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City Weekend
Just getting out of the house, with better food than you have at home.
What this trip actually costs
$317 to $2,559 per head, three nights
City weekends are food and drink money. Lodging is whatever, the bar tab is the budget. Plan accordingly.
The destinations, ranked
Eight of our cities work for a weekend where the city is the point.
Best first. This is an opinion, not a spreadsheet. If the top pick fits your dates and budget, stop scrolling.
01Nashville
BNAThe strip everyone goes to, and how not to spend the whole weekend on it.
See the guide
Check stays02New Orleans
MSYThe cheapest big weekend in America, and the hardest one to survive intact.
See the guide
Check stays03Austin
AUSNashville with better food, better water and thirty percent fewer matching shirts.
See the guide
Check stays04Miami
MIAThe most expensive weekend on this list and the only one that looks exactly like the photos.
See the guide
Check stays06Charleston
CHSThe grown-up version of this trip. Golf, boats and the best food per dollar in the country.
See the guide
Check staysBig groups cannot book a table online
Every reservation site caps out around six or eight. Your group is ten. So the table you want either does not exist or lives behind a phone number.
Above that cap you are usually talking to a private dining or events desk, and the deal changes. Expect a set menu instead of ordering off the card, a food and beverage minimum instead of a per plate price, and a deposit to hold the date. That is not a rip off, it is how a restaurant absorbs the risk of a ten top that does not show up.
Call four to six weeks out for the one dinner that actually matters. Leave the other two nights open. The group will not agree on three dinners anyway, and the good nights are usually the accidental ones.
The bar tab is the budget
Large parties usually carry an automatic gratuity, commonly eighteen to twenty percent, added before anyone gets a chance to argue about it. On a ten top that is real money and it is not optional, so put it in the per head estimate rather than finding it at the bottom of the bill.
Most places will not split a check ten ways either. One card pays and one guy spends the next week chasing nine people. Decide who that is before dinner rather than during, and settle the same night while everyone still remembers what they ordered.
The one thing everyone screws up
Booking three nights in the city centre because it looked convenient.
You are not walking anywhere at two in the morning as a group of ten. You are getting cars either way. Being six blocks out is often close to half the price for the same weekend, and across three nights and ten guys that difference buys the dinner you actually wanted.
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