Cruise Port Guide · 289 cruises visit Boston →
The bucket-list things to do — and the private, expert-led way to do each.
Here’s the bucket list for your day ashore: the most extraordinary thing to do at each stop, and the private, small-group, or expert-led way to make it yours — your own pace, real access, none of the crowd.
A fully bespoke, expert-guided private tour weaving the Freedom Trail's 16 historic sites with insider detours through Beacon Hill's gaslit streets and the North End's storied lanes. Boston's 400-year revolutionary story, told exclusively for your group.
Step aboard the full-scale replica tall ships where colonists dumped 342 chests of British tea in 1773 and re-enact the defining act of American rebellion. A cinematic, actor-led journey through the spark that ignited a revolution.
Join Boston's most acclaimed small-group walking tour through the Freedom Trail, Beacon Hill, and Back Bay with award-winning local historians who bring colonial Boston vividly to life. Intimate groups, extraordinary storytelling.
Ascend to the 52nd floor of the Prudential Tower for jaw-dropping 360° panoramas stretching from Cape Cod to the White Mountains, paired with a premium cocktail at one of America's most spectacular urban observatories.
Board a premium whale-watching vessel from Boston Harbour and cruise to Stellwagen Bank National Marine Sanctuary — one of the world's most reliably productive whale-watching grounds — for close encounters with humpbacks, finbacks, and minkes.
Boston's quintessential cruise-day companion — a fully narrated, hop-on hop-off trolley circuit of 17 landmark stops purpose-built for port visitors. Cover maximum ground in minimum time with live, comedic expert commentary.
⚓ Your bucket-list concierge
Tell us your sailing and we'll send the bucket list for every port — the most extraordinary thing to do at each, and the private, expert-led way to make it yours.
No spam. The honest plan, even when it says skip the ship’s tour.