Boat Briefing Waypoints Yacht Charters


Choose a Category to Easily Find the Answers to Your Charter Questions:

Bareboat Versus Captained Charter

Am I Qualified to Charter a Yacht With Waypoints?

A license or certification is not required to captain a boat; however, you need to have recent experience captaining a vessel of similar size and type to the one you want to charter. Depending on your experience, it may require you to take a Checkout Captain for one or more days or even through the entire charter.

Some essential elements that help determine your competency to handle the boat you would like to charter are:

  • Recent Boating Experience How frequently have you sailed in the last five years? 
  • Boat Familiarity Are the sizes and types of boats you have sailed on in the past similar to the boat you wish to charter? 
  • History of Boat Ownership Have you owned a boat? An understanding of the systems and the inner workings of a boat is essential to happy cruising.
  • Cruising Experience Have you planned a trip from point A to point B requiring navigation skills, decision making, anchoring, mooring, or docking under sail and power?
  • Ocean Experience Have you sailed on the ocean or other large bodies of water such as the Long Island Sound, the Chesapeake Bay, San Francisco Bay, the Great Lakes, and so forth?
  • Twin Screw Vessels Are you experienced in the operation of twin screw vessels? It is a requirement to charter a powerboat and a relevant requirement for a sailing catamaran. A boat with stern drives (inboard outboards) is not considered a twin screw vessel. If you do not have any twin screw experience, plan on spending at least a half day getting up to speed in this area before we let you leave the harbor.
  • Crew Experience Will the crew that is with you actively participate in sailing the vessel? If you are on a large cat or a power yacht, you will need at least one to two good crew members to assist you.
  • Professional Training Have you had any professional or formal training? Have you cruised in the area before?
  • Bareboat Certification A Bareboat Certificate is not necessary to charter a bareboat. While a Bareboat Certification course is valuable training, this document alone may not qualify you to charter. Your overall practical experience is what counts.

What is the Cost to Hire a Captain in the BVI?

We can provide a complete list of licensed captains for you to hire. Captains are available for a day’s checkout sail or the entire charter. Their rates are:

$200for a Checkout Captain (client is responsible to get them back to base)

$300 for a Multi-day Captain (rates are per day)

$350 for an Instructional Captain (rates are per day)

Tipping is customary and greatly appreciated.

Tipping Guidelines

  •   Full-time captain / Instructor:  $75 – $125 per day is encouraged
  •  Check-out captain :  $50 – $100

Full-time captains/instructors will need their own cabin on the yacht, and they do not sleep in the bow cabins. You should plan to include meals for your captain/instructor.

Booking a Charter

When is Your Sailing Season?

October 21 – July 31

Can We Start Any Day of the Week?

Absolutely! Our charters start at noon and if you opt to come the night before to “sleep aboard,” you can board as early as 4:00 pm. 

Our base is closed on Christmas Day and New Year’s Day. Therefore, you cannot start, finish, or sleep aboard on any of those days.

Can We Sleep Aboard the Night Before My Charter Begins?

We offer the convenience of sleeping aboard the night before your charter begins for a reduced fee. This is far less expensive than spending your first night in a hotel and allows you to get your boat provisioned, last-minute shopping completed, and a good night’s sleep prior to your first day on the water. Your sleep aboard will start at 5:00 pm.

Do We Need Passports?


What Currency is Used?

The U.S. dollar is the official currency of the U.S. and the British Virgin Islands. Many spots you may visit have become more sophisticated over the years and now take credit cards, but many smaller establishments still use paper money and coins. Please be prepared. 

What is Included on the Yacht?

Your yacht will come with a fully equipped galley, all linens, towels (bath, hand, face, and kitchen) and beach towels. A propane BBQ, bimini, VHF, charts, Cruising Guide, flashlight, safety gear, stereo (most with BlueTooth), cooler, and a dinghy with an outboard.  

What Do I Need to Bring With Me?

