My favorite island! We finally bought a timeshare there to be able to go every year. What kind of work does your husband do? It's terrific to be able to get some travel money for your visit. The government per diem is not as high as I would expect based on island prices, but I think it's higher than $50 if he has a govt job. I tried for a temporary job there once and looked it up at the time.
Unless you are meeting your dearest friend, it isn't worth wasting an island day to make the trip to Hyannis. Maybe you can persuade her to make the trip over and enjoy Nantucket with you for a day.
That's a terrific flight price. The last time we flew over was more than 25 years ago. We got a cheap flight to Boston, but the Boston to Nantucket leg more than doubled the flight cost.
We cook most of our meals on the island, but always hit the Brotherhood for at least a bowl of Chowder. Sign up for TownPool Nantucket emails at
http://www.townpool.com . They are similar to Groupon and have been having a lot of really nice deals lately. We used one restaurant certificate when we were there in June (for the Hen House, good food) and two for bakeries (nice desserts). I've never made it out there, but the restaurant at the airport apparently has nice food and has some good deals (you'd need a car to get there).
If you won't have access to a car, definitely rent a bike. Youngs Bike Shop at the Steamship Wharf comes highly recommended. The Chamber of Commerce building right downtown has maps and magazines showing all the activities. We go to a different beach every day and always run out of days before we hit all the beaches. They are all very different.
I'm not a big shopper either, but still recommend a stop in Patina for really nice clothing and jewelry and the Hospital Thrift store for books and island goodies. Look for art galleries (our friend David Lazarus just had an show open), and if you're there at the right time, attend an antique auction.
We haven't been in September since our kids started school, but it's probably the nicest time of the year to visit. The trip out to Bartlettt's Farm is always a must do and we always go to Madaket for the sunset every evening. We always drive over to Sconset one day to look at the rose covered houses and visit the Wauwinet House at least once. We haven't been able to do it for several years, but a trip out to Great Point is terrific. You'd need an oversand vehicle to do that. We also try to get in a late afternoon fishing trip and watch the sunset from the boat.
If you have any specific questions, I'll try to answer them. My only regret every year is that we can only stay one week. I'm trying to figure out some way to turn that into two. So much to do that a week just isn't long enough.
Sheila