Short trip suggestions?

October 19, 2006 7:33 AM

The SO and I have been dating for over a year, and we have yet to take a vacation somewhere. I want to know if he and I travel well together, so I need a suggestion of a good city to visit for a long weekend (three days, four max) in the middle of November or December. Parameters inside.

We're in Chicago now. I think we're willing to do just about anything, including outdoor activities (though no downhill skiing), sightseeing, eating, drinking, taking in the arts. It's already been suggested that we go somewhere neither of us is highly familiar with, which will nix Boston, Florida, Los Angeles, San Francisco, Wisconsin, and New York City.

I would like to go somewhere far enough away that we have to fly, is in the US, and has public transportation or things close enough such that we don't have to rent a car (but that's not a deal breaker). We're on a budget, but it's not too strict. Any recommendations? I can supply more details as needed.

posted by bibbit to travel & transportation (25 comments total)

Vegas, baby! Stay on the Stip, walk around. We went for 4 days in September and had a blast.
posted by ThePinkSuperhero at 7:46 AM on October 19, 2006 [1 favorite]

Austin, Tx
posted by JohnnyGunn at 7:46 AM on October 19, 2006

Denver.

Stay downtown (somewhere close to the 16th Street Mall). You can shop, eat, people watch, etc.

When you are ready to get outside, take the ski train up to the mountains.
posted by Sheppagus at 7:48 AM on October 19, 2006

Oh, I forgot to mention that there is RTD (bus) service from DIA to Market Street Station, which is right on the 16th Street Mall.
posted by Sheppagus at 7:48 AM on October 19, 2006

You will probably be able to see a good deal of Washington, D.C., just by using the Metro. You could try Philadelphia, but I really don't know how well SEPTA gets you around. It's not in the U.S., but Toronto seems to fit all your other criteria.

I can't think of anywhere else that you haven't been to (or lived in) that has a decent enough public-transit system for you to see a lot of things without a car.
posted by oaf at 7:48 AM on October 19, 2006

I was going to say, stay out of Texas. The public transportation sucks. But if you do take JohnnyGunn's advice and go to Austin... Rent a car and get a map. Austin is small (but growing) and the traffic is as bad as Houston's traffic but it will make getting around much easier.
posted by nimsey lou at 7:50 AM on October 19, 2006

Memphis.
posted by sulaine at 7:51 AM on October 19, 2006

San Juan, PR. Great outdoor activities, pretty easy to navigate without a car, wonderful people.

I also second Denver/Boulder. It is very relaxing there and you can get into the mountains and wilderness during the day, and hit the restaurants at night.
posted by milarepa at 7:52 AM on October 19, 2006

St. Louis
posted by rglass at 7:53 AM on October 19, 2006

It is not in the US, but Montreal is a romantic city destination. There is plenty to do, good food and just walking around is fun because the city is gorgeous.
posted by caddis at 7:55 AM on October 19, 2006

Philadelphia is great, and SEPTA totally gets you around. Hell, you can get pretty much anywhere you would want to go by walking, and the R1 gets you from PHL right to Center City. There are some kickass museums (Philadelphia Museum of Art, Penn Museum, ICA, Rodin Museum, Mutter Museum, etc), great restaurants, great cafes, and great theater and music (both of the classical and modern varieties). I could give you a ton of suggestions.
posted by The Michael The at 7:58 AM on October 19, 2006

Here's that ICA link again.
posted by The Michael The at 7:59 AM on October 19, 2006

If you need public transport, go Philly. Otherwise, I like Phoenix (really!). There's lots of interesting stuff going on, and there's basebll going on in the Arizona Fall League. But you will have to drive _everywhere_.
posted by sachinag at 8:04 AM on October 19, 2006

I very much second The Michael The's Philadelphia suggestion. Philly's a great town.
posted by Greg Nog at 8:17 AM on October 19, 2006

Email is in my profile; I would be more than happy to expound on stuff to do and places to stay in Philly. My girlfriend and I have been hosting various parents, relatives, and friends quite a bit lately, so I'm prepped for the questions.
posted by The Michael The at 8:28 AM on October 19, 2006

Seattle!

