NBR: Help narrow down our options

Jen748

Next November Brett and I will celebrate 10 years of wedded bliss (that is, if I don't run away from home before then) and we're trying to decide on our anniversary trip. Since I'm a SAHM now, we have to take a long weekend since my parent's have to take off work to watch Emmett. Sammie will be in Kindergarten by then. (UM, WHAT?)

We live smack dab in the middle of the country. We don't have a budget exactly, but no more than a couple grand. We'd like something with relaxation and stuff to do. And, preferably, not something cold weather sport stuff. Why did we get married in Nov?? Super cold in half the country.

Options:
Philadelphia (cold, but history nerds)
Chicago (cold, but not too far so less flight expensive)
Key West, FL
Road trip thru SD, ND and into somewhere in Canada (might not be doable time wise)

We've done: Charleston, Savannah, Fort Myers, San Antonio, San Diego, Branson, MO.

Any suggestions? Thoughts? We could move the trip to sometime in late September or mid-summer. I really wanted to take it right around our actual anniversary but that limits us on places that aren't cold.

sassypants527

The history nerd in me votes for Philly.

krispy83

I've never been to Philly, but the history nerd in me loooooooves Boston, if you can swing that!

Or Key West for a just plain fun option.. DH and I took a cruise a few years ago that docked there for a day and we had an absolute blast!  We're hoping to go back at some point - we had a fantastic time there.

SnShne322

Boston! Of the choices, I'd pick Key West. I've always wanted to go.

sweetrhythms

I'd pick Key West considering it's November. Plus, it sounds the most relaxing!

RevJen

If you did Key West, you could turn it into literary tourism.  Hemingway.  

funkypineapple

Of those options I would pick Key West. I've always wanted to go there. 

Jen748

I forgot to add that we've been to Boston. It was amazing!

I guess I'll look into KW a bit more to figure out cost and such!

ajpufky

Another vote for Key West! We went for our honeymoon at the beginning of November 2 years ago and had an amazing time! The weather was beautiful, i think it was mid 70's the whole time we were there and there is a lot to do. Of course Duval street is a ton of fun (rum drinks!!) but there are also a couple of historical sites and I'd suggest taking the Conch Train tour, it takes you all around town and you can hop on and off all day if you want. We didn't go into Hemmingway's house but did wander by it. We stayed right on Duval street at the Pier House but you really don't need to. There are a TON of bed and breakfasts plus a lot of chain hotels as well just off Duval or on the other side of the island. Just double check the schedule of events the week you'll be there just to make sure it's something you'll enjoy. The week we went was Meeting of the Minds for Parrottheads and we loved it, being Jimmy fans! We flew into Ft. Lauderdale and then took a day to drive down to Key West along A1A, if you are looking to do that make sure you aren't in a rush because it's only 2 lanes so if someone is going slow everyone is going slow!

Read2Me

I love Chicago- so much to do!

MrsJenE

I'm a fan of Philly.

jackiback

I think Key West sounds the most relaxing, but Philly sounds the most interesting. I think it depends on what you're looking for, and if not walking and eating good food and seeing sunshine is your thing (which I know it is I'd probably go for KW. 

nocturnalintimacy

YGPM