Sailing Vacations and Windjammer Cruise Sailing Schedule...
The Liberty Clipper sails in Boston Harbor in the Summer months offering 2-hour harbor cruises. You can find information on our overnight "windjammer cruises" below or get more information on our summer Boston Harbor Cruise.
Windjammer Cruises and Sailing Vacations on the Liberty Clipper. Our schedule of windjammer cruise sailing vacations in New England, the Chesapeake Bay and the Bahamas Sailing Vacations is below (booking policies are at the bottom of the page).
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Bahamas – Out Islands 2011-2012 Sailing Schedule |
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| Date | Description | Cost per person | Book a trip |
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November 2011 Windjammer Cruises |
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| November 20 – 26, 2011 | Bahamas Sailing Cruise - Thanksgiving Cruise! | $ 1,299 | Book it! |
| November 27 – Dec 3, 2011 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| December 2011 Windjammer Cruises | |||
| December 4 – 10, 2011 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| December 11 – 17, 2011 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book It! |
| December 20 – 26, 2011 | Caribbean Holiday and Carnival Parade | $ 1,299 | Book it! |
| December 27 – Jan 2, 2012 | New Years 2012 and Carnival Parade | $ 1,299 | Book It! |
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January 2012 Windjammer Cruises |
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| January 8 – 14, 2012 | Bahamas Sailing Cruise - Only 3 Cabins Left! | $ 1,199 | Book it! |
| January 15 – 21, 2012 | Bahamas Sailing Cruise - Out Islands - SOLD OUT! | $ 1,199 | Sold Out! |
| January 22 – 28, 2012 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| January 29 –Feb. 4, 2012 | Bahamas Sailing Cruise - Only 2 Cabins Left! | $ 1,199 | Book it! |
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February 2012 Windjammer Cruises |
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| February 5 – 11, 2012 | Bahamas Sailing Cruise - Only 5 Cabins Left! | $ 1,199 | Book it! |
| February 12 – 18, 2012 | Bahamas Sailing Cruise - Only 3 Cabins Left! | $ 1,199 | Book It! |
| February 19 – 25, 2012 | Bahamas Sailing Cruise - Only 1 Cabin Left! | $ 1,199 | Book it! |
| February 26 – Mar. 3, 2012 | Bahamas Sailing Cruise - Only 1 Cabin Left! | $ 1,199 | Book it! |
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March 2012 Windjammer Cruises |
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| March 4 – 10, 2012 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| March 11 – 17, 2012 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| March 18 – 24, 2012 | Bahamas Sailing Cruise - Only 1 Cabin Left! | $ 1,199 | Book it! |
| March 25 – 31, 2012 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
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April 2012 Windjammer Cruises |
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| April 1 – 7, 2012 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| April 8 – 14, 2012 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| April 15 – 21, 2012 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| April 22 – 28, 2012 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| April 29 – May 5, 2012 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| May 2012 Windjammer Cruises | |||
| May 6 - 12, 2012 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book It! |
| May 13 – 19, 2012 | Bahamas Sailing Cruise - Only 1 Cabin Left! | $ 1,199 | Book It! |
2011-2012 Season Bahamas Windjammer Cruise Notes:
- All Bahamas sailing cruises board at 5:00pm on the start date and disembark at 10:00am on the end date. On the boarding night, you'll be responsible for dinner ashore in Nassau. All Bahamas cruises are subject to a port fee.
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Offshore Adventure Cruises - Spring 2012 May 2012 Repositioning Cruise Schedule |
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| Date | Description | Cost per person | Book a trip |
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May 2012 - Offshore Adventure Cruise |
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| May 20 – 25, 2012 | Nassau, Bahamas to Charleston, SC - SOLD OUT! | $ 995 | Sold Out! |
| May 24 – June 2, 2012 | Charleston, SC to Boston, MA - 2 Berths Left! | $ 995 | Book It! |
Adventure Cruise Notes:
- This is a repositioning cruise and dates above are approximate based upon weather conditions. Please call our office to discuss the specifics of the trip and to book passage.