Even if you have been to the islands before, it’s easy to forget something. Print out this handy checklist to make sure you have all the basics: 

  • Charter paperwork 
  • Passports – be sure they are signed 
  • Airline Tickets 
  • Cash for incidentals 
  • Sunglasses 
  • Reading glasses 
  • Medication(s) 
  • Sunscreen (multiple bottles) 
  • Aloe Vera Gel (in case you get sunburned) 
  • Mosquito/bug repellent (for no-see-ums on the beach) 
  • Camera 
  • Cell Phone 
  • Cords for your electronic toys 
  • Hats 
  • Flip flops/sandals/ boat shoes
  • Personal Snorkel Gear 
  • T-shirts 
  • Shorts 
  • Swimsuits 
  • Life jackets for children
  • Extra bag for the stuff you will buy in the islands** 
  • Beach towels are provided and available for purchase. If you bring towels, you can leave them on the boat at the end of your trip to be donated to the local animal shelters; this is greatly appreciated!

Note: Most restaurants in the Virgin Islands accept shorts and t-shirts. If you are among the few that pre-plan an elegant dinner out at a high-end restaurant, men should wear long slacks and a collared shirt with boat shoes, and women should wear either a nice dress or an appropriate shirt with a skirt or long slacks and dress sandals. 

Is WiFi Available Onboard the Yacht?

We offer FREE Wi-Fi to our guests while on the docks. While cruising, there is a Wi-Fi plan available for ~ $170 for the week. The client pays for this through the router. Waypoints is not involved with payment for this.  

Can We Rent Water Toys?

Yes, when you make your charter reservation, you can request water toy rentals so they will be ready for you when you arrive. You can also call and place your order anytime before your charter. For a detailed list of available water toys, please contact your personal Charter Experience Specialist.

Blue Water Divers is available for dive equipment and rental of snorkel equipment. They are located in Nanny Cay, a short walk from our base.

Can We Fish From the Boat?

Yes, with a fishing permit. Speak to your Charter Experience Specialist and they can provide you with instructions on acquiring a fishing permit.

Can You Recommend an Itinerary For Me?

Absolutely! Please use the following link to view a sample itinerary. Stay flexible, as the weather can change your itinerary.

If you need suggestions or more details on the itinerary, give us a call, and we would be happy to discuss the options with you.


Where Can I Provision?

You have several options in terms of provisioning for your charter: In-person grocery shopping or provisioning the boat with a grocery store that delivers to our docks on the specified day. Please include your last name and the boat’s name on your order. We will load everything on should it be there before your arrival. Remember to tip your dock staff, as they ensure all your food is put away. 

We have an ice machine at our office. A 10lb bag of ice costs $5.00 per bag. Throughout the islands, you will be able to purchase additional ice. While at Norman Island, Peter Island, and Cooper Island, you will see a small boat selling ice and other assorted goods.  

All yachts are equipped with a Keurig coffee machine. Supplies are limited on the island for the pods. We advise you bring some down in your suitcase with you. There is also a regular filter coffee machine. 

 Grocery Stores 

  • RiteWay Nanny Cay Nanny Cay Marina VG1110 Tortola, British Virgin Islands; +1 284-340-2263. Open 7 days a week from 7:00 am – 7:00 pm: This is a short walk down the dock near Omar’s restaurant. They are good for last-minute purchases and the basics.  
  • RiteWay Provisioning Road Town: Pasea Estate, James Walter Francis Highway, VG1110 Road Town, British Virgin Islands; +1 284-347-1188. You can fill out an online provisioning form from this location which will deliver your items to your boat on the day of arrival. They have a great selection of meats, cheeses, and produce.
  • Bobby’s Supermarket Road Town: Road Town VG 1110 Tortola, British Virgin Islands; +1-954-314-5198. They will also deliver to the yacht. They carry a lot of gluten-free and organic items.
  • One Mart Road Town: Port Purcell, Tortola, British Virgin Islands; +1 284-494-4649. They also have an online provisioning form that can deliver to the yacht.
  • Grape Expectations: Road Reef, Road Town, US Virgin Islands; +1 284-346-9463, This store carries specialty frozen items. They are great for fish, meats , and bread and will deliver. 
  • First Choice Provisioning: Road Town, Tortola, British Virgin Islands; + 1-284-343-6765, Petronella will shop at all major grocery stores to ensure your order is complete. 
  • Steakation Butchers: Waterfront Dr, Road Town, British Virgin IslandsLocated in Road Town. This boutique grocery store offers fresh meat and fish, marinated meats, produce, specialty meat cuts, and more.

