Discover Charlestown with Ramblin' Boston Tours in Boston
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Discover the historic Charlestown neighborhood of Boston with Ramblin' Boston Tours. This private, customizable walking experience takes you through iconic sites like the Navy Yard, home of the USS Constitution and the Constitution Museum, as well as Winthrop Square, the Bunker Hill Monument and battlefield, and the historic Warren Tavern, established in 1780.
Your guide, Tom, is a lifelong Massachusetts resident and a Charlestown local for over 30 years. He’s also the author of "Monumental Man," a book about Solomon Willard, the architect of the Bunker Hill Monument. Additionally, Tom is a licensed US Coast Guard captain, offering scenic tours of Boston Harbor on his sailboat, "Triple Trouble II," through Boatsetter.
This private tour lasts about 2 hours and is perfect for history buffs, families, or anyone eager to explore Boston’s rich past in a relaxed setting. It’s suitable for travelers of all ages, with options for infants and small children to ride in strollers, and requires only a moderate level of physical activity.
Frequently asked questions
How long is the tour?
The tour lasts approximately 2 hours, covering several historic sites in Charlestown.
What’s included in the tour?
Your ticket includes admission fees to attractions and bottled water to stay refreshed.
Are meals or drinks included?
Meals and alcoholic beverages at the Warren Tavern are not included. You can purchase drinks or full meals separately.
Can kids join the tour?
Absolutely! The tour is suitable for all ages, from infants to 120-year-olds. Infants and small children can ride in strollers or prams.
What about accessibility?
Travelers should have a moderate level of fitness. The tour is accessible for those who can walk comfortably; strollers are allowed for small children.
How do I meet the guide?
Meet at Pier 4, the Charlestown Ferry terminal, where your guide Tom will be holding a Ramblin' Boston Tours sign and wearing a white baseball cap.
Free cancellation
Cancel at least 24 hours in advance for a full refund.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 2 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Admission fees to attractions
- Bottled water
Not included
- Any alcoholic beverages or full meals at Warren Tavern
- Parking fees
- Charlestown Ferry round-trip ticket
Itinerary
A 2-hour private walking tour exploring Charlestown’s historic sites, including museums, monuments, and a historic tavern.
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Stop 1
View artifacts and interactive displays about life aboard the USS Constitution.
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Stop 2
Walk through the Bunker Hill Monument District, Winthrop Square, and the Bunker Hill Museum (when open).
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Stop 3
Visit the Warren Tavern, established in 1781, where historical figures like Paul Revere and George Washington once dined. Enjoy complimentary appetizers and drinks, with options to order full meals or cocktails (not included).
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Stop 4
Tour the USS Constitution dockside, with an option for a longer onboard tour when available.
Meeting point & pickup
Meet at the start point in Charlestown.
Pier 4, Charlestown Ferry terminal, in the Charlestown Navy Yard. Look for Tom, who will be carrying a Ramblin' Boston Tours sign and wearing a white baseball cap.
Open in Google MapsCancellation & confirmation
Free cancellation
Cancel at least 24 hours in advance for a full refund.
- 100% refund if canceled at least 1 day prior
- No refund if canceled within 24 hours
- Tour may be canceled due to bad weather
Confirmation within 24 hours
Your booking will be reviewed, and you'll receive confirmation within 24 hours.
From $199.00 per person
- Free cancellation
- Secure checkout with our booking partner
