Cape Cod Sailing Charters

Slide gracefully along beautiful Pleasant Bay and admire the spectacular scenery aboard Maria – one of Cape Cod’s finest sailing charter vessels.  Whether you’re simply looking to sit back and relax, a first-timer hoping to learn or a seasoned pro who wants to take the helm, our captains will help ensure a memorable experience for your entire group!

A few reasons to choose Maria for your next Cape Cod Sailing Charter:

–  “Just right” size.  Most sailboat charters are limited to carrying just 6 passengers at a time.  Beyond that you’ll have to elbow your way onto boats sailing with 50 people or more!  Maria is unique – small enough to remain intimate but large enough to still accommodate your entire group.

–  We sail in protected waters.  Pleasant Bay offers wonderful scenery and exhilarating sailing with less exposure to bad weather and rough ocean conditions.  Our sails carry virtually zero risk of seasickness, so feel free to bring the entire family!

–  Comfort and safety.  All of our passengers sit inside the dry, secure and comfortable confines of Maria’s expanded cockpit.  Customers need not sit uncomfortably on the cabin roof or along the rails, which is common aboard boats this size.

–  Upscale Setting.  Customers enjoy complimentary parking at the world-class Wequassett Resort & Golf Club.  The resort property features several restaurants and sweeping waterfront views.  Also available is the Wequassett’s exclusive On-The-Water catering menu.

Join us to create a unique and lasting memory of your trip Down Cape!

S/V MARIA

Maria began life as a 1966 Glander Tavana, originally built and designed for the shallow waters of the Florida Keys.  With the help of local builders in Chatham, her hull was stripped bare and her cockpit expanded to create a one-of-a kind USCG Inspected 12 passenger daysailer.  Maria’s design includes a retractable centerboard, a 30 HP diesel engine and for passenger comfort, a small head (toilet).

Length:  33 feet       Draft:  3 feet (min), 6 feet (max)

Private Day Sail

PRIVATE CHARTER RATES:

1-6 Passengers    $495.00

 7-12 Passengers  $675.00

Duration:  2 hrs

Kick off the day with a relaxing morning sail!  Morning sails typically offer lighter winds and are perfect for those looking to escape the heat of the day.  If you crave more wind, an afternoon sail will typically be your best bet!  Local winds tend to build in the late morning and stabilize in the afternoons.

No matter the time of day, a Private Day Sail is the perfect choice for Bachelorette Parties, family gatherings and even private photo shoots!

All trips are private – for you and your group only (plus one captain).

Notes:

  • Please refer to our online calendar for exact departure times and live availability.
  • All sailing charters include the services of a licensed captain and complimentary bottled water.  See the FAQ’s at the bottom of this page for information on which food/beverages are allowed to be brought on board.
  • Catering service is also available through the Wequassett Resort’s ON THE WATER DINING MENU.  To place an order please reply directly to your confirmation email at least 24 hours before your tour.  Items will be added to your total and delivered to the boat before departure.

Private Sunset Sail

PRIVATE CHARTER RATES:

1-6   Passengers     $595.00

7-12 Passengers     $775.00

Duration:  2 hrs

Sit back and relax as the summer sun slowly descends over Pleasant Bay.  Undoubtedly our most romantic departure time, Private Sunset Sails are perfect for special occasion’s, anniversary’s and family gatherings.

Sunset sail availability can be limited at peak times.  Book early as these often sell out!

If your desired date is unavailable, consider one of our Sunset Harbor Cruises instead.  We run several powerboats each evening but only the one sailboat!

All trips are private – for you and your group only (plus one captain).

Notes:

  • Please refer to our online calendar for exact departure times and live availability.
  • All sailing charters include the services of a licensed captain and complimentary bottled water.  See the FAQ’s at the bottom of this page for information on which food/beverages are allowed to be brought on board.
  • Catering service is also available through the Wequassett Resort’s ON THE WATER DINING MENU. To place an order please reply directly to your confirmation email at least 24 hours before your tour.  Items will be added to your total and delivered to the boat before departure.

