Sail Dauntless

Now Sailing:

The Hamptons!

Sail Dauntless is the fun, relaxing, memorable all-inclusive sailing charter booking Sunset, Half Day, Full Day and 2-Night Getaway experiences!

Book Now!

Sunset Sail

Enjoy the sunset aboard The Dauntless. Arrive at 5PM and stay aboard until 7:30PM.

Book Sunset Sail

Half Day Sail

Spend four relaxing hours aboard The Dauntless. Board the boat at 10AM and stay until 2PM!

Book Half Day

Full Day Sail

Spend an entire day aboard The Dauntless! Begin your day at 9AM and stay aboard until 5PM.

Book Full Day

2 Night Getaway

Begin your 2-night getaway at 10AM on your start date, and stay aboard until 11AM on your third day!

Book 2 Nights
What’s included in “All Inclusive?”

Specific food/beverage availability is listed under each charter above. Food options range from heavy hors d’oeuvres to full meals and include both alcoholic and non-alcoholic beverage options. Upon booking, please let us know if you have food allergies.

What’s a typical charter like?

Fun, relaxing, memorable. As active or chill as you desire!

After boarding Dauntless from the Water Taxi, the First Mate will provide the beverage of your choice (see specific charters, above,) the Captain will explain the safety of our vessel, and we’re sailing!

Guests may choose to take part in sailing or relax as Dauntless glides through the water.

Depending on the charter length and sea conditions, we may stop at Shelter Island, Montauk, or other suitable destinations. Guests may walk on a beach, play with our water toys or explore on land.

What if I’d like to sail with you for more than just one day?

Contact us!

Phone: +1.703.989.2553 USA (WhatsApp, International)
Email: info@saildauntless.com
Website: saildauntless.com

What if we have bad weather or need to cancel?

The Captain will determine if a charter shall be cancelled due to unpleasant weather. Guests will have the option to reschedule or be refunded entirely.

Our cancellation policy is as follows:

  • 2 weeks in advance for full refund
  • 1 week in advance for half refund
  • Less than 7 days in advance, no refund
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In The News

There could not have been a lovlier couple to take us round the Caribbean Islands! I had such an amazing time & it was a truly special time.

Georgia and Maddy

Had a magical adventure. Many many thanks for your care & attention in making our time unforgettable. Sleek lines and fine sailing followed by turtles, starfish, topped off by delicious food & even a lobster. Outstanding! Thank you Dauntless!

Clare

Thank you so much! We’ve had an excellent few days with you on Dauntless. Captain Jim may have described some of the sailing conditions as robust, but we both loved every minute of it. We’ve seen some breathtaking scenery, beautiful islands and stunning marine life.

Susan

Thank you Captain Jim and Chef Judy for your warm and wonderful hospitality, smooth sailing and generosity. We were able to have much needed and special time to be together – completely stress free – an amazing gift.

Belinda

We have been on many charters and this one had the best combination of blue water sailing, island hopping, snorkeling, hiking and relaxation of them all. Dauntless is a well appointed boat with all the bells and whistles.

Rahul & Elizabeth

What a dream vacation! Between the adventures of snorkeling, diving and sailing to new bays with an expert and wise captain Jim; to eating specially prepared faire by chef Judy; we had a fabulous retreat and highly recommend Dauntless to anyone looking for a peaceful and adventurous vacation!

Mary

Jim and Judy, a belated thanks for very enjoyable week of cruising a bit of the New England coast and visiting beautiful Edgartown on your magnificent Dauntless, with special appreciation for your hospitality, engaging company, focus on safety, and your patience.

Pete

Dear Jim and Judy, thank you so much for sharing your amazing boat with us and showing us around these breathtaking islands! We hope we can see you again and explore more waters together! Thank you!

Gabriela & Nassim

Your tour of the Grenadines was wonderful! Loved all the special snorkeling & swimming spots, lobster grills & delicious & beautiful food. Great place to sail & enjoy time with family.

Cathy & boys

Sailing Dauntless with Jim & Judy Brown was the most bang-for-your-buck adventure vacations I’ve ever taken. Their nich with dovetailing relaxation, luxury and adventure is unparalleled.

John