2025 Sailing Schedule

Price Per Person

All prices listed below are per person.

☆ May 22-26 / Wine, Dine, and Chocolate

4 NIGHTS (THU-MON) $968 / SPACE AVAILABLE – BOOK MY TRIP
Indulge yourself over Memorial Day weekend! Learn more

May 27-30 / Available for Private Charter

Day sail, overnight, or two-night cruise. Enjoy your own private schooner for that special group outing or vacation. Contact us for rates.

May 31-June 4 / Booked for Private Charter

4 NIGHTS (SAT-WED)

☆ Jun 6-11 / Music + Windjammer Gam

5 NIGHTS (FRI-WED) $1,318 / FULL
Live blues and Americana music featuring the Taber house band The Charlie Nobles. Learn more

☆ Jun 12-16 / Gourmet Gastropub

4 NIGHTS (THU–MON) / $1,218 / SPACE AVAILABLE – BOOK MY TRIP
Indulge in classic bistro fare prepared by a special guest Chef James Tranchemontagne of Frog & Turtle Restaurant. Learn more

☆ Jun 17-21 / Summer Solstice + Live Music

4 NIGHTS (TUE-SAT) $1,218 / ONE CABIN AVAILABLE FOR 2 – BOOK MY TRIP
Unwind each evening with Nashville based songwriter Jenn Schott. Learn more

☆ Jun 22-26 / Culinary Explorations

4 NIGHTS (SUN-THU) $1,218 / SPACE AVAILABLE – BOOK MY TRIP
Prepare yourself for la dolce vita as our chef and Fiore Olive Oils and Vinegars impress and delight with every meal. Learn more

☆ Jun 28-Jul 5 / The Great Schooner Race

7 NIGHTS (SAT-SAT) $2,238 / FULL
Join us for North America’s largest annual gathering of tall ships. Learn more

Jul 6-10 / Chocolate With Kate Shaffer

4 NIGHTS (SUN-THU) $1,398 / SPACE AVAILABLE – BOOK MY TRIP
Joining us for this trip will be Kate Shaffer from Ragged Coast Chocolate. Learn more

Jul 11-15 / Weekend Escape

4 NIGHTS (FRI-TUE) $1,398 / SPACE AVAILABLE – BOOK MY TRIP

Jul 16-20 / Four-Night Getaway

4 NIGHTS (WED-SUN) $1,398 / SPACE AVAILABLE – BOOK MY TRIP

Jul 22-26 / Four Nights Booked for Private Charter

4 NIGHTS (TUE-SAT)

Jul 27-30 / Music With Louisa Stancioff and Friends

3 NIGHTS (SUN-WED) $1,248 / SPACE AVAILABLE – BOOK MY TRIP
Louisa Stancioff is an accomplished singer and musician. We will end our lovely sailing days with an acoustic set from Louisa. She has the voice of an angel. Learn more

Jul 30-Aug 2 / Three-Night Getaway

3 NIGHTS (WED-SAT) $1,248 / SPACE AVAILABLE – BOOK MY TRIP

Aug 3-9 / Captain’s Choice

6 NIGHTS (SUN-SAT) $1,848 / SPACE AVAILABLE – BOOK MY TRIP
Captain Noah’s birthday is August 8, so we’ll spend the week indulging in all of his favorite spots and eats.

Aug 10-16 / Perseids Meteor Shower

6 NIGHTS (SUN-SAT) $1,898 / FULL
The best way to see the stars!

☆ Aug 17-20 / Three-Night Getaway

3 NIGHTS (SUN-WED) $1,248 / SPACE AVAILABLE – BOOK MY TRIP

Aug 22-26 / Four Nights Booked for Private Charter

4 NIGHTS (FRI-TUE)

☆ Aug 27-31 / Camden Windjammer Festival

4 NIGHTS (WED-SUN) $,1,358 per person / SPACE AVAILABLE – BOOK MY TRIP
We’ll go out with a bang at Camden’s annual waterfront festivities. Learn more

Sept 1-5 / Four-Night Music With Chicky Stoltz and Ragged Company

4 NIGHTS (MON-FRI $1,328 per person / SPACE AVAILABLE – BOOK MY TRIP
A blend of Americana, alt country and roots rock. Learn more

☆ Sept 7-13 / WoodenBoat Rendezvous

6 NIGHTS (SUN-SAT) $1,638 / Full moon / SPACE AVAILABLE – BOOK MY TRIP
Celebrate true craftsmanship with a trip to a boat-building school. Learn more

☆ Sept 14-20 / Wine, Dine, and Cheese

6 NIGHTS (SUN-SAT)/ $1,698 / SPACE AVAILABLE – BOOK MY TRIP
Visit a different country each evening through its cheese, wine and food. Learn more

☆ Sept 21-25 / Autumn On the Bay

4 NIGHTS (SUN-THU) $1,198 / SPACE AVAILABLE – BOOK MY TRIP
Crisp days, cool nights, a new moon great for stargazing, and a strong breeze defines this autumn sail! Learn more

☆ Sept 26-30 / Autumn On the Bay

4 NIGHTS (FRI-TUE) $1,198 / SPACE AVAILABLE – BOOK MY TRIP
Starry nights define this autumn sail. Learn more

☆ Oct 1-5 / Fall Colors and Half Moon Café

4 NIGHTS (WED-SUN) $1,198 / SPACE AVAILABLE – BOOK MY TRIP
Witness the beautiful landscape of Maine while experiencing some fantastic sailing and live music with Bill Barnes. Learn more

☆ Oct 6-9 / Fall Colors

3 NIGHTS (MON-THU) $958 / Full moon / SPACE AVAILABLE – BOOK MY TRIP
Witness the beautiful landscape of Maine while experiencing some fantastic sailing. Learn more