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


2021
PRE-SEASON SPECIALS
Jun 13 Six-Day $1,045.00
Jun 13 Three Day - 1st half $745.00
Jun 16 Three-Day - 2nd half $745.00
Jun 20 Six-Day $1,045.00
Jun 20 Three Day - 1st half $745.00
Jun 23 Three-Day - 2nd half $745.00
Jun 27 Six-Day $1,045.00
Jun 27 Three Day - 1st half $745.00
Jun 30 Three-Day - 2nd half $745.00
 

SUMMER IN MAINE

2021
THREE AND FOUR DAY CRUISES
THREE-DAY
Board Sun. 5:30pm - Return Wed. 10:00am
Jul 04
Price: $845.00
Jul 11
Price: $845.00
Jul 18
Price: $845.00
Jul 25
Price: $845.00
Aug 01
Price: $845.00
Aug 08
Price: $845.00
Aug 15
Price: $845.00
Aug 22
Price: $845.00
Aug 29
Price: $845.00
FOUR-DAY
Board Wed. 5:30pm - Return Sun. 10:00 am
Jul 07
Price: $945.00
Jul 14
Price: $945.00
Jul 21
Price: $945.00
Jul 28
Price: $945.00
Aug 04
Price: $945.00
Aug 11
Price: $945.00
Aug 18
Price: $945.00
Aug 25
Price: $945.00
Sep 01
Price: $945.00
FIVE DAY & WEEKEND CRUISES
FIVE-DAY
Board Sun 5:30 pm - Return Fri 10:00 am
Jul 04
Price: $1,095.00
Jul 11
Price: $1,045.00
Jul 18
Price: $1,045.00
Jul 25
Price: $1,045.00
Aug 01
Price: $1,045.00
Aug 08
Price: $1,045.00
Aug 15
Price: $1,045.00
Aug 22
Price: $1,045.00
Aug 29
Price: $1,045.00
WEEKEND
Board Fri 2:00 pm - Return Sun 10:00 am
Jul 09
Price: $795.00
Jul 16
Price: $745.00
Jul 23
Price: $745.00
Jul 30
Price: $745.00
Aug 06
Price: $745.00
Aug 13
Price: $745.00
Aug 20
Price: $745.00
Aug 27
Price: $745.00
Sep 03
Price: $745.00

AUTUMN AND FALL FOLIAGE SPECIALS

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

2021
THREE AND FOUR DAY CRUISES FIVE DAY & WEEKEND CRUISES
THREE-DAY
Sep 05
Price: $795.00
Sep 12
Price: $795.00
Sep 19
Price: $795.00
Sep 26
Price: $795.00
FOUR-DAY
Sep 08
Price: $895.00
Sep 15
Price: $895.00
Sep 22
Price: $895.00
Sep 29
Price: $895.00
FIVE-DAY
Sep 05
Price: $995.00
Sep 12
Price: $995.00
Sep 19
Price: $995.00
Sep 25
Price: $995.00
WEEKEND
Sep 10
Price: $695.00
Sep 17
Price: $695.00
Sep 24
Price: $695.00
Oct 01
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 2021 Mistress
THREE-DAY
Board Sun. 5:30pm - Return Wed. 10:00am
Jul 04
Price: $950.00
Jul 11
Price: $950.00
Jul 18
Price: $950.00
Jul 25
Price: $950.00
Aug 01
Price: $950.00
Aug 08
Price: $950.00
Aug 15
Price: $950.00
Aug 22
Price: $950.00
Aug 29
Price: $950.00
FOUR-DAY
Board Wed. 5:30pm - Return Sun. 10:00 am
Jul 07
Price: $1,085.00
Jul 14
Price: $1,085.00
Jul 21
Price: $1,085.00
Jul 28
Price: $1,085.00
Aug 04
Price: $1,085.00
Aug 11
Price: $1,085.00
Aug 18
Price: $1,085.00
Aug 25
Price: $1,085.00
Sep 01
Price: $1,085.00
FIVE-DAY
Board Sun 5:30 pm - Return Fri 10:00 am
Jul 04
Price: $1,220.00
Jul 11
Price: $1,220.00
Jul 18
Price: $1,220.00
Jul 25
Price: $1,220.00
Aug 01
Price: $1,220.00
Aug 08
Price: $1,220.00
Aug 15
Price: $1,220.00
Aug 22
Price: $1,220.00
Aug 29
Price: $1,220.00
WEEKEND
Board Fri 2:00 pm - Return Sun 10:00 am
Jul 08
Price: $815.00
Jul 16
Price: $815.00
Jul 23
Price: $815.00
Jul 30
Price: $815.00
Aug 06
Price: $815.00
Aug 11
Price: $815.00
Aug 13
Price: $815.00
Aug 20
Price: $815.00
Aug 27
Price: $815.00
Sep 03
Price: $815.00

AUTUMN AND FALL FOLIAGE SPECIALS

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

Mistress 2021 Mistress
THREE-DAY
Sep 05
Price: $900.00
Sep 12
Price: $900.00
Sep 19
Price: $900.00
Sep 26
Price: $900.00
FOUR-DAY
Sep 08
Price: $1,035.00
Sep 15
Price: $1,035.00
Sep 22
Price: $1,035.00
Sep 29
Price: $1,035.00
FIVE-DAY
Sep 05
Price: $1,170.00
Sep 12
Price: $1,170.00
Sep 19
Price: $1,170.00
Sep 26
Price: $1,170.00
WEEKEND
Sep 10
Price: $765.00
Sep 17
Price: $765.00
Sep 24
Price: $765.00
Oct 01
Price: $765.00

View 2022 Schedule

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