Down Cape Charters & Boat Rentals is proud to offer the newest and most dependable fleet of sailboats for rent on Cape Cod.  All of our boats come equipped with a dry bag, life preservers and all required USCG safety items.


  • You must be 18 years or older and possess a valid picture ID (driver’s license or passport) to rent a sailboat.
  • Rentals must be secured by a major credit card – Visa, MasterCard or Discover.  Full rental fees required at check-in.
  • Sailing experience is required.  The level of experience will depend on the conditions and which boat you wish to rent.
  • To ensure the safety of our customers, sailboats are limited to staying within our field of vision at all times.
  • Life jackets must be worn at all times.
  • Rental rates do not include MA sales tax (currently 6.25%).



17’ Daysailer

Capacity: 4 people
Sails: Main and Jib

1 HR –                          $105.00

2 HRS –                        $135.00

4 HRS (1/2 day) –     $215.00

16’ Hobie Cat Getaway

Capacity: 6 people (up to 1,000 lbs)
Sails: Main and Jib
Wing Seats

1 HR –                          $95.00

2 HRS –                        $125.00

4 HRS (1/2 day) –     $215.00

14’ Hobie Cat Wave

Capacity: 4 people (up to 800 lbs)
Sails: Main only

1 HR –                          $85.00

2 HRS –                        $105.00

4 HRS (1/2 day) –     $185.00

FAQ : Sailboats

Who can rent a sailboat?

You must be 18 years or older in order to rent a sailboat.  The minimum age for sailing with us is 4 years old.

How much experience do I need? Do I need a license?

No licenses are required.  However, your level of experience should be sufficient to safely handle the boat you request in all conditions.  In general:

  • Less experienced sailors will be steered towards one of our Hobie catamarans.  Hobie’s are simple boats – no metal booms to hit you in the head, only one sail on certain models.  In the event of a capsize, Hobie’s can be righted quickly with little fanfare.
  • Our Daysailer will be reserved for more experienced sailors.  Note that this boat does not come with a motor (nor does it beach itself like a Hobie).  You will be responsible for returning to the dock or a mooring under sail alone.  We will typically not send the Daysailer out in winds over 15 knots unless very comfortable with your abilities.

A $50 rescue fee will be charged for any sailboat that needs to be towed back to our dock or beach for reasons other than mechanical failure.  Typically, this happens because people overstate their sailing experience and struggle to return on time.  Sometimes they struggle to return at all.  For capsizes we will charge a rescue fee to any Hobie renters who are unable to right the boat themselves (most can ­ and we will explain how).  For the Daysailer a capsize automatically ends your rental and doubles the price.  This is because it takes several hours to get the boat righted and bailed.  Typically we lose the boat for the rest of the day.

A one hour lesson costs the same as our rescue fee.  If there is any doubt in your mind about your own abilities, avoid the hassle and take a lesson for an hour.  We guarantee you will get more out of your experience and you’ll end up a better sailor.

Do you offer sailing lessons?

Yes.  Lessons can be arranged on any of our boats, including the larger 33′ Maria.  Please see our Lessons page for more information and rates.

Where can I take the boat?

We recommend you stay within our field of vision at all times.  Pleasant Bay proper, directly in front of our dock, gives you about 4 square miles to enjoy.  In a 1 or 2 hr rental, that is more than enough space.  Those renting for longer often enjoy stopping at one of the islands in the bay during their rental.  Please specify if this is your plan so we can explain your options accordingly.  We’ve found that sailboats that leave our field of vision can:

  • Run into trouble with incoming or outgoing tides.  The current can be surprisingly strong, keeping you from making any headway.
  • Encounter very shallow areas which kick up the rudders and make it difficult to steer.

While these issues aren’t insurmountable for some sailors, especially if you’ve sailed in Pleasant Bay before, many are unable to return by themselves.  But because we cannot see you, we cannot help until either you call us, or until your rental period is almost over and we still cannot see you.  At that point you will be charged our rescue fee.

