1-Day Boston Food, Wine and Shopping Experience for Couples

Boston, Massachusetts

1 days

Leonard P. Zakim Bunker Hill memorial bridge
Downtown cityscape
Skyline from downtown Harborwalk at night
Boston public garden
Skyline of the Financial District

About Boston, Massachusetts

Discover the rich history and vibrant culture of Boston, Massachusetts. Walk the Freedom Trail, a 2.5-mile route that takes you through 16 historically significant sites, including the Massachusetts State House and Paul Revere's House. Explore the diverse neighborhoods, from the Italian-flavored North End to the trendy Back Bay. Visit the world-renowned Harvard University and MIT located in nearby Cambridge. Enjoy a game at Fenway Park, home to the Boston Red Sox. Savor fresh seafood, especially the famous New England clam chowder. Take a relaxing stroll in the Boston Common and Public Garden, the oldest city park in the U.S. Don't miss the Boston Tea Party Ships & Museum and the USS Constitution Museum. With its blend of colonial charm and urban sophistication, Boston offers a unique travel experience.

1-Day Itinerary

Day 1

A Day of Food, Wine, and Shopping in Boston


Start your day with a leisurely stroll through the historic North End, Boston's oldest residential community. Here, you'll find a mix of historic sites, boutiques, and bakeries. Don't forget to stop by one of the many gourmet food shops to pick up some local delicacies.


Enjoy a lunch at a local seafood restaurant. Boston is famous for its fresh seafood, especially its clam chowder and lobster rolls. After lunch, take a walk along the Boston Harborwalk, a public walkway that follows the edge of piers, wharves, beaches, and shoreline around Boston Harbor.


Spend your afternoon exploring the trendy boutiques and designer stores in the Back Bay area. This is also a great opportunity to admire the Victorian brownstone homes that line the streets of this fashionable neighborhood.


For dinner, head to one of the city's renowned farm-to-table restaurants. These establishments pride themselves on using fresh, locally sourced ingredients to create innovative and delicious dishes.


End your day with a romantic walk along the Charles River Esplanade, a beautiful park situated along the banks of the Charles River. The park offers stunning views of the city skyline, especially at sunset.

Attractions in Itinerary (4)

North End

North End

Boston's oldest residential community, where people have continuously inhabited since it was settled in the 1630s.

Food and Drink
Cultural Experiences

Boston Harborwalk

A public walkway that follows the edge of piers, wharves, beaches, and shoreline around Boston Harbor. It's a great place to enjoy the city's waterfront, with views of the harbor and the downtown skyline.

Back Bay

Back Bay

An officially recognized neighborhood of Boston famous for its rows of Victorian brownstone homes.

Charles River Esplanade

Charles River Esplanade

The Charles River Esplanade is a state-owned park situated in the Back Bay area of Boston, Massachusetts. It's a popular destination for outdoor activities like running, biking, and boating, and it offers stunning views of the Boston skyline.


Local Food and Drinks (12)

Clam Chowder

Clam Chowder

A creamy soup made with clams, potatoes, onions, and bacon. It's a staple in Boston and a must-try for seafood lovers.

Lobster Roll

Lobster Roll

A sandwich filled with fresh, succulent lobster meat. It's a classic New England dish and a favorite in Boston.

Boston Cream Pie

Boston Cream Pie

The official dessert of Massachusetts. It's a cake filled with custard or cream and topped with chocolate.

Boston Baked Beans

A traditional dish made with navy beans, molasses, and pork. It's a staple in Boston and a part of the city's colonial history.

Fish and Chips

Fish and Chips

A popular dish in Boston due to its coastal location. It consists of battered and fried fish served with fries.

New England Boiled Dinner

A hearty meal consisting of corned beef, cabbage, carrots, and potatoes. It's a traditional dish in Boston and the New England area.

Sam Adams Beer

A popular local beer named after one of Boston's most famous historical figures, Samuel Adams.



Fresh oysters are a must-try in Boston due to its coastal location. They are often served raw with a side of lemon and cocktail sauce.

Fenway Franks

A type of hot dog that's a favorite at Fenway Park, home of the Boston Red Sox.

Indian Pudding

A traditional New England dessert made with cornmeal and molasses. It's a unique dish that's a part of Boston's colonial history.



