Top Boston Private Sightseeing Tours

(32)

from $387

Forget the crowded hop-on, hop-off buses and rushed group tours where you're just another face in the crowd. Picture Boston is a completely different kind of city experience — intimate, immersive, and carefully curated for people who want to feel this extraordinary city truly. Fully narrated by one of Boston's own expert local guides, you'll glide through neighborhoods rich with history, step out at the city's most photogenic corners, and leave with both a deeper understanding of Boston — and a camera roll that will leave your friends speechless. Whether you're visiting for the first time or rediscovering the city you call home, Picture Boston will show you something you've never seen before.

Boston and Cambridge City Tour

3 hours 30 minutesFree Cancellation

Boston Private 3-Hour Tour by Car

(3)

from $68

(138)

from $550

Private Boston Freedom Trail Walking Tour

1 hour 30 minutesFree Cancellation

(17)

from $450

I know the secrets that no one else knows. You will go on a small private tour where you will learn the amazing origins of everyday things. Enjoy the stories of the great places where liberty was born, told by an amazing guide and driver who really knows his stuff. I will lead you through the interior of Old Ironsides, the battleground and museum at The Battle of Bunker Hill and the incredible history of Harvard while amazing you with information about Boston that most Bostonians don't even know. We provide better service because unlike big chains, we are local and depend on our guests' satisfaction.

Best Boston Private Tour, I know the secrets others don't!

Best Boston Private Tour, I know the secrets others don't!

6 to 8 hoursFree Cancellation

(8)

from $599

Self Guided Classic Freedom Trail Location Aware (GPS) Walking Audio Tour

2 to 3 hoursFree Cancellation

4.4

(277)

from $8

See all of Boston and Cambridge from the comfort of a heated and air-conditioned modern minivan. This is a half-day driving tour that takes you through every highlight of Boston and Cambridge. The drive will include sights such as the Old North Church, Paul Revere's house, Faneuil Hall, Boston Common, Beacon Hill, Bunker Hill Monument, USS Constitution, Harvard, MIT, Copley Square, Boston Public Library and so much more! The tour is mainly driving, however we will (optionally) stop a few times to briefly (5-10 minutes) get out of the car for photo opportunities and a closer look at some sights! Listen to stories about Boston's past, learning about the American Revolution and the city's duality of religious morals and corruption.

Private Half-Day Driving Tour of Boston and Cambridge

4 hoursFree Cancellation

(5)

from $311

This half day private car tour is a perfect way to visit the Revolutionary War towns of Lexington and Concord and see the site where the "shot heard round the world" was fired. We'll take the same route as Paul Revere, stopping at the most significant sites along the way to give a detailed account of what and how things unfolded in April 1775. The travel time from Boston to these towns is 45 minutes each way and you'll be in one of our comfortable private vehicles with an experienced, knowledgeable and licensed tour guide.

Lexington and Concord 3 hour private car tour from Boston

(37)

from $550

Try a unique alternative to a typical night out in downtown Boston with an exciting dinner cruise along the city’s waterfront. This expedition on Boston Harbor features a meal with live entertainment and dancing. Watch the sun set, then take a stroll under the stars and enjoy the view of the illuminated Boston skyline at night, or head to the dance floor for music and fun in the ship’s nightclub.

City Cruises Boston Premier Dinner Cruise on Odyssey

City Cruises Boston Premier Dinner Cruise on Odyssey

2 to 3 hoursFree Cancellation

3.7

(187)

from $133

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

2 hoursFree Cancellation

4.6

(455)

from $71

Boats and various shops located at the harbor in Newport Rhode Island in the setting sun

Experience the best of Newport, Rhode Island on a private, guided day trip tour in a comfortable luxury vehicle. If you value privacy, comfort, and the flexibility to explore at your own pace, our tour is the perfect choice for you. We will take you to all of Newport's most important sights, and our tour is completely customizable to suit your preferences. Whether you want to explore the opulent Gilded Age mansions, take a scenic drive along Ocean Drive, or stroll through the charming downtown area, we will create an itinerary that meets your needs. With our private tour, you can relax and enjoy the sights of Newport without having to worry about keeping a schedule or sharing your experience with strangers.

Boston to Newport Mansions Private Day Trip

9 hours 30 minutesFree Cancellation

(3)

from $1,012

Private 4-Hour Walking and Driving City Tour

from $550

Explore Boston’s Freedom Trail as you wish with this self-guided audio tour. Download the iPhone or Android GPS app and start along the trail when it suits you. As you wander between the sites, dip in and out of their backstories, deep-dive into topics that grab your interest, and stop and resume the audio when you wish. The benefit? You’ll enjoy more flexibility than on a fixed-itinerary tour and have more information at your fingertips than if exploring alone.

