Cape Cod Sailing Charters Overview

Slide gracefully along beautiful Pleasant Bay and admire the spectacular scenery aboard one of Cape Cod’s finest sailing charter vessels.  Maria specializes in 2 hour private sails for up to 12 passengers – with a few public group sails thrown in to satisfy everyone.  Whether you pitch in and help handle the sails or simply sit back and relax, you’re sure to create 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.  Pleasant Bay offers exhilarating sailing with less exposure to bad weather and rough ocean conditions.  Our sails see virtually zero cases 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 a seasoned pro who wants to take the helm or a first-timer looking to learn, 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.

PLEASE REFER TO OUR FAQ’S BELOW FOR MORE INFORMATION

Private Day Sail

PRIVATE CHARTER RATES:

1-6 Passengers    $475.00

 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.  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.

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

During July and August, Saturday and Sunday mornings are typically reserved for our group Rise & Shine Mimosa Sails.  If desired, private groups can still occasionally reserve the entire boat on these popular mornings.  Please see that item for details.

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

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!

During July and August, Friday and Saturday evenings are typically reserved for our group Wind & Wine Sunset Sails.  If desired, private parties can still occasionally reserve the entire boat on these popular nights.  Please see that item for details.

Alternatively, if sunset sail availability is limited, we also offer private Sunset Harbor Cruises aboard motor boats.

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.

~Wind & Wine~

Sunset Sail

PUBLIC CHARTER RATES:

$85.00 per adult (ages 21+)

Duration:  2 hrs

Perfect for those who would rather not book a private charter, or for those looking for a more social outing, our Wind & Wine Sunset Sail offers an upscale yet relaxed atmosphere for up to 12 individually ticketed guests.  These popular sails allow passengers to sample an array of fine wines and upscale beers from around the world.  Join our many repeat customers and make it a yearly tradition!

Notes:

  • Although alcohol is included in your ticket price this is not a booze cruise.  We will serve a couple of rounds but the aim is to create a relaxing, safe and friendly atmosphere for all of our guests to enjoy.
  • Departure times may vary.  Please refer to our online calendar for available dates and exact sailing times.
  • 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 reservations yet for that trip (12 seats show available).  To do so, customers must either: (a) book all 12 tickets to create a Private Wind & Wine Sunset Sail.  Or (b) book 10 tickets if no beer/wine is desired.  Either option is irregardless of actual head count.  At checkout, please add a comment requesting a private trip.
  • 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.

Rise & Shine

~Mimosa Sail~

PUBLIC CHARTER RATES:

$75.00 per adult (ages 21+)

Duration:  2 hrs

Our newest Group Sailing option, the Rise & Shine Mimosa Sail is the perfect start to the day!  Sip on morning mimosas and enjoy an assortment of complimentary pastries while seeing the sights of Pleasant Bay and Chatham Harbor.  This early sail gets you out before the crowds and winds fill in, when the bay is at its most peaceful.  Join us before you hit the beach or shopping in downtown Chatham!

Notes:

  • Although alcohol is included in your ticket price this is not a booze cruise.  We will serve a couple of rounds but the aim is to create a relaxing, safe and friendly atmosphere for all of our guests to enjoy.
  • Departure times may vary.  Please refer to our online calendar for available dates and exact sailing times.
  • Any scheduled Rise & Shine Mimosa Sail can be made “private” if there are no existing reservations yet for that trip (12 seats show available).  To do so, customers must either: (a) book all 12 tickets to create a Private Rise & Shine Mimosa Sail.  Or (b) book 10 tickets if no food/bev is desired.  Either option is irregardless of actual head count.  At checkout, please add a comment requesting a private trip.
  • 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.

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 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 Group 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!