googlecdb1128845f42c47.html VICTORY CHIMES | Maine Sailing Cruise Descriptions

Experience the Music of the Wind and Sea


PO Box 1401
Rockland, ME 04841 

© 2019 All rights reserved | Custom site design, copy & principal photography by Q. Donleavy

Boundless Welcome

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Victory Chimes

Sail Aboard

 Maine Sailing Cruises

Fun descriptions of our upcoming Maine sailing cruises, all departing from the heart of the midcoast, Rockland Maine. 


 Maine Sailing Cruises

Discount Land & Sea Packages:

We board the night on the date listed on the schedule between 6 and 8 p.m., and arrive back in Rockland before noon on the last date on the schedule.

Cancellation Policy

Scroll down or click month


June Cruises

Photo courtesy of Cody Olson
  • Wednesday, May 29 - Saturday, June 1

3 Night Cruise

Private Charter

This private charter is booked by a school trip. Remember when school trips meant hours in a yellow bus? Well, not anymore, these lucky kids will be adventuring around the Maine coast.

If you're interested in having an adventure of your own for your group, whether it's a school trip, business retreat, family outing, or group vacation, get in touch with us to plan your special outing. 

  • Sunday, June 2 - Wednesday, June 5

3 Night Cruise

Private Charter

Don't  be too jealous, you can can do it too. Give us a call to arrange your own ultimate getaway. 

  •  Thursday, June 6 - Tuesday, June 11

5 Night Cruise, $900 per person

Gam Week

What is a Schooner Gam? 

A Gam is where one boat ties up to the other so they create a small floating world.

On this week the schooners will anchor in a harbor together one evening and you will be able to visit other boats and have a look around. "Schooner Party" explains it nicely. Maine is one of the only places in the world where you can see 12 Schooners of this magnitude in the same harbor.


This gathering is to celebrate the unique living Maritime culture of Maine bringing the boats together so that you see them for yourself.

  • Wednesday, June 12 -  Saturday, June 15

3 Night Cruise, $675 per person

Music Cruise with Hubby Jenkins

Hubby Jenkins is a talented multi-instrumentalist who endeavors to share his love and knowledge of old-time American music. Born and raised in Brooklyn he delved into his Southern roots, following the thread of African American history that wove itself through country blues, ragtime, fiddle and banjo, and traditional jazz.


Often performing with the Grammy Award winning Carolina Chocolate Drops, here, he'll be all ours! His repertoire of old-time American music is soulful complement to our storied schooner of 119 years.


His company and concerts will be a memorable treat to top a day at sea and follow our down home cooking. Come sail away with us into a world of exquisite beauty to enjoy three days of relaxation, fine music and good company as we explore Secret Maine with Hubby Jenkins aboard.

Click on the picture to learn more about Hubby Jenkins

and hear his music!

Hubbh Jenkins Sea Great Music portrait.j
  •   Friday, June 21 - Wednesday, June 26

5 Night Cruise, $900 per person

Music & Jamming with Linda McRae

Imagine you are on the beautiful Victory Chimes the vintage wood of deck under your feet while the music wafts through the harbor. We welcome you to bring your instruments and jam with Nashville artist Linda McRae. Performing on banjo, guitar and accordion her warm and world-weary voice, unforgettable melodies and thought-provoking lyrics, make McRae a captivating and sought-after artist.


If you don't play don't be shy come anyway! There will be evening performances, and beautiful sailing and island exploring, something for everyone.

There will be limited spaces available for a songwriting course (+100pp) led by Linda if you are interested please ask!

Click on the picture to learn more about Linda McRae

and hear her music!

Linda McRae 3.jpg
  •   Thursday, June 27 - Sunday, June 30

  3 Night Cruise, $700 per person

Music Cruise with Heather Styka

Join us for two days of stunning scenery, good food and laughter, while you enjoy the sweet music of Chicago born singer songwriter.

Heather Styka who dances where others fear to tread, gleefully cutting to the truth with gutsy vulnerability. She combines the lyrical intricacy of folk with a catchy melodic pop sensibility and the grit of classic country in songs that are smart and disarming. Her witty acoustic music promises to add a special touch to this taste of the Maine Coast.

Click on the picture to learn more about Heather Styka & hear her music!

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July Cruises

The Great Schooner Race is a local event that celebrates the culture of sailing and wooden boats that is present and strong in Maine until this day.


Join us for a week of cruising islands and outdoor adventure featuring The Great Schooner Race where the whole of the Schooner fleet will be invited to Race a full days course with a plentiful amount of friendly competition, ending in an evening awards ceremony and party.