Boston Freedom Trail Self-Guided Tour with Audio Narration & Map

3 to 4 hoursFree Cancellation

4.4

(113)

from $10

Boston's Freedom Trail: A Self-Guided Tour of All 16 Sites

Are you looking for a way to see all 16 Freedom Trail sites without joining a tour group? Explore at your own pace with this self-guided walking tour. • Find out about Samuel Adams, the one man on whom you could maybe blame the entire American Revolution and other key Freedom Trail players • Hear from producer Daniel Berger-Jones, a local educator and tour guide • Do it all in 120 minutes or linger at stops along the way with complete control over when you start and finish • Get unlimited use before your booking date and after it • Use the virtual tour option at home Once you’ve booked, you’ll receive a ticket with instructions and a unique code listed under “Before You Go”. Then simply install the Voice Map app and enter your code. The app displays directions to the starting point, and when you’re in the right place, pop in your headphones, and just tap start. Voice Map has automatic GPS playback, with turn-by-turn directions. It also works offline.

Boston's Freedom Trail: A Self-Guided Tour of All 16 Sites

2 hours to 2 hours 40 minutes

(14)

from $15

Boston Harbor Narrated Sunset Cruise

1 hour 30 minutesFree Cancellation

4.2

(563)

from $29

Private Day Tour of Salem and Boston

7 hoursFree Cancellation

(28)

from $418

Discover the thrilling history of Boston on this immersive walking tour of the Freedom Trail. Hear tales of Redcoats, smugglers, riots, and midnight riders while reliving the American Revolution as you explore all 16 official sites of the trail. Learn about Boston’s leadership in abolition, women’s rights, education, and immigration over its 400-year history. Explore downtown Boston, hearing stories of legendary figures such as Paul Revere, John Hancock, and lesser-known pioneers and patriots.

Boston's Freedom Trail: A Revolutionary Walking Tour

Boston's Freedom Trail: A Revolutionary Walking Tour

2 hours 30 minutesFree Cancellation

Experience the epitome of luxury with our private helicopter tour of Boston. Discover a world of wonder as you soar above the ever-evolving skyline and breathtaking surroundings of this vibrant city. From the moment you arrive, our pilot will cater to your every need, ensuring an unforgettable journey that is tailored exclusively to you. Sit back, relax and capture stunning photos, and prepare to be amazed as you ascend into the skies. Witness the majestic Downtown Boston, the shimmering Seaport District, and the harmonious blend of nature and urban life at Boston Common. Marvel at iconic landmarks like the Hancock Tower, Prudential Tower, and Zakim Bridge, while soaking in the beauty of Boston's renowned park. Whether you're marking a special occasion or seeking a truly immersive escape, our helicopter tour promises an engagement with Boston that transcends the ordinary. Book now and let us elevate your adventure to new heights of opulence and wonder.

(1,618)

from $31

30-Min Private Helicopter Skyline Tour of Boston

30-Min Private Helicopter Skyline Tour of Boston

1 hourFree Cancellation

(7)

from $349

Boston Walk Through History Private & All-Inclusive Tour

3 to 6 hoursFree Cancellation

4.6

(11)

from $339

3-Hour Private "Cold Weather- Warm Van" Driving Tour of Boston

4.7

(22)

from $495

It can be tough to take in all of Boston’s historic sights on your one in just one day, so this private combination car and walking tour of Boston and Cambridge is here to help. Follow in the footsteps of famous academics exploring Harvard and MIT, learn about Boston’s storied history and the American Revolution at Beacon Hill and the Bunker Hill Monument, and explore the artisanal food options available at the US’s oldest tavern and restaurant.

Private City Tour of Boston and Cambridge

7 hoursFree Cancellation

(42)

from $440

The Full Revolutionary Story Epic Small-Group Boston Walking Tour

Explore the best of Boston at your own pace on a hop-on hop-off trolley tour of the city. Choose from a 1- or 2-day pass and see Boston’s top attractions, including the USS Constitution, the original bar from TV show “Cheers,” and the Faneuil Hall Marketplace, to name a few. The pass includes discounted admission to the Boston Tea Party Ships and Museum, to enjoy during or after the tour.

(2,697)

from $59

Boston Hop-On Hop-Off Trolley Tour with 13 Stops

Boston Hop-On Hop-Off Trolley Tour with 13 Stops

2 hoursFree Cancellation

4.3

(5,830)

from $51

Boston: Freedom Trail History Small Group Walking Tour

2 hours 30 minutesFree Cancellation

Boston Pizza Lovers Food and History Walking Food Tour

(7,421)

from $39

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Top Attractions in Boston

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Attractions

What are people saying about Boston

Amy_C, Jul 2026

Must do

This was one of the best tours we’ve ever taken! Dan was funny, informative, and made the entire experience so enjoyable. The pizza was delicious, and the meeting instructions were clear and easy to follow. Five stars all the way - this is a must-do when visiting Boston!

