Bareboat Yacht Charter Guide for Beginners: How to Take Your First Sailing Vacation

Virgin Gorda Sound sunset with Saba Rock in the background (Pre-Irma)

Photo: spectacular evening in North Sound, BVI on our first bareboat yacht charter trip

Why go on a bareboat charter trip?

To me, there is no better vacation than a bareboat yacht charter. 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 yacht 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 Tahiti.

In this bareboat yacht 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!

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.

These same charter companies, however, can provide you with a skipper and will assist you with provisioning arrangements.

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.

Fowl Cay in the Exumas
Lunch snorkel spot in the Exumas

Skills that you need

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.

Catamaran downwind sailing
Easy downwind sailing in 10 knots

Sailing

Do you need to know how to sail? No! You can always hire a skipper (what is referred to as 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.

Dodging squalls
Getting ready to deal with an isolated squall

Weather 

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).

Systems

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.

Navigation

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

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.

our first sailing trip in virgin gorda sound
Aboard a 37 foot monohull in North Sound, BVI - the trip that started it all for the Yacht Warriors

What to consider when choosing a 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.

Age

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.

Brand

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.

Bali 5.4 in the Exumas
Plenty of room for the whole crew on this Bali catamaran

Charter Company

We’ve used several charter companies including Navtours, the Moorings, Sunsail, and Dream Yacht Charter. We usually focus more on which boat we want and where it is available. The charter company is a less important factor in our decision.

I will say after dealing with many larger operators, customer service leaves much to be desired. I’ve heard much better things about smaller independent operators. They may not have quite the yacht variety, or availability, but there are always tradeoffs.

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.

painkillers at the soggy dollar bar in white bay jost van dyke
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 bareboat 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! 

Provisioning

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 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.

Palm Cay sunset
One of the marina bases that you might use - this one in the Exumas

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

Check-in

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

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.

The Indians, BVI
Popular snorkel spot: The Indians in the BVIs

Charter destination for your first trip: British Virgin Islands

There is no better first time chartering destination 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 British Virgin Islands sailing itinerary

We’ve visited the BVIs four 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).

You can also visit this link to see my other articles I’ve written about the British Virgin Islands. My FAQs will also address the most common questions.

If you want more information about how to navigate to Anegada and what to do there, check out this write up.

Travel day
Day 1: Travel day
Arrive, get settled in, and stow away your provisions. Familiarize yourself with the boats systems if you'd like. Crack a beer - you've made it!
Travel day
Cooper Island Beach Club
Day 2: Cooper Island
Plan for an easy, short sail on your first full day on the water. Cooper Island Beach Club is a perfect stop. Grab a mooring ball and head ashore to enjoy the facilities, bar, and restaurant. Arrive early - the mooring balls fill up quickly! You may also enjoy a snorkel at Cistern Point to the south.
Cooper Island Beach Club
The Baths & North Sound
Day 3: Baths & North Sound
Get an early start and sail up the Sir Francis Drake Channel. Stop for lunch at The Baths, a must see visit. Swim ashore and hike through the monstrous boulders to Devil's Bay.

Round Virgin Gorda and enter North Sound through the well-marked channel. There are many places to choose from including the Bitter End Yacht Club, Saba Rock, and Leverick Bay. Plenty of mooring balls are available.
The Baths & North Sound
Sunset at Setting Point in Anegada
Anegada & Setting Point
Day 4: Anegada
Some will say to avoid Anegada if you are a beginner, but I disagree. The channel is well marked and it is only a couple hours sail offshore. Check with your charter company. Anegada is a low lying, coral island making up part of Horseshoe Reef - the 4th largest barrier reef in the world. Rent a car and visit the spectacular beaches on the north shore. Enjoy a freshly caught spiny lobster dinner at one of the many Setting Point restaurants.
Sunset at Setting Point in Anegada
Anegada & Setting Point
sunset at Cane Garden Bay in the BVIs
Cane Garden Bay
Day 5: Cane Garden Bay
Head back south and sail counter clockwise around Tortola. Monkey Point at Guana Island is a great snorkel lunch stop. Cane Garden Bay is a picturesque spot with lots of room and plenty of mooring balls. This is a great opportunity to head ashore and shop for additional provisions if you need them. There are lots of restaurants to choose from if you want to eat ashore.
sunset at Cane Garden Bay in the BVIs
Cane Garden Bay
Sandy Spit BVI
Sandy Spit
Day 6: Sandy Spit & Great Harbour
Make your way north and try your hand at anchoring near Sandy Spit. This is a fun day spot. Dinghy ashore for a picnic. Great Harbour at Jost Van Dyke is home to the famous Foxy's Bar. Enjoy some late night live music and dancing. Over the weekend, they have a famous Beach BBQ.
Sandy Spit BVI
Sandy Spit
swimming at white bay jost van dyke
White Bay & the Soggy Dollar Bar
Day 7: White Bay & The Soggy Dollar Bar
Get an early start to grab a mooring ball on the east side of the bay. Check with your charter company to make sure it is not off limits. Enjoy a full day of beach bar relaxing and fun. The Soggy Dollar Bar is world famous for its invention - the Pain Killer. If you're a beginner, I don't recommend anchoring at White Bay. Stay at Great Harbour and dinghy over, or walk.
swimming at white bay jost van dyke
White Bay & the Soggy Dollar Bar
The Indians, BVI
The Indians & the Bight
Day 8: The Indians & the Bight
Pass nearby St. John, USVI and head for a lunch stop and snorkel at The Indians. Make a loop around the rock formations and enjoy the abundant sea life. Stay overnight at the Bight and join the party at Willy-Ts, the famous floating pirate ship bar and restaurant. The Pirate's Bight restaurant is also a very good choice for a last night send off.
The Indians, BVI
The Indians & the Bight
Travel Home
Day 9: Travel Home
Leave early enough to motor back to the base to comply with checkout procedures. Radio your charter company on your way back in if you'd like help docking the boat.
Travel Home