A traditional New England meal that includes lobster, clams, corn on the cob, and potatoes. It's a popular dish in Boston, especially during the summer.

Harpoon IPA

A local craft beer that's a favorite in Boston. It's known for its strong hop flavor and crisp finish.

Best time to visit

The best time to visit Boston, Massachusetts is from June to October. Summer is peak season when the city's parks are green and bustling, and the weather is warm and pleasant. Fall is also a beautiful time to visit as you can witness the stunning fall foliage. However, if you're looking to avoid crowds and get better deals on accommodation, the shoulder seasons of spring and late fall are also good times to visit.

National holidays

Here you can find the national calendar of all public holidays for the year. These dates are subject to change as official changes are announced, so check back regularly for updates.

DateDayHoliday Name

January 1


New Year's Day

January 15


Martin Luther King Jr. Day

February 19


Presidents' Day

May 27


Memorial Day

June 19



July 4


Independence Day

September 2


Labor Day

October 14


Columbus Day

November 11


Veterans Day

November 28


Thanksgiving Day

December 25


Christmas Day

Please note that during national and public holidays, opening hours for establishments, museums, etc. may vary. Don't forget to check in advance!

How to get around

The Massachusetts Bay Transportation Authority operates the fourth largest subway system in the U.S., known locally as the 'T'. It consists of four lines: Red, Orange, Blue, and Green. It's a convenient and efficient way to get around the city and surrounding suburbs.

The MBTA also operates a comprehensive bus network, which complements the subway system. Buses can take you to areas of Boston not served by the 'T'.

For longer distances, the MBTA operates a commuter rail service. This is ideal for day trips to places like Salem, Lowell, or Worcester.

Ridesharing services like Uber and Lyft are widely available in Boston. They offer a convenient and often cost-effective way to get around, especially if you're traveling with a group or have a lot of luggage.

Boston's bike share program, Bluebikes, offers a healthy and environmentally friendly way to get around. There are hundreds of stations across the city, and the first 30 minutes of each ride are free.

Renting a car can be a good option if you plan to visit areas outside of Boston, but keep in mind that parking in the city can be expensive and difficult to find. Also, Boston's narrow, winding streets can be challenging for unfamiliar drivers.

The MBTA operates several ferry routes, which can be a scenic and relaxing way to travel. Routes include service to the Boston Harbor Islands, as well as commuter service to places like Hingham and Hull.

Taxis are readily available throughout Boston, although they can be more expensive than other options. They can be hailed on the street, picked up at taxi stands, or booked in advance.

Boston is a compact and walkable city, with many attractions located close together. Walking can often be the quickest and most enjoyable way to get around, especially in areas like the Freedom Trail and the Back Bay.

While we strive for accuracy in our "How to get around" section, the information may not always be up-to-date or 100% accurate; we highly recommend cross-checking with local resources before your travel.

Important information

Currency$ USD

Time zoneUTC-5

Driving sideRight

Emergency phone911

Drinking waterYes

Power sockets

Power socket type APower socket type B

Voltage120 V

Things to know about Boston, Massachusetts as a first time visitor


Boston is a walkable city, so pack comfortable shoes.


The city is known for its unpredictable weather, so pack layers and always carry an umbrella.


Boston is a historic city with many cobblestone streets, which can be difficult to navigate for those with mobility issues.


The city is very bike-friendly, with many bike lanes and bike rental services available.


Boston's public transportation system, the 'T', is extensive and can get you almost anywhere in the city.


Taxis and rideshares are also readily available, but can be more expensive than public transportation.


Boston is a foodie city, known for its seafood, Italian food in the North End, and diverse international cuisine.


Tipping is customary in Boston. It's standard to tip 15-20% at restaurants, bars, and taxis.


Boston is a sports-loving city. If you're in town during baseball season, try to catch a Red Sox game at Fenway Park.


The city is home to many colleges and universities, which can make certain areas very busy during the school year.


Boston is a safe city, but like any major city, it's important to stay aware of your surroundings, especially at night.


The city's legal drinking age is 21, and it's strictly enforced.


Boston's sales tax is 6.25%, which is added to most goods and services.


The city is in the Eastern Time Zone (ET).


Boston's peak tourist season is in the fall, when the leaves change color, and in the spring, during the Boston Marathon.


Boston's winters can be very cold, with temperatures often dropping below freezing (32°F/0°C).


