You can by almost anywhere with just English and waving your arms around - you can do a "fish" gesture if you want to order fish, flap your arms up and down and go gwak-gwak-gwak if you want to order chicken, and go "p-shawwww" while holding your arms out if you want a taxi driver to take you to the airport. And that's in countries where no one speaks English, most places there's enough people who speak it. Once you meet someone local and get along, try to get a few phrases at least for politeness' sake - thank you, hello, "I don't understand the language, sorry" are a good first three. "Happy" is another good versatile one in most languages.
The bigger piece of advice than "where?" is "how?" How you travel makes all the difference. You're probably going to make tourist mistakes when you start traveling, and pay between twice as much and five times as much as you should for what things cost and get lower quality in the process. Hey, it's how it goes, I was staying in a so-so hotel in London near Victoria Station the first time I went, and I wound up paying 12 pounds for bad Mexican food in Leicester Square. Ouch. Now if I was going back I'd either short-stay rent an apartment, or if I was going cheap I'd stay at Picadilly Backpackers for cheap. I'd eat at all you can eat Indian and Chinese buffets once a day for a very large meal, and have a small meal from a grocery store the other meal. I'd live really cheap in London and save any/all money for when it can be better spent elsewhere.
But you learn those things over time. Don't book too far in advance at any hotel if you don't know the area. Like, if you booked "downtown" in Los Angeles, you'd be staying in the middle of nowhere. LA has no real center, but the area called "downtown" happens to suck and not have anything really significant, whereas Santa Monica and West Hollywood areas are more interesting. But again, you wouldn't know that if you didn't know that, so don't book too far in advance. If it's a walking city, I like to just turn up and ask people in the airport what area is nice, then go walk around that area until I find somewhere to stay.
That sounds crazy, but it's not. You can always find an internet cafe and start making calls to places if you don't find a place within a few hours. One time I showed in Kuala Lumpar, Malaysia without anywhere to stay, and it happened to be their 50th anniversary of their independence, and a major air-and-space convention was in town. That was the hardest it ever was for me to find a room, but I still found one after a number of hours. Usually it's much simpler.
Very, very glad my first time to Taipei I just showed up, because Guting doesn't show up as a "top area" on anyone's tourist lists, but I love it and it's perfect for me. Again, showing up and walking around (though I got into Taipei in the middle of the night, so I stayed at an airport hotel the first night).
Anyway, how is more important than where. How - stay flexible and mobile on your accomodations so you can move around if you don't like the area. Eat where the locals eat, especially laborers if you can find them. That's the best value for healthy, high energy food. If I see construction guys going somewhere at lunch, I know it's going to be good value for good, hearty food.
Street food can be very good for cheap in some countries. Walk into all sorts of small, local restaurants that you can't understand the sign with no English and look at the prices. If you're not a picky eater, just point to something and there's a decent chance it'll be okay. (I used to do this before I refined my diet down to just a few things) Convenience stores or grocery stores sometimes have really good value, depending on the country. South Korea and Taiwan both have flavored hard boiled eggs for quite cheap that are delicious. You pick that stuff up when you get around.
If you have a return ticket from a major airport like Schripol in Amsterdam or anywhere in London, you're free to bum around Europe and and find somewhere that suits you. Also possible in Japan, but less possible in most of Asia. These days I'm pretty comfortable going one way and I figure I'll get a one way ticket to return whenever from wherever I'm at, though occasionally (rarely) you get burned on price, especially if you have to get back on a certain day. Again, I'm usually okay doing it this way, but I remember once or twice I paid a fair bit. I still think it's worth it and still usually do it this way.
Ah, there's so much more to say... look at travel lists of recommended places from people who have similar tastes as you. My recommendations:
-Easiest to get around with just English: London, Amsterdam, Toronto, New York, Hong Kong, Taipei (Taipei less so than the rest, but really it's not bad at all, my Chinese is almost nonexistent)
-Good beach weather: Italy, Spain, Southern France, Austin (need car), Los Angeles (need car), Thailand depending on the season
-My favorite cities overall: Tokyo (by far, but it's not relaxing), Barcelona, London (not really relaxing), New York (...maybe not relaxing), Nice France, Florence Italy.
Southern Europe might get you the best bang for your buck, get a return flight from a big city and you can travel until you find a city you really like and then spend most of your time there. Taipei is a fine choice if you like Asian culture, it's extremely clean, safe, modern, and inexpensive for the quality you get. Japan is amazing but can be crazy. Thailand is hit or miss - I actually wasn't crazy about it while I was there, but in retrospect I had a great time. Note that some people do really dislike Thailand, it's kind of... in your face. Sensory overload at times, lots of vibrant smells, prostitution is everywhere and very aggressive, lots of drinking and drugs in the tourist areas. The type of traveler in mid/low end places in Thailand is different too - not really my kind of people, I like the people I meet in Europe and Taipei much more, lots of very hippie stoned out people but to each his own.
Lots of thoughts there. Drop me a line if you've got any questions or reply here and I'll try to check it, I've been to a fair number of places in Europe, North America, and Asia over the years.