Skip to main content

Favorite Weekend Cruise: Boston Harbor Islands

We dropped anchor in the lee of an uninhabited island and pulled the dinghy up the sandy beach. Soon we had a campfire blazing and the entire island to ourselves.

We dropped anchor in the lee of an uninhabited island and pulled the dinghy up the sandy beach. Soon we had a campfire blazing and the entire island to ourselves. Then an American Airlines 777 came in for a landing amazingly close to the top of our mast and almost blew our fire out. As we learned during a magical weekend spent cruising among the 34 islands that comprise Boston Harbor Islands National Park, watching (and at times feeling) the planes land is all part of the fun.

We started our cruise in Hingham on Boston’s south shore, but any harbor within a 25-mile radius of the city puts you within easy striking distance of this unique cruising ground. We got a late start and didn’t sail far that first day, but that’s one of the benefits of cruising Boston Harbor: you don’t have to sail far to find the fun, and most “passages” can be completed in a couple of hours. The sailing is also typically fast and flat among the protected islands, the majority of which are wild and uninhabited, in spite of the close proximity to the city; the channels between the islands are deep and well-marked; and the islands are so close together that the pilotage is as easy as pointing and saying, “Head over there.” You do, however, have to watch out for commercial traffic. Tankers, cruise ships, whale watchers and high-speed ferries churn up the channels with regularity.

Our time was limited, so we sailed straight to Grape Island, just off Hingham, and pitched a tent ashore, since we were sailing aboard a pocket cruiser with limited space. In fact, sleeping in the tent added such a wonderful dimension to the cruise that since then, I’ve encouraged all my cruising friends to bring camping supplies, even if they are aboard boats with more palatial accommodations. Camping is allowed on many of the harbor islands and you can confirm campsite availability at bostonharborislands.org.

The next morning we sailed out with the current (it can get up to 5 knots) through Hull Gut and around America’s first lighthouse, Boston Light, which was built in 1716 and then rebuilt in 1783 after the British destroyed it during the Revolu tionary War. Like the nearby city, these islands are steeped in history. Boston Light on Little Brewster Island is the last manned lighthouse in the United States, and Grape Island not only has a number of ancient shell middens but was also the site of an early Revolutionary War skirmish. Fort Warren, on Georges Island, was used as a prison for captured Confederate soldiers during the Civil War and is reported to have a ghost. Nearby Lovells Island still showcases Fort Standish’s old concrete watch towers and gun emplacements—which like Fort Warren remained active through both World Wars—in addition to the stellar beach where we built a campfire for our final night out.

While we were sitting around the campfire, basking in the glow of our fantastic day of sailing and adventuring among stunningly beautiful and culturally interesting islands, it dawned on me: wait a minute, I live here.

And maybe that’s the best part of all. We’re not the only people who live within a 25-mile radius of these wonderful islands that are hidden in plain sight. But as the fire crackled, the crickets chirped, the tiny wavelets lapped up the beach and the Boston skyline lit up, we sure felt like it. Just then, British Airways flight 213 banked in on its final approach into Logan, straight from London, and we had the best seats in the house.

Related

Background-02

Notice to Mariners: A Blog from the SAIL Editors

As a teenager, I stumbled across a copy of Derek Lundy’s Godforsaken Sea in the back room of a used bookshop. I had never heard of the Vendée Globe and frankly found all the boat-speak in the first 50 pages a little difficult to get through. But Lundy’s storytelling and the draw ...read more

Screen-Shot-2022-01-13-at-9.26.59-AM2048x

VIDEO: Celestial Navigation Episode 2

Celestial navigation is an invaluable tool for all kinds of sailors. In episode two of the celestial navigation series, learn the basic elements of navigation and the sight reduction process using declination and GHA to determine the Geographic Position and navigate using a ...read more

Film-poster

Cruising: Year of the Sea Shanty

Along with other timeless pursuits, like baking sourdough and gardening, singing sea shanties surged back into popularity during the recent lockdown, thanks, in part, to the app TikTok and its “duet” feature, which allows singers from around the world create music together. By ...read more

Book-Cover-9780712353700

Book Review: Sailor Song

Sailor Song is the ultimate guide to the music of working sailors during the 18th and 19th centuries. The book includes lyrics and sheet music for 50 of the most beloved sea songs with fascinating historical background on the adjoining page. Chapter introductions provide ...read more

Screen Shot 2022-01-12 at 10.42.33 AM

Race Update: RORC Transat

With the fleet leaders about halfway to Grenada, the 2022 RORC Transatlantic is shaking out to be a tactically interesting one. The race, now in its 8th edition, began on Saturday with 30 teams ranging from 70-foot catamarans to a 28-foot JPK 1010. Early in the race, light winds ...read more

01-LEAD-IMG_1585

Experience: Fire Down Below

Due to the Covid-19 pandemic, local racing had resumed with household crews only. My wife, though, while always up for a pleasure sail, was not up for this kind of thing, so, for the fifth time in what was any measure an unusual sailing season, I found myself singlehanding my ...read more

BestBoats2022-logo

Best Boats 2022

In case you hadn’t heard, the fall 2021 boat show season was one for the record books. If there was ever any doubt the sailing public still enjoys making its way to Newport, Rhode Island, or Annapolis, Maryland, to see the latest in boat design, those doubts were put to rest ...read more

01-LEAD-Dominique-David-2048x

Mulithull Show Coming to La Grande-Motte

After a year without boat shows, 2021 proved to be a blockbuster summer and fall for events around the globe, and the International Mulithull Show is looking to continue that trend in 2022. First held in 2010, the show, which takes place in La Grand-Motte, France, on the shores ...read more