The city's summers can be hot and humid, with temperatures often reaching into the 80s°F (27-32°C).


Boston has strict parking regulations, and parking can be expensive. Consider using public transportation instead.


Boston is a city of neighborhoods, each with its own unique character and charm. Explore beyond the downtown area.


Bostonians are known for their distinct accent. Don't be surprised if you hear 'pahk the cah in Hahvahd yahd'.

Packing List

  • Clothing

  • Comfortable walking shoes

  • Light jacket or sweater

  • Umbrella or raincoat (depending on the season)

  • Sunglasses

  • Hat or cap

  • Change of clothes

  • Toiletries

  • Travel-size toothpaste

  • Toothbrush

  • Travel-size shampoo and conditioner

  • Deodorant

  • Hand sanitizer

  • Face mask

  • Sunscreen

  • Travel documents and essentials

  • Valid ID or passport

  • Credit and/or debit card

  • Cash

  • Health insurance card

  • Hotel reservation confirmation

  • Car rental reservation confirmation (if applicable)

  • Electronics and gadgets

  • Smartphone

  • Charger for smartphone

  • Portable power bank

  • Camera (if not using smartphone for photos)

  • Charger for camera (if applicable)

  • Headphones or earbuds

  • Miscellaneous items

  • Snacks

  • Water bottle

  • Travel guide or map of Boston

  • Backpack or daypack

  • Travel pillow (for the journey)

  • Travel first aid kit

Weather Conditions

Boston, Massachusetts, is a city that experiences all four seasons, each with its own unique weather conditions. In the winter months, from December to February, Boston can get quite cold, with temperatures often dropping below freezing. It's not uncommon for the city to experience snowfall during this time, so if you're planning a visit, be sure to pack warm clothing, including a heavy coat, gloves, and a hat. Temperatures can range from 22°F to 41°F (-6°C to 5°C). Spring, from March to May, sees a gradual warming with temperatures ranging from 33°F to 73°F (1°C to 23°C). It can be a bit unpredictable, with some days feeling more like winter and others more like summer. It's a good idea to pack layers so you can adjust to the changing conditions. Summer, from June to August, is typically warm and sometimes humid. Temperatures can range from 60°F to 82°F (16°C to 28°C). It's a great time to explore the city's outdoor attractions, but don't forget to pack sunscreen and a hat to protect yourself from the sun. Fall, from September to November, is a beautiful time to visit Boston. The temperatures range from 39°F to 76°F (4°C to 24°C) and the city's many trees change color, creating a stunning display. It can get chilly, especially in the evenings, so be sure to pack a light jacket or sweater. Regardless of when you visit, it's always a good idea to check the forecast before your trip so you can pack appropriately. Boston's weather can be unpredictable, so it's best to be prepared for a range of conditions.

MonthHi / Lo (°C)Weather Overview


4° / -6°

January is the coldest month in Boston, with snowfall common. Dress warmly and enjoy winter activities like ice skating.


4° / -5°

February is still quite cold, with snow and ice. It's a great time for indoor activities like visiting museums.


8° / -2°

March sees the start of spring, with temperatures slowly rising. You might still need a coat, but the snow starts to melt.


13° / 3°

April is a transition month, with both rain and some late snowfall. The city starts to bloom, making it a beautiful time to visit.


20° / 8°

May is a pleasant month with moderate temperatures. It's a great time to explore the city and its parks.


25° / 13°

June marks the start of summer, with long, sunny days. It's perfect for outdoor activities and exploring the city's waterfront.


28° / 17°

July is the hottest month in Boston. It's a great time to visit the beaches and enjoy outdoor concerts.


27° / 16°

August is still quite hot, but with more rainfall. It's a great time to visit the Boston Harbor Islands.


24° / 12°

September is a comfortable month, with less humidity. It's a great time for sightseeing and attending festivals.


17° / 7°

October sees the start of fall, with beautiful foliage. It's a great time to go on a fall foliage tour.


12° / 2°

November is a cooler month, with the first signs of winter. It's a great time to visit historic sites and enjoy Thanksgiving celebrations.


7° / -3°

December is a festive month, with Christmas lights and snow. It's a great time to enjoy holiday shopping and festive events.

Did you know?

Did you know that Boston is one of the oldest cities in the United States, founded in 1630 by Puritan settlers from England?

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