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Sail Aboard

Victory Chimes

2021 Adventures

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

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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.

Click Month or Scroll to Explore


JUN 2 - JUN 5

WED - SAT, 3 Night Cruise

Available for Charter

Group reward, family get together, school trip, reunion or wedding - make it whatever you want it to be by chartering the ship for your own adventure!

JUN 6 - JUN 10

SUN - THU, 4 Night Cruise

Standard Cabin Price $795

Join us for 4 nights at sea, while we island hop and enjoy fine feasts. At day's end we'll anchor in secluded coves. You can explore them in one of our small boats to enjoy the changing colors. Imagine being aboard our fine ship for a full and leisurely adventure.

Sailing Adventure

JUN 11 - JUN 15

FRI - TUE, 4 Night Cruise

Schooner Gam Week

Standard Cabin Price $805

A “Gam” is an old sailing term that referred to a social visit between whaling ships.


Today, it’s a whale of a good time and it includes the entire fleet! During this trip we all raft up together for a wonderful “social visit” with music, mingling and visits to each others ships.


We’ll be bringing our own music along, for the full trip - Fiddlehead Field will be sailing with us!


This trip will show you the best of Maine and introduce you to the full family of windjammers and our community of sailors and captains. It’s a beloved tradition and an extra special trip.

JUN 16 - JUN 20

WED - SUN, 4 Night Cruise

Spring Music Fling with Rising Appalachia!

Standard Cabin Price $1200

Sometimes, what you take with you on a trip can be as important as what you leave behind.

On this special trip, we’re bringing along the fantastic talent of Rising Appalachia! With Southern roots and global influences, Leah and Chloe have traveled the world for decades, building their fanbase and gathering influences.


And what are we leaving behind? Schedules, worries and the idea that you can’t have it all. Loud food, delicious scenery and warm concerts will be our recipe to serve up lifetime memories, every day. This is going to be so special!

JUN 21 - JUN 26

MON - SAT, 5 Night Cruise

Classic Five Nights at Sea 

Start your day helping to hoist sail, spend the day reading on deck or enjoying the scenery and the company of those around you as you sail past uninhabited islands and small fishing villages. Enjoy delicious meals and exploring missions to small islands. Spend your evening surrounded by peaceful beauty as you enjoy the harbor around you, and finish your day in a cozy bunk. And... Repeat!

Standard Cabin Price $972


JUN 27 - JUL 3

SUN - SAT, 6 Night Cruise

Boothbay Windjammer Festival

Standard Cabin Price $1,117

Join us for a six night sailing adventure as we make our way south to Boothbay where we will be one of several Schooners featured and honored at the Boothbay Windjammer Festival 2021!

JUL 4 - 10

SUN - SAT, 6 Night Cruise

Standard Cabin Price $1,316

Join us for the annual Great Schooner Race! This is the event of the year where we join the 8+ schooners that reside in Maine for a breathtaking spectacle sailing across Penobscot Bay. The Race is followed by a lovely ending ceremony with music and desserts put on by the Windjammer Association. 

Great Schooner Race Week

JUL 11 - 17

SUN - SAT, 6 Night Cruise

Journey Down East with Mike & Amy Aiken

Standard Cabin Price $1,325

This trip will be filled good music and laughter featuring Mike and Amy Aiken. Longtime sailors, living 24 years on their own boat, they play as a beautiful acoustic duo and will regale us with stories and songs as we join them for a voyage Down East to explore our magnificent Maine Coast from the vantage point of the sea. It always seems more beautiful from the water!

JUL 18 - 21

SUN - WED, 3 Night Cruise

Comedy on the Sea, featuring Gary Crocker

Standard Cabin Price $850

A fun couple of days island hopping and exploring while laughing until your sides hurt with Comedian Gary Crocker. Known for his down-home Maine humor, Gary is sure to let you in on a side of Maine you probably haven't heard about. And of course, don't forget all the good food you will be eating!

JUL 21 - 24

WED - SAT, 3 Night Cruise

Summer Jewel 

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. 

Standard Cabin Price $850

JUL 25 - 31

SUN - SAT, 6 Night Cruise

This full week of exploring islands and sailing our renowned local waters will be a real event. A week aboard gives you fuller time to relax and find your rhythm. Sailing with us will be Skylark, a trio playing a variety of traditional music ranging from old-time tunes, English and Irish ballads to jazz. Sailing with the musicians makes their concerts a more intimate experience and this longer trip connects you deeper to the island rhythm of exploring the Maine coast by sail. 

Standard Cabin Price $1,316

Sailing & Music Adventure with Skylark


V I D E O 

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AUG 1 - 6

SUN - FRI, 5 Night Cruise

Classic Summer Sailing with Chilvarous Crickets

Standard Cabin Price $1,210

Explore, relax, refresh. Five nights of summer sunsets and wonderful meals and, at night, live music by the Chilvarous Crickets. It's always cooler on the water and more relaxing under sail. This trip makes the dog days of summer purr like a kitten. Join us for five nights that you'll remember for a lifetime. 

