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.  From mid-May through October, Maria is available for 2 hour private sails for up to 12 passengers.  In July and August, scheduled Group Morning Sail’s are also offered.   Join us to create a unique and lasting memory of your trip Down Cape!

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

–  “Just right” size.  Most sailboat charters are limited to carrying only 6 passengers.  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 (up to 12).

–  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!

–  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.

–  Flexibility.  Whether you’re simply looking to sit back and relax, a first-timer looking to learn or a seasoned pro who wants to take the helm, our captains will help ensure a memorable experience for your entire group!

Please see answers to Frequently Asked Questions at the bottom of this page.

The Boat

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 remodeled as a 12 passenger daysailer.  Maria’s one-of-a-kind design includes a retractable centerboard and a 25 HP diesel engine.  For passenger comfort, a small head (toilet) was also incorporated.

Length:    33.0 feet
Draft:        3.0 feet (min), 6.0 feet (max)

Original Design:  Glander Boats, Tavernier, FL
Redesign:  Richardson’s Marine, Chatham, MA

The Name

Maria borrows her name from the legend of Captain Sam Bellamy and the pirate ship Whydah.  Known as “Bellamy’s bride”, Maria Hallett plays an important role in the lore of Cape Cod’s pirate past.

Private Day Sail

PRIVATE CHARTER RATES:

1-6 Passengers    $475.00

 7-12 Passengers  $675.00

Duration:  2 hrs

WE ARE CURRENTLY LIMITED TO A MAXIMUM OF 10 PASSENGERS PER STATE REGULATIONS.

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.  Or 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.

The perfect choice for Bachelorette Parties, family gatherings and even private photo shoots.

No matter the time of day, you can’t go wrong with a Private Day Sail!

Notes:

  • Please refer to our online calendar for exact departure times and live availability.
  • Standard 2 hr charters are available for direct online booking.  If you would prefer a longer (or shorter 1 hr) sail please contact us directly at 508-241-4070.
  • All sailing charters include the services of a licensed captain and complimentary bottled water.
  • Additional food and beverage service is available through the Wequassett Resort.  Click here to download the ON THE WATER DINING MENU.  To place an order please reply directly to your confirmation email or call/email us at your convenience.  Items will be delivered to the boat before departure.

Private Sunset Sail

PRIVATE CHARTER RATES:

1-6   Passengers     $555.00
7-12 Passengers     $755.00

Duration:  2 hrs

WE ARE CURRENTLY LIMITED TO A MAXIMUM OF 10 PASSENGERS PER STATE REGULATIONS.

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.  Book early as these often sell out!

Notes:

  • Please refer to our online calendar for exact departure times and live availability.
  • Sunset sail availability can be limited at peak times.  If your desired date is unavailable, please consider one of our Sunset Harbor Cruises instead.
  • Standard 2 hr charters are available for direct online booking.  If you would prefer a longer (or shorter 1 hr) sail please contact us directly at 508-241-4070.
  • All sailing charters include the services of a licensed captain and complimentary bottled water.
  • Additional food and beverage service is available through the Wequassett Resort.  Click here to download the ON THE WATER DINING MENU.  To place an order please reply directly to your confirmation email or call/email us at your convenience.  Items will be delivered to the boat before departure.

~ Rise & Shine ~

Morning Group Sail

PUBLIC CHARTER RATES:

$55.00 per adult

$35 per child (12 and under)

Infants free (2 and under)

Duration:  2 hrs

Due to the Social Distancing guidelines of the Massachusetts Reopening Plan, we will not be offering this item until further notice.

Perfect for those who would rather not book a private sailing charter or for those looking for a more social outing, our Rise & Shine Morning Group Sail offers a relaxed atmosphere for up to 12 individually ticketed guests.  This early sail gets you out before the crowds and winds fill in, when the bay is at its most peaceful.

Our Morning Group Sail includes a selection of fresh pastries, coffee and juice.  Join us before you hit the beach or shopping in downtown Chatham!

Notes:

  • Departure times may vary.  Please refer to our online calendar for available dates and exact sailing times.
  • Our Morning Group Sail includes the services of a licensed captain and a selection of fresh pastries, coffee, juice and bottled water.
  • We ask that groups larger than 6 book a private charter as they can sometimes overwhelm other guests who are not part of your group.
  • In the rare instances where there are no reserved seats 12-24 hrs before a scheduled departure, we may call off our captain for that specific sailing time.  To help ensure captain availability and on-time departures, it is important that reservations are made in advance for any of our group tours.

STAYING HEALTHY  (Updated 5/20)

As we prepare to reopen, additional protocols and procedures have been added to adhere to current state guidelines.  These include:

  • All passengers and employees will be required to wear face coverings that meet DPH/CDC standards.
  • Employees will be screened daily, including temperature checks.
  • Additional cleaning and sanitizing procedures will be added for vessels, equipment and frequently touched surfaces.  
  • Hand sanitizer will be available at all times.
  • Online transactions for payments and waivers will be utilized whenever possible. 

A full list of additional protocols will be emailed to each customer at the time of booking.

TRAVEL INTERRUPTION  (Updated 5/20)

Our standard 48 hr cancellation policy will apply for the entire 2020 season.  However, to reflect the current uncertainty surrounding the travel industry, exceptions may be made on a case-by-case basis for: 

  • Interrupted travel due to COVID-19 travel restrictions.
  • Customers who are feeling ill or are advised to avoid travel by a medical professional.

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 2 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 storms.  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 (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.

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 Sailing Charters – both private and group sails – 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?

We currently do not allow pets on any our vessels.

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).

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!