Boston Bound: Business by Day, Adventure by Night how to spend 48 hours

Andrea Thompson

ByAndrea Thompson

March 17, 2025
Boston,City,Skyline,Over,The,Charles,River,In,Massachusetts,,Usa.

Boston, Massachusetts, is a city where history meets modernity, offering a rich tapestry of experiences for business travellers and their families.

Whether you’re here for a conference or a quick getaway, this guide will help you make the most of your 48 hours.

Day 1: Dive into Boston’s History and Culture

Morning:

Start your day with a walk along the Freedom Trail, a 2.5-mile red-brick path that takes you through 16 historical sites, including the Boston Common (America’s oldest public park), Paul Revere’s House, and the Old North Church. This trail is a perfect introduction to Boston’s pivotal role in the American Revolution.

Lunch:

Head to the North End, Boston’s Little Italy, for a hearty meal. Try Mamma Maria for authentic Italian cuisine or grab a quick bite at Regina Pizzeria, a local favourite.

Afternoon:

Explore the Museum of Fine Arts or the Isabella Stewart Gardner Museum for a dose of art and culture. If you’re traveling with family, the New England Aquarium is a hit with kids.

Dinner:

Dine at Legal Sea Foods for a quintessential New England seafood experience. Their clam chowder is legendary.

Evening:

Unwind with a stroll along the Charles River Esplanade, offering stunning views of the city skyline. For a more lively evening, catch a game at Fenway Park, home of the Boston Red Sox.

Day 2: Business Meets Leisure

Morning:

Kick off your day with a power breakfast at Tatte Bakery & Café, known for its pastries and strong coffee. Then, head to the Seaport District, a hub for innovation and business, where you can also enjoy waterfront views.

Lunch:

Try Committee, a modern Greek restaurant offering shareable plates perfect for a business lunch or a family meal.

Afternoon:

Take a Boston Duck Tour, an amphibious vehicle tour that combines sightseeing with a splash into the Charles River. Alternatively, visit the Boston Tea Party Ships and Museum for an interactive history lesson.

Dinner:

For a sophisticated dining experience, book a table at No. 9 Park, located near the Boston Common. Their French and Italian-inspired menu is perfect for impressing clients or treating your family.

Evening:

Wrap up your trip with a drink at Haley. Henry, a cosy wine bar offering an extensive selection of small-production wines. If you’re with family, consider a night time harbour cruise for a magical view of the city lights.

Tips for Business Travelers:

Stay at hotels like The Langham or Fairmont Copley Plaza, which offer excellent amenities for both work and relaxation.  Use Boston’s efficient public transport system, the MBTA, to navigate the city with ease.

With it’s unique blend of history, culture, and modern amenities Boston makes an ideal destination for business travellers looking for “bleisure”.