Location Boston

Boston’s rich history, vibrant culture, and stunning landscapes make it a destination unlike any other. From the historic charm of Beacon Hill to the modern energy of the Seaport District, the city offers a perfect blend of old-world elegance and cutting-edge innovation. Explore the Freedom Trail, where colonial-era landmarks and revolutionary sites tell the story of America’s past. Wander through the lush greenery of the Arnold Arboretum or stroll along the picturesque Charles River Esplanade. For outdoor enthusiasts, the Blue Hills Reservation provides breathtaking views and scenic trails, while the Boston Public Garden offers a serene escape in the heart of the city. Whether you’re drawn to history, nature, or urban excitement, Boston delivers an unforgettable experience.

Private Sightseeing Tours

Private Customized Walking Tour of Boston

Explore Boston in a way that interests you on a private walking tour that can be customized to your preferences. You'll follow a flexible itinerary tailored to include attractions that you want to see, such as Boston Common, Freedom Trail,…

From: 595.00$
Half-day Tours

Boston Private Walking Food Tour With Secret Food Tours

Explore the cobblestone streets of Boston’s North End and taste your way through the neighborhood with this private food tour. Meet your guide for a half-day tour that includes some of the city’s best Italian food and go off-the-beaten-path to…

From: 395.00$
Private Drivers

Boston Restaurant Week

If you are In the City and Looking To Enjoy a Great Evening, Allow The Chiefton Group to Be Your Chaperon! Enjoy the Scenic Ride To and/or The Scenic Ride Back From An Exclusive Eatery Of Your Choice. We Will…

From: 120.54$
Water Tours

Boston Mother's Day Premier Brunch Cruise

This Mother’s Day, create family memories that will be treasured forever with an amazing day on the water! Treat the mom in your life to a special Mother's Day Premier Brunch Cruise on Boston Harbor. While onboard, your family will…

From: 142.06$
Mountain Bike Tours

Boston's Emerald Necklace Guided Bicycle Tour

Discover Boston’s fall beauty on this guided, 4-hour, small-group bike tour around the North End of the city. Explore the historic Emerald Necklace, a 1,100-acre chain of parks linked by parkways and waterways in Boston and Brookline. Visit the shaded…

From: 89.00$
Day Cruises

Boston Harbor Holiday Brunch Cruise

Combine an indulgent brunch with a sightseeing boat tour on this two-in-one festive outing. Meet at Rowes Wharf, and hop aboard the Northern Lights: a 1920s-style yacht. Over the course of several hours, you’ll see landmarks ranging from the Seaport…

From: 104.53$
Historical Tours

Beacon Hill: Small Group Tour of Civil War Boston

Experience the Black Heritage Trail and get to know more about Civil War-era Boston on this small-group walking tour. In the company of a guide, head out into Beacon Hill and hear stories about the Underground Railroad, Boston Brahmins, and…

From: 35.00$
Private Drivers

Private transfer: Boston to Boston Airport (BOS)

English-speaking, affordable airport drop-off. Enjoy a safe, comfortable ride from wherever you need ‘ hotel, short-term rental or a meeting. Tour the chic Hamptons on this private, full day tour from New York City See the best of the Hamptons…

From: 97.24$
Airport & Hotel Transfers

Private transfer: Boston Airport (BOS) to Boston

Make your arrival in Boston hassle-free with this one-way private transfer from Boston Logan Airport to anywhere in the city of Boston. Receive your driver’s information before your plane lands and meet your driver directly at the airport. Relax on…

From: 97.24$
Private Transfers

Three Hour Private Chauffeur Service from Boston

Enjoy the personal service of a private driver as you explore Boston by booking a fully customizable car service that’s tailored to your needs. Whether you’re arriving at the Boston airport or doing some sightseeing, this half-day booking takes you…

From: 275.80$
Half-day Tours

Plymouth half day private tour from Boston, groups 1-4

If you've always wanted to see Plymouth Rock, this 4 hour tour lets you check it off the bucket list. It can fit snuggly into a Boston city break without using up too much of your time in the city.…

From: 675.00$
Architecture Tours

Guided Walking Tour of Copley Square to Downtown Boston Freedom Trail

Explore elegant neighborhoods, historic streets, and American landmarks on a Boston walking tour from the Back Bay to Beacon Hill and downtown portions of the Freedom Trail. Learn about Boston’s history and culture as you stroll brownstone-lined avenues and walk’the…

From: 45.00$