Thanks for reading my bareboat yacht charter guide for beginners and making it all the way to the end! If you enjoyed it, please subscribe or check out some of my other articles, like this one about my secret anchorages in the BVIs.

Sailing Songs – The Best Yacht Rock Playlist

I am on an endless quest to create the perfect sailing playlist. These are the tunes that are meant to be jamming when we’re boating:  the sun’s out, the sails are up, and the trolling lines are in the water. 

Our sailing playlist – Yacht Warriors Rock – is the culmination of multiple edits over the last 8 years since we embarked on our first sailboat adventure. It’s not perfect, but we think it’s pretty close and keeps getting better with age.

The name, Yacht Warriors Rock, is a play on the Yacht Rock genre which was coined in 2005. It features primarily soft rock bands from California that produced music in the 1970s and 1980s. 

We honor a few of those artists, but our playlist is intentionally much more diverse in style. You’ll find something for everyone – classic rock, country (mostly Zac Brown Band), reggae, caribbean soca, sea shanties, Jimmy Buffett, Kenny Chesney, and more.

Here are some of the best sailing songs that are included in our playlists below.

  • Rich Girl – Hall & Oates
  • Southern Cross – Crosby, Stills, & Nash
  • Peaceful Easy Feeling – Eagles
  • Africa – TOTO
  • Steve Winwood – Higher Love
  • Running on Empty – Jackson Browne
  • Into the Mystic – Van Morrison
  • Smooth Operator – Sade
  • Come Sail Away – Styx
  • Vahevala – Loggins & Messina
  • Sailing – Christopher Cross
  • Carolina in my Mind – James Taylor
  • Sailing – Rod Stewart
  • Sail Away – David Gray
  • Knee Deep – Zac Brown Band (featuring Jimmy Buffett)
  • Banana Boat – Harry Belafonte 

There are a couple other playlists with links below that you should add to your arsenal. In the morning, we love starting our day on the catamaran with the soft sound of steel drums in the background. In the evening, nothing is more appropriate than eating a meal (hopefully something freshly caught) with Boccherini from Master and Commander: The Far Side of the World.

Dancing to sailing songs in the British Virgin Islands
Getting in that boat trip mood

Yacht Warriors Rock Sailing Songs

Check out the latest version of our hand curated Yacht Warriors Rock selections. Play these sailboat tunes with a cold beverage in hand and no other sound besides the water lapping against the sides of the hull.

Yacht Rock Starter Playlist

If you’d prefer to take a DIY approach with your sailing songs, check out this starter playlist. We pulled together the top 40 songs that should be on anyone’s sailing playlist. If you want to go heavy on the Jimmy Buffett, copy these tunes over in the Spotify desktop app and build the rest out in your own style!

Morning Jams - Summertime Steel Drums

Everyone’s got their own morning routine on the boat – ocean dip, yoga, breakfasting, etc. While everyone gets ready for the day, this Spotify playlist is the perfect background music to energize the crew for another great day on the water.

Dinner Music Playlist - Master and Commander

The film Master and Commander with Russell Crowe is one of my favorite movies of all time, so perhaps I’m biased with my recommendation here. But, you should give it a shot – this Master and Commander inspired playlist is an excellent choice for dinner music while rocking gently and lying at anchor. Close your eyes and you can picture yourself aboard the HMS Surprise listening to a Boccherini duet by the main characters Jack Aubrey and Stephen Maturin.