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Bareboat Versus Captained Charter

Am I Qualified to Charter a Yacht With Waypoints?

A license or certification is not required for you to captain a boat, however, you need to have recent experience captaining a similar size and type of vessel that you want to charter.  Depending on your experience, it may require you to take a Checkout Captain for 1 or more days, or even through the entire charter.   As part of the Application Process submitted through our Portal, you will describe your experience and a team member will review and respond to your application request within 48 hours.

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

  • 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 boats 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 Long Island Sound, 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 USVI?

We can provide a complete list of available licensed captains for you to hire.  These captains are available for a day’s checkout sail or for the entire charter.  Their rates range from $275 up to $300 per day. Guests must make sure the checkout captain gets back to the base. You should plan to include any meals for your captain/instructor. Tipping is customary and greatly appreciated.  

Tipping Guidelines

  •   Full-time captain / Instructor:  $75 – $125 per day is encouraged
  •  Check-out captain (8 hours):  $50 – $100

Full-time captains/instructors will need their own cabin on the yacht, and they do not sleep in the bow cabins. Once you hire your captain, they will reach out to you directly to discuss plans for the charter.

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 4:00 pm.

Do We Need Passports?

Yes, but…If you are visiting the USVI and not leaving the USVI, standard airline IDs are required. If you are visiting the BVI, every person on board MUST carry a valid passport as proof of citizenship. This includes minor children of any age who are US citizens. Minor children that are not accompanied by both parents have special rules so check with the State Department. You will be stopping at Customs and Immigration in both the BVI and USVI. Make sure all passports are signed and valid. No other IDs are accepted.

This advice is tailored for Americans; if you are visiting from overseas, please check with the State Department for the most current information, including whether or not a VISA is required for the US or the British Virgin Islands.

What Currency is Used?

The U.S. dollar is the official currency of the U.S. and 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.

St. Thomas and Tortola have several banks with ATM machines.  While you will find some access to money machines, it is best to plan ahead and bring money with you! 

What is Included on the Yacht?

Your yacht will come with a fully equipped galley, all linens, and towels (bath, hand, face, and kitchen). A propane BBQ, bimini, VHF, charts, Cruising Guide, flashlight, safety gear, stereo (most with BlueTooth), cooler, and a dinghy with an outboard. We offer snorkel fins (but not masks and snorkels). 

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 WiFi to our guests while on the docks.

Once you leave, we have a limited number of routers available (first come, first served) that can be used while on charter to activate internet service.   Since you are in the US waters, the internet is widely available, and most US carriers work just fine.

Can We Rent Water Toys?

We work with West Indies Windsurfing, a local USVI water toys company to provide water toys to our guests.   They offer a wide range of toys for your charter and offer free delivery to the boat.  Ask your Charter Experience Specialist for more details.

Can We Fish From the Boat?


Can You Recommend an Itinerary for Me?

Absolutely! Please use the following link to view our sample itinerary for the USVI. 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:  either in-person grocery shopping, quasi-online grocery shopping with pickup at the store (by you or taxi), or full provisioning.

Grocery Stores

  • Time Saver VI: They are professional, reliable, and very close to our base.
  • Anna’s Market St Thomas VI:  Fine Food Afloat Online ordering of groceries and liquor for delivery in St Thomas and St John, USVI.
  • VI Provisioning: You order, they shop and they deliver directly to the boat. 
  • Moe’s Market: Less than a 10-minute walk to Moe’s Market on the Waterfront. Moe’s will have everything you need but does not have an overwhelming selection of any one item. You will need to take a taxi back to our base with groceries.
  • Pueblo Supermarket:  This store is about a 15-minute walk from our office. Most people walk there and taxi back with their groceries. Pueblo is a U.S.-style supermarket with all the items you’d expect to find in a major grocery store (although the brands may be different than you have at home.)
  • Cost-U-Less: Similar to a Costco or Sam’s Club. This is better suited for large groups who want to buy things in bulk.

During your charter, you can pick up additional provisions in Cruz Bay, St. John, West End or Road Town on Tortola, or Spanish Town on Virgin Gorda.

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 dish towels
  • 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 microfiber small 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 as well. If you have a few headlamps or small flashlights, they are a must-have for riding in the dinghy at night. In St. Thomas, you will probably want to buy extra rolls of toilet paper, additional rolls of paper towels, and paper napkins.

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 BVI?