Wine and Beer 

  • TICO: Pasea Estates Near RiteWay; 284-494-2211 X323. You can order online or over the phone. 
  • Caribbean Cellars: Lower Estate, Road Town, British Virgin Islands; +1 284-393-4470. You can order online or over the phone. 

Note: TICO and Caribbean Cellars do not deliver on Sundays.  If you need to have it delivered on Sunday, please request a Saturday delivery, and our team will ensure it is secure for your arrival. 

Can I Have My Meals Catered?

From Farm to Yacht. Elite Culinaire is a catering company that can accommodate your dietary requirements. We specialize in creating handcrafted meals that have an excellent taste. From farm to yacht, you may obtain ready-to-eat meals or prepared ready-to-cook meals from the top catering service in its league. For additional information, please contact Elite Culinaire directly at

What Will Be Included When We Board?

We provide the basics aboard the boat to get you started.

In The Galley

  • One sponge 
  • A small bottle of dish soap 
  • One small roll of paper towels 
  • Multiple dishtowels 
  • One garbage bag 

In Each Head 

  • One roll of toilet paper 
  • Two small bars of soap 

Recommendations: Bring a few extra kitchen sponges, including one for each of the heads, a small microfiber towel for the galley, several boxes of different-sized resealable plastic bags, six to eight tall kitchen garbage bags, and aluminum foil. We also recommend a tiny bottle of air freshener for each head. If you have a few headlamps or small flashlights, they are a must-have for riding in the dinghy at night.

Note: If you choose to use the ocean for bathing/shampooing (with fresh water rinse on deck), Prell is the only shampoo that will sud well in salt water. It can only be found at a larger drug store or a shop similar to a Dollar Store. 

Sailing Area / Boundaries

Can We Go to the USVIs?

Yes, however, you must clear in and clear out of the BVI and USVI. For details on this, please contact a Waypoints Team member.

Boat & Equipment

How Much Fuel Will I Use?

It is different for every charter, but here are some general guidelines: 

Sailboats will burn about a half gallon of fuel per hour per engine; don’t forget the second engine if you are chartering a cat. For most sailboats, you will probably run the engines for about 6 hours per day (12 in total for a cat) for propulsion and battery charging. 

If your boat has a generator, you will need to add about three-quarters of a gallon per generator per hour to your total. Most boats with generators return with about 60 hours on the generator – more if you run the generator all day and all night to enjoy the air conditioning. 

Does the Boat Have a BBQ grill?

Please inquire with your Charter Experience Specialist to see if your chosen yacht has a BBQ grill. 

Can We Upgrade to a Larger Dinghy?

Unfortunately not. Every Waypoints yacht is individually owned and comes with a 10′ – 12′ tender and 15hp outboard. I

Can I Use My Hair Dryer on the Boat?

On most yachts – Yes. Most of the Waypoints yachts are equipped with generators that allow for the use of hair dryers; however, please ask during your chart briefing about the rules of power management. Most guests allow the sun and gentle Caribbean breezes to dry their hair naturally! 

Will My Computer/Phone Work on the Boat?

Yes, all Waypoints yachts are equipped with inverters that will allow you to charge your cell phone and laptop but HEY – you’re on vacation – leave the laptop at home! 

Do you Have Children’s Life Jackets and Netting?

No. You should bring properly sized life jackets to fit any children in your crew, as well as netting that can be attached to lifelines. 

Upon Arrival / On Charter 

How Far Away Are You From the Airport? Do You Have a Shuttle Service?

Waypoints BVI is located at Nanny Cay Marina on Tortola. We are situated on the south side of the island about 3 miles west of the capital, Road Town. 

There are two ways to get to the Waypoints BVI charter base: You can choose to fly into St. Thomas to Cyril E. King Airport  (STT), U.S. Virgin Islands, and catch a short ferry or water taxi to the island of Tortola. If coming from the USVI, public ferry services depart from the Charlotte Amalie Harbor (a short 15-minute taxi ride from the airport on St. Thomas). 