Great Schooner Race

  • Monday, July 1 - Saturday, July 6

5 Night Cruise, $1000 per person

What better inspiration than gorgeous scenery, Historic vessels and the music of the wind and the sea for your creative efforts? This trip will Feature a parade of the Schooner Fleet which will be an amazing time to get that perfect shot of a ship under full sail. This trip is open to everyone and will have all the usual and wonderful things we offer, great sailing, good food, and good company.

We will be bringing a special guest Jesse Stuart, an incredible local photographer who will offer a photography workshop for an extra 75$ to those interested!

And, when it's getting too dark to take pictures, we'll have the talented musician Dennis Warner aboard to play some of his wonderful acoustic music after dinner!

Parade Week & Photography Workshop with Jesse Stuart

Also featuring musician Dennis Warner

  •  Sunday, July 7 - Saturday, July 13

6 Night Cruise, $1035 per person

A full week on the Victory Chimes gives you a chance to enjoy the experience to its fullest giving you time to get into your groove and explore more islands.


With more time we can go further offering a chance for you to get a real feel for Maine. The food will be great and the company better, and with Captain Sikkema as your guide, your Maine experience will be exceptional.

Classic Windjamming Week

  •  Sunday, July 14 - Saturday, July 20

6 Night Cruise, $1035 per person

The annual Maine Humor cruise. Comedian Gary Crocker will be sailing with us for his 8th year making you laugh harder than you knew you could. This while you enjoy the Summer sunshine and rocky coast of Maine, as we show you what our exquisite archipelago has to offer.

Click on the picture to learn more about Gary Crocker

and hear his humor!

Humor Cruise with Gary Crocker

  • Monday, July 22 -  Thursday, July 25

3 Night Cruise, $700 per person

Maine Sailing laughter.jpg

In the peak of Maine's summers, beautiful boats fill the waters in the day and stars fill the skies at night. The air is mild and the sunsets glow warmly. We sometimes have dinner on deck and watch as the sun's showy finale dims to the darkest blue of dusk. 

Every spot on deck is front row to the best of Maine. Don't miss it.

Closeout July Sailing Week

  • Friday, July 26 - Wednesday, July 31

5 Night Cruise, $950 per person

 Maine Coast Cruises 

Experience the Muisc of the Wind & Sea



August Cruises

Captain Kip Files owned and sailed VICTORY CHIMES for 30 years, from 1988-2018. Legend has it that, if you book this cruise, you can still see him at the helm and walking the decks. Spooky. 

Actually, he's invited back for this engagement, so don't be shocked when you see him! He's back to enjoy the height of summer for this "Cameo Cruise" along the Coast of Maine. 


August tends to be warmer and be less gusty than other months. But what it lacks in wind is made up for with more leisurely sails and sweet Maine sunshine.


Time to tan and read your book, have a stroll on an island and eat a delicious meal on deck. An ideal chance for swimming and enjoying a fresh salad and an ice cold drink. 

Also, with Captain Kip Files back for this trip, you'll get to hear some tales from his storied time with this sweet ship.

Summer Cameo Cruise

  • Thursday, August 1 - Monday, August 5

4 Night Cruise, $900 per person

Join us for two days of summer fun and island exploring accented by musical performances by the locally renowned and wandering band of Miners Creek with the VICTORY CHIMES as your backdrop.

Miners Creek play Contemporary Bluegrass at its best; they meld Bluegrass with pop, rock, jazz, folk, Latin, Appalachian, gospel and blues. 
The magical experience of gathering together on deck while the music wafts through the harbor is a truly unforgettable experience.

Click on the picture to learn more about Miners Creek and hear their music!

Music Cruise with Miners Creek

  •  Tuesday, August 6 - Friday, August 9

 3 Night Cruise, $700 per person

Miners Creek Summer concert series victo

Dyado an eclectic indie rock and folk duo from North Carolina will be joining us for this trip, to fill the harbors with glorious harmonies and creative original and traditional songs.


Cousins Matt Lohan and Louisa Stancioff the creators of this heartfelt duo are sure to be good company, and as excited as you to enjoy this Maine experience. And as excited to eat the food!

Click on the picture to learn more about Dyado and hear their music!

  •  Saturday, August 10 - Tuesday, August  13

 3 Night Cruise, $700 per person


The Full Moon will fall on the 15th, so our first night out will be your first chance to experience the wondrous, glowing, slow-motion Wow that is the moon rising on the water.

For this cruise, to deepen the experience, and to just add more Neato, in our Victory Chimes way, we've invited Mercedes Foster along for yoga and meditation sessions open to all levels, intro to expert. Trained in both Yin Yoga & Meditation, with a focus on body-positive teaching, she will host three sessions per day. Morning will be a meditation before breakfast with an afternoon yoga session and the evening capper will be either a session of Restorative Yoga, Yin or Guided Nidra Yoga.

