I am planning a trip to either Martha's Vineyard or Nantucket from October 6 - 16. Is this a good idea? Will things be open? Will we be able to go on a whale watching cruise? Which island is better? We would like to relax, take walks, ride bikes, go to restaurants, shops, whale watching...

Each island has its charms and virtues.

Nantucket is more compact, with a single town in the middle and villages at each end. Martha's Vineyard has multiple towns, each with its own character, and is more spread out. Each has lots of historic architecture, but Nantucket has the edge here since so much is visible in a small space.

You can walk, ride bikes, shop, and eat well in both places. Most of Nantucket is accessible by bike if you are moderately fit. The Vineyard is bigger, so you would probably want a car. Everything (well, almost everything) will be open, and you have Columbus Day weekend that will bring lots of people.

It will be too cool to swim (unless you are from Quebec) but it should be good for walking on the beach. Most beaches in Massachusetts are private, but Nantucket property owners generally let orderly users on their beaches to a greater degree than on the Vineyard, where this is a real issue.

My friends in the tourist business will hate for me to say this, but it is my impression that neither place is ideal for classic whale watching. I think the North Shore (Salem, Gloucester, Cape Ann in general) is a lot closer to big whales, and I am not even sure they are around at this time of year. You could spend a week on one of the islands, then go north of Boston for three days IF the whale watch companies are still running then.

Well, you can certainly stay on either island for this time and generally the weather is good in October. However, it is hurricane season and you should take that into consideration for your planning.

You may wish to consider staying on the mainland and visiting either place on a daytrip - that way you can pick the day that will have good weather.

Whale watching goes on until the end of October but out of Boston or Cape Ann or P'town, Salem, etc.At times, the whale watching can be terrific at this time since the whales are "ganging up" to take the trip south.