Walk the Historic Freedom Trail with Costumed Guide

Tracy_M, Jun 2026

Zoey, our guide, was...

Zoey, our guide, was terrific!! I went with my husband and a friend, both who grew up just outside of Boston. They were amazed to learn so much about places they had been walking by for years. A very fun and educational way to walk around Boston!! Thank you Zoey!!

Boston's Beacon Hill Underground Railroad Audio Walking Tour

Cynthia_O, May 2026

Great little company!!

Unfortunately, didn’t get a chance to go this time but when we’re back in Boston, we’ll definitely check it out!! I was extremely pleased with how professional and kind my communications were with the company. They reached out every step of the way. We had plans to do the Underground Railroad in addition to the JFK library but the day quickly we got ahead of us and we weren’t able to do the railroad. My only disappointment was that the railroad excursion started a little late in the day. I had plans to do the railroad first since our tickets for the JFK Museum wasn’t until noon. Good luck with your business.

Boston Harborwalk & Tea Party Self-Guided Walking Audio Tour

Jennifer_M, Apr 2026

Lovely and informative.

Park at Harbor Garage for this experience, it starts around the N.E. Aquarium. The walk is like a sidewalk thing around the buildings, right against the water and the buildings so it is right against, it curves with the landscape. VERY nice experience. When you get to one of the spots with the app, it automatically tells you about the area which you arrived. Super interesting and a great job/informative.

Boston Private 3-Hour Tour by Car

Katherine_F, Apr 2026

Don't hesitate to book!

Joan was the best! We had a great time cruising around Boston, and learned a ton. It was a wonderful combination of historical facts and fun. Doing a private tour let us ask all kinds of questions and have the tour fully customized. Joan was flexible with where she dropped us off at the end too. My 12 year old son said it was his favorite part of our trip to Boston! Highly recommend!

Lexington and Concord 3 hour private car tour from Boston

Clinton_E, Mar 2026

A highly recommended, brilliant tour!

We absolutely loved our tour of Lexington and Concord with Martin, the best tour guide in New England! He picked us up from our hotel right on time in a clean, new minivan. He gave us a brief photo review of the land-filling that created the Back Bay (as our hotel was there). He then gave us a drive-through bonus tour of a bit of MIT and Harvard on the way to Lexington. We were able to briefly walk the long corridor of MIT and see the unbelievable freshman dining hall at Harvard. Both on the road and when out of the van in Lexington and Corcord, Martin demonstrated a captivating style of history telling that really intrigued the listener. He is clearly passionate about the details of the events of April 19, 1775. I was easily able to visualize the incredible drama that unfolded in these towns on that day. Because of this, standing on Lexington green was very moving for me. Near the end of our tour, he gave us a bonus drive-by of Bunker Hill and provided us with some additional history. He then walked us in to the Warren Tavern, so to insure that we found a great seat. This was my fifth or sixth trip to Boston, and can say without hesitation that this or any of Martin’s company’s tours will stand above the rest (we also took the full-day private tour of Salem and the coast with Martin)!

Boston Freedom Trail Self-Guided Tour with Audio Narration & Map

Chris_B, Mar 2026

Great storytelling - get two for one!

Great narration throughout the tour. The tour tracked our location using GPS and automatically started the narration as we approached different stops. Pro Tip: For two people, just buy one tour and each of you can wear an earbud for the tour...two for one!

Boston's Freedom Trail: A Self-Guided Tour of All 16 Sites

Jenna_P, Dec 2025

Such a great way to...

Such a great way to explore Boston solo! I didn’t want to do a formal group tour and was so impressed with this entire audio experience. I had never done anything like it before and it was so easy to download and use and I loved how the audio would automatically start when I got to the next location.

Boston Sightseeing Tour - a fully-narrated driving tour

Dyan_K, Oct 2025

Fantastic tour w/Peter

Peter was punctual & full of historic information + he was funny. We had a wonderful time with him. He filled us in on all the points of interest, giving us from the time the British and other countries came here all the way through about the 1950s. If we needed to make a stop, he was willing to do that. And all the anecdotal information that you can’t find in a book was such fun to hear.

Boston City View Bicycle Tour: History and Landmarks

Laura_A, Sep 2025

DO THIS! We loved every minute!

This was the absolute best way to see Boston and to put its neighborhoods and landmarks into context. The tour leaders who rode with us were funny, friendly, and engaging, and I felt safe knowing they were looking out for us at intersections. I’m not in perfect biking shape but found it easy to tackle the hills without an e-bike. I ABSOLUTELY recommend this to anyone who wants an active, fun, educational way to understand Boston!