I would expect Boston to be covered in snow right now - a veritable winter wonderland. It's not. Nature has an ironic sense of humor I think. I traveled to Boston for the first time over Thanksgiving weekend and was quite mesmerized with how beautiful a city it is. Thankfully, when I was there it didn't snow. Was beautiful and sunny for two days and rainy for two days. Got the best and worst.
Much of America's "young" history began here, and I love it when history comes alive. I spent my weekend hanging out with a bunch of internationals for the most American of holidays. Here's our itinerary.
Day One - North End "Little Italy" Market Tour
The interesting thing for me was that Boston was a lot smaller than I had imagined. For some reason I expected it to be bigger, but it's compact size and easy to use subway system makes it fun to navigate. It's first and foremost a walking city.
Started off with a 3-hour food tour of the North End or "Little Italy" as it's commonly known. The North End is one of America's oldest neighborhoods with immigrants settling here for centuries. Michele Topper Food Tours takes you through "American history, ethnic heritage and authentic Italian food." We started at the V. Cirace & Son Wineshop, 173 North St and ended at Maria's Pastry Shop, 46 Cross St.
My favorite stop was the Salumeria Italiana. I tried the most awesome balsamic vinegar I've ever had from Modena called Rubio Aged Balsamico. It's amazing - goes great with berries, aged cheeses and grilled and roasted meats. Great gift for any of your foodie friends.
Dinner: Check out Lucca for dinner (Hanover Street) or the famous and No.1 pizza spot in Boston - Pizzeria Regina, where there's always a pretty long line.
Day Two - Boston Freedom Trail
I think this is the easiest way to see the sights of Boston. The Freedom Trail is a "2.5 mile red-brick walking trail that leads to 16 nationally significant historic sites, every one an...American treasure." You go through parks, cemeteries marking the names of Pilgrims - sights that tell the story of the American Revolution. Faneuil Hall, the "Cradle of Liberty," was gorgeous and really festive as they had just put up the huge Christmas tree, lights and decorations. Boston's Holocaust Memorial is striking and simple with the numbers of the victims etched in glass.
Had a great time. No need to really ask for directions, but Pippa, our wonderful host told us how she loves asking locals for directions - just to hear that famous Boston accent.
We ended up at the Prudential Center for some shopping and chowder at Legal Seafood, a well-known New England chain. You can also pick up tickets for the Boston Duck Tours at the Prudential as well.
Day Three - Boston Duck Tours
Took in a church service at Union United Methodist in Boston's South End. Boston's brownstones have a remarkable history. Was the center of Boston's African-American community at the turn of the last century, with renowned jazz clubs. Stop by Wally's Cafe, Boston's oldest jazz club, later in the evening for some great live music.
Boston Duck Tours is a must. It's a bus-boat that takes you through Boston's streets and harbor. A tour is always a great way to get fun history anecdotes and absolutely loved it!
Cambridge. We headed to Harvard, to check out the campus and get our photo taken with the gold toe statue. Cambridge is a cute little town. Some fun shops and restaurants.
Dinner: Elephant Walk. Cambodian-French food to die for near Boston University - good cocktails. Nice wine list.
Day Four - Cheers!
Checked out Newbury Street with its trendy shops and restaurants. Johnny's Cupcakes is a trendy t-shirt shop. Me - being obsessed with cupcakes thought it was a real cupcake place. But cool t-shirts. Ended our visit doing the most gawdy of tourist things and having dinner and drinks at Cheers. It's a classic. Had to do it. Food not that bad. Then, home sweet home. Thanks Pippa and Kudzai!
Websites
Michele Topor Food Tours of Boston - www.foodtoursofboston.com
Salumeria Italiana - www.SalumeriaItaliana.com
Pizzeria Regina.com - www.Pizzeriaregina.com
The Freedom Trail - www.thefreedomtrail.org
Elephant Walk Restaurant - www.elephantwalk.com
Boston's South End - www.south-end-boston.com
Daily Candy Boston - www.dailycandy.com/boston
Johnny Cupcakes (Cook T-Shirts) - www.johnnycupcakes.com
Wally's Cafe Jazz Club - www.boston.com
Credits: Photographs by Pippa Mpunzwana, except Boston Aerial.

Wow. You know what? As I was reading your blog, I just felt like I'm also there goofing around Boston. Thanks for sharing.
-liz
Posted by: fun weekend getaways | January 13, 2010 at 11:53 PM