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A Weekend in Boston | Where to Go, What to See, Where to Stay

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Make the most of a weekend in Boston. You don’t want to miss out on some must-see places, so use this guide to plan your trip.

Early Autumn day in Boston Gardens. Note the Swan Boat ride!

How do I get from the South Shore to Boston?

Any place on the South Shore is an easy trip to Boston.

Coming from the South Shore, simply get on and stay on Route 3 North.
Depending where in the city you wish to begin your adventure will depend what exit you
take off the highway.

You may be lucky enough to find on-street parking, but you may want to check out Best Parking to find and prepay a parking spot.

Hingham Ferry departing from Hingham Shipyard off Route 3A North from the South Shore.
Please note there are 18 trips daily beginning at 6:50 am. The last trip into Rowes Wharf, Boston departs at 8:30 pm.
Because transportation schedules do change I am adding a link to the Hingham Ferry here: The cost for ferry tickets and how to purchase tickets are also available following link below. Prices are subject to change and it is best to be advised at the time of your particular travel.
Ferry Schedule

Hi Speed Train:
Also available from the South Shore to Boston is a high speed commuter train. I am familiar with the Greenbush line located in Scituate. This is about a 50 minute trip to the South Station for example.
The train and ferry service are both operated by the MBTA, Mass Bay Transit Authority, and many of the same rules apply. Here is an example of of the train schedule:
Train Schedule

Plymouth & Brockton Street Railway Co. This bus company operates daily service from several towns on the South Shore, including Plymouth, Marshfield, and Scituate, to Boston. The buses run frequently throughout the day, and fares are reasonably priced.

How do I get around the city?

Some days I go into the city to wander aimlessly without time constraints. On these days I prefer to drive in because I am lucky and always get an on street metered parking space that I can easily pay for using my ‘PARK BOSTON’ app. You may prefer to take public transportion, Uber/Lyft, or rent a bike. My favorite mode of transportation in the city is walking. I can walk for hours in the city.

If you are taking the Ferry from the South Shore please do be mindful of the ferry schedule home. It would be a very long walk back to the South Shore if you miss the last ferry!

Are dogs allowed on MBTA transportations?

The policy is not crystal clear. The following information is from the MBTA list of rules:

  • Service animals are always allowed on the T at all times.
  • Non-service dogs are not allowed on the T during rush hours: 7-10 AM and 4-7 PM.
  • During off-peak hours, T operators may allow non-service dogs. Dogs should be on leash and cannot take up a seat. Please ensure your dog can be quiet and calm on the T.
  • Small animals like cats and rabbits should be kept in pet carriers. Please keep the carrier on your lap if possible and away from vehicle doors, especially during rush hour.

Things to Do on a Weekend in Boston

Pizelle cookies from the North End of Boston
Steve Snodgrass, CC BY 2.0 https://creativecommons.org/licenses/by/2.0, via Wikimedia Commons
  • Ducktour: A tour that combines land and water transportation on a vehicle that looks like a duck.
    There are 3 easy departure locations to leave for a Ducktour. See the locations and ticket information here.
  • Freedom Trail: A 2.5-mile walking trail that highlights 16 historically significant sites in Boston.
    Because Boston has so much to offer visually the Freedom Trail is best seen by foot. Here are suggested itineraries depending on the amount of time you have.
  • Downtown: The central business district of Boston.
  • North End: A neighborhood in Boston known for its Italian-American community and delicious Italian food. Please treat yourself to a meal while visiting the North End. You may never leave! A trip to Mikes Pastry or Modern Bakery is a must too!
  • South End: A trendy neighborhood in Boston with many restaurants, art galleries, and Victorian brownstones.
  • Museums: Boston has a variety of world-class museums, including the Museum of Fine Arts, the Isabella Stewart Gardner Museum, and the Museum of Science.
  • Seaport & ICA: The Seaport district is a newly developed area in Boston that features modern architecture and the Institute of Contemporary Art.
  • Newbury St: A trendy street in Boston lined with high-end shops and restaurants.
  • Charles St: A charming street in Boston’s Beacon Hill neighborhood with boutique shops and cafes.