You can also fly directly to Tortola (Beef Island, EIS) at Terrance B. Lettsome International Airport BVI and take a taxi to Nanny Cay marina.

Island Time BVI and Chillout Charters, located in Nanny Cay Marina, are the preferred private water taxi providers. They will meet you at the airport and take you to Red Hook to board the private taxi across to our base.

Short flights from Puerto Rico to Tortola are also available. You will need a taxi to get to the marina from Tortola (Beef Island, EIS) at Terrance B. Lettsome International Airport.

What is Your Physical Address?

If you have ordered rental equipment or are coming by car yourselves, our physical address is: 

Waypoints Yacht Charters
Nanny Cay Marina
Roadtown Tortola, BVI

What Facilities Do You Have at the Base?

We have air-conditioned bathrooms and showers with hot water and a swimming pool for our guests. We also offer free Wi-Fi on the dock and are just a short walk to many restaurants in Nanny Cay. 

What Happens When I Arrive at Waypoints?

  • When the taxi drops you off, leave your bags in front of the office (tented area for shade available) and walk right into our reception office. One of our friendly team members will welcome you and help you finalize your paperwork and deposit.
  • You’ll receive pre-departure checkout forms and be directed to your yacht.
  • Before you unpack, you’ll want to go through the yacht to verify that the inventory items on the checklist are all aboard.
  • If you ordered full provisioning, your food will be on board when you arrive – you’re ready to go.
  • If you plan to do some grocery shopping, now is the time to do it. Send crew members off while the captain and first mate get acquainted with your yacht.
  • A team member will go over the yacht’s systems and operation and go through a chart briefing with you. Both the captain and the first mate must attend the briefing! After the briefing, we’ll help you off the dock.

What Time Can I Board the Yacht?

Officially, your charter starts at noon on the first day and finishes at noon on the last day of your charter. If you booked a sleep aboard the night before, you can board the boat at 4:00 pm on that day. 

Will Someone Be in the Office After 5:00 p.m.?

No, we all head home at 5:00 pm. About one week before you arrive, call our office to receive information regarding the name and location of your yacht.  If you choose to sleep aboard the night before, the yacht will be left open for you in a well-lit area. Make yourself at home. The following morning, check in with one of our staff members wearing a navy Waypoints shirt. Our contact details will be listed in the boat folder on board should you need after-hours assistance

What Time and How Long Are Briefings?

You will need to do a full briefing at the start of your charter which should take about 1 ½ to 2 hours, depending on how many questions are asked.  

How Long Does it Take to Get Off the Dock?

For the majority of our charters, all pre-departure requirements are typically completed within  60-90 minutes if you and your crew are organized. Please allow 2 hours for those who need a full briefing. Allow extra time if you need to do some grocery shopping. 

Where Can I Expect to Get Off the Docks on the First Day?

If you leave before noon (sleep aboard option), you can start sailing to Norman Island and try snorkeling the Indians or the Caves. You can also go to Pirates Bight, which has access to pristine beaches and a family-oriented beach bar. When you’re ready to settle in for the evening, head to the infamous Willy-T to enjoy the sunset!

Can I Sail After Dark?

No. You should be securely anchored on a mooring buoy or docked by 5:00 pm. Our Insurance will not allow our guests to cruise between sundown and sunrise. Get to your anchorage early to enjoy the sunset with a beverage and have a refreshing swim before dinner. 

What Happens if the Boat Breaks Down?

It is highly unlikely that your boat will break down. However, If you have mechanical trouble, just call the service number that you were given during your briefing. If we can’t talk through a solution to the problem by phone, we’ll make arrangements for you to receive help at a nearby repair center, or for a reputable repair person to come to the boat.

What Do We Do if a Hurricane is Approaching?

All prudent mariners should listen to the marine weather daily. There is a page in the vessel operations or general info manual that lists numerous broadcast radio weather sources. In the unlikely event that a hurricane or tropical storm is in the forecast, please contact us for instructions. If it appears that we will experience a severe weather event, we will instruct you where to leave the boat and where to seek shelter. 

