Escape to Castle Island, a premier Boston destination where rich American Revolution history meets breathtaking coastal beauty. Immerse yourself in unforgettable Boston Harbor adventures, from scenic sailing cruises and guided walking tours to relaxing nature escapes. Whether you are exploring historic landmarks, enjoying sunset views, or seeking family-friendly activities, Castle Island offers the perfect blend of culture and relaxation. Book your top-rated maritime experience today and discover why travelers love this stunning seaside gem!
$54–$106 typical
Wide range from $38 to $1,086
4.7★ average
Based on 2,001 pooled reviews
Cruise and Sailing
92% of available options
2 hours median
Typically ranges from 1.4 to 4.2 hours
Book in advance
42% of tours are likely to sell out
Free cancellation
Offered by 67% of tour providers
20 Products
See the sights. Experience the history. Boston's inner and outer harbors are awash in legend and lore, not to mention beauty. On this fully narrated 60-minute Historic Sightseeing Cruise of Boston Harbor, we’ll regale you with hero tales of the Revolutionary War, local legends of the sea, and storie...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Experience a beautiful Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. This elegant sailing experience will be aboard either Schooner Adirondack III or Adirondack IV. Both sailboats are classically styled schooners and offer a...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Getting started Meet your crew at the boarding point mentioned on your ticket. After a quick security scan, head to the high-speed catamaran. Departure is from One Long Wharf, located between the Long Wharf Marriott Hotel and the New England Aquarium. What to expect Enjoy the luxuries of the boat—sp...
Getting started Meet your crew at the boarding point mentioned on your ticket. After a quick voucher and security scan, head to the boat. Departure is from One Long Wharf, located between the Long Wharf Marriott Hotel and the New England Aquarium. What to expect Enjoy the comforts of the boat, spaci...
After a busy day sightseeing or working, what could be nicer than relaxing onboard one of Boston's finest boats for a cruise on the harbor? Watch the sun setting below the horizon as you glide by the skyscrapers of the downtown. And you can't miss the booming cannons of the U.S.S. Constitution, Amer...
For a full refund, cancel at least 24 hours before the scheduled departure time.
This dog friendly cruise allows you to beat the heat of the city while enjoying the sights and sounds of Boston Harbor. The live narration provides historic information as well as current updates to a very lively working harbor.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Enjoy a delicious 2-hour brunch cruise and take in historic sights along the water including Castle and Deer Island, Spectacle Island, Long Island, Lovells Island, Georges Island, Independence Fort, Bunker Hill Monument, USS Cassin Young, USS Constitution, Old North Church, Boston’s Seaport District...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Escape the heat and enjoy amazing views of Boston’s beautiful skyline and the historic USS Constitution as the sun sets behind the city. As evening sets in, sunset colors fade to a twilight sky and the city comes alive with lights. Our 90-minute narrated sunset cruise will highlight popular and famo...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Our afternoon Boston Premier Brunch Cruise is ideal for group celebrations, couples, or just capping off an incredible weekend with someone special. Enjoy a delicious menu, stocked with breakfast and lunch favorites, full-bar service, onboard entertainment, and City Cruises' distinctive hospitality ...
For a full refund, cancel at least 24 hours before the scheduled departure time.
Getting started Meet your crew at the boarding point mentioned on your ticket. After a quick voucher and security scan, head to the boat. Departure is from One Long Wharf, located between the Long Wharf Marriott Hotel and the New England Aquarium. What to expect Enjoy the comforts of the boat—spacio...
Landmarks travelers visit on the same route as Castle Island.