I'll vote for landing on the ice runway in February.
Before that, how about a turkey farm at Thanksgiving or a tree farm at Christmas?
My birthday is in January so I'm sure you'll take me somewhere.
I am always up for block island. The cafe stays open in the winter but is not super large inside. Only one restaurant in town ope. After 10/15.
I still need to try Mansfield and see Tom on his turf.
Martha’s Vineyard is great for me too as is Nantucket.
Westerly is getting a new restaurant but it won’t be open until next Spring. The FBO at Westerly, Dooney has a nice operation where I am sure we could have a lunch if we bring our own food like we did at Montauk. Fuel is reasonable, $6.50 and they pump it for you.
Going West there is a dinner at Sussex that has already said they would give us also me special pricing.
KMVY is absolutely lovely - KACK only a little less so - in both places, with a little planning, either the FBO or a local van for a small fee could bring the group to/from a nice place in town for a lunch et al.......... which is a fabulous spot to hang -
the arrival to either island is stunning -- a favored destination when I'm taking family for an outing.