Large Sailing Ships Vacation Ideas

Large Sailing Ships Vacation Ideas #1: The Schooner Timberwind sails out of the harbor at Rockport, Maine and she’s a beautiful sight under full sail as she leaves the Rockport breakwater in her wake. Just think, no phones, no faxing, no honking cars and the boss can’t get in touch with you as you sail in the protected waters and Islands of Penobscot Bay. The Timberwind offers 3, 4 and 6 day cruises. These cruises are known for their A+ cooking and typically include, of course, Maine lobster.

No, you don’t have to help with the sailing chores, but most voyagers like to assist so that they’ll have some good stories to tell their friends back home. The cruises on the Schooner Timberwind could be considered a family affair as the owner and his wife are part of the crew.

#2: The Liberty Fleet of Tall Ships sails out of Boston, the Chesapeake Bay and the Bahamas. This is windjammer sailing at its best. There are several options for the specific voyage course at each of the three base locations. Each windjammer vacation is always completely unique.

If you take a train ride you are limited to where the tracks were laid. When you sail on a tall ship the choices of where to sail are limited only by the tides, the winds and the desires of the passengers.

The goal is to have a cruise that is exciting and yet relaxing and memorable. The crews typically welcome the passengers to take part in the operation of the ship.

You can learn to plot the course, raise the sail, or even man the helm with the captain by your side. The crews of these ships include a professional chef so you can expect some great food.  

All of the sailing is done from mid-morning to mid-afternoon which provides relaxation time for reading, napping and fellowship with fellow voyagers. One thing to remember is that you are anchored in the middle of a large swimming pool so take a refreshing dip.

The second thing to remember is that, on the water, sunrises and sunsets are fully visible so have your camera ready when night falls. This brings up the best part which is being rocked to sleep like a baby by the gentle tides.

Typical sailing courses out of Boston are north to the coast of Maine or South to Cape Cod and the Islands (Martha's Vineyard and Nantucket). Chesapeake Bay cruises typically leave from Baltimore inner harbor and cruise to Annapolis or along the eastern shore near Saint Michaels. The Bahamas Cruises home port is Nassau and they visit the many islands in that area.

Schooner Zodiac
Schooner Zodiac
Large Sailing Ships Vacation Ideas #3: The Schooner Zodiac sails out of Bellingham, WA and has a very robust schedule of cruises. They specialize in multi-day cruises with a special twist. For instance, they have 4 day winery tours, 6 day tall ship festival cruises and a 3 day artists’ workshop cruise plus many more.

They also have several short day sails for special events such as an evening dinner sail, a mother’s day sail and a 4th of July sail. The artists’ workshop cruise is particularly interesting as it offers well-known artist, Austin Dwyer on board for the journey. Painting and sailing, now that’s a creative marriage.

The Zodiac can handle up to 26 passengers for multi-day voyages and the accommodations and the food are top rate. The ship and the cruises are owned and managed by the Zodiac Corporation.  

#4: Star Sail Cruises has many ships and thus offers a variety of cruises in both the Pacific Northwest and in the Bahamas islands of the Caribbean. One of Star Sails’ specialties is training want-to-be sailors how to handle a schooner. With a licensed captain and an experienced crew you can learn how to sail the larger traditional sailing ships.

Star Sail Cruises has several vessels which can be used for these the training cruises. These are real hands-on, adventure cruises for future captains and future crew members. The schooner Martha is frequently used for these training trips. Martha has an overall length of 84 feet with a deck length of 68 feet and a 2,250 square foot sail area.

You will join the crew and help raise the sails, stand watches, chart the course, and take the helm. Other skills to be mastered are navigation and knot tying. You’ll sail the San Juan Islands, Desolation Sound and the Gulf Islands which are all just north of Seattle, WA.  

Large Sailing Ships Vacation Ideas #5: The Arabella is probably one the three most beautiful windjammer sailing vessels in existence. She is so stunning that when she enters a harbor everybody stops what they are doing to stare.

She has three masts and at least six sails and is 160 feet in length. Everything from the private bathrooms to the teak decks is modern first class. In the summer the Arabella offers the finest 5 or 6 night vacation cruises in the New England and Chesapeake Bay areas.

In the winter it’s off for several of the favorite cruises in the Caribbean. For more information contact Capt. George Sloane at Just search “Windjammer Arabella” on the internet and check out the photos.

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