drewmiller0531

We have a group of 8 friends that get together end Sept-First of Oct for a long weekend trip each year. We have been to Seaside FL, Charleston SC, and Rosemary Beach FL. Looking for recommendations for our trip this year, Sept 30 - Oct 3. A few ideas we have had for this year but are far from settled on anything are, Boston MA, Old Town Scottsdale AZ, New Orleans LA and Savannah GA. Coastal destinations are always a bit more appealing but wouldn't be a deal breaker if not.

Couple things that weigh heavily on our selection is the food scene, not looking for big name popular chains, but love finding and trying out that unique joint that you might overlook unless someone suggests you go there. We love to walk or bike around town taking in the the history and uniqueness of wherever we are, no museums though. Also finding that house/apartment with a space to hangout in the backyard around a firepit for those late nights kicking back with a glass of wine, some bourbon and a cigar is key.

Bonus points if its within an hour of a major airport since we are traveling from different states in the eastern US.

Jean

At that time of year, Scottsdale would be too hot for me. New Orleans and Savannah would be borderline. Your tolerance may be higher.

I like Santa Fe, but evenings may be too chilly. Nantucket?

clarkgriswold

If budget is a concern for anyone in the group, Boston can be expensive at that time of year due to leaf-peeping tour buses coming through town, college football games, parents weekends at Universities and baseball crowds. Also Boston has some home-share situations available but a house sleeping 8 would probably be hard to come by. Cape Cod is not too crowded then so might be a nice idea, but nights can be chilly towards the end of September. It's not clear if you need 8 beds or if you're 4 couples, but this place looks really nice: https://www.vrbo.com/7841247ha Del Mar Bistro nearby is excellent, and Branches Grill is your "hidden gem" spot. Lily's Diner for breakfasts.


Scottsdale would most likely be around 90 degrees though you could by chance hit a cooler week, or unfortunately a hotter heat wave. New Orleans might be a more pleasant 80 degrees, but hurricane season can always disrupt plans at that time of year as you probably know.

drewmiller0531

Thanks Jean and clarkgriswold for the info. I see that I did miss mentioning that its 4 couples not 8 individuals.

KTtravel

I'd vote for New Orleans and hope for good weather.

HappyTrvlr

Do not consider going to AZ until at least November! And then do not choose Old Town Scottsdale.
How about Santa Barbara or San Diego?
Or Chicago? All have very good food scenes.