Weekend Getaway Ideas
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Weekend Getaway Ideas

By WookieMan following x   2017 Sep 20, 2:22pm 593 views   22 comments   watch   quote     share  


Wife and I are looking to get away for a long weekend, no kids. Maybe a Friday to Monday or Thursday to Sunday type setup. Would probably do this in October/November. Anyone got good recommendations within a 2hr flight of Chicago (~1,000 miles)? New York/Boston to the East, Atlanta to the Southeast, Dallas Southwest, Denver West & basically Minneapolis to the north since there's not much else. Would be flying out of Midway on Southwest using up some points.

Don't mind city experiences, but would probably want to be south in that scenario where it's warmer. Prefer cabin, rural type places, but don't want to drive three hours from the destination airport after landing. 2 hours max drive due to the short length of the trip. Don't mind cold if it's scenic. Prefer resorts, B&B's or even a vacation rental, but don't want a Holiday Inn off the highway. $600/night or under if possible.

Fire away with suggestion or ignore. I don't care either way. I know a lot of you guys are West coast, so if you have something out there I'd still be willing to hear it to book another time. Dig me some Cali.
1 NuttBoxer   ignore (1)   2017 Sep 20, 4:23pm   ↑ like (0)   ↓ dislike (0)     quote        

You could hitup the southwest desert, may be a little hot this time of year though. There's a ton of parks in Utah. Or maybe Yosemite. Could also head up to the Rocky's from Denver. Estes park is nice.
2 Blurtman   ignore (1)   2017 Sep 20, 5:35pm   ↑ like (0)   ↓ dislike (0)     quote        

Check out DC, a beautiful city with lots to do.
3 Patrick   ignore (0)   2017 Sep 20, 6:04pm   ↑ like (0)   ↓ dislike (0)     quote        

Chicago itself has years of things to do. Once had a great weekend trip there with my wife. Stayed at the hotel Nikko, ate good deli food, got comedy shows, walked by the lake.
4 WookieMan   ignore (0)   2017 Sep 20, 6:36pm   ↑ like (0)   ↓ dislike (0)     quote        

Patrick says
Chicago itself has years of things to do. Once had a great weekend trip there with my wife. Stayed at the hotel Nikko, ate good deli food, got comedy shows, walked by the lake.

I hear you, but I work in the city and surrounding suburbs. Also lived in the city for about 6 years. Without giving away too much, my job has had me on pretty much every block in the entire city at some point or another over the last 12 years. Even many of the shitty parts. I'd venture to guess I know the city as a whole better than 98% of people that think they know it well.

We've got the Southwest companion pass, so we can go pretty much anywhere within two hours flight for like 10-20k points and the $11 9/11 fee round trip. Have done local places, city (chicago) included and are looking for something different. I'm thinking places like Chattanooga, TN; Charleston, SC; upstate NY; Washington D.C. area; and north of Boston (Maine, NH & Vermont). Did Denver this summer with some buddies. Had a great time, but getting to scenic/cool places from the airport is at least a two hour drive and a pain in the ass.

Just wasn't sure if someone had traveled to a random part of the midwest or east coast that might have a recommendation.
5 jvolstad   ignore (0)   2017 Sep 20, 7:41pm   ↑ like (0)   ↓ dislike (0)     quote        

Some of the best pizza in the Chicago area, IMHO, was located in a small store front in Naperville. I lived nearby and worked in downtown Chicago.

http://www.adamospizzaandcatering.com/
6 EastCoastBubbleBoy   ignore (0)   2017 Sep 20, 7:45pm   ↑ like (2)   ↓ dislike (0)     quote        

go leaf peeping Columbus day weekend in the northeast
7 WookieMan   ignore (0)   2017 Sep 20, 7:48pm   ↑ like (0)   ↓ dislike (0)     quote        

jvolstad says
Some of the best pizza in the Chicago area, IMHO, was located in a small store front in Naperville. I lived nearby and worked in downtown Chicago.

Haven't had it. I'm sure it's good and will likely check it out. Would love to pump my pizza place, but I live in too small a town and don't need my public personality known here.
8 Strategist   ignore (0)   2017 Sep 20, 8:08pm   ↑ like (1)   ↓ dislike (0)     quote        

WookieMan says
Fire away with suggestion or ignore. I don't care either way. I know a lot of you guys are West coast, so if you have something out there I'd still be willing to hear it to book another time. Dig me some Cali.


Where can you find a better place to visit than So California in Oct/Nov? Do come over and bring lots of money, because we need to pay the fucking pensions of the public employees of California.
9 WookieMan   ignore (0)   2017 Sep 20, 8:15pm   ↑ like (0)   ↓ dislike (0)     quote        

Strategist says
Where can you find a better place to visit than So California in Oct/Nov? Do come over and bring lots of money, because we need to pay the fucking pensions of the public employees of California.

