Grand Tour of Boston

Boston is one of the greatest cities in the world to visit by bike: it’s relatively flat, geographically small, and logistically manageable. Boston has a great cycling infrastructure with a growing number of bike lanes, dedicated bike paths, and plenty of green spaces and public gardens connecting two-wheeled visitors to all the lovely sites with minimal pedaling effort.

For new visitors or local residents who know and love it well, cycling in Boston offers a unique perspective and an up-close deep dive into multiple layers of New England and American history. With the majority of sights and places of interest within a 3-mile radius, you will be delighted by Boston’s collection of architectural treasures, charming neighborhoods, a harbor like no other, and tales of fascinating personalities who have left their mark everywhere throughout our beloved Beantown.

This four-hour bicycle tour of Boston will begin in Italian North End, one of the oldest neighborhoods in America and where Paul Revere began his famous ride. From here we pedal a zigzagging and quiet loop of downtown Boston taking us through North Station, up and over Beacon Hill, along the Charles River to Kenmore Square and Fenway Park for selfies with the Ted Williams statue. We will make our way to The Fens, roll down St. Botolph Street, and enjoy the pristine and peaceful South End. Onto Copley Square, the Public Gardens, the Commons and the heart of Boston–the Financial District where good ole Ben Franklin was born!

After a nod to the Old State House, it’s onto to the grand finale, a ride to the new and sparkling Seaport District, and along the beloved Boston Harbor where a pristine bike path offers a magnificent panorama of the entire city. We ride past Castle Island to the John F Kennedy Museum and hear about one of Boston’s Favorite sons.

For four hours, your native Boston expert tour guide will not only escort us safely from point to point but will share humorous stories and a flowing and in-depth history of Boston that is only possible by bicycle. Food stops will be available and there will be ample time to stop, ask questions, and take photographs.