After three years of travel restrictions to the British Virgin Islands territories, we are ecstatic to announce that starting in January 2023, many of our USVI boats have been licensed to travel freely between the U.S. Virgin Islands and British Virgin Islands. Please check with your Charter Sales Specialist to confirm eligibility of the boat(s) you plan to charter or are chartering. Some boats may not be eligible to go into the BVI.

What do we need to do to clear in/out of the BVI?

To clear into the BVI you will need to register with SailClear to enter the BVI 24 hours in advance.    

To re-enter the USVI, you will need to download and register using the App CBP ROAM by US Customs and Border Protection APP on your phone.

Entry fees do apply. To include, Customs fees, National Park Fees, Cruising Taxes, and VISAR donations.

Can We Go to the Spanish Virgin Islands?

In order to sail to the Spanish Virgin Islands, we require the following, and a waiver will need to be signed and returned to your Charter Sales Specialist prior to arrival:

  • Second qualified skipper
  • 4 adults
  • Paper charts (purchase online or upon arrival at the base)
  • Suitable weather

Can We Go to St. Croix?

In order to sail to St. Croix, we require the following:

  • A waiver will need to be signed and returned to your Charter Sales Specialist prior to arrival
  • Second qualified skipper
  • 2 adults
  • Paper charts (purchase online or upon arrival at the base)
  • Suitable weather

Note: Traveling to St. Croix with only a 7-night charter can be a challenge. It’s a full day sail there, a full day back, and presumably, you’d want to spend at least a day there. There is so much you would be missing out on in taking the time away from St. Thomas and St. John.  

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.

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.

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.   

Do You Have Snorkel Gear?

Due to COVID-19 we have stopped providing our loaner masks and snorkels. Fins are still available to borrow in adult sizes.

Do You Have SCUBA Equipment and Kayaks for Rent?

We work with several local shops to provide SCUBA and other water sports equipment. You will be able to reserve this equipment during the charter reservation process.  Speak to your Charter Sales team member for a list of available equipment to rent.

Upon Arrival / On Charter

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

This is so cool — we are less than 15 minutes away by taxi! If you choose to pre-order your taxi (done through the Portal), we will make arrangements for a driver to meet you at the baggage claim and bring you straight to the marina where your yacht will be waiting for you.  However, if the driver isn’t there, don’t panic, and don’t even wait.  Just jump in the first available taxi.  Fares run about $12 – $15 per person (depending on group size).

What is Your Physical Address?

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

Waypoints Yacht Charters
3562 Honduras #4
Frenchtown Marina
St. Thomas, VI 00802-5741

What Facilities Do You Have at The Base?

We have air-conditioned bathrooms and showers with hot water.  We also offer free WiFi on the dock and are just a short walk to many restaurants in Frenchtown.  Nearby is Oceana, a lovely waterfront restaurant (reservations required), the French Quarter Bistro, and the Frenchtown Deli known for the best sandwiches on the Island.  Twisted Cork and Sea Le Vie are also great options. We do recommend reservations at all restaurants for groups of 4 or more.

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 staffers 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.
  • Select snorkel gear from our dock box and stow it on board.
  • 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 and give you a chance to briefly sail the yacht with one of our crew aboard so that you can be satisfied everything is in order before you leave the harbor.

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. Note that you need to make arrangements to be at the fuel dock early enough on your last day to return to the marina, dock the boat, debrief the boat and depart by noon. In some instances, depending on flight times, you may need to return to our docks on the last night of your charter. Please let us know ahead of time so that we can plan for your arrival back at the base.

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. Briefing start times vary depending on arrival times and the client’s schedule.

How Long Does It Take to Get Off the Dock?

For the majority of our charters who have the option to do an Online Briefing, you should be able to complete the paperwork, pre-departure checklist, and chart briefing in about 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’ll easily get to one of the anchorages at St John, Christmas Cove, or even Honeymoon Bay. If you leave after 2:00 pm, you can still anchor at Honeymoon Bay on Water Island. Check out our sample cruising itineraries for more information. 

Can I Sail After Dark?

No. You should be securely anchored, or 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 so that you can 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 on a daily basis. 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 the Virgin Islands 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, and then call us on Channel 16 as you leave the fuel dock. A Waypoints team member will dinghy out to meet you to do a post-charter sail check and help you bring the boat into the 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 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?

At the end of your charter, a Waypoints representative will meet you at your boat to conduct a debriefing and a dive check.  If everything is in order and there is no damage to the boat or dinghy, your deposit will usually be refunded within 48 hours.

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 & Insurance?

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 INSURANCE FEE – The 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.

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