Annapolis FAQ

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 must have recent experience captaining a vessel of similar size and type to the one you want to charter. Depending on your experience, you may be required 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?

We can provide a complete list of available licensed captains for you to choose from and hire. These captains are available for a day’s checkout sail or for the entire charter. Costs range from $175 up to $350 per day (overnights). ASA Instructors are also available at the rate of $450 per day.
You should plan to include meals for your captain and also include gratuity as it’s customary to tip.

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?

Our sailing season in Annapolis opens on April 1st and closes on October 31st.

Can We Start Any Day of the Week?

Absolutely! Our charters start at 9:00 am, and if you opt to come the night before to “sleep aboard,” you can board as early as 43:00 pm. 

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 it allows you to get your boat provisioned, last-minute shopping completed, and a good night’s sleep before your first day on the water. Your sleep aboard will start at 4:00 pm.

What Currency is Used?

The U.S. dollar is the official currency of the U.S. Most restaurants will accept credit cards as well.

What is Included on the Yacht?

Your yacht will come with a fully equipped galley, all linens, towels (bath, hand, face, and kitchen), a propane BBQ, Bimini, VHF, charts, Cruising Guide, flashlight, safety gear, and stereo (most with Bluetooth). Most boats are not outfitted with a dinghy with an outboard; however, we have a few for rent. Inquire with your Charter Experience Specialist for more details.

What Do I Need to Bring With Me?

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

Plan on packing in a soft, mid-sized bag. This makes it easier to store your suitcase, as yachts typically have less drawer and closet space than you’re likely accustomed to.  

  • Charter paperwork 
  • Cash for incidentals 
  • Sunglasses 
  • Foul weather gear 
  • Reading glasses 
  • Medication(s) 
  • Sunscreen (multiple bottles) 
  • Aloe Vera Gel (in case you get sunburned) 
  • Camera 
  • Cell Phone 
  • Cords for your electronic toys 
  • Hats 
  • Flip flops/sandals/boat shoes
  • Sweater/light jacket
  • T-shirts 
  • Shorts 
  • Swimsuits 
  • Life Jackets for Children

Is WiFi Available Onboard the Yacht?

No. Since you are in US waters, the internet is widely available, and most US carriers work just fine.

Can We Rent Water Toys?

Unfortunately, at this time, we do not rent water toys.

Can We Fish From the Boat?

Yes, with a fishing license. Visit the Maryland Department of Natural Resources (DNR) to purchase a Fishing License.

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, quasi-online grocery shopping with pickup at the store (by you or a taxi), or full provisioning. 

We have a few local grocery and liquor stores within a short drive, or you can opt to have your groceries delivered through any local app. We will load everything on should it be there before your arrival. The dock staff will ensure all your food is put away for you, so please remember to tip.

Grocery Stores 

  • Giant: 948 Bay Ridge Rd, Annapolis, MD 21403: 410-267-0228 
  • Graul’s Market: 607 Taylor Ave, Annapolis, MD 21401; 410-269-5103  
  • Safeway: 1781 Forest Dr, Annapolis, MD 21401; 410-626-2710   
  • Delivery Options: InstaCart App,,

Liquor Stores 

  • Eastport Liquors: 1007 Bay Ridge Ave, Annapolis, MD 21403 
  • Eastport Shopping Center 1023 Bay Ridge Ave. Annapolis, MD 21403 
  • Bay Ridge Wine and Spirits (They also deliver): 111 Hillsmere Dr, Annapolis 
  • Annapolis Wine and Spirits: 1307 Forest Dr, Annapolis, MD 21403 

Can I Have My Meals Catered?

Yes! Various local caterers can craft delicious meals for your trip. 


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, extra paper towels, toilet paper, 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. 

Sailing Area / Boundaries

Where Can We Sail?

Out of Bounds Area: The sailing area shall be restricted to the waters of the Chesapeake Bay and navigable tributaries, and not to navigate South beyond Norfolk or North into the C & D Canal. Kent Narrows and Tilghman Island are also restricted due to shallow waters and strong currents.

Boat and 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?

Yes, our larger monohulls and all catamarans have BBQ grills powered by Propane. Please inquire with your Charter Experience Specialist for smaller boats.

Do You Have Dinghies Available?

Our catamarans are equipped with dinghies, and we have a limited number of dinghies available to rent for our monohulls. Reach out to your charter experience specialist for complete details!

Can I Use My Hair Dryer on the Boat?

Yes, all Waypoints yachts are equipped with inverters that allow for the use of hair dryers; however, please ask during your chart briefing about the rules of power management.

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?

The Nearest Airport 

Baltimore Washington International Thurgood Marshall Airport (BWI), has plenty of ground transportation options. Your personal Charter Experience Specialist can help you make arrangements. 

Driving Directions 

Driving south from New Jersey, Pennsylvania: Follow I-95 South to Baltimore, then I-695 East toward Glen Burnie, then I-97 South toward Annapolis and Route 50 East, and follow the directions below. 

Driving east from Washington DC: Take Route 50 and follow the directions below. 

Driving Delaware/Maryland Eastern Shore: Take Route 50/301 West to the Bay Bridge and follow the directions below. 

Driving Directions from Route 50: Take Route 50 East to Aris T. Allan Blvd, exit right, and keep to the left. Continue through the light at Chinquapin Round Road, and Aris T. Allan Blvd becomes Forest Drive. Stay in the left lane, make a left turn at Hilltop Lane, and stay in the right lane of Hilltop Lane. Continue straight through lights at Spa Road and Primrose Road. Make a left at the light and turn on Bay Ridge Road. Follow straight down to the left turn on Sixth Street (Royal Farms on the left). Make your first right turn onto Severn Ave, and follow straight down to the left into our parking area. We are located near the water in “The Hut” in front of Pier 3.* 

What is Your Physical Address?

Our physical address is: 

Waypoints Yacht Charters
222 Severn Avenue
Bldg 15 “The Hut”
Annapolis, MD 21403

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 or water taxi ride to many restaurants in Eastport and Downtown Annapolis.

What Happens When I Arrive at Waypoints?

  • Please come into the “Hut” and speak with a team member. One of our friendly team members will welcome you and help you finalize your paperwork and security 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 operations and go through a boat 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 9:00 a.m. If you booked a sleep aboard the night before, you can board the boat as early as 3:00 p.m. on that day. 

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

No, we all head home at 5:00 p.m. 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 after 8:30 a.m., check in with one of our staff members wearing a navy Waypoints shirt. Our contact details will be listed on the black clipboard on board should you need after-hours assistance

What Time and How Long are Briefings?

We normally begin your briefing at 9:00 a.m., however, times may vary depending on many factors.  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.

Can I Sail After Dark?

No. You should be securely anchored on a mooring buoy or docked by 5:00 p.m. 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 and then call the service number you were given before you arrive at the fuel dock. A Waypoints team member will walk over to meet you at the fuel dock to help you bring the boat into the dock.
  • We will meet you at your boat with the post-charter paperwork to conduct a debriefing. 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?

If everything is in order and there is no damage to the boat or dinghy, your deposit will usually be refunded within 48-72 hours.

Booking Process and 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. Since our season is short, we book up, leaving little last-minute availability.

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 & Cancellation 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.

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 Refuel the Tank Before Returning the Boat?

Your boat will be ready for you with a full tank at the start of your charter. 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. Check and ACH payments do not include the fee.