Joyride Charters - Sailing Everywhere

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Joyride Charters - Sailing Everywhere Small-group sailing experiences Connecticut and Worldwide. For solo travelers, couples & friends. And yes, 🐾 is part of the experience!

Come solo or bring your crew… you’ll never feel out of place here. Enjoy a unique sailing experience aboard Pure Joy. Joy and her crew understand everyone needs pampering. Pure Joy is the perfect place to unwind, relax and let the coast go by. Sailing On Sale – Monday thru Thursday afternoons and evenings. Great for a special event or celebration or just to watch a unique sunset. Bad weather? No worries, your deposit is fully refundable!

Eighth year sailing Greece. Do you think we love it? 🇬🇷⛵️💙 Join us again May 2027
10/25/2026

Eighth year sailing Greece. Do you think we love it? 🇬🇷⛵️💙
Join us again May 2027

🇭🇷 Croatia, you have been wonderful to us.A few glimpses from our Joyride Charters adventure so far — sailing between be...
09/24/2026

🇭🇷 Croatia, you have been wonderful to us.
A few glimpses from our Joyride Charters adventure so far — sailing between beautiful islands, swimming in impossibly blue water, wandering through old stone towns, discovering local food and w**e, and sharing a whole lot of laughter along the way.
What I love about our small-group sailing trips. We unpack once, let the boat carry us from one beautiful place to the next, and have the freedom to experience each destination at a slower, more personal pace.
And Croatia has certainly delivered. ⛵️💙
Here are a few favorite moments so far… and we’re not finished yet!

⛵ BVI Update — Just 2 Cabins Left at the Current Price!I know a few of you have been talking it over, checking schedules...
08/31/2026

⛵ BVI Update — Just 2 Cabins Left at the Current Price!
I know a few of you have been talking it over, checking schedules and trying to decide if the BVI is going to happen. 😊 So I wanted to give you a little heads-up before these last two cabins are gone.
I was able to get a great price on our first boat and passed that savings along to everyone joining me. We now have just 2 cabins left on that boat at the current price.
Once those are booked, I’ll be adding another boat — but the cost of that boat is higher, so the price for the next group will be higher as well.
So if you’ve been saying, “I really want to do this…” this might be the time to make it official. 🌴⛵
A week sailing the British Virgin Islands, warm water, beautiful beaches, island hopping, great company and plenty of fun along the way.
Message me if you’ve been thinking about joining us or want to grab one of the remaining cabins.

Family requested privacy. Scupper requested publicity. 😂🐾⛵So while everyone else is hiding behind doggy faces, Scupper w...
08/30/2026

Family requested privacy. Scupper requested publicity. 😂🐾⛵
So while everyone else is hiding behind doggy faces, Scupper would like you to know he is available for photos, autographs and belly rubs. 🐶🧡

⛵ We still have a few openings between now and Labor Day weekend!Summer isn’t over yet. ☀️ Come squeeze in one more sail...
08/29/2026

⛵ We still have a few openings between now and Labor Day weekend!
Summer isn’t over yet. ☀️ Come squeeze in one more sail, feel the breeze, get out on the Sound, and enjoy these last beautiful days of summer.
Bring your favorite people, something to sip, and leave the rest to me.
Let’s make the most of summer while it’s still here! ⛵🌊
Message me for available dates and times.
Connecticut Day Trips Explore Connecticut

Address

63 Pilots Point Drive
Westbrook, CT
06498

Telephone

+12035305037

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