Great people-watching, excellent coffee (and food, of course); lots to see and do - and the part of their public transportation that operates downtown is free. The weather may not be stellar, but it will certainly be warmer than Chicago.
posted by rtha at 8:44 AM on October 19, 2006

Key West!

I'm going there on vacation next month (the first for my SO and I..and we will have been together for a little over a year at that point).

The flight is much cheaper if you fly the Miami instead of Key West on some of the vacation websites (though we're flying straight there, and staying in a B&B for about $1200 total). If you do fly into Miami, there are many shuttles that will drive you down to Key West, though I'm not sure of the prices.

Now this city can be somewhat expensive since it basically survives on overcharging tourists...but isn't that the fun of going on vacation?

We're staying at the Heron House Court (there's a regular Heron House).
They're offering a "4 nights for the price of 3" special ($477)

You won't need a car, since the whole island is only something like 4 miles by 2 miles. You can rent mopeds, and regular bikes too.

And what's better than going somewhere warm, when it's getting cold up north?
posted by picture_yellow at 8:51 AM on October 19, 2006

Fellow Chicagoan here... I second the Montreal suggestion, although it will be cold that time of year.

Portland is an amazingly relaxed city, so it might be a good choice if you don't want to pair a frenetic pace with your first vacation experience.

Louisville is a great city for a weekend away, and just a short, cheap flight away via Southwest. (It will also be slightly warmer.) On the downside, public transport isn't great there.

(If you want to go on a one night trial run before your big weekend away, why not spend a night in Milwaukee? It's a a great city, a short drive/train/busride away, and pretty fantastic.)
posted by j-dawg at 8:52 AM on October 19, 2006

I have a friend that toured many of the southern states and she raved about Charleston, SC. It's a 19 hour drive from Chicago, so I suppose flying would be the way to go. She emphasised it would be particularly nice for a couple.

I don't have a lot of details, otherwise, but it might be worth looking into.

Have fun!
posted by backwards guitar at 8:53 AM on October 19, 2006

Hey, guys, these are all great. Art museums in the cold cities would be a great thing. And in the warm cities, I suppose we could get out and do a lot of walking around. Keep the suggestions coming...and reasons why are helpful.

The Michael The, if we pick Philly, I'll definitely be emailing you for pointers.
posted by bibbit at 8:55 AM on October 19, 2006

Someone else suggested Montreal - I spent an extended weekend there with my SO last spring and it was very nice. I don't know what it would be like in November/December, though. If it weren't for the November/December thing I would suggest Mackinac Island. I'm afraid I'm not very well-traveled in places that are in any way hospitable in the winter. :)
posted by srah at 9:21 AM on October 19, 2006

For a more rural suggestion I recommend Maine - Vinalhaven for example or Deer Isle. Its gorgeous, there is tons to do, and once you get to the islands you can get around by walking, biking, sailing, ferries, buses and taxis.
posted by zia at 9:43 AM on October 19, 2006

Why pollute with air travel when you could drive around in a car? There's nothing like a long road trip to get to know each other better. Travel the highways and byeways of Illinois, and just find things en route ;)
posted by badlydubbedboy at 9:50 AM on October 19, 2006

New Orleans!

Okay, the public transportation is basically non-existent, but who needs it when there's the French Quarter! And you can take the streetcar to City Park (and the New Orleans Museum of Art and Sculpture Garden.)

I don't think you'll find a city more appreciative of tourists than New Orleans.
posted by pyjammy at 12:18 PM on October 19, 2006

I second Austin. There aren't a whole lot of touristy things to "do," but it's a great city for just hanging out - numerous cool bars, cafes, etc., and great live music, of course. A rental car is not absolutely essential, but would definitely make things easier.

Montreal would be great in many ways (unique, romantic, great restaurants, good transit), but the amount of walking around you can do might be limited by the weather, which may or may not be full-bore Canadian winter by Nov/Dec, depending on the year. I love Toronto, and weather there will likely still be fall-like at that time of year, but you may not find it dramatically different from Chicago in terms of urban feel.

Also, flights to Canadian cities will be much more expensive than flights within the US. (However, if you are willing to consider Canada, let me suggest Vancouver as well.) Feel free to email (in profile) with specific questions about any of the destinations I've mentioned. Have a great trip!
posted by Urban Hermit at 4:43 PM on October 19, 2006