Freedom of Too Many Choices

We’re probably not going to make it to Maine.

There. I said it out loud, wincing a little. We’ve been looking forward to the challenges and joys of cruising in Maine since we realized we weren’t going to be far enough along on boat projects to get to the Bahamas or the Caribbean before hurricane season. The Maine Cruising Guide was even one of Jeremy’s Christmas presents; we’ve eagerly accosted anyone we come across who has any Maine sailing connection and used their guidance to mark up the book.

Between getting a later start than we wanted, the need to wait for weather (or even be shoved backwards by a certain hurricane, ahem Henri), and the hard deadline to be in Annapolis by the end of the first week in October, it just doesn’t really feel feasible. Not the way we like to cruise anyway.

You’d never know it from that first week push, but our preferred way of cruising involves exploring. Picking up the hook and leaving an anchorage with no real destination other than a general direction, a few likely spots picked out depending on how the sailing is. When we left Port Jefferson on Wednesday, August 25, we happily ghosted along for hours before we realized we couldn’t even make our closer destination before midnight without turning on the engine, so on went the Yanmar. After the hook was set at Charles Island, we dug out the paddle boards and circumnavigated the island, then had sundowners on the bow. In the morning, we took the dinghy ashore to circumnavigate by foot before leisurely picking up anchor and sailing under code zero, awning up in the fierce heat, all the way to the Thimble Islands, a whopping 15 miles east. We saw blazing speeds of 2-3 knots. It was perfect.

*Code Zero plus awning = great shady ghosting*

Of course we could make it to Maine. It would be a “tag you’re it” kind of thing, where we pushed hard to get there only to turn around and head south again. That’s not our style of cruising but we could do it. Why, though?

*Evening light catches a perfect fishing boat in the Thimble Islands*

There’s so much to see out here it can be overwhelming. Or maybe, just maybe, it’s liberating. We ducked into the Thimble Islands because we wanted to get somewhere under sail and it was close enough to be able to do that in the super light winds. What we discovered was a magic spot of rocks and trees, impossible buildings on what seem to be inhospitable terrain. An unexpected national park with a dinghy dock (time limit 1 hour on weekdays) and informative signs. We took the dinghy for an explore, circling some of the reported 365 islands and creating stories about the houses and the families who own them.

We didn’t see Block Island, other than the anchorage. Haven’t tucked into Essex or explored Mystic. Newport and Woods Hole are still places of myth in our world. All of those are “must see” spots on a New England cruise. If we’d raced from one of those to another, we’d have missed the Thimbles. That would have been sad indeed.

Maybe by realizing we can’t see it all, we can slow down and discover our own “must see” spots. Because they’re everywhere. If you give yourself the chance to find them.