Oct 13, 20115 min read

Roadtrip! Food and Fun :: Boston & Martha’s Vineyard

Boston Waterfront

I took the most amazing trip to Boston and Martha’s Vineyard over Labor Day holiday and fell in love. Boston is one of those places that feels like a big city but is actually pretty small and low-key if you ask me. I loved the slower pace, the still quietness of the South End on a Saturday night. The views of the harbor, the blue and white hues of sailboats and water surrounding the city’s edge. The amazing Italian food in the North End, the historic architecture all over the city and along the Freedom Trail, and the beautiful campus of Harvard University.

Charles River Sunset

Watching the sunset at dusk over the Charles River. Amazing lobster and seafood on the harbor with views to match…and for a big city girl like me, I think I could live here one day.

The Colonnade Hotel Rooftop Pool

We stayed at the amazing Colonnade Hotel (with a rooftop pool and bar!) in Back Bay.

Shop in Back Bay, Boston

The next day, we headed to Newbury Street in Back Bay for shopping…

Public Gardens, Boston

then we wandered through the Public Gardens, heading to historic Charles Street to see all the beautiful old homes in Beacon Hill

The Hill Tavern

before we stopped at The Hill Tavern for drinks and lunch.

Old City Hall

We spent most of the day hiking the Freedom Trail to see all the old historic buildings and sites around town.

Shrimp & Polenta, Sibling Rivalry

That night we had amazing dinner in the South End at Sibling Rivalry and had some delicious seafood.

Harvard University

Our last day there, we made our way to Harvard University and trekked around Cambridge! Boston is definitely small enough to see in a few days, but the views and slower pace will make you want to stay a lot longer.

Here’s a few places I went to that you don’t want to miss on your next trip to Boston:

The North End, Boston

North End (Boston’s Little Italy): If you are in the mood for Italian food and pastries, this is the place to go. Just head straight to Hanover Street and you’ll find a multitude of shops, restaurants and cafes, delis, pizzerias, bakeries, pubs and taverns. Many have lines out the door on a Friday night so reservations are highly recommended!

Lucca, The North End Boston

We had an amazing dinner at a really nice Italian restaurant called Lucca on N. Hanover Street (Grilled Veal with Truffled Mash and Asparagus) and Lobster Tagliatelle!

Cannoli from Mike’s Pastry

Then we hit Mike’s Pastry for amazing cannolis and gelato. Um, YUM!

Giacomo’s, The North End

Here’s a list of my favorite places in The North End that you don’t wanna miss: Lucca, Strega, Neptune Oyster, Giacomo’s, Fiore, Cantina Italiana, Dino’s Pizza and Subs, Mike’s Pastry, Modern Pastry.

Newbury Street, Back Bay

Back Bay/South End – These are two of Boston’s nicest neighborhoods in my opinion. Back Bay is the best place for shopping, art galleries, gardens, cuisine and culture in Boston. There are gorgeous historical homes and churches, clothing boutiques, spas and salons and fabulous restaurants to explore. Head to Newbury Street and make your way to the Public Garden to check out the Swan boats or just hang out in the park. The Charles River Esplanade is a great place to get a gorgeous view of the harbour and stroll along the river on a sunny day.

Sibling Rivalry, South End

The South End is a tree-lined neighborhood known for its fine dining, art galleries, open market, restaurants and high end martini clubs and jazz bars. Head to Tremont Street and check out Sibling Rivalry, Stella, Tremont 647 for a nice dinner.

Enjoying a Blueberry Martini @ 28 Degrees

Then hit 28 Degrees for some great martinis..

The Beehive

and The Beehive for amazing live jazz and blues.

Seaport, Boston Harbor

Waterfront/Seaport District – If you want a great view of the Boston Harbor, then you need to go to Waterfront and Seaport District. You can start in the North End near the Bunker Hill Bridge and then continue around Atlantic Ave to Christopher Columbus Park and view the harbor islands. From here you can walk to the Aquarium where there are several cruise lines that take you around the harbor. Head down to Rowes Wharf to check out the show cruise ships and Boston Harbor Hotel and Towers and then cross the old Northern Bridge to the Seaport District.

Legal Seafood

The two places I recommend for Waterfront Dining are the famous seafood restaurants Legal Sea Foods and across the street the Legal Test Kitchen

Shrimp Cocktail at LTK

(we ate at LTK and I had the most amazing Shrimp Cocktail

Truffled Lobster Mac & Cheese, LTK

and Truffled Lobster Mac ‘n Cheese – to die for!)

Tia’s on the Waterfront

For casual dining and terrific cocktails on the harbor, there’s no other place than Tia’s Restaurant and Bar on the Waterfront! Closer to the North End than the Seaport, but awesome place for happy hour and watching the sunset..

Martha’s Vineyard, MA

VIEW SLIDESHOW OF PHOTOS FROM MARTHA’S VINEYARD

Vineyard Haven Harbor, MV

If there is ever a place I would like to go after retiring myself from the hustle and bustle of New York City, Martha’s Vineyard has to be top of my list. This charming island is the epitome of beautiful architecture, history, charm, quietness, tree-lined streets, locals, antiques and oh, seafood.

Vineyard Haven, MV

We took a train to Woods Hole from Boston and then took a ferry to Vineyard Haven, a lovely area of the island full of shops, restaurants, beautiful homes and even more stunning views of the ocean.

Black Dog Tavern

We strolled the streets for awhile and then made our way to the famous Black Dog Tavern, a restaurant and pub established in 1971,

Black Dog Clam Chowder

famous for their Quahog (Clam) Chowder. Read my full review and get the recipe here!

The Edgartown Inn

Then we made our way to Edgartown, a quiet, beautiful little village on the island to check in to our Bed & Breakfast, The Edgartown Inn.

South Beach, Martha’s Vineyard

We decided to hit the beach immediately, so we headed to South Beach, the smaller, quieter beach on the South side of the island.

The Edgartown Lighthouse

After relaxing and watching the sunset, we decided to head over to the Edgartown Lighthouse

House in Edgartown

and take in the views of the beautiful old homes,

Edgartown Harbor

harbors and the Harbor View Hotel.

Lobster Bisque

That night we hit The Seafood Shanty for some delicious Lobster Bisque, Seafood Pasta, and Grilled Scallops and Shrimp. Situated right on the harbor, this is a great place for fresh seafood and great waterfront views. The prices are pretty reasonable too! After we stuffed our faces, it was time to have some fun.

The Atlantic Restaurant

We headed down to a fun area near the harbor and stopped at a local pub, and ran into a wedding party who pretty much took over the whole center of town. To top off the night, we went to the Atlantic Fish & Chop House for a drink and headed back to crash out!

Vineyard Breakfast at Edgartown Inn

The next day it was raining so our plans to hit Aquinna Beach on the other side of the island were ruined, but we had an amazing “Vineyard Breakfast” at our B&B with homemade apple cinnamon coffee cake,

Awesome Breakfast at Edgartown Inn

scrambled eggs and bacon and some juice and coffee. Such a cute place!

Chappy House

We walked off breakfast by strolling around on N. Water Street for awhile..

Main Street, Edgartown

and then we took a stroll down Main Street to check out more beautiful old homes, bookstores, shops and antique stores before we had to leave.

Murdicks Fudge, Edgartown

One of my favorite finds was Murdick’s Fudge – delicious creamy fudge in about 10 different flavors! Who can resist that?

The Vincent House

The Vincent House was also really cool – the original home built in 1672 was actually transported into Edgartown and you can tour the house to see the classic Vineyard architecture and antique furnishings.