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Schooner Race

Great Chesapeake Bay Schooner Race

Example 5 Day Cruise aboard Liberty Clipper
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Join the Liberty Clipper on this 5-day racing cruise, sailing amongst a fleet of tall ships and schooners as you race from Baltimore to Portsmouth. This adventure includes a parade of sail and a crew party in Baltimore, and the schooner race and the awards ceremony with pig and oyster roast in Portsmouth. Join the crew as they look to earn another victory in the race - 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. Experience the thrill of racing amidst a fleet of tall-ships! 

Day-by-Day Summary

Day 1 : Baltimore | Embark
Days 2-4 : The Great Chesapeake Bay Race
Day 5 : Portsmouth | Disembark


  • Experience the thrill of racing amidst a fleet of over 50 tall ships
  • Enjoy sunset under full sail in Chesapeake Bay and some night-time sailing
  • Savor the chef's wonderful food to keep you going during the race


Liberty Clipper

Places Visited


Trip Type

  • Small Ship

Activity Level


Trip Snapshots

Schooner Race Baltimore's Inner Harbor Chesapeake Bay Bridge in Early Morning Portsmouth, New Hampshire Sail along the Potomac River

Day 1 Baltimore | Embark

Board the ship between 12:00 noon and 3pm to kick off this annual Windjammer Race event! The Liberty Clipper participates in the Parade of Sail at 5:00pm and sails 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 can join the party ashore later that evening at the Schooner Party held in the Latin Room. The festivities continue with the Sailors' Evening in Fells Point.

Day 2-4 The Great Chesapeake Bay Race

  • Ship
  • 3 Breakfasts, 3 Lunches, 3 Dinners
In the morning feel the excitement in the harbor as the Fleet heads out into Chesapeake Bay and heads towards the starting line of the Great Chesapeake Bay Schooner Race with a starting gun at 1:00pm. The Liberty Clipper is the 2005 Champion - this is the year to win back the title!

The 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 can enjoy sunset under full sail in Chesapeake Bay and some night-time sailing. Your Chef prepares wonderful food to keep you going during the excitement of the race.

Once you arrive at the finish line, 127 miles south in Portsmouth, Virginia, stay for the award ceremonies and explore the town.

Day 5 Portsmouth | Disembark

  • 1 Breakfast
Disembark in the morning, at 10:00am 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.

This cruise is a favorite and space is limited so book your spot now for this historic race down the Chesapeake!

Liberty Clipper

Per person starting at
Accommodations aboard the Liberty Clipper
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Standard Cabin
4 cabins located on the port and starboard sides of the midship area, with two single-size bunks, skylight hatch, and close access to a shared bathroom.
Cabins aboard the Liberty Clipper
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Premium Cabin
3 cabins slightly larger than standard cabins with single sized upper bunk, wider lower bunk, skylight hatch, and access to a shared bathroom.
Accommodations aboard the Liberty Clipper
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Private Bath
5 cabins with single sized lower bunk, wider upper bunk, skylight hatch, and private attached toilet and shower room.


All rates are per person based on double occupancy. A select number of premium cabins are available for an additional fee.

Cruise fares do not include port taxes, an additional 5% of total cost.

Rate Includes:
  • 1 bunk space in a standard double-occupancy cabin
  • All meals for the duration of your trip* Excluding Sunday night dinner
  • Coffee, tea, and juice (unlimited)
Note: bottled water, soda, and alcoholic beverages are not included and may be purchased separately on board, or consider one of our Drink Passes (see below)
  • All linens – sheets, blankets, bath towels, beach towels, pillows
  • Use of all on-board water toys, such as snorkeling gear, kayaks, paddleboards, etc
Rate Excludes:
  • Port fees (calculated as tax)
  • Travel expenses (Airfare, train tickets, taxi fare, etc) to/from the vessel boarding or disembarking locations
  • Hotel stays prior to or following cruise
Note: for transits or schooner races, you may be able to stay on board the night prior to departure for an extra fee -
Please contact for details.
  • Meals prior to or following cruise
  • Travel Insurance
  • Personal expenses such as souvenirs
  • Meals taken in place of those provided on board
  • Crew Gratuity – Our crew work very hard throughout your trip, and gratuities are always greatly appreciated. At the end of your trip you will have the opportunity to add this on to your cruise - we accept both cash and credit card on board. 15% of total cruise cost is recommended.
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The trip might have been the absolute best of our lifetime (thus far). We particularly want to commend our guide Peter in the Guilin area-he was so incredibly attentive, energetic, enthusiastic-and absolutely dedicated to ensuring that our meals were 100% vegetarian.
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