Let's not get into that whole discussion again (layovers are not "off" time)
Let's see, since I now live in southwest FL, it is hard to think of a better place to be in winter than home. I love to go fishing in the 80 degree weather and call my sister, who lives in northern IL and rub it in!
But hey, best overnights for us? Depends on what you like. I have favorites for the hotel, restaurants, stuff to do, etc. Our hotels change all the time, they mostly take away all the good ones that we like and replace them with others.
Best overnight hotels:
BOS Hilton - at airport, close to train into downtown, free internet, flat screen TV. They have since renegotiated with our airline and we no longer get the good discount at the restaurant and no more 24 hr. room service, but still nice.
Embassy Suites - ANY! Suite and free breakfast (with omelet guy!)
BNA - Radisson - Applebee's downstairs and close to Grand Ol' Opry and huge mall
ORF Sheraton - We stay on the bay and hotel has balcony rooms facing the sunset and water. Newly remodeled and nice!
Best overnight towns:
PWM - great bars and restaurants, shops, and waterfront activities (better in summer, obviously)
SAV - We now stay near the airport, but back in the day, it was great to be close to the River Walk
PHL - If time allows, home to mom and dad's for a home cooked meal
ABE - same as above (they live between the two)
CLE! - The Brown City! Very brown and ugly, but a great area to hang out is the Warehouse District! Also, R&R Hall of Fame, and summer activities by the waterfront.
BOS - Not only the hotel, but the town is great too!
ROC - Ok, Dinosaurs BBQ! Not much else, but good food!
DCA - Stay in Alexandria, VA - King Street! Also, great excercise trail and bike rental along the river!
RIC - Nice walking town
YHZ - Great in summer! Seafarer town, and great summer wx! Winter can be fun too, if you get snowed in and just hang out with a good crew!
YYZ - We had a bad hotel, close to bars and restaurants. Now we are at a nice hotel, not near anything. Free internet and HBO & Showtime. Still not sure of the new place. Expensive menu, but pizza delivery was cheap.
Many others I'm sure, but it's late and I can't think of them right now
Worst Overnights:
HSV - Hotel in airport, miles from anywhere! No food choices except subpar hotel restaurant.
JAN - nothing to do
GSO - Hotel at airport, miles from anywhere! Very expensive hotel menu, no free internet.
ORD - Great City, just that we stay near airport and hotel has very expensive restaurant and bar, no other food nearby, no free internet
MEM - Many years traveling here (actually based there in USMC years ago) and my conclusion....Beale Street, that's all there is, and that gets old too.
YUL - Sorry, not a fan. French Canadians, no free internet, no food close by...all bad.