What times can I rent a boat?

Sailboat rentals generally run 1, 2 or 4 hours and begin on the ½ hr (ie. 1:30, 2:30).  This helps to relieve some congestion while also renting powerboats on the hour.  ½ day rentals (4 hrs) can start at either 9:30 or 1:30.  One or two hours rentals will be slotted where available.  During our spring and fall season we can generally be more flexible with the start times.

Are there costs other than the rental fees? Is insurance available?

For sailboats, the only other cost is sales tax (currently 6.25%).

We do not sell insurance for our sailboats.  You are responsible for returning the boat in the same condition in which you received it, complete with all additional equipment.  Normal wear and tear items will be covered by us. Additional damages and lost equipment will be paid for by the renter in full.

What forms of payment do you accept?

We accept cash, Visa, Mastercard or Discover.

Do I need a reservation?

Yes.  In the summer season it is not uncommon for us to have no availability on busy days.  Please, do not count on just showing up and getting a boat.  Even in slower periods a reservation allows us to make sure your boat is clean and fueled before you arrive ­ – no waiting.

The less flexible you are, the earlier you should make your reservation.  Especially on weekends and holidays.  If you want a specific boat, on a specific day and at a specific time, you should reserve well ahead.  If you are flexible enough to take any boat at any time, you will need less notice.

What if I need to cancel my reservation? What if there is bad weather?

For cancellations made 48 hours or more in advance we will issue a full refund.  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.

Rentals will not be allowed out in hazardous weather conditions such as heavy rain, thick fog, high winds or thunder and lightning.  However, we will operate as usual in overcast conditions, light fog and in intermittent sprinkles.  No guarantees can be made that every day will be perfectly sunny.  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 rental short, we will prorate the unused portion.

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

What should I wear? What should I bring?

First you will need a form of payment and a valid photo ID (driver’s license or passport).  Most renters bring water, a towel, hat, sunglasses and sunscreen.  You will be on the water so we recommend wearing clothing and shoes that you don’t mind getting wet.

We are happy to provide a small dry bag for your valuables.  This might include a cellphone (to contact us in an emergency) or a camera.  If you will not be bring a phone, make sure somebody has a waterproof watch.  It is YOUR responsibility to bring the boat back on time.  We will not be able to signal you or warn you.

Can we bring food or alcohol on board?

Your group is more than welcome to bring food.  We do ask that you avoid glass containers for safety reasons and clean up of all related trash will be your responsibility.

State and federal boating regulations prohibit the operation of a boat while intoxicated.  Boating Under the Influence (BUI) is a federal offense, subject to fines and even jail time.

No hard liquor will be allowed on any rental boat.  Small quantities of beer and wine will be allowed provided it is not in a glass container.  Each group should have a designated driver.  The bay is regularly patrolled by both Coast Guard Station Chatham and the harbormasters from Orleans, Harwich and Chatham.  Random checks are not uncommon.  Any groups believed to be intoxicated before the rental begins are subject to cancellation without refund.  No exceptions.

How early should I show up for my reservation?

To leave enough time for our check-in procedure, we recommend your party arrive at least 15 minutes before your scheduled rental time.  Leave yourself some margin for traffic or parking related delays, pre-departure bathroom stops, etc.  There will be no refunds for those arriving late.  Boats are often reserved multiple times per day and keeping a strict schedule ensures that all of our reservations are honored.  An additional charge of $75 per ½ hr will apply, beginning 15 minutes after your appointed return time, for late returns.

Our responsibility is to have your boat at the dock/beach, clean and fueled at the appointed time.
You are reserving the rights to use that boat for a specific block of time (ie. 9am-­1pm).
Your responsibility is to arrive early and return the boat on time.

Do you deliver boats to other locations?

