Boston - 14 Days Itinerary

Arrive in Boston

Arrive at Boston Logan International Airport (BOS), collect luggage, and head to your accommodation.

The flight includes one stop.

Check into Hotel

Check into your hotel in the Back Bay area of Boston, unpack, and settle in.

Conveniently located with good amenities.

Boston Public Garden Stroll

Enjoy a leisurely walk through America's first public garden, admiring the Victorian landscape and iconic Swan Boats (seasonal).

A beautiful oasis in the city center, perfect for a relaxing start to your trip.

Tracy Morgan Live

Enjoy an evening of stand-up comedy with Tracy Morgan at The Wilbur Theatre.

Wilbur Theatre Parking is available at the link below. Consider arriving early for dinner nearby.

Freedom Trail History Tour

Walk Boston's principal role in launching the American Revolution, linked by the brick-lined Freedom Trail, with an expert historian.

This tour also offers a brewery taste, but you can opt for the history only.

Old State House Visit

Explore the Old State House, Boston's oldest public building and a key site on the Freedom Trail, for a deeper dive into colonial history.

Entry fees may apply. Check for guided tours for additional insight.

Lunch at Quincy Market

Enjoy a casual lunch at Quincy Market, offering a wide variety of food stalls and local specialties.

A lively spot with options for every taste.

The Princess Bride: An Inconceivable Evening with Cary Elwes

Spend an afternoon with Cary Elwes, star of 'The Princess Bride', as he shares behind-the-scenes stories and answers audience questions.

Wilbur Theatre Parking is available at the link below.

Dinner Downtown

Enjoy dinner at a restaurant in the downtown area, reflecting on the historical sites and cinematic experience of the day.

Boston Harborwalk Stroll

Enjoy a refreshing morning walk along the Boston Harborwalk, taking in views of the harbor and city skyline.

A great way to experience Boston's waterfront.

Explore Long Wharf

Visit Long Wharf, a historic pier that offers great views and is a hub for ferry services.

Grab a coffee from a nearby cafe.

Boston Tea Party Ships & Museum

Step back in time to the Boston Tea Party with interactive exhibits, replicated 18th-century sailing vessels, and a fully guided experience.

Booking recommended, especially for peak times. Check website for current admission fees.

Lunch in Seaport

Enjoy fresh seafood or other cuisine at one of the many restaurants in Boston's modern Seaport District.

Back Bay Chocolate & Art Tour

Explore one of Boston's most beautiful neighborhoods, admiring Victorian-era architecture, visiting art galleries, and sampling local chocolates.

A delightful way to discover the charming streets and artistic side of Back Bay.

Dinner in Back Bay

Savor dinner in the elegant Back Bay neighborhood, known for its upscale dining options.

Beacon Hill Exploration

Wander through the picturesque streets of Beacon Hill, famous for its gas lamps, cobblestone streets, and charming brick row houses.

Don't miss Acorn Street, one of the most photographed streets in America.

Boston Public Library

Visit the historic main branch of the Boston Public Library, America's first free publicly-funded municipal library.

Admire its architecture and art.

Take a self-guided tour or check for free guided tours.

Lunch near Copley Square

Enjoy lunch in the Copley Square area, surrounded by architectural landmarks like Trinity Church and the John Hancock Tower.

Shopping on Boylston Street

Indulge in some retail therapy along Boylston Street, featuring a mix of national retailers and local boutiques.

Darcy & Jer: Average At Best Tour

Catch Darcy & Jer on their 'Average At Best Tour' for an evening of laughter at the Boch Center Shubert Theatre.

Consider dinner before the show in the Theater District.

1 Hour Boston Segway Tour

Explore Boston's historical landmarks and modern attractions on a fun and unique Segway tour, starting near the waterfront.

A great way to cover a lot of ground quickly. Be prepared for a short training session before the tour.

Private North End Neighborhood Tour

Dive deep into Italian culture and savor incredible food on a walking tour of Boston's Little Italy, with personal stories from a local.

Yelp's 2025 pick for Massachusetts #1 food tour. Come hungry!

Visit Old North Church

See the Old North Church, Boston's oldest standing church and the location of Paul Revere's famous 'one if by land, two if by sea' signal.

Explore the interior and gift shop, and learn about its pivotal role in the American Revolution.

Dinner in the North End

Enjoy a delicious Italian dinner in Boston's historic North End, capping off a day of culinary and historical exploration.

Numerous excellent Italian restaurants to choose from.

Boston Public Library

Explore the historic Bates Hall and McKim Building of America's first free, publicly-funded municipal library.

Admire its impressive architecture and art.

Free to enter and explore. Guided tours might be available.

Lunch in Back Bay

Enjoy lunch at a charming cafe or restaurant in the picturesque Back Bay neighborhood.

Votes for Women History Tour

Discover Boston’s pivotal role in the American fight for women’s suffrage on this engaging walking tour through Back Bay's elegant streets with an expert historian.

Wear comfortable shoes for walking. This is a Viator experience.

Hadestown (Touring)

Experience the acclaimed musical Hadestown, a captivating intertwining of two mythic love stories – that of Orpheus and Eurydice, and King Hades and Persephone.

Check for show exact run time closer to the date. This is a Ticketmaster event.

Boston Public Garden

Stroll through America's first public garden, a Victorian-era botanical masterpiece.

See the famous Swan Boats and intricate landscaping.

Entry is free. A peaceful oasis in the city.

