All Over: Where To?

After working tirelessly day and night for the past three months, weekends included on a very big project (you may have heard of it?), I'm treating myself to a delightful two weeks off. The only problem -- I have no idea what to do with my time! I fear that a two-week staycation will drive me insane, so I'm planning a possible long weekend retreat with anyone who's willing to join (I know vacay days for most are few and far between right now).

Here are my top choices for nearby destinations. More suggestions welcome!

Courtesy of www.sabalhomessc.com

Charleston

I've heard so many wonderful things about this town between the architecture and the seafood. However...is the south somewhere I want to be right now? I dunno.

Courtesy of GQ Magazine

Havana

I think its already way too late to be calling this a hidden gem, but that doesn't make it any less appealing. Havana in summer might be miserable weather-wise, but it also means cheaper hotels.

Courtesy of Eater

Toronto

Staci and I had a great time up north last summer, and I suspect that Toronto would be equally as fun! 

Courtesy of Travel and Leisure

Portland, Maine

One of my oldest friends, Julia, moved here just a few months ago and her pictures are giving me some serious envy. Any chance I can crash on your couch for a few days, J.Bro??

-Jen

p.s. If you're in Times Square today, get your free glasses and astronaut ice cream!