need?
  • Settled weather - you can expect steady trade winds out of the east year round. If you avoid the summer months when tropical systems can develop, there is little risk of a major weather disruption.
  • Easy navigation - there are few navigational hazards and you can usually see the islands you are navigating towards.
  • Mooring balls - there are plenty of well maintained balls available, making it easier for beginners.
  • Well established bareboat yacht charter industry - lots of operators, a deep bareboat charter fleet, plenty of restauraunts that serve boaters, and many services to help make your trip easy.
If you have a cruising ground close to home that offers some of these same features, that could be a great option too!
North Sound in Virgin Gorda, BVI

First time BVI bareboat charter sailing itinerary

We've visited the BVIs five times now, and every time our itinerary gets a little bit better. Here's what I would do on a first time visit. (update - here's a more in depth post about a first time BVI sailing itinerary).

Check out my most recent story about our BVI bareboat charter here. You can also visit this link to see my other articles I've written about the British Virgin Islands. The FAQ section also address many common questions.

My sailing plan also assumes you take the sleep aboard option on your first day.

When is your next yacht charter?
Consider booking with the Yacht Warriors.

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