top of page

Sailing LI Sound

Sailing is  the perfect way to break the routine, unwind, relax and let the coast go by.


Sailing on Sale

Pure Joy is located in Westbrook, Connecticut. We’re available for hourly, half and full day charters. Whether it’s a small family gathering, a romantic sunset sail, pop-the-question, birthday, therapeutic sail, lessons or memorial at sea, Joyride Charters is here to make it possible. We’re committed to making your sailing experience a memorable one. Great for a special event or celebration or simply enjoy a unique sunset. Have something special in mind? Captain Joy can tailor your sail to meet your needs.

Please note: Weekend rates are slightly higher.

See Pricing below in "What You Need to Know" section.

20200618_215716 (2).jpg


Joyride Charters offers afternoon and sunset sails (approx. 2.5 hours long)

Our apologies, we do not have wheelchair access to our vessel. However, there are stairs to step aboard easily.

$550 for the first 4 people. $100 each add’l person (Friday and weekends $600) add’l person $100

Each extra hour $125

Please, no red wine, black soled shoes or heels!

Includes unlimited bottled water and soda. Feel free to bring your own beverages and snacks (please no red wine, greasy or messy foods)

For an extra fee, Joy Ride Charters would be happy to provide food and beverages

A deposit is required in advance for all cruises.

  • Venmo (@joysherman)

  • Zelle Joy Sherman - 2035305037

  • PayPal

Balance should be cash, Venmo or credit card (cc service fee add’l).

Customize your perfect outing - contact Joy for more information!

  • Where do our guests come from?
    Our guests come from diverse backgrounds with their own personal stories, like you. They are professional working people, retired or semi-retired and physically active. Our trips are a way to exploring dreams, visiting places via sailboat. The one common thread of everyone is a love for being on the water and sailing. Or it could be just being on the water! Leave the sailing to us.
  • What are the demographics of your charters? Gender? Age?
    We are roughly 30 – 70 split with women making up the larger number. Ages range from 40’s to 50’s with most of our clients in the 50-70 age range. However, we welcome all! Some of our best charters are mixing the young with the older young!
  • Do I need to have experience?
    Not everyone who comes on our charters has experience. We welcome all levels. You can participate in learning more about sailing or simply lay on the bow with a good book or a snooze in the sun.
  • Who is captain Joy?
    She has been leading charters since 2004 and has completed over forty five charters, but who’s counting? She has spent her entire life around or on the water. She has her USCG Master 100 ton license. Even in her spare time, you may find her sailing. You are in good hands with Joy.
  • What should I expect and what will be expected of me?
    You may be arriving on your own. Once you and your fellow crew members arrive at the boat, we will help you get settled in your cabin. Our boats are mostly large luxury catamarans. They are super comfortable with lots of space for your belongings. If there is a hostess/cook on your charter, they are there to help ease into the evening with a cold beverage. The friendships you make aboard, will most likely be lifetime friends.
  • What will my cabin be like?
    Most of the boats have one or possibly two single cabins available for purchase. Most of our clients don’t mind being placed in a double cabin with someone of the same sex. You may also choose to purchase a double cabin as a single. You can read more about the boats and their cabin arrangements on each trip detail page. The cabin you choose when you make a booking is the one you’ll have when you arrive. If we need to change your cabin, we will only upgrade at no extra charge.
  • What happens on the first day?
    This time is spent getting familiar with the boat. We will go through a safety briefing and our plan for the week will be discussed. You will get to know your fellow mates, what’s aboard as far as provisions. Some of our charters include some alcohol. It is recommended that you purchase your favorite alcoholic beverages before you arrive. If there is a liquor/grocery store nearby we will let you know. We may go out to dinner that evening (if there is a good place nearby) or will have dinner aboard.
  • What do I need to know about charters with a cook onboard?
    Some of our charters include hostess or cook. (hostess makes breakfast and lunch while cook makes three meals a day) Whether there is a cook on board your charter or not, we will go over the provisions aboard. The food will have been put away. Meals are planned based on local provisions available and taking into account what you submitted on your questionnaire. Captain Joy is an early bird and will have coffee ready for you upon waking. Breakfasts and lunches may offer a variety of local fruit, eggs, bacon, cereal, yogurt, toast. Lunches may be salads, wraps, sandwiches which you might assemble yourself. Guests are asked to take turns doing dishes. Either lunch or dinner will be provided, with the other meal being ashore. Of course a cook will most likely prepare more extensive meals. If the meals are being prepared by everyone aboard at different times, there will be a loose schedule for you to sign up for a meal or two to make additionally, if you love to cook and are on a charter where there isn’t an assigned cook, we encourage meal prep sharing and doing dishes. It becomes a community effort. A lot of great conversations take place in and around the galley!
  • How long do we sail each day?
    This varies on how far we travel to the next stop and of course the weather. We try to make a stop mid day to swim, snorkel, have lunch and relax or go to the location for the evening, earlier so you have time to explore on shore. Expect sailing of 2-3 hrs each day give or take. When we arrive at port for the night, we arrive so there is plenty of time for you to explore.
  • What type of shape do I need to be in?
    You must be able to get in and out of a dinghy. Some docks require using a ladder to climb up to the dock. You should be able to handle your own body weight. You can participate in sailing for a bit, a lot, or not at all.
  • Do I need travel insurance?
    Travel insurance is highly recommended. Because the charter companies have strict non refundable policies, travel insurance will give you peace of mind your investment will be protected.
  • What if the weather changes?
    We always hope for wonderful sailing weather. From time to time we may encounter a rain shower or heavy winds which may keep us on our mooring. Captain Joy reviews the weather predictions days before so that we are prepared to “wait it out” if need be. Safety is our first priority
  • What types of boats do you typically sail?
    Joyride Charters typically sail 45 to 50ft catamarans.

Our Experience





Looking for a Personalized Option?

We'd love to talk with you about a personalized sailing option! With offerings all week long, we're ready to sail. Please note: Weekends incur slightly higher rates.

bottom of page