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Best North American City to Spend a Week?


Gator Dave

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I have 3 weeks until my 10 year anniversary and I need to plan a trip. Last-minute planning due to not being able to find a taker for the kids (now resolved). So for those with more travel experience than me, if you could pick one city to spend a week (not NY, been there), what would it be? Some preliminary ideas (but definitely not limited to these) are: San Diego, San Francisco, Savannah, Charleston, Chicago. We're not too picky, we like breweries/wineries/beaches/historical sites/good food and nightlife. Somewhere with interesting areas that are walkable with restaurants/bars/other points of interest. A nice balance of sightseeing and relaxation. I'll hang up and listen.

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16 minutes ago, midtown said:

Montreal? 

My very first thought ^^^^. Everything I've heard about Montreal makes it one of my bucket list cities. Many call it the most beautiful city in N. America, like stepping into Europe for a day without flying across the Atlantic.  

Time of year is crucial. February, probably no bueno, unless you like arctic cold, and lots of snow.  Spring, Summer, and Fall glorious.  I believe the Lonny is a bit weak to the dollar as well, so that's a bonus.

Amazing amazing food, word class architecture are 2 of it's traits.

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47 minutes ago, jimmyjazz said:

Savannah is phenomenal, but a week might be too much.

Agreed. Savannah is great for a long weekend, but you’d be bored staying there a full week.

Casting another vote for San Francisco.  Lots to do in the city, with hiking in Muir Woods and wine tasting in Sonoma not far away.

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San Francisco hits all the marks.  The big question is do you want to go North to Muir Woods/ Napa/Sonoma/Russian River or South to Carmel/Monterrey/Big Sur.  You could do it all but that would be way too much car time.

 

I would probably go north, because I like the Napa valley and the amazing restaurants you can hit while you are there.  

 

Make sure you time the trip to catch an afternoon Giants game.

Edited by MAROON
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Do the Charleston-Savannah duo: two hour drive between the two. Food, underrated beer scene, coastal drive and beaches between the two. Tybee Isaland and Folly Beach pretty good beaches. Open drinks in Savannah. Plsu, it will be cheaper than anything San Fran or San Diego wise.

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San Francisco.

I mean, I would just spend a week in NYC regardless of whether you've been there or not, but if you really don't want to return (and haven't been there) then San Fran. 

 

Edited by ztejas
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Vancouver. End of story. Good coffee on a sidewalk shop downtown. Aquarium. Stanley Park. Day trip to whistler. Wife can shop at Granville island. Victoria Day trip. Very dog friendly place  some places allow you to bring your dog to work. Can also visit Seattle in same trip  

Have always said if I win lottery I would live there 7-8 months a year. 

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Another vote for SF but also drive down and spend a night or two in Monterey/Big Sur:
 
[url=https://www.surlyhorns.com/board/index.php?/topic/6973-pebble-beachmonterey-things-to-do/&tab=comments&do=embed&comment=883054&embedComment=883054&embedDo=findComment#comment-883054][/url]  


Realized the link I added didn’t work. How about this one:

https://www.surlyhorns.com/board/index.php?/topic/6973-pebble-beachmonterey-things-to-do/
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3 hours ago, Jerry Callo said:

No beaches, but Washington D.C. checks many of your boxes.  You would not run out of things to do.

Echo Washington.  There is so much within 3 hours of the city, it's like 50 different countries/climates.  Nowhere like it.  Plus it has great beaches within 2 hours.  However the water is still pretty cold in May.   Otherwise it checks out with everything else on your list.  Still my favorite city/region, largely because within 3 hours you have ocean, mountains, white water, urban atmosphere, bay life, etc. etc.

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My very first thought ^^^^. Everything I've heard about Montreal makes it one of my bucket list cities. Many call it the most beautiful city in N. America, like stepping into Europe for a day without flying across the Atlantic.  
Time of year is crucial. February, probably no bueno, unless you like arctic cold, and lots of snow.  Spring, Summer, and Fall glorious.  I believe the Lonny is a bit weak to the dollar as well, so that's a bonus.
Amazing amazing food, word class architecture are 2 of it's traits.

Quebec City is pretty awesome. It’s pretty much what described about Montreal, just much smaller.
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Based upon OP’s description, Savannah could totally work for a full week. Take in the District, do the kitschy stuff, do the fine dining stuff, time to debauch, time to relax, lots of safe walking, historic day trips, Tybee Island, take some tours, do the museums, party with the natives, etc., etc.  

People always try to cram shit into their vacations and wear themselves out. I usually enjoy just staying put (wherever) and just absorbing the town...good or bad. 

Although...the Savannah / Charleston double feature recommended above is a solid rec as well, if you’re one of those restless travelers. 

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Your woman will love you lots for SF, Napa and Sonoma and Big Sur. That might be too much to cover in a week but holy crap that’s top notch. I like Big Sur/Carmel over Napa.

 

I’d say Seattle and Vancouver could be good too.

 

Montreal is intriguing. Don’t know much about it.

 

Not in NA per your request but ... The other option is to spend a week traveling through parts of Central America. Mexico is amazing, Costa Rica, Panama, you could make an awesome trip out of Columbia and Ecuador or hit Brazil or Argentina. 10 years is a big deal. Blow that shit out right and going south your dollars go much farther.

 

 

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