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New England / Chesapeake Bay / Offshore Passages 2012 Summer & Fall Sailing Schedule |
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| Date | Description | Cost per person | Book a trip |
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Coastal Cruies and Offshore Adventure Sails |
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| September 1 – 3, 2012 | Boston: Gloucester Schooner Race - SOLD OUT! | $ 650 | Sold Out! |
| Sept 29 - Oct 5, 2012 | Boston to New York: Islands of New England Cruise | $ 950 | Book it! |
| October 5 - 9, 2012 | New York to Baltimore: Coastal Cruise | $ 650 | Book it! |
| October 10 - 14, 2012 | Chesapeake Bay Schooner Race Cruise | $ 850 | Book it! |
OFFSHORE ADVENTURE CRUISES |
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| October 14 - 23, 2012 | Portsmouth, VA to Amelia Island, FL (Jacksonvile area) | $ 750 | Book it! |
| October 28 - Nov 1, 2012 | Amelia Island, FL to Freeport, the Bahamas! | $ 650 | Book it! |
New England Sailing Cruise Notes:
- Gloucester Schooner Race: You will board the vessel in Boston at 8:00am Saturday, September, 1st. Breakfast and lunch are included. The ship will set sail by 9:00am on Saturday September 1st for Gloucester and return to Boston by 6:00pm on Monday, the 3rd.
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Bahamas – Out Islands 2012-2013 Sailing Schedule |
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| Date | Description | Cost per person | Book a trip |
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November 2012 Windjammer Cruises |
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| November 18 – 24, 2012 | Bahamas Sailing Cruise - Thanksgiving Cruise! | $ 1,299 | |
| November 25 – Dec 1, 2012 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | |
| December 2012 Windjammer Cruises | |||
| December 2 – 8, 2012 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | |
| December 9 – 15, 2012 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book It! |
| December 16 – 22, 2012 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book It! |
| December 23 – 29, 2012 | Caribbean Holiday and Carnival Parade | $ 1,299 | Book it! |
| December 30 – Jan 5, 2013 | New Years 2012 and Carnival Parade | $ 1,299 | Book It! |
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January 2013 Windjammer Cruises |
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| January 6 – 12, 2013 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| January 13 – 19, 2013 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book It! |
| January 20 – 26, 2013 | Bahamas Sailing Cruise - Out Islands - SOLD OUT | $ 1,199 | Sold Out! |
| January 27 –Feb. 2, 2013 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
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February 2013 Windjammer Cruises |
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| February 3 – 9, 2013 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| February 10 – 16, 2013 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book It! |
| February 17 – 23, 2013 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| February 24 – Mar. 2, 2013 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
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March 2013 Windjammer Cruises |
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| March 3 – 9, 2013 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| March 10 – 16, 2013 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| March 17 – 23, 2013 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| March 24 – 30, 2013 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| March 31 – Apr 6, 2013 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| April 2013 Windjammer Cruises | |||
| April 7 – 13, 2013 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| April 14 – 20, 2013 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| April 21 – 27, 2013 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| April 28 – May 4, 2013 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book it! |
| May 2013 Windjammer Cruises | |||
| May 5 - 11, 2013 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book It! |
| May 12 – 18, 2013 | Bahamas Sailing Cruise - Out Islands | $ 1,199 | Book It! |
2012-2013 Season Bahamas Windjammer Cruise Notes:
- All Bahamas sailing cruises board at 5:00pm on the start date and disembark at 10:00am on the end date. On the boarding night, you'll be responsible for dinner ashore in Nassau. All Bahamas cruises are subject to a port fee.
Booking policies:
- A 50% deposit is due when you make your reservation.
- The balance is due 60-days prior to your cruise.
- The deposit, less a 10% handling fee on the cost of the entire cruise, is refundable up to 60-days prior to your cruise date, after which date the deposit is non-refundable and the balance is due in full.
- All prices are per person, based upon double occupancy. Single supplement fees may apply.
Please keep in mind the Liberty Clipper is a working sailing ship. Your safety and comfort are important to us. If you require any special assistance, have any dietary concerns, or any other special circumstances, please contact us so that we may make adequate arrangements to ensure a pleasurable and safe voyage.
We recommend travel insurance. We are an authorized re-seller for Travel Guard Insurance. Please call or email our office to book your trip specific policy. For general information, you can visit Travel Guard's website at http://www.travelguard.com.