Make way for ducklings decked out for St Patricks Day
Ducklings decked out for St Pats day.
  • Public Gardens: A beautiful park in Boston that is home to the famous “Make Way for Ducklings” statue and offers Swan Boat rides during the warmer months. There is also a large underground parking garage across the street from Public Gardens.
  • State House Tours: Visitors can tour the Massachusetts State House, a historic building that houses the offices of the Governor and state legislature. The 40 minute tours are given weekdays year-round from 10:00 am to 3:30 pm, and are free of charge. Tour schedule info
Commonwealth of MA State House
Commonwealth of MA State House
  • Theatre: Boston has a vibrant theater scene, with many theaters offering a range of performances from Broadway shows to experimental productions.
  • Symphony: The Boston Symphony Orchestra is one of the most renowned orchestras in the world and performs at Symphony Hall. For info on Free 1 to 1.5 hours tours please visit this link.
  • Charles River: A scenic river that runs through Boston and offers opportunities for boating, jogging, and picnicking.
  • Red Sox game: Boston is home to the legendary Fenway Park, where visitors can catch a game of the Boston Red Sox.
  • Old Faneuil Hall Marketplace: A historic marketplace in Boston that dates back to the 18th century and is now home to many shops and restaurants.
  • Great walking city: Boston is a compact and walkable city with many historic sites, charming neighborhoods, and scenic parks to explore on foot.
  • Rent Bikes: Boston has a few bike-sharing program and many bike rental shops throughout the city. Bluebikes is a popular bike rental service.
  • Copley Place: A luxury shopping mall in Boston’s Back Bay neighborhood.
Blue Bike rental at Copley, Boston
Blue Bike Rental at Copley
Boston Public Garden
Take a stroll through Public Gardens

What are the best places to eat and drink?

Here’s a list of restaurants in Boston to suit all budgets:

  1. Legal Sea Foods: A popular seafood chain that offers affordable options for budget-conscious diners.
  2. Giacomo’s Ristorante: A cozy Italian restaurant in the North End with delicious food at reasonable prices.
  3. Sam LaGrassa’s: A sandwich shop in the Financial District that offers hearty sandwiches at reasonable prices.
  4. The Friendly Toast: A funky diner in the Back Bay that serves breakfast all day and has affordable prices.
  5. Union Oyster House: A historic seafood restaurant in the Downtown area that offers affordable seafood dishes.
  6. Tasty Burger: A casual burger joint in the Fenway area with affordable prices and delicious burgers.
  7. Flour Bakery + Cafe: A popular bakery and cafe in the South End and other locations that offers affordable breakfast and lunch options.
  8. Shabu Zen: A Japanese hot pot restaurant in Chinatown with affordable prices and an all-you-can-eat option.
  9. Bon Me: A Vietnamese food truck and restaurant chain with affordable prices and delicious banh mi sandwiches.
  10. Regina Pizzeria: A Boston institution that serves affordable and delicious pizza in multiple locations around the city.

How much money should I bring for a weekend in Boston?

A common question travelers have is how much money should they expect to spend in Boston.
Generally speaking, Boston isn’t cheap, but there are lots of low cost and free things to do. The renowned MFA, Museum of Fine Art, has free admittance on Weds afternoons. And walking the Freedom Trail or enjoying the Public Gardens is free as well.

What is the best time of year to visit?

Tourism picks up in Boston in the Spring and Summer because the city is especially gorgeous in warmer weather. Public Gardens and Boston Garden have an explosion of color with all the plantings. The city workers do a terrific job at keeping these high traffic areas extremely clean for you to enjoy.

Christmastime in the city is beautiful as well. Traditionally, Canada gifts the city a Christmas Tree each year. Why is Canada so generous? Well as the story goes back in 1917 when 2 ships met tragically a horrific explosion ensued. Boston responded immediately sending aid and relief to the hundreds of injured, homeless folks in Nova Scotia. Almost 2,000 people died this horrific day. It is the generous and fast response of the City of Boston to our friends to the North that is remembered each year by Boston’s Canadian friends.

People gather for the lighting of the tree. Throughout the city you will see little clear sparking lites lining the streets along with other holiday gatherings and traditions creating a festive atmosphere.

What are some off the beaten path hidden gems?

