While I love taking big, multi-destination trips, I’m also a really big fan of weekend getaways. In fact, I think some cities are meant for weekend trips and not much longer than that. And I say that in the best way possible. Some places really shine when experienced in two to three days while others need longer for you to appreciate them. And some places could be both!

Every year, I like to do a mix of big trips and weekend getaways, partially because it’s a good way to space things out personally and professionally (can’t always be on vacation at work, amirite?) and also because always doing big trips or always doing weekend getaways feels like too much of one thing and not enough of the other.

So, anyway, back to the weekend getaways. These are the places I’ve loved experiencing the most in two to three-day stints:

Chicago, Illinois - Home of the deep dish pizza, the fun architectural river cruise and so much more, Chicago makes for a great weekend adventure, especially in the summer. My one tip: go to Girl and the Goat and make reservations beforehand!

Miami, Florida - Miami is a good getaway pretty much any time of year, but it’s most valuable in that November to March timeframe when you’re desperate for some warm weather (assuming you live in a colder place like me).

Los Angeles, California - I’ve only done LA in multiple two to three day stints, and while I don’t think one weekend is ever enough for this city, you can cover a lot of ground in a weekend. Make sure part of that ground is at the beach.

Savannah, Georgia - Savannah is one of those cities that shines over the duration of a weekend. You can enjoy the beautiful squares full of Spanish moss and the Southern hospitality and wander around to your heart’s content.

Philadelphia, Pennsylvania - I have always felt that Philly is an underrated city, for both living and visiting. One of my good friends lives in Philly, so I get there once a year or so, and I always have a good time.

Dover, Vermont - I’ve been to Dover twice now to go skiing, and it’s exposed me to how beautiful Vermont is in the winter. I hear it’s even more stunning in the fall, so I’ll have to plan a fall weekend getaway soon!

Sedona, Arizona - I didn’t actually spend an entire weekend in Sedona but I did spend enough time there to know it would be a great weekend getaway. It’s also an easy drive from Phoenix and can be combined with a variety of nearby places for a nice longer trip.

Montreal, Canada - Should I even say how much I love Montreal? I feel like I’ve said it so many times on this blog that it goes without saying. This is a place I will gladly go to for many more weekend getaways to come.

New York, New York - I couldn’t not list New York as a weekend getaway. While you will only skim the surface with two to three days in New York, I actually think it’s a good way to start. Dip your toe in, experience the craziness of the city, take a break and then come back again.

Napa, California - I haven’t been to Napa yet, but that’s going to change very soon, and when it does I am sure it will be a favorite weekend getaway. How could it not be? Update: I went, I drank all the wine and I had a blast :)

What are your favorite weekend getaways?