Immerse yourself in American history with Tripshepherd, Boston’s best small group tours (max. 7 guests).

Our tour includes complimentary pick-up and drop-off from your downtown Boston hotel, as well as admission fees to all attractions. Say goodbye to long wait times with our skip-the-line entry, maximizing your valuable vacation time.

Begin your adventure with a scenic and narrated drive through Downtown Boston. Marvel at the architectural beauty of the Old State House, explore the historic Granary Burying Ground, and admire the majestic Massachusetts State House. We'll even make a stop at the iconic Cheers Bar Boston.

Continuing the adventure, visit View Boston, where panoramic views await. Located in the heart of downtown Boston, this state-of-the-art observation deck offers 360-degree vistas of the cityscape, from historic landmarks to modern skyscrapers.

Next, embark on a leisurely walking tour of the North End. Our guide will share fascinating stories and insights as you visit landmarks such as the renowned Skinny House, the historic Old North Church, the elegant George Robert Fountain, and the iconic Paul Revere Statue and House. Along the way, indulge in a delectable Boston Cream Pie at a local bakery.

At the end of the tour, your guide will ensure a comfortable and convenient experience by taking you back to your downtown hotel.