Top 10 Private Sightseeing Tours in Boston

Destination: Boston.
This private car tour is the perfect way to orientate yourself to Boston, to see not just the historic sites, but the entire city. On this tour we'll take you into all the city neighborhoods and along the sites of the Freedom Trail. We'll share the history and legends of the city, keep it topical with current day fun facts and light hearted stories. All guides are fully licensed and approved Boston tour guides, driving luxury and livery insured vehicles. Please message for pricing if your group is larger than 4.
Known For: Boston Historical Tours, Boston Shore Excursions, Boston Worry-Free Shore Excursion, Boston Ports of Call Tours, Boston Port Pickup, Boston City Tours, Boston Private and Luxury, Boston Car Tours, Boston Bus Tours, Boston Luxury Car Tours, Boston Half-day Tours, Boston Private Sightseeing Tours.
Duration: Around 3 hours.

Destination: Boston.
Private tours are priced per GROUP, not per person. This amazing tour is for those who want more than a driving tour but not a ton of walking.(aprox. 90 minute walk) Stroll through the historic North End. Have a snack from a famous North End pastry shop. Go inside the Old North Church and see Paul Revere's house, Explore Copp's Hill Burial Ground and learn about the "Spite House", the "Brink's Job" robbery. and the Great Molasses Flood. Visit the USS Constitution, and go up Bunker Hill where the first organized battle of the Revolutionary war took place. Learn how the Colonists lost that battle but won at the same time. Ride through Downtown, up Beacon Hill, The Back Bay, Fenway and over to Cambridge to see Harvard & MIT. You will see the entire city in half a day. ​Learn all about our history as well as what makes Boston such a great 21st century city. We can confirm tour start time after booking is complete. Weekday tours during the school year tours can only start after 2:30PM
Known For: Boston Private and Luxury, Boston Historical Tours, Boston Shore Excursions, Boston Bus Tours, Boston Half-day Tours, Boston Cultural Tours, Boston Walking Tours, Boston Ports of Call Tours, Boston Port Pickup, Boston Private Sightseeing Tours, Boston City Tours.
Duration: Around 4 hours.

Destination: Boston.
Yelp's 2025 pick for Massachusetts #1 food tour! Create food memories with one of Boston's original food tours. Our North End Neighborhood Tour offers a view of Boston's Little Italy from the perspective of our founder, a native Bostonian, with topics ranging from best eats to history to crime to movies, and personal stories that you can't Google! We've included some surprises, too, including FOUR sites that aren't what they appear to be, and two hidden gems in a very unexpected place. And, if you're lucky, you might meet a neighbor or two!
Known For: Boston Half-day Tours, Boston Private and Luxury, Boston Private Sightseeing Tours, Boston Food & Drink, Boston Walking Tours, Boston Cultural Tours.
Duration: Around 3 hours and a half.

Destination: Boston.
Immerse yourself in our colonial history! On this six-hour driving tour, you will see the sights and hear the stories of Boston's colonial past narrated by a professional historian and experienced guide with ample opportunities for taking pictures. This is an excellent tour for seasoned historians and students alike. A meal break will be taken in Concord or elsewhere as directed.
Known For: Boston Private and Luxury, Boston Private Sightseeing Tours, Boston Historical Tours, Boston Bus Tours, Boston Half-day Tours, Boston Day Trips, Boston City Tours, Boston Shore Excursions, Boston Port Pickup.
Duration: Around 6 hours.

Destination: Boston.
If you've always wanted to visit this infamous town, then let's do it during your visit to Boston. This half day Boston to Salem tour consists of: - Downtown Boston pick up, ~45 minute drive to Salem - Stories of what happened before, during & after the Salem Witch trials - Walking tour of movie scenes, sites and fun facts of Salem - Go into one of the main Salem attractions (entry fee not included, and availability not guaranteed) - 45 minute drive back to Boston If you'd rather skip going into any of the sites, we use that time to take you to Marblehead for some amazing ocean views. The return journey and tour is 4 hours, we're happy to customize it to accomplish the things you're most interested in. If you want to spend more time in Salem and see the coastline then check out our full day option. Please message for pricing if your group is larger than 4.
Known For: Boston Historical Tours, Boston Shore Excursions, Boston Cultural Tours, Boston Worry-Free Shore Excursion, Boston Ports of Call Tours, Boston Port Pickup, Boston Private and Luxury, Boston Bus Tours, Boston Luxury Car Tours, Boston Half-day Tours, Boston Walking Tours, Boston Private Sightseeing Tours.
Duration: Around 4 hours.

Destination: Boston.
Hire a private tour guide for your 90-minute walking tour of the Freedom Trail. Take your time, and ask any questions you want! We cover the first 11 historic sites starting in Boston Common at the Visitor Information Center, and end at Faneuil Hall. Ask your guide to give you local's recommendations for spots to go after your tour! Entertaining and educational, this tour is centered on American history with a focus on the Revolutionary War. You'll learn patriotic, fascinating stories of America's founding by great patriots in Boston. Great for school groups, work outings, and families ranging all ages! A highlight of many people's visit here. A must-do. Any start time can be arranged for your convenience.
Known For: Boston Historical Tours, Boston Walking Tours, Boston Private Sightseeing Tours, Boston City Tours, Boston Private and Luxury.
Duration: Around 1 hour and a half.

