Chris and I have entered into an ages old dilemma when it comes to travel. With a few extra days of vacation left in both of our pockets, we’ve decided to actually take a trip together this year, when we thought originally that this wouldn’t be possible.

So let the decision-making fun begin. There are a few factors we’re using to narrow down the choices:

1. We won’t leave the country for this vacay
2. We’ll keep the flight and hotel stay to under $500
3. We’ll choose a “relaxing” vacation this time, as opposed to something where we’ll feel the need to run around and sight see all the live long day
4. We’ll shy away from the West Coast for this trip, since it will only be for a couple of days

We tossed around the idea of picking a place where a specific action would do the guiding—as in “We went to Arizona because they have the best sky diving”—but I think we may have decided against that.

A quick goggle search of the Top 10 cities to visit in the U.S. left me feeling a bit jipped.

1. San Francisco– West Coast
2. Charleston, SC—Been there
3. Santa Fe, NM—Possibility
4. NYC—Live there
5. Chicago—Possibility
6. Honolulu—Been there
7. Carmel, CA—West Coast
8. Savannah, GA—not sure I see the draw
9. San Diego—West coast
10. Boston—Been there

After adding New Orleans and Phoenix to the list, we still only had a couple of good options.

So we threw the list out, and I think we’re going to go with Florida. It’s cheap. It’s tropical. I know my way around it. Now the decision is this:

St. Augustine—where I used to live, but could be fun to show Chris around the place, and I know the best places to go/stay/eat
The Everglades—neither one of us has been, but we’re dying to see some alligators

This might be a tough one….