Frequently Asked Questions

What is your cancellation policy? What if there is bad weather?

For cancellations made 48 hours or more in advance a full refund will be issued.  Cancellations made less than 48 hours in advance will be charged 50%.  No-shows and cancellations made less than 3 hrs before the trip will be charged full price.  We regret that we cannot make exceptions for personal emergencies as a cause for late cancellation.

We will not operate in hazardous weather conditions such as heavy rain, thick fog, high winds or thunder and lightning.  However, no guarantees can be made that every day will be perfectly sunny.  So we will operate as usual in overcast conditions, light fog and in intermittent sprinkles.  The final decision on weather related cancellations rests with us and reservations should be considered upheld unless you speak with us directly over the phone.  If weather cancels your reservation we will make every effort to reschedule for another day.  Otherwise, a full refund will be issued.  If weather cuts your trip short, we will prorate the unused portion.

All refunds will be at the sole discretion of Down Cape Charters & Boat Rentals, Inc.

How early should I show up for my reservation?

To leave enough time for our check-­in procedure, we recommend your party arrive 15-20 minutes before your scheduled departure time.  Leave yourself some margin for traffic or parking related delays, pre-departure bathroom stops, etc.  Group tours will leave at the regularly scheduled departure time – no exceptions.  Private charters arriving late must still return at the regularly scheduled time.  There will be no refunds for those arriving late.  Trips are often scheduled multiple times per day and keeping a strict schedule ensures that all of our reservations are honored.

Will I get seasick?

In all of our years of operation, we have had zero instances of seasickness within the protected waters of Pleasant Bay.  The ocean swell and chop that you might encounter on the ocean or Nantucket Sound is simply not present for any of our sailing trips.  Nevertheless, concerned passengers are welcome to experiment with over-the-counter remedies containing ginger, which has been shown to calm an upset stomach.  Consult your physician if you have any further questions or concerns.

What should I wear? What should I bring?

The only things you need for your charter are a form of ID and your personal items (snacks, hat, sunglasses, sunscreen – preferably not the spray kind, camera).  It is always a little cooler on the water so a windbreaker or sweatshirt might come in handy.  Please wear boat shoes, non-scuffing white-soled sneakers or relax and sail barefoot.

May food and drinks be brought on board?

Yes, feel free to bring your own food and beverages.  All of our trips include complimentary bottled water.  Additionally, we recommend finger foods (small sandwiches, cheese and crackers, etc) as they are easiest to eat on a boat.  Foods with sauces will stain clothing and upholstery so are not recommended.  For adults over 21, reasonable amounts of beer and wine are also allowed (please minimize glass containers).  No hard liquor allowed.

Any excessive use of alcohol will result in the immediate termination of the trip with no recourse.

Are there any age restrictions or physical restrictions?

Our Private Sailing Charters are appropriate for all ages and have no age restrictions.

Those with mobility issues must be able to walk down the resort dock (which has ramps) and step up into the vessel.  Very rarely is this an issue, but it should be mentioned.  Our team will assist in any way they can to ensure that those with mobility issues are comfortable.

Are pets allowed on your sailboat?

As a concession operating from within a resort property that currently does not allow dogs, we have to restrict our boats to service dogs (with valid paperwork) only.

Do you provide life jackets for children?

Yes, we have life jackets for all shapes and sizes (even infants).  While we recommend that everybody wear a life jacket on our boats, by law only those 12 and younger have to wear one at all times.  Your boat will have enough life jackets on board for everybody in your group.  Younger children are welcome to bring their own life jacket if they are more comfortable, provided it is Coast Guard approved (no arm floaties, please!).

We have a group of 13. Can we squeeze onto a trip listed at a 12 person capacity?

Unfortunately, no.  Each of our vessels is rated for a certain capacity by the United States Coast Guard and the USCG does not differentiate between children and adults.  A 12 person capacity means twelve human beings – regardless of age.

Book online now!