Portland, Oregon is like that kid in high school you wish you would have gotten to know better. A little weirder than average but emitting intriguing vibes of originality and depth, this city has personality to spare and often turns out to be a much better vacation companion than traditionally popular spots. It takes time to become fully acquainted with all that this lovely and offbeat place has to offer, but be assured that each step is an enjoyable one.

An interesting history is always a good start, as it provides a solid foundation for all that a city will become. Trivia lovers take note: we could just as easily be calling this town Boston right now, as two original settlers actually flipped a coin in order to determine who would name the place after his hometown. Luckily, confusion was bypassed when the man from Portland, Maine won the toss. Those two probably didn't realize that the modest grounds they stood upon would one day be a thriving cultural mecca and haven for nature lovers, beer brewers and so much more.

Thanks to future-thinking zoning laws, an inherent earth-friendliness and a dedication to preservation and sustainability, Portland is consistently ranked one of the country's most livable cities. Skyscrapers will never obscure the stunning vision of Mount Hood and farmland has kept its place alongside the business buildings. Despite a growing population and high level of energy, Portland has maintained an intimate and small town feeling that locals cherish and visitors soon fall in love with.

The wonderful year-round weather (mild winters, warm dry summers) and the surrounding mountains, wilderness trails, lakes and streams make this and outdoors-oriented destination. Day trips to Mount Hood, Mount Saint Helens, the Willamette Valley and the Colombia River Gorge are easy and tempting so be sure to pack your hiking boots and a camera in order to fully explore and remember this low-key and lovely region of the country.

Oregon's natural gifts are easily accessible from the city of Portland, but don't underestimate the wide array of things to see and do within the perimeter of this quietly bustling, oh-so-cool hot spot. Hippies, hipsters and green thinkers definitely add their influence to Portland's scene, but it can't be boiled down into a few simple labels. Rather, the city exists as a friendly confluence of progressive ideas, artistic endeavors, culinary creativity and open-mindedness.

Portland is very pedestrian friendly and has an unusually easy to navigate mass transit system. Inviting spots like Governor Tom McCall Waterfront Park, which replaced a four lane freeway, and Pioneer Courthouse Square, known as ?Portland's living room? are free places to soak in public art, people watch and further appreciate the individuality of this fun, fresh-air loving city. Biking is also a good way to see the sights, both in the city and around the nearby countryside.

As for art and culture, Portland will probably dish out more than you can take. In addition to just strolling through the artsy and colorful neighborhoods (like the Pearl District, Chinatown, Hollywood and Hawthorne Boulevard) and letting fate take its course, there are specific places to visit as well. The Portland Zoo, the International Rose Test Gardens, the Portland Art Museum, Salmon Street Springs and The Grotto Gardens are a few to get you started, but believe that there's plenty more where that came from. Depending on what time of year you're here, you might be able to see the vast displays of fragrant flowers that have given Portland its nickname as the ?City of Roses.?

Many famous yearly festivals dot the calendar as well, including the Rose Festival, the Bite of Oregon food and music fest, and the Oregon Brewers Festival, which showcases another of Portland's talents as a microbrewery capital and beer loving crowd of folk. Great shopping, a healthy music scene, lots of bookstores and coffee shops and many fine restaurants fill in any gaps, ensuring that every visitor will be able to leave sated and impressed with this thoroughly savvy town.

Letting Portland rub off on you is always a pleasant experience, and can be enjoyed even more by renting a vacation home in one of the funky neighborhoods or near downtown. Living like a local allows for all the secrets of the city to more easily be revealed, and having the comforts of home in a home-away-from home lays the foundation for a relaxed and rejuvenating trip. Explore the available and prepare to enjoy an enlightening trip to one of the country's coolest cities.