Schedules & Reservations


Welcome to Maine Windjammer Cruises

The Original Windjammer Fleet

Explore our overnight cruise schedules & Plan Your Trip Today!

Questions? (800) 736-7981

No matter when you sail with Maine Windjammer Cruises you will experience amazing scenery, lighthouses, wildlife, stunning sunrises and sunsets, congenial shipmates, delicious meals and of course Lobsters!

SCHOONERS GRACE BAILEY & MERCANTILE

Four cruise options weekly

SELECT A DATE TO BEGIN YOUR RESERVATION

Printable Schedule Click Here


2022
PRE-SEASON SPECIALS
May 20 Weekend $675.00
May 22 Four-Day Preseason $845.00
May 22 Six-Day $1,045.00
May 22 Three Day - 1st half $745.00
May 25 Three-Day - 2nd half $745.00
May 27 Weekend $695.00
May 29 Three Day - 1st half $745.00
May 29 Six-Day $1,045.00
Jun 01 Three-Day - 2nd half $745.00
Jun 05 Six-Day $1,045.00
Jun 05 Three Day - 1st half $745.00
Jun 08 Three-Day - 2nd half $745.00
Jun 12 Three Day - 1st half $745.00
Jun 12 Six-Day $1,045.00
Jun 15 Three-Day - 2nd half $745.00
Jun 19 Three Day - 1st half $745.00
Jun 19 Six-Day $1,045.00
Jun 22 Three-Day - 2nd half $745.00
Jun 26 Three Day - 1st half $745.00
Jun 26 Six-Day $1,045.00
Jun 29 Three-Day - 2nd half $745.00
 

SUMMER IN MAINE

2022
THREE AND FOUR DAY CRUISES
THREE-DAY
Board Sun. 5:30pm - Return Wed. 10:00am
Jul 03
Price: $845.00
Jul 10
Price: $845.00
Jul 17
Price: $845.00
Jul 24
Price: $845.00
Jul 31
Price: $845.00
Aug 07
Price: $845.00
Aug 14
Price: $845.00
Aug 21
Price: $845.00
Aug 28
Price: $845.00
FOUR-DAY
Board Wed. 5:30pm - Return Sun. 10:00 am
Jul 06
Price: $945.00
Jul 13
Price: $945.00
Jul 20
Price: $945.00
Jul 27
Price: $945.00
Aug 03
Price: $945.00
Aug 10
Price: $945.00
Aug 17
Price: $945.00
Aug 24
Price: $945.00
Aug 31
Price: $945.00
FIVE DAY & WEEKEND CRUISES
FIVE-DAY
Board Sun 5:30 pm - Return Fri 10:00 am
Jul 03
Price: $1,095.00
Jul 10
Price: $1,045.00
Jul 17
Price: $1,045.00
Jul 24
Price: $1,045.00
Jul 31
Price: $1,045.00
Aug 07
Price: $1,045.00
Aug 14
Price: $1,045.00
Aug 21
Price: $1,045.00
Aug 28
Price: $1,045.00
WEEKEND
Board Fri 2:00 pm - Return Sun 10:00 am
Jul 08
Price: $795.00
Jul 15
Price: $745.00
Jul 22
Price: $745.00
Jul 29
Price: $745.00
Aug 05
Price: $745.00
Aug 12
Price: $745.00
Aug 19
Price: $745.00
Aug 26
Price: $745.00
Sep 02
Price: $745.00

AUTUMN AND FALL FOLIAGE SPECIALS

September offers what we consider some of the best sailing of the season!

2022
THREE AND FOUR DAY CRUISES FIVE DAY & WEEKEND CRUISES
THREE-DAY
Sep 04
Price: $795.00
Sep 11
Price: $795.00
Sep 18
Price: $795.00
Sep 25
Price: $795.00
FOUR-DAY
Sep 07
Price: $895.00
Sep 14
Price: $895.00
Sep 21
Price: $895.00
Sep 28
Price: $895.00
FIVE-DAY
Sep 04
Price: $995.00
Sep 11
Price: $995.00
Sep 18
Price: $995.00
Sep 25
Price: $995.00
WEEKEND
Sep 09
Price: $695.00
Sep 16
Price: $695.00
Sep 23
Price: $695.00
Sep 30
Price: $695.00

MISTRESS

Each week, the Mistress sails either a three-day trip & four-day trip or a five-day trip & weekend trip. The length of the first reserved trip determines what the other trip will be. Reservations are by double only (2,4,6). Prices are per person.

NA indicates Not Available and F indicates Full

SUMMER IN MAINE

Mistress 2022 Mistress
THREE-DAY
Board Sun. 5:30pm - Return Wed. 10:00am
Jul 03
Price: $950.00
Jul 10
Price: $950.00
Jul 17
Price: $950.00
Jul 24
Price: $950.00
Jul 31
Price: $950.00
Aug 07
Price: $950.00
Aug 14
Price: $950.00
Aug 21
Price: $950.00
Aug 28
Price: $950.00
FOUR-DAY
Board Wed. 5:30pm - Return Sun. 10:00 am
Jul 06
Price: $1,085.00
Jul 13
Price: $1,085.00
Jul 20
Price: $1,085.00
Jul 27
Price: $1,085.00
Aug 03
Price: $1,085.00
Aug 10
Price: $1,085.00
Aug 17
Price: $1,085.00
Aug 24
Price: $1,085.00
Aug 31
Price: $1,085.00
FIVE-DAY
Board Sun 5:30 pm - Return Fri 10:00 am
Jul 03
Price: $1,220.00
Jul 10
Price: $1,220.00
Jul 17
Price: $1,220.00
Jul 24
Price: $1,220.00
Jul 31
Price: $1,220.00
Aug 07
Price: $1,220.00
Aug 14
Price: $1,220.00
Aug 21
Price: $1,220.00
Aug 28
Price: $1,220.00
WEEKEND
Board Fri 2:00 pm - Return Sun 10:00 am
Jul 08
Price: $815.00
Jul 15
Price: $815.00
Jul 22
Price: $815.00
Jul 29
Price: $815.00
Aug 05
Price: $815.00
Aug 12
Price: $815.00
Aug 19
Price: $815.00
Aug 26
Price: $815.00
Sep 02
Price: $815.00

AUTUMN AND FALL FOLIAGE SPECIALS

September offers what we consider some of the best sailing of the season!

Mistress 2022 Mistress
THREE-DAY
Sep 04
Price: $900.00
Sep 11
Price: $900.00
Sep 18
Price: $900.00
Sep 25
Price: $900.00
FOUR-DAY
Sep 07
Price: $1,035.00
Sep 14
Price: $1,035.00
Sep 21
Price: $1,035.00
Sep 28
Price: $1,035.00
FIVE-DAY
Sep 04
Price: $1,170.00
Sep 11
Price: $1,170.00
Sep 18
Price: $1,170.00
Sep 25
Price: $1,170.00
WEEKEND
Sep 09
Price: $765.00
Sep 16
Price: $765.00
Sep 23
Price: $765.00
Sep 30
Price: $765.00

Our schooners are available for single day trips and charters on Wednesdays and Sundays. In the pre-season, they may be available for additional dates. Most trips are from noon to 4 p.m. On daysails, our larger schooners can hold from 29 to 49 guests each. Smaller parties can be accommodated on the Mistress. Please call for availability and pricing. Learn more about Charters & Daysails