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2 min readWinter

A Quieter Kind of Valentine's Weekend

Boston is a lovely city fifty-one weekends of the year. Valentine's is not one of them. Forty-five minutes north is a different proposition.

By Dotti Maguire

Eastern Point Lighthouse and breakwater at sunset, Gloucester

Every Valentine's weekend Boston's prix-fixe menus run $180 a head and the reservations go at 4pm or 10pm. Forty-five minutes north of the city, none of this is true.

Here is how we would spend it.

Friday Night

Check in late afternoon. Walk Main Street in Gloucester or Bearskin Neck in Rockport before sunset. Buy something you didn't plan to buy: a handmade soap, a print from one of the galleries, a bottle of wine for the weekend. Head back to the house. Light a fire. Open the wine.

For dinner, keep it easy. Short and Main on Main Street for the pasta, Franklin Cape Ann for something a little more ambitious. The Rhumb Line on Fort Point if you want a bar with a jukebox and a harbor view instead. When you arrive, reply to your confirmation email and we will tell you which has a table and which one fits your mood.

Saturday

Sleep late. The beauty of Cape Ann in February is that nothing is open before 10am and nobody expects it to be.

A long walk somewhere cold: the Atlantic Path in Rockport, the Annisquam loop, or Dogtown if the trails are dry. Lunch at a coffee shop with a water view is the right energy for the middle of this kind of day.

Afternoon nap at the house is encouraged. Mid-afternoon light through a window in February is the second-best light of the year.

Saturday Night

This is the night you book in advance. The Gloucester House on the waterfront for the fireplace and the harbor view, or Tonno on Main Street for a proper Italian dinner. Rockport's dinner roster is thinner in February, so if you are staying in Rockport, drive into Gloucester. The Emerson Inn dining room is the exception, with two fireplaces and the kind of quiet that Valentine's wants.

Ask us the morning of. We know who is open and who has a table that night.

After dinner, a walk along the harbor in the dark. The fishing boats are all lit for winter work. The lighthouse signals are visible in the distance. Hold hands. This is why you came.

Sunday

Coffee somewhere quiet. A drive to Essex for antiques or to Ipswich for more antiques. A late lunch at one of the year-round spots along Route 133 that has been feeding people for decades. Home by dusk.

Why This Works

The thing about a Valentine's weekend away is that the weekend itself is the gift. Not the prix fixe, not the overpriced champagne, not the waiting for a table. The gift is the slowness and the space. Both are in abundance here in February.

Book the house early. The few winter weekends with real demand are Valentine's, school vacation, and the weekend around St. Patrick's. They go fast.

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