Cape Cod Sailing Charters

Slide gracefully along beautiful Pleasant Bay and admire the spectacular scenery aboard MARIA.  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 a medium sized 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.

Length:  33 feet

Draft:  3 feet (min), 6 feet (max)

Private Day Sail

PRIVATE CHARTER RATES:

1-6 Passengers              $600.00

Additional Passengers       $75.00 each

Max of 12 passengers

Kick off the day with a relaxing Private Day Sail – the perfect choice for intimate gatherings, family groups and even Bachelorette Parties.

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.

This is a 2hr private tour – for you and your group only (plus one captain).  Please be sure to read through the FAQ’s located at the bottom of this page.

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 to read our food/beverage policies.
  • Catering service is also available through the Wequassett Resort – see menu link below.  Reply to your confirmation email with your order at least 48hrs before departure and we’ll take care of the rest!

Private Sunset Sail

PRIVATE CHARTER RATES:

1-6 Passengers              $750.00

Additional Passengers        $75.00 each

Max of 12 passengers

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 occasions, anniversary’s and family gatherings.

Sunset Sail availability can be limited at peak times.  We recommend booking 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!

This is a 2hr private tour – for you and your group only (plus one captain).  Please be sure to read through the FAQ’s located at the bottom of this page.

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 to read our food/beverage policies.
  • Catering service is also available through the Wequassett Resort – see menu link below.  Reply to your confirmation email with your order at least 48hrs before departure and we’ll take care of the rest!

Frequently Asked Questions

What is your cancellation policy?

For a full refund, a minimum of 7 days notice is required.

Cancellations made less than 7 days in advance – but more than 48 hrs before departure time – will be charged 50%.

No-shows and cancellations made 48 hrs or less before departure time will be charged full price.

What if there is bad weather?

Safety is ultimately our top priority.  We will not operate in hazardous weather conditions such as heavy rain, thick fog, high winds or thunder and lightning.  If severe weather cancels your reservation we will make every effort to reschedule for another day.  Otherwise, a full refund will be issued.

However, no guarantees can be made that every part of every day will be perfectly sunny.  So we will operate as usual in overcast conditions, light fog and in intermittent sprinkles.  Guests should dress appropriately for changeable weather and bring a positive attitude!

The final decision on weather related cancellations rests with the captain and reservations should be considered upheld unless we contact you directly.  

How early should I show up for my reservation?

To leave enough time for our check-­in procedure, we recommend your party arrive 20 minutes before your scheduled departure time.  Leave yourself some margin for traffic or parking related delays, pre-departure bathroom stops, etc.

There will be no refunds or credits for customers arriving late.  Trips are scheduled multiple times per day and to ensure that all of our reservations are honored, your tour will still have to return at its regularly scheduled time.

What should I wear? What should I bring?

WHAT TO BRING:

  • A valid form of ID (only necessary for the person who has made the reservation).
  • If your tour/rental has not been prepaid, you will need to bring a form of payment.  We accept all major credit cards and/or cash.  Guests of the Wequassett Resort can also charge to their room account if they prefer.
  • An additional layer of clothing.  Even if its t-shirt weather in your driveway, always assume it will be cooler on the water.  For shorter tours, a sweatshirt or a light jacket is often enough.
  • Please wear boat shoes, non-scuffing white-soled sneakers or relax and go barefoot.
  • Snacks/beverages.  Please see additional FAQ’s for restrictions.
  • Sunscreen (non-spray only).
  • Polarized sunglasses.
  • Camera

DO NOT BRING:

  • Spray sunscreen.
  • Marking shoes or sandals.
  • Hard alcohol.
  • Cigarettes/cigars/vapes (no smoking allowed).
  • Drugs of any kids.
  • Beer bottles or glass containers.  (Wine bottles are fine.  Beer in cans is also fine).
  • Red Wine.
  • Anything that can easily blow away.
  • Dogs or other pets.
  • Large coolers.  Each of our vessels already has a large cooler onboard.  Feel free to bring a small cooler and small bags.
  • Large meals.  It just doesn’t work well on an open, moving boat.  Keep food/snacks simple!

May food and drinks be brought on board?

All of our trips include complimentary bottled water.  Additionally, customers are welcome to bring their own snacks and beverages.

Please remember that you will be eating/drinking on a boat that is moving, open to the wind and may or may not have a table or cup holders (we operate several vessels and each is equipped differently).  Our advice is to KEEP IT SIMPLE and don’t bring anything that you aren’t prepared to eat in your lap.  Smaller snacks and finger foods are easiest and less likely to stain your clothing and our upholstery.

For adults over 21, reasonable amounts of beer and wine are also allowed.

RESTRICTIONS:

  • Leave the red wine at home.  On a moving boat it will stain clothing and upholstery.
  • No hard alcohol.
  • Please opt for cans and minimize glass containers in general.  Wine bottles are allowed but no beer bottles.  We will provide plastic cups if needed.

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

What happens if my group size changes after booking?

After booking, don’t worry if your party grows or shrinks.  Your final rate will be adjusted based on the headcount that shows up on the day of your charter.  Please remember that our sailboat can accommodate a maximum of 12 passengers regardless of age/size per Coast Guard regulations.  Just don’t show up with 13 and everything will be fine!

We have a group of 12 plus a baby. Can we squeeze onto your sailboat?

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.

Please note that we can accommodate groups of up to 18 on our largest motor boat.

Will I get seasick?

Tours that stay within the protected waters of Pleasant Bay carry virtually zero risk of seasickness.  The swell and chop that you might encounter on the open Atlantic Ocean or Nantucket Sound is simply not present within the bay.

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.

Are there any age restrictions or physical restrictions?

Our 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 (pictured on our About Us page) and step up into the vessel.  Rarely is this an issue, but it should be mentioned.

Are dogs allowed on your charters?

We do not allow dogs on our sailboat.

However, in certain circumstances, we may allow dogs on some of our motor boat tours.  See our Harbor & Seal Tour, Beachcomber Tour and Sunset Cruise items for more information.

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!).

Book online now!