Newbury Street Exploration

Wander down Newbury Street, known for its elegant 19th-century brownstones housing boutiques, galleries, and sidewalk cafes.

Back Bay Chocolate & Art Tour

Indulge in a delightful tour exploring Back Bay's architectural beauty, art galleries, and sampling exquisite chocolates along the way.

Come hungry for chocolate! This is a Viator experience.

Pete Correale: As I Was Saying

Enjoy a night of stand-up comedy with Pete Correale at The Wilbur.

Parking is available nearby.

Plan to arrive early for good seats. This is a Ticketmaster event.

Boston Common

Start your day at Boston's oldest public park, a historic green space that marks the beginning of the Freedom Trail.

Great for a morning stroll or a picnic.

Old State House

Visit the Old State House, Boston's oldest public building and a key site on the Freedom Trail where the Boston Massacre took place.

Admission fee usually applies. Check current hours.

Lunch at Faneuil Hall Marketplace

Explore the bustling Faneuil Hall Marketplace and Quincy Market for diverse lunch options and local treats.

Boston Rock & Roll Tour

Take a walking tour through Boston’s Fenway neighborhood, guided by a local musician, exploring the city's rich rock and roll past and present.

This is a Viator experience. A unique perspective on Boston's music scene.

Dinner in Fenway

Enjoy dinner in the lively Fenway neighborhood, with many restaurant options near the ballpark.

Museum of Fine Arts

Spend your morning at the Museum of Fine Arts, one of the largest art museums in the United States, featuring collections from ancient to contemporary art.

Check for special exhibitions and free admission days.

Lunch near MFA

Grab a bite at one of the cafes within the museum or nearby.

Charles River Esplanade

Enjoy a leisurely walk or bike ride along the scenic Charles River Esplanade, offering beautiful views of the river and city skyline.

Perfect for relaxation and enjoying the outdoors.

Dinner in Beacon Hill

Dine in the charming and historic Beacon Hill neighborhood, known for its gas lamps and brick row houses.

Boston Tea Party Ships & Museum

Relive one of America's most pivotal historical events with interactive exhibits, replicated 18th-century sailing vessels, and a dramatic reenactment.

Book tickets in advance, especially during peak times.

Lunch in Seaport District

Enjoy lunch in the modern Seaport District, known for its diverse culinary scene and waterfront views.

1 If By Land Walking Tours

Embark on a walking tour of Boston, exploring historical sites and viewing historical photos of the exact spots you're standing on, bringing the past to life.

This is a Viator experience. Be prepared for walking.

Dinner at Downtown Crossing

Explore the vibrant dining options in the Downtown Crossing area for your evening meal.

Private North End Food Tour

Dive deep into Italian culture and savor incredible food on a guided walk through Boston's historic Little Italy, the North End.

You'll enjoy personal stories from a lifelong local.

Yelp's 2025 pick for Massachusetts #1 food tour! Book in advance as tours can fill up.

Old North Church Visit

Explore the Old North Church, Boston's oldest standing church and the place where Paul Revere's famous 'one if by land, two if by sea' signal was sent.

Consider taking a guided tour to learn more about its rich history.

Dinner in North End

Enjoy an authentic Italian dinner at one of the many renowned restaurants in the North End.

Favorites include Regina Pizzeria for casual pizza, or Giacomo's Ristorante for seafood pasta.

Boston Public Library

Visit the historic main branch of the Boston Public Library, America's first free, publicly-funded municipal library.

Admire its stunning architecture and collections.

Enjoy the Bates Hall reading room and the courtyard.

Explore Harvard University

Take the MBTA to Cambridge and spend the afternoon exploring the historic Harvard University campus, including Harvard Yard, and browsing the shops in Harvard Square.

Consider joining a student-led tour for insights into university life and history.

MIT Campus Walk

Walk through the campus of the Massachusetts Institute of Technology, known for its innovative architecture and contributions to science and technology.

Look for unique public art installations and the impressive Stata Center.

Dinner in Cambridge

Enjoy dinner at one of Cambridge's diverse restaurants, offering a wide range of cuisines.

From casual eateries to upscale dining, Cambridge has options for every taste.

A Taste of the Freedom Trail

Sample Boston’s most iconic dishes on a delicious journey through history.

Taste Boston’s history with every bite, from creamy chowder to buttery seafood.

A perfect way to combine historical insights with local culinary delights.

Stroll Boston Harborwalk

Enjoy a leisurely walk along the Boston Harborwalk, offering picturesque views of the harbor and city skyline.

Discover hidden parks, public art, and historic wharves.

A great way to relax and take in the maritime atmosphere.

New England Aquarium

Visit the New England Aquarium, home to thousands of aquatic animals, including sharks, sea turtles, penguins, and more.

Check their schedule for animal encounters and shows.

Boston After Dark Walking Tour

Meet the real Boston after dark, uncovering terrifying serial killers, infamous gangsters, urban legends, bizarre industrial accidents, unsolved crimes, and ghost stories.

A unique and thrilling way to experience the city's darker history.

Last Minute Souvenirs

Enjoy some last-minute souvenir shopping or revisit a favorite spot in Boston before heading to the airport.

Grab some Boston-themed gifts or treats to remember your trip.

Casual Lunch

Have a relaxed lunch near your hotel or in a convenient location before your departure.

Many cafes and casual restaurants are available throughout the city.

Limo Transfer to Logan Airport

Enjoy a private limo transfer from your Boston accommodation directly to Logan International Airport for a stress-free departure.