Eat Something Great
New Orleans, Chicago, New York, Santa Fe, Savannah, and Atlanta can each justify a trip around what you're going to eat—and what neighborhood you'll explore afterward.
You don't need a week to have a vacation. Sometimes three or four nights, the right hotel, and one really good reason to go are exactly what you need.
Let's Get Out of TownA great getaway might start with a city you've always wanted to see. But it might just as easily start with a concert, an NFL game, a food festival, a Broadway show, Halloween, an anniversary, a three-day weekend—or simply, “I need to get out of town.”
Pick the reason, and we can find the place.
Weekend trips work best when we know what we're trying to get out of them.
New Orleans, Chicago, New York, Santa Fe, Savannah, and Atlanta can each justify a trip around what you're going to eat—and what neighborhood you'll explore afterward.
Broadway in New York. Comedy in Chicago. A residency in Las Vegas. Live music in New Orleans. Sometimes the ticket comes first and the vacation grows around it.
Football, baseball, a festival, Halloween, a concert, a food weekend, or a holiday celebration can be the reason to go rather than something we add after choosing the city.
San Francisco, Asheville, Santa Fe, Savannah, and the California coast prove a short trip can feel much longer when the scenery and pace are completely different.
Orlando is the obvious example, but a getaway built around theme parks, attractions, golf, spas, museums, or a favorite activity works almost anywhere.
A long weekend doesn't have to stop at the border. Riviera Maya is one example of how the right flights and resort can turn a few nights into a real international escape.
I've personally visited all of the destinations featured on this page, most of them several times or more, and I've even lived in some of them. That matters on a short trip. When you only have three or four days, where you stay, how you get around, what deserves your time, and what isn't worth crossing town for can make a huge difference.
I also already have detailed trip ideas and planning experience for many of these places. We can use one as a starting point, change it completely, or build something new around what you want to do.
A four-night trip has different rules than a two-week vacation. Flight times matter more. Airport-to-hotel time matters more. Hotel location matters more. Changing hotels usually makes less sense. And an attraction that takes half a day to reach needs to be worth half a day.
The goal isn't to cram a week's vacation into 72 hours. It's to make those 72 hours feel well spent.
Sometimes the best weekend isn't a place you've been dreaming about for years. It's where something great is happening next month. A concert, comedy show, football game, festival, food event, seasonal celebration, or unusual local tradition can give us the destination—and then we build the hotel, restaurants, neighborhoods, and extra experiences around it.
The event gives us a reason to go. The rest of the weekend turns it into a vacation.
Build the weekend around the performance instead of treating it like one more item on the schedule.
One game can anchor a weekend of restaurants, neighborhoods, museums, and nightlife.
Go when a city is showing off what it does best.
Halloween, Christmas, special exhibitions, local traditions, and those wonderfully specific events that only happen once a year.
I can start with a trip I've already built, use a destination I know well, or begin with nothing more than your dates and the sentence, “We want to go somewhere.”
Start with something proven. Change anything you want. Or start with a blank sheet of paper.
Give me a few days, who is going, and what sounds fun. We'll figure out where the weekend should take you.
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