What Happens at the End of My Charter?

  • Allow enough time to refuel the yacht as explained in your pre-departure briefing. Call us on either Channel 16 or on the contact number provided as you approach the fuel dock. A Waypoints team member will meet you at the fuel dock and after fueling, help bring you into your slip on our dock.
  • We will meet you at your boat with the post-charter paperwork to conduct a debriefing and a dive check. While the crew is packing, we will go through the checklist to make sure the boat and all equipment is in order.
  • We will return the paperwork to the office along with the fuel receipt. If everything is in order and there is no damage to the boat or dinghy, your deposit will usually be refunded within 48 hours.

How Do I Get My Deposit Back?

If everything is in order and there is no damage to the boat or dinghy, your deposit will usually be refunded on the spot.

Booking Process / Costs

When is the Best Time to Book My Charter?

We recommend booking as far in advance as possible. That way you can choose the boat and the exact dates for your charter vacation, especially if your dates aren’t flexible. December through April book well in advance as they are our busiest times of the year. 

What is a DRA or Damage Reduction Agreement?

This is a fee that Waypoints collects per day for your charter that will limit your exposure from possible damages or loss while on charter. There is a deductible per incident dependent on the yacht charters. 

What is the Cancellation Policy & Reschedule Insurance Fee?

CANCELLATION POLICY – Payment for the charter is non-refundable once your boat is booked and the deposit has been received. In the case of unavoidable cancellation, any money received by Waypoints will be forfeited.

CANCELLATION FEE – he Cancellation Insurance Fee of $200 will be automatically added to your booking. You have the option to decline this fee prior to making the initial deposit. Once the deposit has been made, this becomes non-refundable. Please read our Cancellation Policy below.

  • If a charter is canceled within 91 or more days of embarkation, a $300.00 administration fee will be deducted from the deposit monies. Alternatively, all funds paid can be held on account and applied to a new charter within 24 months.
  • If the charter is canceled within 90 and prior to 61 days of embarkation, the penalty is 50% of the total charter fee, including the sleep aboard fee. Alternatively, all funds paid can be held on account and applied to a new charter within 24 months. 
  • If the charter is canceled within 60 days to 31 days of embarkation, the full charter fee, including the sleep aboard fee, is forfeited less the cost of additional extras. Alternatively, 50% of the total charter fee can be held on account and applied to a new charter within 24 months.
  • If the charter is canceled within 30 days of embarkation, the full charter fee, including the sleep aboard fee, is forfeited less the cost of additional extras, except for pre-paid Skipper fees. 

Cancellation insurance can only be used once. In the event of cancellation, where Cancellation insurance is used and a charter is rebooked, the new dates are considered non-refundable. Cancellation insurance is not available to purchase for ‘rebooked’ charters.  In the event of a refund, Credit card surcharges, wire transfer fees or any fees occurring through any other method of payment will not be refunded.

The charterer is also advised that Travel Insurance is highly recommended for all travelers to all destinations.

Where Can I Get Travel Insurance?

We advise and highly encourage all charterers to purchase Travel Insurance for all travelers to all destinations. We recommend Travel Guard as a good source for coverage.  

Will I Have to Re-Fuel the Tank Before Returning the Boat?

Your boat will be ready for you with a full tank. After your charter, we require that you refuel the tank completely before returning your vessel. Fuel prices vary depending on the market.

I’m Ready to Book a Boat. What’s Next?

Contact our Sales office at 443-225-4355 x1 and let us know what you want to book. A team member will send you a quote. If you like what you see, there is an option to book it right from the quote.  

What is the Payment Schedule?

Within 7 days of booking, a 50% deposit will be required to secure your charter. Your final payment is due within 60 days prior to the first day of your charter.

What Type of Payment Methods do you Take?

We accept Credit Cards (Visa, Mastercard, American Express, and Discover), ACH, Wire Transfers, and Checks. If paying with a credit card, a surcharge of 3% will be added to the final payment. Check and ACH payments do not include the fee.

Waypoints Wanderers Photo Contest Is Live – Grand Prize is a $500 Gift Card!