Schooner Races

GCBSR 2013 02

The LIBERTY CLIPPER participates in two schooner races each year – the Gloucester Schooner Race and Schooner Festival held in Gloucester, Massachusetts, and the Great Chesapeake Bay Schooner Race where dozens of schooners race from Baltimore, Maryland to Portsmouth, Virginia! Schooner races are a thrilling look into the past – with so many tall ships sailing together, it is easy to imagine yourself transported to another time.


Great Chesapeake Bay Schooner Race

Trip Info
Dates: October 10 - 14, 2018
Route: Chesapeake Bay Schooner Race – Baltimore MD to Portsmouth, VA
Pricing: $825 per person
Passengers: 24
Board in Baltimore: 12:00 – 3:00 PM on Wednesday, October 10, 2018
Disembark Portsmouth: 10:00 AM Sunday, October 14, 2018


GCBSR 2013


BOOK the Chesapeake Bay Schooner Race NOW!

You'll experience the thrill of racing amidst a fleet of over 30 tall ships. In 2012, the LIBERTY CLIPPER sailed at 14.7 knots and set a new ship speed record! This was done while sailing past the mouth of the Potomac River - what a thrill it was! This cruise is a favorite and space is limited so book your spot now for this historic race down the Chesapeake.



2018 Intinerary & Scheduled Events


12:00 – 3:00 PM: You'll board the ship between 12:00 noon and 3 PM to kick off this annual tall ship event!

5:00 PM: The Liberty Clipper will participate in the Parade of Sail and sail Baltimore Harbor in the company of a fleet of tall ships! Be sure to have your camera ready as over 50 ships participate in this event. As a guest aboard the Liberty Clipper, you will be eligible to join the party ashore later that evening at the Schooner Party. The festivities will continue with the Sailors' Evening.


As the sun comes up this morning you will feel the excitement in the harbor as the Fleet moves into the Chesapeake Bay and heads towards the starting line of the Great Chesapeake Bay Schooner Race. The Liberty Clipper is the 2005 Champion - we'll give it our best to win back the title this year!

1:00 PM – Starting gun of the Great Chesapeake Bay Schooner Race!

Racing through the Chesapeake Bay

This itinerary of this cruise is determined by the winds. The fastest race time to date is 11 hours 18 minutes, set in 2007. If the winds are light, unusual at this time of year, the race can be significantly longer and may last up to 20 hours. In either event, you will enjoy sunset under full sail in the Chesapeake Bay and some night-time sailing. Our Chef will prepare wonderful food to keep you going during the excitement of the race.  (Last year, there was perfect wind from the start, all the way to the end. Winds were out of the ENE around 20 knots, gusting up to 25 knots at times. Those who could flew spinnakers, while the big boats almost danced with glee.)

Once we arrive at the finish line, 127-miles south in Portsmouth, Virginia, we will stay for the award ceremonies and give you a chance to explore the town.





10:00 AM – Disembark in Portsmouth. The Norfolk and Newport News airports are very close or you may take an easy train ride back to Baltimore for a round-trip flight.

For more information about the Great Chesapeake Bay Schooner Race, please visit the Race's official website.

GCBSR 2012


PLEASE NOTE:  Events that are scheduled by the Great Chesapeake Bay Race Organization are planned and controlled by that organization. 
Please be aware that the race organization reserves the right to make venue changes as well as changes in their planned events. 
That said, we'll make sure you'll have one heck of a time on our Liberty Clipper, as THAT we can ensure!

34th Annual Gloucester Schooner Festival

2018 Trip Info
Dates: September 1, 2018 to September 3, 2018 (Labor Day Weekend)
Cruise Options: 3 day overnight cruise ($600/person)
Single all-day cruises:
·        Sep. 1: Boston-Gloucester offshore transit ($100 Adult / $75 Youth)
·        Sep. 2: Gloucester Schooner Race ($125 Adult / $100 Youth)
·        Sep. 3: Gloucester-Boston offshore transit ($100 Adult / $75 Youth)
Capacity: 24 Overnight guests
12 day passengers (in addition to overnight guests)


Gloucester Schooner RaceSet sail on the Liberty Clipper for the Gloucester Schooner Race and Schooner Festival on Labor Day Weekend! Gloucester is a wonderful seaport village steeped in maritime history and lore. In 2017, over 30 schooners plied the waters off of Cape Ann, Massachusetts during this annual gathering of tall ships. This weekend of special sailing events is an annual favorite and space is limited, so book today!

BOOK The 3-Day Gloucester Schooner Race Event!


2018 Itinerary & Scheduled Events

All cruises include breakfast and a BBQ lunch served on deck.

Saturday, September 1, 2018:  Boston to Gloucester Offshore Sailing

8:00 AM: Boarding begins for our offshore adventure. Enjoy coffee and breakfast on deck as we prepare the ship to get underway. If you are coming in from out of town, you may stay on board the night before – call us for details!

9:00am - 4:00pm: The ship will sail offshore from Boston to Gloucester, MA. The ship will sail out of Boston Harbor and pass Boston Light while making passage to the beautiful Cape Ann. On this leg of the cruise, you may see whales in Massachusetts Bay and will likely sail in the company of other schooners on their way to Gloucester for the Gloucester Schooner Race.

7:30 – 10:00 PM (approx.) Lighted Boat Parade & Fireworks Cruise: The Liberty Clipper will sail in Gloucester Harbor to watch a lighted Parade of Sail and spectacular fireworks!

Book the Boston-Gloucester Sail!


Sunday, September 2, 2018: Annual Gloucester Schooner Race Cruise!

8:00 – 8:45 AM:  Boarding for day cruise passengers. We will depart promptly at 8:45 AM to line up for the race.

9:00am - 4:00 / 5:00 pm (approx.): The Liberty Clipper will compete in the Mayor's Cup, racing in the coastal waters off of Cape Ann against a large fleet of tall ships! Be sure to bring your camera - events like this present the rare opportunity to get some great pictures of a fleet of tall ships pressing forward under sail!

Book the Gloucester Schooner Race Day Event!


Monday, September 3, 2018: Gloucester to Boston Offshore Sailing

8:00 AM: Boarding begins for day cruise passengers.

9:00am - 4:00pm:  The ship will sail offshore from Gloucester, MA to Boston, MA. The ship will sail out of Gloucester bound south for Boston. As on the transit up from Boston, we may have the opportunity to see whales in Massachusetts Bay and will likely sail in the company of other schooners on their way home from the race. Hear the crew tell their stories of the race and parties ashore. We'll be having a special lunch prepared, courtesy of our Professional Chef!

Book the Gloucester-Boston Sail!