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3 Day Itinerary in Boston | Part 1

One of the oldest cities in the United States, Boston offers the perfect mix of new and old - where The Freedom Trail landmarks stand beside cutting edge restaurants. Given its age, Boston’s streets aren’t arranged in a grid or anything remotely resembling an organized structure. Given that each Boston neighborhood tells its own story - it's the perfect place to get lost. Just be careful when walking on cobblestone!

USS Constitution Museum

Begin your day a the USS Constitution, which is the world’s oldest commissioned warship afloat. This ship had sailed 52,370.5 miles around the world from May 1844 to September 1846. The greatest glory for Constitution came during the War of 1812, when its crew defeated four British frigates during three separate engagements. She earned the nickname "Old Ironsides" because the cannon fire from enemy ships seemed as if they couldn't penetrate her strong oak hull. The Navy operates the ship as a historic site in cooperation with the National Park Service. The ship is located on the Freedom Trail, where it’s open free of charge for public visitation throughout the year. The museum has a suggested donation of $5-$10 for adults, $3-$5 for children, and $20-$25 for families.

Neptune Oyster

Neptune, a North End oyster bar that’s probably Boston’s best-known restaurant, is known for having some of the most pristine seafood in the city and is the perfect spot for lunch. There is always a wait for the tiny dining room. You line up for the host to take your phone number and tell you to walk around for a couple hours, then you’ll come back and wait a little more. The raw bar, for starters, is fantastic, with a collection of some of the freshest shellfish from up and down the Eastern Seaboard. Aside from the oysters, you should go for the uni or razor clam cocktail. Their warm lobster roll is also one of the best that Boston has to offer. The chowder is also a must have. Go hungry because this will be one of the best meals in Boston you'll ever have!

Spend the afternoon exploring "Little Italy" aka North End

The North End, a one-square-mile corner on Boston’s waterfront, is a maze of narrow streets with some of the city’s oldest buildings.

  • The heart of the Freedom Trail is in the North End neighborhood. The 2.5 mile walking path includes 16 sites that are linked to tell Boston’s story of the American Revolution. In the North End, heading north, the Freedom Trail comes from Haymarket and Blackstone Street through the Greenway parks to Cross Street. It heads down Hanover Street, passing the Paul Revere House, into the Prado – Paul Revere Mall park and the famous statue of Paul Revere to the Old North Church and Copp’s Hill Burying Ground before heading out of the North End toward Charlestown.

  • The Old North Church features a steeple that is 191 feet high. At the time, the Church represented the strong Puritan beliefs of the Massachusetts Bay Colony. At the beginning of the Revolution, most of the Old North congregation were loyal to the King of England. However, the church is most well-known for when Robert Newman, church sexton, held two lanterns on April 18, 1775 giving the famous “one if by land, two if by sea” signal to Paul Revere that the British were going to Lexington and Concord by sea. Still standing next to Old North is the Clough House, built in 1712, and representative of colonial architecture. There is an admission fee - this will get you entrance to the entire Old North Church & Historic Site, including the Old North Church, Captain Jackson’s Historic Chocolate Shop, Patriots Corner and access to the five gardens of Old North’s campus.

  • Paul Revere’s House is a c.1680 home owned by Paul Revere from 1770-1800. The wooden house is the oldest building in downtown Boston. The famous patriot was living here when he made midnight ride to Lexington on April 18, 1775, well-known through the famous poem of Paul Revere’s Ride by Longfellow. Next to the Paul Revere House is the Pierce Hichborn House, a 1711 brick building built in 1711.

  • The famous Paul Revere equestrian statue, created by sculpture Cyris Dallin, is a must-visit site of the North End. The Prado, officially known as the Paul Revere Mall, was designed by Boston architect Arthur Shurcliff and is located between the Old North Church and St. Stephen’s Church on Hanover Street.

  • Designed by Stanley Saitowitz, The New England Holocaust Memorial consists of six glass towers. Each tower symbolizes the six major concentration camps from the Holocaust: Majdanek, Sobibor, Chelmno, Belzec, and Auschwitz-Birkenau. The six towers also represent the six years from 1939-1945 when the most deadly phase of the Holocaust, the “Final Solution,” took place. Engraved on the outside walls of each tower are groups of numbers representing the six million Jews that were killed, along with quotes from survivors of each camp. Visitor’s may walk underneath the towers as steam rises up through metal grates, symbolizing smoke rising from charred embers at the bottom of these chambers, to remember the horrors of the extermination. The Memorial is located in Carmen Park on Congress Street near Faneuil Hall and Quincy Market.

If you prefer to do a walk along the water instead, the Harborwalk is a free public walkway along the waterfront with parks, public art, seating areas, cafes, exhibit areas, interpretive signage, water transportation facilities and a wide range of other amenities. In the North End, the Harborwalk is largely completed and among the most well-maintained and highly visited in the city. It encompasses the wharves along Boston Harbor and several parks.

Today, Little Italy is also known for being a hub of Italian-American culture and cuisine. Italian restaurants, coffeehouses, pastry shops and old-school delis pack the area, especially on lively Hanover Street. Aside from the numerous long-time Italian restaurants and bakeries, there are feasts that take place each summer. Starting in June and running through early September, the North End hosts a number of Italian feasts and festivals, all in honor of a different saint and put on by the community’s religious societies. Large crowds gather for the decorations, marching processions, and food vendors selling Italian dishes. The biggest festival is the Saint Anthony’s Feast over the last weekend in August. The three-day feast celebrates Saint Anthony of Padua and Santa Lucia and ends with a 10-hour grand procession with street bands and floats.

Enjoy dinner at Giacomo's North End

With nearly 100 restaurants, cafes, and markets in the North End, there are endless food and dessert options. The busiest street is Hanover Street. Authentic, family owned Italian restaurants and bakeries line the streets - make sure to explore the cobblestone alleyways as well - making choosing nearly impossible!

If you need a recommendation - go to Giacomo's. This is a no-frill, true Italian restaurant. How authentic is this place? It's cash-only authentic. Be careful, there is always a line outside this seafood and pasta spot. The budget-friendly restaurant offers piles of butter-saturated garlic bread, $20 bottles of wine, to go with your zuppa di pesce, a beautiful platter of linguine with lobster, shrimp, scallops, calamari, clams, mussels with your choice of sauce. The pasta is made fresh-in-house, and their sauce is what made them famous.

As for bakeries, Modern Pastry (Italian cakes and cookies) and Mike’s Pastry (cannoli) are the most famous in the neighborhood (Modern is available for an after dinner treat, but Mike's is only open during the morning / early afternoon).


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