I did. Went this last January 2017 to Palm Springs. Sparrows Lodge. Nice little place. Did some golfing and good amount of eating. One thing about California, at least the limited places I've been, food is very average for a high price. Chicago has AMAZING food for an average price. I would miss that if I were to ever move full time.

Feb 2016 we also did San Diego, Escondido and Disneyland over a week with the kids. Cali has close to $10k of my dollars over the last two years. I'm doing my part for you all.
10 Strategist   ignore (0)   2017 Sep 20, 8:27pm   ↑ like (0)   ↓ dislike (0)     quote        

WookieMan says

Feb 2016 we also did San Diego, Escondido and Disneyland over a week with the kids. Cali has close to $10k of my dollars over the last two years. I'm doing my part for you all.


Thank You. We need everything we can get to make sure our public employees have enough champagne and caviar when they retire at 55.
11 APOCALYPSEFUCK_is_ADORABLE   ignore (5)   2017 Sep 20, 8:30pm   ↑ like (0)   ↓ dislike (0)     quote        

Quebec City. Bring walking shoes and a solid point and shoot camera. A complete hoot. Medieval walled city. Great food. Walkable scale. Most locales with a view of the St Lawrence. Maybe an hour or so flight time.
12 Strategist   ignore (0)   2017 Sep 20, 8:36pm   ↑ like (0)   ↓ dislike (0)     quote        

APOCALYPSEFUCK_is_ADORABLE says
Quebec City. Bring walking shoes and a solid point and shoot camera. A complete hoot. Medieval walled city. Great food. Walkable scale. Most locales with a view of the St Lawrence. Maybe an hour or so flight time.


Traitor.
13 WookieMan   ignore (0)   2017 Sep 20, 8:38pm   ↑ like (0)   ↓ dislike (0)     quote        

APOCALYPSEFUCK_is_ADORABLE says
Quebec City. Bring walking shoes and a solid point and shoot camera. A complete hoot. Medieval walled city. Great food. Walkable scale. Most locales with a view of the St Lawrence. Maybe an hour or so flight time.

This is the kind of suggestion I like. Unfortunately for a long weekend, closest airport for Southwest airlines is Portland, Maine. From there it's a 5 hour drive. Which means I'd literally be driving/flying 16 hours round trip roughly on a long weekend.

Added to the list though. My brief research makes it seem like a cool place, affordable and fun.
14 Patrick   ignore (0)   2017 Sep 20, 8:40pm   ↑ like (1)   ↓ dislike (0)     quote        

I second Quebec City. Just don't go in winter. Brutal.
15 Philistine   ignore (0)   2017 Sep 20, 10:33pm   ↑ like (0)   ↓ dislike (0)     quote        

WookieMan says
Palm Springs. Sparrows Lodge. Nice little place. Did some golfing and good amount of eating. One thing about California, at least the limited places I've been, food is very average for a high price.

Don't judge California food based on Palm Springs. I go several times a year and am captivated by PS, but their food scene is incredibly average, whether it's the stalwarts or their special occasion restaurants or their hipster renaissance (Workshop is almost notable). LA, SF, Napa, and Sonoma have impeccable food, but you will pay for it. Definitely not like Chicago or NYC where cheap and delicious are around every corner.

Seconding Quebec City. Had a picturesque time there. Good food, at that. People are daffy and loveable. Jazz clubs. French Canadians must be my jam.
16 APOCALYPSEFUCK_is_ADORABLE   ignore (5)   2017 Sep 20, 10:40pm   ↑ like (1)   ↓ dislike (0)     quote        

Patrick says
I second Quebec City. Just don't go in winter. Brutal.


I had a gig in November. Came in the snow. Plane kind of slid into the gate. Fantastic. No one was there except for locals. It was hard to leave.
17 BayAreaObserver   ignore (1)   2017 Sep 21, 2:33am   ↑ like (1)   ↓ dislike (0)     quote        

@WookieMan - Looking at the SW Route Map and adding in places I have been here a few suggestions for a two hour or less flight window.

Charleston - Very Walkable, Lots of Great Food and Historical Sights, Antiquing (if you or your wife are into that), and also the Charleston City Market for things like handmade Sweetgrass Baskets. Lots of history in the area.

Buffalo - Go straight to the Canadian side of the falls and use this as your base. Niagara on the Lake quite nice, easy trip over to Toronto for a day, take in the Welland Canal and the lock system, lots of great wineries in the area. U.S. side go to Fort Niagara and surrounding areas - Robert Moses Power Plant tour if you want something educational. A lot of the small towns on the Welland Canal system are very nice, Canadian Beer is awesome and so is the Ice Cream. Must do if you go - evening dinner in the revolving restaurant on top of the Skylon Tower, the views are amazing, food was not bad either - reservations suggested.

