Cape Cod Sailing Charters Overview

Slide gracefully along beautiful Pleasant Bay and admire Cape Cod’s spectacular coastline aboard our newest luxury daysailerCertified by the USCG to carry up to 12 passengers, Maria offers the area’s finest sailing experience.  Whether you pitch in and help handle the sails or simply sit back, relax and enjoy the scenery, Maria provides the perfect backdrop for a unique and lasting memory of your trip Down Cape!

A few reasons to choose Maria for your next sail:

–  “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.  While other boats have to carefully plan around the rough conditions often found on Nantucket Sound and the Atlantic, Pleasant Bay offers the exhilaration of sailing with less exposure to bad weather and minimal risk of seasickness.

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

–  Flexibility.  Pitch in and help handle the sails or simply sit back, relax and enjoy the scenery.  Whether you’re a seasoned pro or a first-timer, our captains will help ensure a memorable experience for your entire group!

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 Captain

Captain Chris Sammartino has been a sailor his entire life, learning to read the winds and currents under the watchful eye of his father aboard their Cape Dory Typhoon.  Since earning his USCG 100 Ton Masters License and Sailing Endorsement in 2000, Chris has provided thousands of passengers with safe and enjoyable experiences on the waters of Cape Cod.  When he’s not out on Pleasant Bay, he can be found sailing and maintaining his 38′ Shannon ketch with his wife on Nantucket Sound and wintering under the Caribbean sun.


Private Sailing Charters

RATES:               2 hrs      Add’l hrs
1-6   Persons      $475      $175 each
7-12 Persons      $675      $175 each

Whether you’re celebrating a special day or hosting out of town guests, a private sailing charter will provide a unique experience not soon forgotten.  Maria is available for private charter with captain any day of the week – from afternoon sails to romantic sunset trips.

Please refer to our online calendar for exact departure times and live availability.


  •  Only our standard 2 hr sailing charter is available for direct online booking.  If you would prefer a longer (or shorter 1 hr) sail please contact us directly at 508-241-4070 to reserve.
  • 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.

Wind & Wine Sunset Sail

RATES:  $85 per adult. 

Ages 21+ only.  12 passengers max.

DURATION:  2 hours

Watch the summer sun slowly descend over Pleasant Bay on our popular Wind & Wine Sunset Sail!  Featuring an array of fine wines and upscale beers from around the world, this evening cruise offers an upscale, yet relaxed atmosphere for up to 12 guests.

Offered only on Friday and Saturday evenings during our busy “summer season”.  Please refer to our online calendar for available dates and exact departure times.


  • Includes the services of a licensed captain, bottled water, wine and beer.  All required extras (cooler w/ice, cups, napkins, bottle openers, cork screws, etc) will be on board.
  • Passengers are welcome to bring their own preferred beverages – just be prepared to share!
  • Any scheduled Wind & Wine Sunset Sail can be made “private” if there are no existing passengers booked yet for that trip.  To book a private Wind & Wine Sunset Sail you must book 10 individual tickets.  Upon booking, reply directly to your confirmation email advising that you would prefer a private cruise.

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 payment 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 avoid 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?

Private charters have no age restrictions.  Our scheduled Wind & Wine Sunset Sail’s are reserved for adults over 21 only.

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 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.  Ignoring that capacity is against the law and endangers everybody on board.  A 12 person capacity means twelve human beings – ­ the USCG does not differentiate between children and adults.

Book online now!