How does Should I Travel To … rate cities?
At Should I Travel To …, we believe the best travel decisions come from understanding both the advantages and the tradeoffs of a destination.
Highlights are important, but we think it’s just as important to understand the crowds, costs, transportation, and other factors that shape the overall experience.
That’s why every city on this site is evaluated using the same consistent framework.
Our goal isn’t to declare one city “better” than another.
Instead, our goal is to help you decide which destination best fits the kind of trip you want.
How Should I Travel To … Rates Cities: 10 Categories
Cost & Value
How expensive is a typical trip?
We consider factors such as accommodations, transportation, dining, and the overall value visitors receive for their money.
Weather
How comfortable is the destination for the average traveler?
We look at seasonal conditions, temperature, humidity, and the likelihood that weather will disrupt a vacation.
Crowds
How busy will the destination feel?
Some travelers love energy and excitement. Others prefer quieter experiences. We consider overall visitor volume and how crowded major attractions typically feel.
Walkability & Transportation
How easy is it to get around?
Some destinations are best explored on foot or by public transportation, while others are easier to reach by car. We evaluate how convenient the average visitor’s experience is likely to be.
Things To Do
How much can travelers realistically fill their itinerary?
We consider the variety and quality of attractions, landmarks, museums, entertainment, outdoor activities, and experiences available.

Food & Dining
How rewarding is the destination for travelers who enjoy eating out?
From local specialties to internationally recognized restaurants, we look at both quality and variety.
Tourist Comfort & Safety
How comfortable is the average visitor likely to feel?
Rather than relying on statistics alone, we consider the overall visitor experience, including ease of navigation, common tourist concerns, and the general atmosphere.
Culture & Character
Does the destination have a strong sense of identity?
Some places feel unlike anywhere else in the world. Others offer a more familiar experience. We look at history, architecture, traditions, and local personality.
Cleanliness & Infrastructure
How well does the destination function for visitors?
We consider factors like general upkeep, transportation systems, public spaces, and the quality of tourist infrastructure.
Uniqueness
Can you get this experience somewhere else?
Some destinations offer something truly one-of-a-kind. Others may provide experiences that are easier to find elsewhere.
No Destination Is Perfect
Every city has strengths.
Every city has weaknesses.
New York City is exciting, but crowded.
Boston is historic, but winters can be challenging.
Orlando offers incredible family entertainment, but it isn’t a traditional city experience.
Those tradeoffs aren’t flaws. They’re simply part of what makes each destination unique.
The Scores Are a Starting Point
Our ratings are designed to help you compare cities consistently, but they aren’t meant to tell you where you should travel.
Some travelers actively seek out busy cities.
Others don’t mind paying more for a once-in-a-lifetime experience.
The best destination isn’t always the one with the highest score.
It’s the one whose strengths match what you’re looking for.
We present 3 pros and 3 cons so you can decide where you should travel to next.