If you have 4 days to spare, Boston and the nearby coastal island of Martha’s Vineyard make for an unforgettable quick getaway from the city. Get ready to crisscross historical Boston on foot while taking in the rich American history before heading out to the quaint seaside towns and beaches of the Vineyard. Here’s a 4 day itinerary that hits the highlights:
Day 1 – Boston’s Freedom Trail Kick off your long weekend with a self-guided walking tour along the iconic Freedom Trail to view 16 historical sites related the American Revolution. Soak in sights like the gold-domed Massachusetts State House, the harborside Paul Revere House, the Old North Church, and Faneuil Hall. Fuel up on lobster rolls or clam chowder before some evening bar hopping.
Stay: Wyndham Boston Beacon Hill
Day 2 – Day Trip to Martha’s Vineyard Catch a ferry from Boston Harbor out to the coastal island of Martha’s Vineyard for a day of beachfront bliss. Browse the gingerbread cottages and sea captain homes in the whaling town of Edgartown before setting up camp at one of the public beaches. Don’t miss the photo op with the red and white striped Gay Head Lighthouse. Grab dinner in one of the local hangouts like The Newes or Nancy’s Restaurant before heading back to mainland Boston.
Stay: Wyndham Boston Beacon Hill
Day 3 – Harvard Square and Fenway Exploration Spend your third day poking around two classic Boston neighborhoods – Harvard Square in Cambridge with its bohemian vibe and Fenway near Kenmore Square where you’ll find Boston’s hallowed baseball stadium. Peruse the indie boutiques and grab a pastry from Tatte Bakery in Harvard before venturing over to Fenway to catch a baseball game or tour Fenway park depending on the season.
Stay: Hotel Commonwealth near Fenway
Day 4 – Shopping and Seafood Feast On your last day, take time to hunt for souvenirs and boutiques along Newbury Street and at Quincy Market. Then sample Boston’s most iconic cuisine – fresh lobster and clams -with dinner at Yankee Lobster Co or James Hook Lobster Co near the harbor. Toast to new discoveries as your Boston trip wraps up!
First up is a visit to the Massachusetts Institute of Technology (MIT). As an engineering geek, I can’t wait to take a campus tour and see some of the innovative projects underway at MIT’s labs and research centers. It’ll be inspiring to walk the halls where so many great minds have learned and pioneered new technologies.
After an invigorating dose of genius, I’ll head over to Newbury Street to soak up some charm and character at Boston’s iconic shopping street. As an architecture buff, I’ll enjoy admiring the elegant brownstones as I weave through the unique boutiques, galleries, and cafes. I even have reservations at Contessa, an upscale Italian restaurant located right on Newbury, for what I’m sure will be an unforgettable meal.
I’ll be fueling up on pasta and vino for a marathon shopping session! My credit cards are ready for some damage at all the fabulous fashion and accessories stores. By the time I stumble back to my hotel room, my feet will be sore but my bags will be full.
Before I collapse for the night, I have one last stop – a luxurious European facial at a swanky Boston day spa. I’ll be pampered with cleansers, toners, masks and creams made from natural ingredients. My skin will look as glowing as I feel after this whirlwind Boston getaway!
I can’t wait to share more about my adventures in Beantown. For now, I need to start packing and plotting my itinerary. This is going to be an epic girls weekend! Stay tuned for more dispatches from my Boston travels.
Bring layers. Boston weather can be very changeable, even within a single day. Pack some lightweight sweaters, long-sleeve shirts, jackets, etc. that you can layer on or take off as needed. Also be sure to bring a warm coat, hats, gloves, and scarf.
Pack waterproof shoes. Boston gets a fair amount of precipitation, so having waterproof boots or other shoes that can withstand some rain and snow is important.
Bring some casual clothes that can go from day to night. Boston has a pretty casual vibe, but you’ll likely want to head out to some nice dinners or bars at night where you may want to look a bit sharper. Items that transition well are key.
Pack a lightweight umbrella and/or rain jacket. As mentioned, Boston often sees rainy weather, so having an umbrella and outer layer to throw over your clothes is essential.
If visiting in winter, pack snow/winter accessories. This includes heavy socks, winter hat, insulated gloves, scarf, and boots that have good traction for icy sidewalks. You’ll want to bundle up if visiting in the colder months.
Bring comfortable walking shoes. Boston is an incredibly walkable city. Make sure to pack sneakers or other comfy shoes for exploring by foot.
Pack medications you may normally use. Don’t count on finding your specific over-the-counter medicines or prescriptions while traveling. Bring what you may need.
I hope this gives you a good starting point for packing for your Boston trip! Let me know if you need any other recommendations.
