Not every vacation is right for every traveler.
New York is exciting, but crowded.
Orlando is magical, but touristy.
Boston is historic, but winters can be harsh.
At Should I Travel To, every city is evaluated using the same consistent framework so you can decide which destination fits your travel style.
Featured Destinations
If you’re visiting the United States for the first time, or want to explore a new destination, these are some of the country’s most iconic city vacations.
New York City
World-class attractions, incredible food, and endless things to do, but expect crowds and high prices.
Los Angeles
The entertainment capital, diverse neighborhoods, and perfect weather, but expect a car-dependent experience.
Orlando
Unmatched theme parks, family-friendly fun, and year-round sun, but expect crowds, tourist zones, and summer heat.
What Makes Should I Travel To … Different?
Travel Isn’t One-Size-Fits-All
Most travel websites tell you why every destination is worth visiting.
We think every trip involves tradeoffs.
That’s why every city is evaluated using the same ten categories, including:
- Cost & Value
- Weather
- Crowds
- Walkability & Transportation
- Things to Do
We don’t tell you where to travel.
We help you decide.
Popular Comparisons
Which Trip Is Right For You?
- NYC vs Chicago
- NYC vs Boston
- NYC vs Washington, DC
- Disneyland vs Disney World
- Los Angeles vs San Francisco
Our Philosophy
Almost Every Great City Is Worth Visiting Once.
Some travelers love New York.
Others prefer Chicago.
Some people dream of beaches.
Others want museums.
The best destination isn’t the one with the highest score.
It’s the one whose strengths match what you’re looking for.
3 Pros. 3 Cons. You Decide.
Latest City Guides
- Anaheim vs. Orlando
- Should I Travel To … Anaheim?
- Should I Travel To … Los Angeles?
- Should I Travel To … Orlando?
- Should I Travel To … New York City?
Not sure where to start?
Explore our complete collection of city guides and find the destination that’s right for you.