Albuquerque - You can head up to Sante Fe from here for the art, food etc. - annual The Albuquerque International Balloon Fiesta which is quite the sight to see at sunrise or just before as they are taking flight and look like flying luminaries. Sandia Peak tramway in Albuquerque worth a shot, Old Town was so-so on my last visit. Sante Fe is a better bet to set up base. Home of Georgia O'Keefe and tons of great artists.

Rochester - the Finger Lakes Region of upstate New York is also worth a visit, especially if you are into wine (so many wineries and so little time) and general sightseeing with fall colors etc. Geneva on the Lake is really nice. Also worth a look, the 1000 Islands Region and take in Boldt Castle, as well as taking in sights on along the St. Lawrence Seaway System. Take in the Erie Canal system.
18 WookieMan   ignore (0)   2017 Sep 21, 9:57am   ↑ like (0)   ↓ dislike (0)     quote        

Philistine says

Don't judge California food based on Palm Springs.

I did actually forget to mention that I think it was Wednesdays and Saturday, Sparrows Lodge where we were staying does a dinner. That was actually really, really good. Again it was pricey, but they bring in different chefs on site and change the menu etc. Hotel guests get first dibs, but I think the day before or day of they open it up to the public. So it might be an option for someone in the area those days. Really cool little resort.

Philistine says
Workshop is almost notable

That's funny, we did end up eating there. Sat at the long concrete table in the middle. I would definitely rate it above average to pretty good. We like our drinks, but pretty sure our bill was around $150 for 2. Probably $100 for the food. Not totally unreasonable, but that's just two main dishes and no appetizer. I give it 4 stars and would recommend, but don't expect your socks to get knocked off by any means.

We are thinking about a Central/Northern Cali trip in the next 12-18 months, maybe even next summer with the kids. For this long weekend trip of 3 nights, it's just too long of a flight and I'm guessing getting out of SF at certain times can be a bitch. This place did catch my eye though: http://www.postranchinn.com/ That looks very relaxing.
19 WookieMan   ignore (0)   2017 Sep 21, 10:00am   ↑ like (1)   ↓ dislike (0)     quote        

BayAreaObserver says
@WookieMan - Looking at the SW Route Map and adding in places I have been here a few suggestions for a two hour or less flight window.


Really appreciate the suggestions and tips. Upstate New York was definitely top 3 and so was Charleston. If anyone has been, we were also thinking of flying to Atlanta then swing North toward the Chattanooga area. Been there a couple times driving through on the way to the FL panhandle, but haven't really had much more than an afternoon there. Seems like a cool spot and you still get the Smokey Mountain vibe I feel like. Plus Chicago to Atlanta is next to nothing in SouthWest points depending on the day of the week. So it would allow future trips to not burn too many on this one.
20 BayArea   ignore (0)   2017 Sep 21, 10:31am   ↑ like (0)   ↓ dislike (0)     quote        

Some great weekends I've had:

Paso Robles, CA - Great little wine town, excellent restaurants, over 300 wineries on the perimeter. It feels a bit like Napa without the crazy crowds and tourists. My wife and I rented an AirBnB cottage and had an awesome weekend here.

Scottsdale, AZ - When the rest of the country starts cooling down, head to Scottsdale. What a fun city! It's full of energy and there's lots to do. I've been here with the wife and also had my bachelor party a few years before that. This city might have the highest concentration of beautiful women that I've seen of any city in the USA.

Chicago, IL - Covered by others above... I consistently hear great things from people and have enjoyed my weekend trip there.

Some places I'd like to check out in the future: Vancouver, Austin, Park City, Nashville.
21 BayAreaObserver   ignore (1)   2017 Sep 21, 12:39pm   ↑ like (0)   ↓ dislike (0)     quote        

@WookieMan - forgot to mention flying into Islip on Long Island and then going out and doing the Hamptons, Montauk etc. - its really great post Labor Day when the crowds have gone plus the prices for lodging drop way off. Montauk Point and the lighthouse would be a must as well as local seafood places. It can get crowded on some weekends in the fall but not anything near to summer. Nice time as well for beach walking with almost no one else around. Spent two years out in Hampton Bays while in the service - great place if you can afford it.

Another option is Colonial Williamsburg etc. accessed out of Richmond. Never been but on the "to do" list. Richmond itself has quite a bit to offer depending on your interests.

Upstate New York though starting in Rochester gives you a really wide choice of places to access within your driving window limit. Probably good to plan what you can do in rainy weather as well since the fall is a transitional season. Should you opt for that - try and catch a sunset from Lake Ontario as well. No shortage of stuff to do and see.

Was going to toss in the Blue Ridge Parkway but not sure where you would want to fly into to catch it from either end. Only been through the airports in that area or else stuck at a conference center.
22 bob2356   ignore (1)   2017 Sep 21, 3:27pm   ↑ like (0)   ↓ dislike (0)     quote        

WookieMan says
Would probably do this in October/November.


Too big a time period for specific suggestions. You would want to do New England if early Oct when it's still hot and oppressive in a lot of the south or the south if late November when New England is already under snow.

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