With so many cities to be explored it's hard to know how to prioritize them. For every city I visit I'll give it a ranking to share my insight and offer help if you are having a hard time deciding. Obviously these rankings are based off my experiences and what I look for when I travel and may be different than yours.
Some of these ratings may seem low but I enjoyed all the cities on the list. I just didn't want to be handing out 10s and 9s to every city. I tried to look at the city has a whole and take into consideration the things to do, the ease of getting around, and the food and drinks.
The best way to use these rankings is if I were to recommend someone visit a city it would be in this order. For example, I really liked Amsterdam and found the history to be fascinating but I'd say you should visit Munich because I felt there was so much more to do.
If you want to see what I bring when I'm exploring a new city you can do that here!
New York City, New York: 10/10
This rating is a little unfair because I love New York. I first went when I was 15 (so like 2005) and was captivated by the lights and energy of the city. I loved watching people selling knock off handbags, it was so interesting to me! They had a system of when they heard cops were coming they'd wrap up their stuff, throw it over their shoulder and were on their way. I respected the hustle! I've then gone back in 2011, 2014, 2015 (lived in Brooklyn for 8 weeks), 2016, 2017, and 2018. It helps that two of my best friends live here.
New York has everything you could want. There are famous landmarks, historical places, great food and drinks, public transportation to easily get around, historic museums, cultural events, free events, and more. The city isn't perfect, it can be hot during the summer and cold during the winter, overly crowded and expensive, but hey, I've yet to see the perfect city. If you want a quiet day you can go into Central Park and you'll forget you are in one of the biggest cities in the world. If you're bored on a Tuesday you can go to the Comedy Cellar and might run into Paul Rudd, Adam Driver, and Jonah Hill as they watch Judd Apatow do stand up like I've done. You may be visiting your friend at the coffee shop he works at and see a Seth Meyers sketch be filmed. There are speakeasies, rooftop bars, and some of the best cocktail or craft beer bars in the world (check out As Is). From my experience, there really is no other place like it!
For more information on New York click here.
Seattle, Washington: 9/10
Growing up in the desert I always thought I'd like Seattle because it rained so much there. Well, it didn't rain when I was up there and still really liked the city! I thought the downtown area was cool, super modern, but also very clean. I think what really skewed my perception of the city was actually getting out of the downtown area though. The things I enjoyed the most were the falls, the parks, beaches, hiking, and taking the ferry over to Bainbridge Island.
I obviously didn't do some of the more iconic things like going to the Space Needle, Chihuly exhibit, go whale watching or experience the rain but thought the Seattle was awesome!
For more information on Seattle click here.
Milwaukee, Wisconsin: 8/10
This may be one of my most shocking rankings I’ve given. I came into Milwaukee with moderate expectations and left thinking the city was really cool. The city really has a lot of things to do during the summer whether that is kayaking on the river or biking around town. If you are into beers they have brewery tours or you can take a distillery tour. If you want to relax they have beaches, a public market or neighborhood markets. If you are a sports fan they have an NBA and MLB team with the Green Bay Packers somewhere near by. There are museums, cool houses, and a lot of parks in the city. , places to eat, and plenty of beers to be drank looking over a river. Milwaukee has a wide variety of decent restaurants and a growing food scene and is easy to get around. Everything seemed to be a 15-20 minute walk with the most extreme being 30 minutes.
I went in June and the temperature was in the 50s some days and heard July and August is when the weather is the best. If I went in the middle of winter this ranking would probably look vastly different!
For more information on Milwaukee click here.
Grand Junction, Colorado: 7.5/10
This is a hard city for me to rank because I lived in Grand Junction for almost 3 years. But I do stick by this ranking. If you are into free wine tasting, breweries, doing outdoorsy stuff like hiking, river adventures, or taking day trips into the mountains this is your spot. You will need a car to get around and there aren't a whole lot of food options that are high class but there are several good options.
For more information on Grand Junction click here.
Pagosa Springs, Colorado: 6.5/10
This rating seems lower than how much I actually liked my time in Pagosa. I enjoyed all the hikes and thought the scenery was gorgeous. There were great coffee places to go to and a cute downtown area to check out the shops. The reason the ranking is low is because if you are looking for another else out of a travel destination than outdoor activities it may be hard to find that here. I do highly recommend it though!
For more information on Pagosa Springs click here.
HELLO AND WELCOME!
I'm Jake, a dude interested in personal finance and travel creating the life I choose.
In 5 years I went from living in a basement with Craigslist roommates to paying off 90k of debt, backpacking 3 continents, getting a house for myself and 5 rental units.
Read my story in the about me section.
All photos on the blog are from my travels
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