"It's rare to find a singer/songwriter with the personality,
vocals and presence to captivate and hold an audience
the way Dennis did last week. He's one performer who
can effectively walk in with his guitar and engage even
a savvy, musically inclined crowd all by himself.
Dennis' style is reminiscent of the great story
tellers like Harry Chapin and James Taylor."

Meghan Diamond; Walnut Creek, CA

"Dennis is a terrific performer with
an outstanding sense of humor.
He's always welcome to play here."

John Hunt; Southeast Alaska State Fair (AK)

PILOT ME #8 on world folk music radio charts August 2020. - Folk DJ	SEEDS Named one of the top albums in Folk Music - 2012 by FolkDJ based on radio play around the world

Now in its Ninth Printing! Dennis' popular children's book

Come sailing with me among the beautiful islands of coastal Maine!

AUGUST 16-22, 2026 

SOLD OUT! 

Six nights aboard the beautiful schooner Grace Bailey

Built in 1882, this ship is a majestic
piece of American history. It's not a
replica. It's the real deal!

My friend Captain Sam Sikkema is a highly talented and experienced skipper. I've sailed with him many times. We're in good hands.

We'll have our own chef on board! Carnivores and vegetarians are all well cared for.  Let them know your preference when you make your reservation. They will gladly accommodate special dietary needs.

This isn't a big, luxury cruise ship. There are only 15 cabins.
No TV's or radios (headphones are acceptable!) It's a chance to escape our noisy world, disconnect from the crowds and our daily schedules, to live in nature with like minded people experiencing the raw beauty of the islands and the wildlife of Maine sailing aboard an historic vessel.

We'll be transported back in time while also being pampered with great food and friendship!

During the week I'll perform three concerts, all acoustic with no sound system. Suggest to me your favorite DW songs and I'll do my best to accomodate.

MORE INFO: www.SailGraceBailey.com

Book Now!

Riding the Enoch (dinghy) for our daily shore
excursion on one of the countless islands!

One of the many lighthouses along the Maine Coast!