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Plan your own voyage of discovery for Columbus Day weekend

The Windjammer Angelique sails out of Camden (Maine) Harbor for a three-day Columbus Day Foliage Cruise.Yoon S. Byun for the Boston Globe/Globe Freelance

This Columbus Day weekend, do like Columbus and set your sights on a sail. The leaves are colorful, the air is crisp, and the sea temps are still warmish. Take an organized sail with a skipper and crew — just show up, sit back, and enjoy the ride along the foliage-studded Maine coast or to the Boston Harbor Islands. Or, maybe you’re an experienced sailor and want to rent a sailboat for a couple of hours — the Charles River is a lovely escape. So, before winter knocks the wind out of your sails, consider these nautical ideas for getting out on the water during the long holiday weekend.



The Sailing Capital of the World is naturally a good fit for an autumn day sail. The quintessential Newport experience: a two-hour sail on a yacht from the America’s Cup days. During the Columbus Day weekend, you can sail on two of the America’s Cup 12-meter yachts — the Columbia and Heritage. Columbia won the America’s Cup in 1958, and Heritage, the last wooden America’s Cup yacht, raced in 1970. Kick back — or go for an all-hands-on-deck sail and join the crew who will show you how to grind the winches to raise the sails, and even let you take the helm. You’ll sail out of Newport Harbor into Narragansett Bay and glide by photo-worthy sights, including like Hammersmith Farm, the Rose Island Lighthouse, Fort Adams, and the rocky shoreline. The cost is $79 per person, and you can bring your own food, beer, and wine.


A sail on the Charles is an easy way to spend a day or couple of hours out on the water.

Courageous Sailing If you’ve got sailing chops you can rent and skipper your own sailboat from this nonprofit located on Pier 4 in Charlestown Navy Yard. If not, you’ll be set up with a skipper for your sail. The one-day sail rentals begin at $95 (without an instructor), depending on the boat. Courageous is all about helping Boston kids build life skills through sailing, as well as bringing sailing to the community.


Community Boating Qualified skippers 18 and older can rent a 15-foot keel version Cape Cod Mercury sailboat (for up to four adults) from this Charles River sailing center that’s celebrating its 70th year. You can sail the Charles from the Longfellow Bridge to the Harvard Bridge. (Note that the skipper must verbally demonstrate sailing ability to a dock master before a rental will be approved). The cost is $79 for the day.

Classic Harbor Line Pack a picnic and take a schooner sail on one of two classically styled sailing vessels out of Boston Harbor. The 80-foot all-wooden Adirondack III is a throwback to an 1890s pilot schooner with teak decks, mahogany rails, two towering Douglas fir masts, and almost 2,000 square feet of sail that stretch to the heavens. The elegant Northern Lights is a nod to the Gatsby era and the New England commuter yachts that offered quick transport for the uber-rich from Fall River to New York City. Beer, wine, and cocktails are available for purchase, and water and soda are complimentary.

You have many options over Columbus Day weekend — board Northern Lights for a one-hour inner Harbor Cruise, a Boston Harbor Islands Cruise, Sunset Cruise, Boston Celtic Cruise, and Boston Jazz Cruise. Or, opt for a day sail on Adirondack III.



Got a seafaring dog? Kennebunkport is a seaworthy spot for a pet-friendly sail. The Pineapple Ketch departs from The Nonantum Resort marina off of Ocean Avenue (a half mile from Dock Square). Pack a picnic and BYOB — and your own dog — and take the sunset sail that heads out past the breakwater and beaches to Walker’s Point, better known as the Bush compound. All dogs are welcome but “we do limit our canine sailor to one per trip,” says boat owner John E. Martin, “so we need to be alerted to them when you make a reservation.”


Coastal Maine typically reaches peak foliage this time of year, and over Columbus Day weekend, there are three windjammer sailing opportunities out of Rockland and Camden.

The Windjammer Angelique sails out of Camden Harbor for a three-day Columbus Day Foliage Cruise. The ship is reminiscent of a 19th-century sailing ship that once fished off the coast of England. The Schooner Stephen Taber, a National Historic Landmark, sails out of Rockland for a four-day journey. Schooner Ladona, also from Rockland, is a newly restored ship and is offering a four-day sail. A Downeast lobster bake is a highlight on each of the cruises, and there are also opportunities for paddleboarding into fishing villages or remote islands.

Laurie Wilson can be reached at