AUG 7 - 10

SAT - TUE, 3 Night Cruise

Standard Cabin Price $880

If you've ever gotten a cinnamon bun and wanted to just scoop out the delicious, chewy center and indulge yourself in the best part - then this is your trip. It's August. It's the height of summer. It's the best time to be on the water, and away from any crowds.  This trip is a nugget of summer gold


Imagine feeling like you've really figured out how to summer. We'll explore Secret Maine and experience the best of what a Maine summer has to offer: peaceful scenes, exciting sailing, happy guests, fun island visits, and wonderful meals. 

August Gold

AUG 11 - 16

WED - MON, 5 Night Cruise

Adventure & Music with Dennis Warner

Standard Cabin Price $1,210

In the words of Dennis Warner himself, "It's not enough to show up and sing a few songs. I'm an entertainer at heart. My concert is more than music. I want it to be fun and hopefully a bit thought provoking too."   Join us to Explore our incredible Penobscot Bay and sail through its sparkling waters. While we enjoy Dennis Warners wonderful songs and celebrate his Birthday with him! If we are lucky this week may coincide with the Perseids meteor shower.

AUG 17 - 21

TUE - SAT, 4 Night Cruise

Sailing, Irish Music and Yoga,

a 20 year Chimes' tradition!

Standard Cabin Price $995

Join us for 4 nights, 3 days, of sailing, healthful food, Yoga on deck, and Irish Music in the evenings. What a combo! Pretty sure it only happens here, on this week in Maine. Joining us will be a longtime group of friends who make up an important piece of our Chimes family. They have sailed with the ship for almost 20 years and come every year to add workshops on mindfulness, healing and reiki sessions and beautiful performances of Irish music to the crisp September air by day and the peaceful anchorages by night.

AUG 22 - 28

SUN - SAT, 6 Night Cruise

Music and Sailing with Tim Grimm & Friends

Singer-songwriter Tim Grimm will be joining us for 6 nights of music-packed sailing adventure. He will be bringing a select guest artist to join us as well as himself. He specializes in leading groups on tours across several countries, helping his guests understand the musical cultures around them. We are thrilled to have him onboard with helping to connect the world of Maine's islands through the musical traditions around us.

Standard Cabin Price $1,350


V I D E O 

AUG 29 - SEP 4

SUN - SAT, 6 Night Cruise

Sweet Fleet Threepeat

Standard Cabin Price $1,325

6 night island hopping and exploring punctuated by a gathering of the fleet! It's always a treat to gather the fleet, and this will be the first time we do it three times in one season! Explore Secret Maine and meet up for family-style get together for this week of summer gold along the Maine coast. 

SEP 5 - 11

SUN - SAT, 6 Night Cruise

Standard Cabin Price $1,117

If you love adventure and exploring this is your trip! Weather permitting we will make our way Down East to Acadia to experience the celebrated national park from the vantage point of the water. The coast line is an exquisite backdrop to the tasty food and great friends you will be making along the way.

Annual Labor Day Cruise 

SEP 12 - 18

SUN - SAT, 6 Night Cruise

Wooden Boat Sail In

Standard Cabin Price $1,117

Maine is celebrated for being the home of countless beautiful traditional wooden boats and rich and thriving Maritime culture. This is your opportunity to get a taste of this culture! The Wooden Boat School set in the beautiful Blue Hill region will host us along with other traditional boats for an afternoon of fresh local steamed mussels and live music. The rest of the week be full of as much sailing as we can squeeze in and all our usual good food and small boat fun!

SEP 19 - 23

SUN - THU, 4 Night Cruise

Fall is in the Air; September Sail

Standard Cabin Price $905

Join us for 4 nights of sailing; with the crisp September winds picking up, this is sure to be an exciting adventure. 4 nights is a perfect sweet spot of not too long, not too short. You are sure to enjoy your island exploring and hearty delicious meals, with warm cider coming off the stove in the afternoon, and the talented duo of The Whiskey Geese playing for us in the evening. Listen here! This lovely trip will carry you deep into fall with warm memories.


SEP 24 - 27

FRI - MON, 3 Night Cruise

Classic Three Nights at Sea

As the air turns crisp and we start to feel fall in the air, join us for three nights on Penobscot Bay. Island hopping, exciting sailing as the winds in September pick up and apple cider hot off the stove!  

Standard Cabin Price $793

SEP 28 - OCT 2

TUES - SAT, 4 Night Cruise

Crisp fall air, exciting September winds, hot cider off the stove, acoustic music wafting across the harbor - the list goes on! The memories of the scenery around you and the water glistening in sunrises and sunsets will stick with you into the winter. Join us for these last 4 nights of our third season owning the unique VICTORY CHIMES.

Standard Cabin Price $868

Out with a Bang! Music & Fall Colors on the Sea

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V I D E O