Currently we only deliver our boats inside Pleasant Bay, meaning we will deliver to your location by water but not by trailer.  For the Daysailer you must have access to a dock or mooring.  For a Hobie you must have a secure beach location or a mooring.  Deliveries may be subject to a fee.

Are pets allowed on your equipment?

We do not allow pets on our rental boats.

Do you offer multi­ day discounts?

We encourage you to check out our Loyalty Program page.  It offers information and options for repeat renters.  If you still have questions please call us to discuss.

We have a group of 7. Can we squeeze onto a boat listed at a 6 person capacity?

No.  Each of our boats is rated for a certain capacity by the United States Coast Guard.  Ignoring that capacity is against the law, it strains our boats and it endangers everybody on board.  A 6 person capacity means six human beings – ­ the USCG does not differentiate between children and adults.

Can our group of 10 take turns on one boat?

With Hobie catamarans, yes.  Renters are allowed access to the beach away from the designated resort guest beach chairs.  Groups can drop­ off and pick­up from the beach as much as they like while some remain back (please read next question).  For safety reasons and to limit potential damage to our boat, we prefer our Daysailer not return to the dock until the rental is fully complete.

If I am renting a boat, does that allow me access to the resort facilities?

Down Cape Charters & Boat Rentals is not owned by the Wequassett Resort.  Using our services does not entitle you use of any resort facilities outside of the restrooms and parking lot.  The resort pool, deck area and beach chairs are strictly reserved for resort guests only.

Renters are allowed access to any part of the resort that is normally open to the public.  This includes four restaurants: the Outer Bar & Grille, Thoreau’s, Twenty­Eight Atlantic and the waterfront bar, LiBAYtion.  (Please note: LiBAYtion and the beachfront terrace open to the public after 4:30pm during the summer season).

Should I be concerned about sharks?

Despite the recent media attention garnered by Chatham’s shark population, chances of encountering a shark during your rental are remote.  Consider that our entire rental team, with many years combined experience, has never seen a shark (in the bay or otherwise).  Some fun facts:

  • You are statistically more likely to be injured by a cow or a vending machine than a shark in the United States.
  • Shark attacks in North Carolina in one month last summer outnumber those in Massachusetts over the last 100 years.

We obviously recommend always being aware of your surroundings.  It’s probably best not to swim/surf near a group of seals (potential shark food and wild animals themselves).  And we would probably not swim in the open ocean with a bleeding wound (common sense).  Otherwise, each day hundreds of people swim and surf in the open ocean off of the Cape Cod National Seashore.  Inside the bay, ­ even further from where sharks potentially roam, ­ its frankly an afterthough

Does everyone need to wear a lifejacket? Do you have children’s sizes?

PFD’s must be worn be everybody using our equipment.  The life jacket will keep you afloat if you are tired or cold and is a critical piece of safety gear.  It is very difficult to put on a life jacket when you’re in the water, so better to wear it all the time.

We have life jackets for all shapes and sizes.  Younger children are welcome to bring their own life jacket if they are more comfortable, provided it is Coast Guard approved (no arm floaties).  Otherwise we have several kids sizes. Note that the age minimum is 4.

Can I keep equipment out longer if we are enjoying ourselves?

Possibly.  If there are no other existing reservations for your boat then we’d be happy to extend your rental period (assuming we are not about to close).  We ask that you check in with us at the conclusion of your rental or call us 30 minutes before your rental period is over.  If we have a reservation the boat will have to be returned as scheduled.

Can it be too windy to sail?

Occasionally, yes.  We become very conservative with our sailboats once winds climb over 15-20 knots.  This is both for the safety of our customers and for the well­ being of our boats.  We are more likely to allow a Hobie rental in high winds than the Daysailer, even for experienced sailors.  Please see our Weather Information page for the general forecast.

Will I need to rig the boat myself?

We will rig the boat and have it ready for your arrival.  No hassles.  Just hop on and sail.  At the end of your rental, just walk away.  We’ll handle everything.