Destination: Boston.
Take a break from your Boston city break with this scenic private tour. There's lots of ocean views, rocky coastline, a bit of shopping and even some witch history. We keep this full day itinerary flexible to let you customize the tour but here's a feel for what we'll see. Pick up in Downtown Boston, taking the 60 minute highway drive to Manchester-by-the-Sea, where we pick up the scenic back roads. We'll take a picturesque country road to Gloucester, where we stop to walk along the waters edge to the Fisherman's memorial statue. We'll continue the scenic drive to Rockport, where there's a great collection of cute stores to browse and views to admire. Then drive to Salem, where we have time for a short walking tour around the main sites and historic spots. To finish out the day we'll squeeze in a few more ocean views on our drive back to Boston. We'll stop along the way for lunch (not included in price of tour). Please message for pricing if your group is +4.
Known For: Boston Historical Tours, Boston Private and Luxury, Boston Luxury Car Tours, Boston Bus Tours, Boston Car Tours, Boston Day Trips, Boston Half-day Tours, Boston Cultural Tours, Boston Private Sightseeing Tours.
Duration: Around 6 hours.

Destination: Boston.
Start the day in Little Italy, with traditional cannoli and espresso at the oldest Italian café in Boston. Proceed through the historic "Little Italy" neighborhood to learn about Boston's history! Listen to stories about the neighborhood's ties to the American Revolution such as the ride of Paul Revere. Try traditional sandwiches from an Italian Salumeria. Drive through Boston's historical downtown while learning about the city's colorful past. Walk through Beacon Hill, Boston's most prestigious neighborhood. Visit Boston Common, the oldest public park in America. Stop at a local seafood chain for lobster rolls and New England clam chowder. Take a drive through Back Bay, Boston's man-made neighborhood lined with 19th century Victorian houses. Take a quick drive through Cambridge for stunning views of Boston and MIT. End the tour with seeing the stunning Copley Library! Be sure to come hungry! The tour includes pick-up and drop-off anywhere in the Boston area (up to 6 people).
Known For: Boston Day Trips, Boston Bus Tours, Boston Half-day Tours, Boston Ports of Call Tours, Boston Shore Excursions, Boston Private Sightseeing Tours, Boston Food & Drink, Boston Private and Luxury, Boston Port Pickup, Boston Walking Tours, Boston City Tours.
Duration: Around 5 hours and a half.

Destination: Boston.
This full day private tour is comprehensive enough for any history buff, but as interesting in other ways for non history nerds. It's a unique combination of the Revolutionary War sites in Boston and Cambridge that you won't have seen. Then onto Lexington and Concord to see the towns where the "shot heard round the world" was fired. We'll take the same route as Paul Revere, stopping at the most significant, and lesser known sites along the way giving a detailed account of events in April 1775. For those less interested in the details of the battles, there's the option to visit the home of Louisa May Alcott or just take some time to enjoy the pretty main street of Concord. The itinerary gives the list of sites we'll visit, but timings are flexible to let us spend time at the places you're most interested in. We'll also stop for lunch (not included in price of tour) and there's plenty of photo opportunities. If your group is larger than 4, message for group pricing.
Known For: Boston Private Sightseeing Tours, Boston Port Pickup, Boston Day Trips, Boston Ports of Call Tours, Boston Bus Tours, Boston Half-day Tours, Boston Historical Tours, Boston Shore Excursions, Boston Cultural Tours, Boston Car Tours, Boston Private and Luxury.
Duration: Around 6 hours.

Destination: Boston.
This is an action packed private day tour of the sites, history and events of the Revolutionary War era in Boston, Cambridge Lexington & Concord. We drive the Freedom Trail with stories of the city's 400 year history, the events, people and sites which led up to the war. In the oldest neighborhoods of the city, we'll give context to historic events like the Boston Tea Party, Boston Massacre and Battle of Bunker Hill. We'll take a quick walking tour of Harvard, explain the role it played in the start of the war and where George Washington himself spent time. A 10 mile drive gets us to Lexington Green where we take in the significance of the site and the story of what happened that night in April 1775. Next the picturesque town of Concord, to the Old North Bridge and how the second battle of the war took the British by surprise. Pick up and drop off in Downtown Boston, a stop for lunch along the way (not included in price of tour) and as light or heavy on history as you'd like.
Known For: Boston Shore Excursions, Boston Day Trips, Boston Private Sightseeing Tours, Boston Private and Luxury, Boston Car Tours, Boston Half-day Tours, Boston Bus Tours, Boston Luxury Car Tours, Boston Historical Tours, Boston Ports of Call Tours, Boston Cultural Tours, Boston Port Pickup.
Duration: Around 6 hours.