There are many many hidden gems which is why I prefer to walk around.
I consider the day I found Mike’s Pastry Shop in the North End of Boston one of the best days of my life.
In addition to absolutely everything in the Italian bakery, founded in 1946, I have been known to drive in to North End just to visit Mike’s and buy a box of Marzipan!

Mike’s Pastry Shop 300 Hanover St, Boston, MA 02113  
(617) 742-3050 open til 11pm!

Delucas Market is on the corner of Charles & Beacon Streets. This intersection gives a colorful example of Boston drivers so be careful before you step off sidewalk. Wouldn’t hurt to proceed with caution on the sidewalk too! I like Deluca’s because they have maintaned a successful community market since 1905 and showcase fun Italian Specialty foods. Be sure to stroll the lengths of Charles & Newbury Streets when you are visiting!
11 Charles St and 329 Newbury St Boston, MA.
(617) 523-4343

DeLucas Market on Charles Street, Boston
DeLucas on Charles Street

Jamaica Plain

Jamaica Plain neighbors the City of Boston and has two of my favorite places to visit:

The Arnold Arboretum in conjunction with Harvard University is a 281-acre landscape featuring over 15,000 accessioned plants, many liliac bushes! The Arboretum is open daily and free for all to explore. Adults, kids and leashed dogs alike can enjoy a carefree walk among the gorgeous plants and wildlife or learn the science and lore of the plants. There is so much to do and the Visitor Center is eager to help you do it.

Jamaica Pond is about 1.5 miles around the largest body of water in the City. Available for rent at the on-site Boat House are kayaks, rowboats and sailboats.


Charlestown is accessible by the MBTA orange line. This Boston neighborhood is home to Old Ironsides, The Bunker Hill Monument and The Warren Tavern.

The USS Constitution, also known as “Old Ironsides,” is located at the Charlestown Navy Yard. The ship is a historic landmark and a popular tourist attraction. It is the oldest commissioned warship afloat in the world and is still a commissioned U.S. Navy vessel..


8 Tips On How To Travel Safely In Big Cities

I find common sense to be my best friend.
Keep the amount of cash you are carrying minimal.
Travel light.
Don’t advertise valuables – leave home or in a safe.
Put your phone away.
You may want to put your backpack on the front of you when in a crowded situation.
Before you leave home, make a list of your serial numbers on electronics etc.
Dress like the locals. Crooks tend to look for folks that stand out in a crowd.

Best Places to Stay for a Weekend in Boston:


HI Boston Hostel
19 Stuart St Boston, MA 02116
617 536 9455
Hostels are a great way to travel with or without family when you are on a budget.

The Copley House: A budget-friendly option in the Back Bay area that offers apartment-style accommodations with kitchenettes.

Boston Fenway Inn: A budget-friendly hostel located near Fenway Park with affordable dormitory-style accommodations and private rooms.


  • Hotel 140: A mid-range hotel located in the Back Bay area that offers comfortable accommodations at reasonable prices.
  • The Verb Hotel: A retro-style hotel located in the Fenway area that offers stylish accommodations at reasonable prices.
  • The Midtown Hotel: A mid-range hotel located in the Back Bay area that offers comfortable accommodations at reasonable prices.


  • The priciest hotel in the city of Boston is the Four Seasons Hotel
    Rooms range in price of 500-1000$ per night.
    1 Dalton St.Boston MA 02115
    617 377 4888
  • The Liberty, a Luxury Collection Hotel: An upscale hotel located in the Beacon Hill area that offers luxurious accommodations and amenities.
  • Kimpton Nine Zero Hotel: An upscale hotel located in the Downtown area that offers stylish accommodations and amenities.
  • The Godfrey Hotel Boston: An upscale hotel located in the Downtown area that offers luxurious accommodations and amenities.


  • The Revolution Hotel: A boutique hotel located in the South End area offerING unique and stylish accommodations at reasonable prices.
  • The Eliot Hotel: A boutique hotel located in the Back Bay area that offers luxurious accommodations and amenities.
  • The Boxer Boston: A boutique hotel located in the Downtown area that offers stylish accommodations and amenities.

Remember to check out Vrbo.com listings too.
You can find some reasonably priced lodging advertised in these rental listings in Boston and neighboring communities with the added benefit of having a kitchen to reduce costs of eating out.

We wish you the best time while visiting our city!

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