Maine has a reputation for being the ultimate cruising ground. Lots of nooks and crannies and miles of coastline to explore. So when we realized we wouldn’t get there, it was a bit of a disappointment.

Not for long. New England cruising, the little we’ve done, has captured our hearts in a way we never, never expected. Sure, there are drawbacks - I’ll touch on a few of those at the end of this - but overall? Sheer amazingness.

The water is blue. No Chesapeake brown up here, except for the rare jaunt up a river. There’s the dark blue of deep water, the light blue/green that indicates a sandy bottom, the patches of visible-from-far-away brown that indicate rock to avoid.

The terrain is varied. We’ve seen river banks and fields and craggy sheer cliffs, rock islands and wide beaches, all within day sail distances. There are towns (even cities!) to explore or uninhabited islands to anchor off of, and each has its own flavor. We didn’t get to anyplace in Martha’s Vineyard other than Vineyard Haven, but apparently the three main towns on that small island each has its own very very unique vibe.

The boat-watching is superb. There have been a number of places where just taking the dinghy around the anchorage to check out all the really really cool boats has been a favorite way to spend the afternoon. From impeccably maintained wooden boats of all sizes to fleets of Nonsuch to awesome fishing boats, there’s something to gawk at everywhere you turn.

The sailing has blown us away. It might be that we finally have decent sails, including a code zero for light air that has seen a lot of use, but most days we have wind to move the boat. This is a big difference from what we usually have in the Chesapeake in the summer. We also see many, many more boats actually sailing up here, as opposed to motoring on perfect wind days which seems to be the norm for sailboats everywhere.

We’ve discovered places we’d never heard about (Thimble Islands), been awed by others (Newport and Hadley Harbor), explored beaches (Block Island) and walked towns (Essex) and watched sunsets (everywhere!). We’ve only scratched the surface and will be back for sure.

There are a few things to get used to up here. 

Mooring fields. A lot of harbors are filled with moorings, many of them empty, some available for rent from the town itself. Space that has no moorings is buoyed off with “NO ANCHORING” markers, meaning you need to anchor far out in unprotected water or in super deep places. It feels a bit like someone’s staking out a great parking place and sticking an orange traffic cone across it even if they’re not there. We haven’t seen much to indicate this is anything other than a revenue move by locales. Certainly their prerogative. If we spend money on a mooring, we won’t have money to spend on other things like eating out or renting bikes. We have thus far found anchoring spots that are fine with us even in places where there are mooring fields.

Dinghy docks. Sometimes difficult to find. Often accompanied by signage that indicates it’s “touch and go only - 30 minute maximum” unless you have an annual, residents-only dinghy permit. Frequently filled by dinghies that are tied tight to the dock with their engines tipped up.

Currents. We’re just not used to currents of any strength! Paying attention to when you’ll be moving with the current can make your sailing day a lot shorter. It’s also way more fun to check your speed over ground when you’ve timed it right.

Massachusetts beaches. Beaches on private islands in Massachusetts, at least the ones we saw (the Elizabeth Islands), all had MASSIVE signs every 100 feet or so. These signs are visible (though not readable) from a mile or further away. Some signs read “Visitors welcome” or “Beach open”; others read “NO TRESPASSING KEEP OUT PRIVATE BEACH”. The signs mar what would otherwise be beautiful scenery, even if you are allowed to walk. Mass state law, dating back to 1641, deeds the private land all the way to the low water mark; most places deed private land ownership only to the high water mark, meaning the intertidal areas are supposed to be open to the public. 

Ticks. The deer ticks that carry Lymes are so rampant around here that in Massachusetts, every trail head sign had a prominent laminated flyer warning of tick presence. Not having any shoes other than our flip flops, and definitely not wearing long pants and long white socks, we did not explore off the road. Note to self: source some lightweight long pants, long white socks, and shoes that are not open-toed. Plus some good tick repellant. We’re not interested in getting Lymes, thank you very much.

We arrived in New England on August 19. Since then, we’ve been largely skipping around to cool new places every night. 

Block Island, RI

Fisher’s Island, NY

Bridgeport, CT (Hurricane Henri)

Port Jefferson, NY

Thimble Islands, CT

Branford, CT

Thimble Islands, CT

Essex, CT

Mystic, CT

Ram Island, CT

Wickford, RI

Bristol, RI

Newport, RI

Jamestown, RI

Cuttyhunk, MA

Tarpaulin Cove, MA

Vineyard Haven, MA

Hadley Harbor, MA

Dutch Harbor, RI (back side of Jamestown)

Block Island, RI

East Harbor, Fishers Island, NY

We haven’t even hit the crown jewel of New England and we’re already besotted. New England. 10/10. Would recommend.