Sailboat Rentals

Pleasant Bay, Cape Cod

Down Cape Charters & Boat Rentals is proud to offer the newest and most dependable fleet of Hobie Catamarans for rent on Cape Cod.  Come experience the charms of Pleasant Bay – considered by most to be tailor-made for small boat sailing.


  • At least one participant must be 18 years or older and possess a valid picture ID to rent a sailboat.  Minimum age of participants is 5 years old.  All participants must be able to swim.
  • Rentals must be secured by a major credit card – Visa, MasterCard or Discover.  Full rental fees required at check-in.
  • Adequate sailing experience is required.  Instructors are available for hire.
  • To ensure the safety of our customers, sailboats are limited to staying within Big Pleasant Bay at all times.
  • Life jackets will be provided and must be worn at all times.
  • Rental rates do not include MA sales tax (currently 6.25%).

Private Sailing Lessons

Learn the life sport of sailing with Down Cape’s private sailing instruction.  Our experienced instructors cover the basic principles involved, vocabulary, techniques and good seamanship.  Participants will gain on-the-water experience from the very first lesson.  Couples and families are encouraged to learn together.

RATES:       1HR  –  $165        2HRS  –  $235

Please contact us directly to schedule a Private Sailing Lesson!


Hobie Cat Wave

Length: 14 ft
Capacity: 4 people
Sails: Main only

1 HR –                           $85.00

2 HRS –                        $110.00

4 HRS (1/2 day) –      $185.00

Please refer to our online calendar for available rental times.

Hobie Cat Getaway

Length: 16 ft
Capacity: 6 people
Sails: Main and Jib

1 HR –                           $105.00

2 HRS –                        $135.00

4 HRS (1/2 day) –      $215.00

Please refer to our online calendar for available rental times.


For the safety of our customers and employees, additional protocols and procedures have been added to adhere to current state COVID guidelines.  These include:

  • All customers are asked to wear face coverings that meet DPH/CDC standards when checking in and boarding. 
  • All employees will wear face coverings at all times.
  • 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. 

We look forward to getting your group out of the house and onto the water in a safe and socially responsible manner!

Frequently Asked Questions

Who can rent a sailboat?

At least one person in your group must be 18 years or older in order to rent a sailboat.  The minimum age for sailing with us is 4 years old.  All participants should be able to swim.

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

Your level of experience should be sufficient to safely handle a catamaran in all reasonable conditions.  In general:

  • Less experienced sailors will be steered towards a Hobie Wave, which features only one sail.  In the event of a capsize it can also be righted quickly by one average sized adult.
  • Our Hobie Getaway will be reserved for more experienced sailors.  A larger boat, featuring two sails, the Getaway will be take two adults to right in the event of a capsize.

A $50 rescue fee will be charged for any sailboat that needs to be towed back to our 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).

A lesson costs roughly the same as a rental plus 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.  Please refer to the the top of our Sailboat Rentals page.  Lessons can be conducted on either model of Hobie.  Please note that the capacity of each boat will be reduced by one to account for the instructor.

Where can I take the boat?

We recommend you stay within our field of vision at all times.  Big Pleasant Bay proper, directly in front of our dock, gives you about 3.5 square miles to explore.  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.

Sailboats that leave our field of vision often:

  • 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.
  • End up paying a rescue fee.

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 sailboat rentals.  You are responsible for returning the boat in the same condition in which you received it, complete with any provided 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 ready for your arrival ­ – 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.

Note:  Dry bags are not perfect.  Down Cape Charters & Boat Rentals assumes no responsibility for items stored in a dry bag. 

How early should I show up for my reservation?

To leave enough time for our check-in procedure, we recommend your party arrive 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 will apply, beginning 15 minutes after your appointed return time, for late returns.

Do you deliver boats to other locations?

Currently we will only deliver our equpment inside Pleasant Bay, meaning we will deliver to your location by water but not by trailer.  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 any our rental boats.

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

Unfortunately, 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).

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?

Though statistically rare, encounters between sharks and humans on Cape Cod tends to happen near large concentrations of seals – off the coast of the Cape Cod National Seashore and Monomoy Island (ie. in the ocean).

To date, there has never been a confirmed shark sighting within the area where you will be allowed to sail.

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 for sailing with us 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 knots.  We also reserve the right to cancel any existing reservations once speeds reach 20 knots.  This is both for the safety of our customers and for the well­ being of our boats.  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.

Book online now!