Not only with this cruise provide a great outdoors experience, but we'll also be offering a valuable inner experience too. None of the sessions are required, but both yoga and meditation are proven to be beneficial and - it'll never be easier to try than on this cruise. If you know you'll be doing it, please bring your mat. Click the picture to learn more. 

Full Moon Yoga Cruise

  • Wednesday, August 14 - Monday, August 19

       5 Night Cruise, $1000 per person

Maine Moon sailing .jpg

Beat the heat and loll in the breezes! No matter how hot it gets on shore, it's always cooler on the water.


The islands are nice too, always catching the sea breezes, so we'll be going ashore wherever we happen to be. The wind and tides set our itinerary, so you'll enjoy the indulgence of "Chimes" time, which has no schedule but the meals. 

Three times a day you'll be spoiled and gathered together to share the simmering joy of summer sailing off the coast of Maine. Our trips are a pure experience of wind and sea; the music of sailing and the beauty of the sea. 

  • Tuesday, August 20 - Sunday, August 25

5 Night Cruise, $950 per person

Maine is a community rich in Maritime history and culture. The Camden windjammer festival is our communities recognition of the part that these vessels play within that culture.


The quaint seaside town of Camden will welcome us to their harbor for an evening of fun events including the annual crew talent show, not to be missed!


The rest of your week will spent sailing and exploring islands giving you a real taste of what the story of Maine has to offer.

Camden Windjammer Festival

  •   Monday, August 26 - Saturday, August 31

 5 Night Cruise, $1035 per person



September Cruises

  • SUN, September 1 - SAT, September 7

6 Night Cruise, $1035 per person

Annual Labor Day Cruise

A bit of a tradition on the VICTORY CHIMES, this cruise has many people who have been sailing with us for a long time. They like to sail hard and make tracks.


With the coming of September, the winds in Maine begin to pick up, and with the combination of the incredible coast and the growing level of the wind, the weeks in September offer some of the best coastal sailing you can find in the world.

  •  SUN, September 8 - SAT, September 14

 6 Night Cruise, $1035 per person

Wooden Boat Sail-In

Wooden Boats! Maine is full of them; it is one of the things that makes this place so special. On this week, the windjammer fleet will sail into Wooden Boat harbor, and the Wooden boat school of Brooklin Maine will invite us to stroll through their beautiful grounds, tour the school and have steamed mussels with them.


It is a gathering they hold for the windjammers ever year, offering an opportunity to see the fleet underway, and is a beautiful tradition of Maine.

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  • SUN, September 15 - THU, September 19

4 Night Cruise, $925 per person

Music Cruise with Piper Hayes   x

On this trip, while you enjoy the exquisite scenery and the fresh September wind, Canadian folk/roots singer, songwriter and social activist Piper Hayes and her partner Carson Ritcey-Thorpe will be joining us to regale you with their shining personalities. Their intricate guitar style, and beautiful harmonies are as authentic and as they are!

Click on picture to learn more about Piper & Carson,

and hear their music!

Wellness Cruise 3.jpg
  • FRI, September 20 - TUE, September 24

4 Night Cruise, $900 per person

Yoga, Wellness & Irish Music Cruise

What a combination! On this trip enjoy the peace and quiet of the Maine Coast without the sound of cars and city lights.


Nourish your body with healthy meals, and take in the beauty around you while you enjoy a massage or reiki session. Your evenings will be filled the beautiful and ancient melodies of traditional Irish Music. A wonderful combination!

Click on picture to learn more about this unique cruise we host!

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  • WED, September 25 - SAT, September 28

3 Night Cruise, $650 per person

Music Cruise with Nat Hussey

Would you like to know more about the Maine that not many get to see or experience? If you are the sort of traveler who loves to know the locals this is the trip for you. Nat Hussey, of Matinicus Island, Maine native, lobsterman, musician (and lawyer too) will be joining us to tell you about his story, through his original blues, folk and rock.

Click on the picture to learn more about Nat and hear his music!

  •   SUN, September 29 - WED, October 2 

  3 Night Cruise, $600 per person

Last Sail of the Season, with a Whiskey Chaser

Close out the season with us and come on this last trip to celebrate the season and toast it farewell with a Whiskey Tasting aboard. 

September winds will be at their finest, which will make this trip feel full of adventure.  As we enjoy the last few days of sailing for the year, it may be a little chilly, but crisp fall air lends a feeling of nostalgia to the surroundings, and as the leaves begin to turn, it will only make the scenery that much more breathtaking. And don't worry, there is always a fresh mug of hot tea or coffee waiting for you any time of the day.


Click images to read captions, because some are really good. 



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