One of the most underrated cities to vacation in is Boston, Massachusetts. I know you're already getting visions of front-bitten fingers, cranky new Englanders, and Ben Affleck. But Boston has more to offer than that. From early history sites to the Arts to great food to enthusiastic fans of some of the best sports teams in the country, this great city is a city like no other. You will cherish the time you spent there and you will find the Boston-ites to be some of the most genuine and fun-loving of all the cities you'll visit.The two biggest challenges are the weather and finding your way around the city. If you are not used to the cold weather it can come as quite a shock to the system. And if it does snow it can really jam up transportation. On the good side, the snow will make the holiday time that much more special as it adds another special dimension to sites. Finding your way around is another challenge altogether. Boston is not organized in a grid-like manner like other cities. I lived there and it took me quite a while to figure it out. I suggest getting a good map and treating it like a game and have some fun with it. Remember, you are on vacation. Despite that you're going to have a great time in Bean-town. Here's some of my favorite things to do when I'm there:Food, Art, and Fun at Faneuil Hall - An absolute must. This section of town makes me think about what life must have been like 100 years ago. The cobblestone streets, the statues, and historic architecture are fantastic. You'll find great shops, food, and performance art (get your dollar bills ready). You have this great culture that is a mixture of the local colleges, the fast-paced financial district, and a thriving urban city. It's hard to put into words. This is a special place. Food - There is so much delicious food to eat. You are in a "Seafood Haven" so you can't leave without having a 1 lb lobster or two . What about real clam chowder (chowdah!)? Be sure to grab a slice of fresh hot pizza from "Regina", authentic Italian food in the North End (La Famiglia is my favorite but you can almost go to any restaurant), and the best cannoli from Mike's Pastry.Newbury Street - I suggest you park at the Marriott Copley down the street. Some the best shopping and outdoor cafes on the East Coast. High-end designers like DKNY and Versace as well as many others in beautiful boutiques up and down the street (the local boutiques have better prices than the brand names so check it out). This street is a mixture of great clothing designers and fantastic (non-chain) restaurants and cafes. You can eat from almost any international cuisine you seek. If you live in a city or town that is overrun with chain restaurants you'll appreciate this even more with food flavors and selections that are uncommon. Well, let's go to school - Harvard that is - Take a walk around one of the most famous universities in the entire world. Then head on over to Harvard Square and see the performers and feel the energy of the area. Then grab dinner at "Fire and Ice", a Mongolian wok restaurant with the best Prickly Pear Margaritas. Catch an independent film at Kenmore Square and say hi to Ben Affleck while you're there.The Boston Museum - This is an incredibly diverse museum with rare paintings, sculptures, and artifacts that range from ancient China to modern day. Local tip: Wednesday Night is Citizens Bank night - free entrance! I could go on and on and we haven't even mentioned Fenway Park yet. Boston is one of my all-time favorite cities. You'll love the art, the culture, the food, AND the people. Whether you stay in a hotel or in a timeshare with Intervalworld or RCI.com, you will enjoy this unique city very much. But be careful, you might have so much fun, you might leave with a "wicked cool" accent!
