Not sure where to start?
Whether it’s your first trip to the United States or you want to pick the right next getaway, we usually recommend starting with one of these three destinations:
New York City: America’s most iconic urban experience.
Washington, DC: History, museums, and national landmarks.
Orlando: The country’s premier family vacation destination.
Explore Cities
Every city offers something different.
Some are famous for history. Others are known for food, beaches, nightlife, or world-class museums. Some are easy to explore without a car, while others require a little more planning.
Note: Some cities appear in multiple categories because most destinations offer more than one type of experience.
At Should I Travel To, every destination is evaluated using the same framework so you can compare places more easily.
3 Pros. 3 Cons. You Decide.
Featured Cities
- New York City
- Los Angeles
- Chicago
- Orlando
- Boston
- Washington, DC
Browse By Travel Style: Best Of
First-Time Visitors
- New York City
- Washington, DC
- Orlando
History Lovers
- Boston
- Philadelphia
- Washington, DC
Food Cities
- New York City
- Chicago
- New Orleans
Without a Car
- New York City
- Boston
- Washington, DC
Family Vacations
- Orlando
- Anaheim
Beaches & Weather
- Honolulu
- Miami
- San Diego
Nightlife
- Las Vegas
- New Orleans
- Miami
Museums
- Washington, DC
- New York City
- Chicago
Browse By Region
Northeast
- NYC
- Boston
- Philadelphia
- DC
South
- Orlando
- Miami
- Nashville
- New Orleans
Midwest
- Chicago
- Detroit
- Minneapolis
West
- Los Angeles
- San Francisco
- Seattle
- Las Vegas
Pacific
- Honolulu
Compare Cities
Maybe you’re stuck trying to pick between one city or another. Our comparisons aim to make that decision easier for you.
Popular Comparisons
- NYC vs Chicago
- NYC vs Boston
- NYC vs Washington, DC
- Disneyland vs Disney World
- Los Angeles vs San Francisco
- Boston vs Philadelphia
Explore more City Comparisons
How We Rate Cities
Every city on this website is evaluated using the same ten categories:
- Cost & Value
- Weather
- Crowds
- Transportation
- Things to Do
- Food
- Safety
- Culture
- Cleanliness
- Uniqueness
Learn more about our methodology: Should I Travel To … Rating Framework