Help me pick a destination
 

I have a commitment outside WDC 22 September and then need to be in Chicago 29 September. A week to do anything in between, flying or driving. Thoughts of hurricanes somewhat of an impediment as far as settling on a destination.

Possibilities:

1) History driving tour to Richmond and then to Williamsburg. This is not exciting me even though I know it's a good idea and I would be glad I went. Husband hankers to see the Museum of the Confederacy in Richmond.

2) Have never been to Bermuda. But, hurricane season. Ditto for Bahamas, Turks & Caicos, etc.

3) Paris has been mentioned...I struggle with jet lag and multiple time zones, but for Paris, it might be worth it.

4) Montreal? Quebec?

5) Fly to Chicago and take a driving trip up to Traverse City area? Have never been there either. Hear that Glen Arbor is a nice area.

6) Thought about going to Palm Beach and basking at The Breakers but, again, hurricanes, and I hear it is even more beastly hot in Florida in September than the rest of the hellish summer months.

Have already done St. Michael's, Philadelphia, Gettysburg, Fredericksburg and I live part-time in NYC so those are not on the list.

I tend to be a planner, but am considering the possibility of just waiting until a week before and gauging the weather. Am I likely to find bargains if I do that?

I know everyone here is a savvier traveler than I am so am looking for suggestions.

Icelandair has flights to Iceland from New York, Chicago, and Washington D.C.
Some dates are as low as $423 roundtrip.

Montreal & Quebec City! The Canadian dollar should help you find good bargains! :D

You mention some historical sites. So how about Boston? You can spend a couple of days touring historical sites.

Richmond can easily be done from DC as a day trip - the Confeferacy Museum is not big, but is very well done - the exhibits provide some keen insights.

When I visited about 15 or so years ago I remember being impressed by the "fairness" and objectivity of the depiction of the conflicts, both military and home front. No jingoism at all.

Skip Williamsburg - tourist trap.

You would then have plenty of days for one or more other destinations.

Ocean City, MD? One other thing I would say is to take Amtrak from WDC to ORD rather than flying, a leisurely trip across eastern US

Never thought of Iceland. Will look into that. Love the idea of the train. Had considered making the trip to Chicago by car and stopping off at The Greenbriar for a few days but haven't gotten resounding recommendations from friends who have been there. Grateful to be gotten off the hook with Williamsburg - I know I should want to go there but maybe will save that one to torture grandkids with at a later date.

Good to hear positives about the Museum of the Confederacy. We spent 3 days in Gettysburg last year and my husband has gone way down the rabbit hole with reading about the Civil War.

Have never been to Ocean City. Does it compare well with St. Michael's? I am always drawn to destinations on the water.

Fully intend to visit Boston and hopefully the Berkshires sometime soon but we will probably make that a side trip from our home base in NYC.