Boston Harbor Cruise: 1920s Yacht, Skyline & USS Constitution

Summary

Boston’s skyline, storied ships & harbor islands from the water

You’ll glide past Boston’s skyline on a classic 1920s yacht, hear stories from your captain as you pass Spectacle Island and “Old Ironsides,” and relax inside or out on deck with a drink in hand. It’s an easygoing cruise where you’ll catch new angles on familiar sights — and maybe find yourself lingering over one or two moments after you’re back ashore.

What’s the experience like?

We stepped onto the Northern Lights just as the last bit of sun hit the harbor — that kind of gold you only get near the sea. The deck smelled faintly of salt and varnish, and someone behind us was already laughing about how their hair would never survive the wind up top. I headed straight outside anyway. There’s something about seeing Boston from the water that makes it feel like a different city — all those glass towers and old brick buildings lined up along the edge, with gulls swooping low enough to make you duck (or maybe that was just me).

The captain started pointing out landmarks in this easygoing way — not too much talking, just enough so you knew what you were looking at. We drifted past Spectacle Island, which our guide said used to be a literal dump but now it’s all green hills and walking trails because of the Big Dig project. I didn’t expect to care about an island’s backstory but honestly, it stuck with me. The breeze kept shifting between warm and chilly, so I ducked into the grand salon for a coffee (I could’ve gone for wine but didn’t want to risk getting sleepy). The woodwork inside felt solid under my hand — old-school in a comforting way.

We glided by the USS Constitution next. The crew called her “Old Ironsides” — I’d read about her in school but seeing her from this angle, with her masts sharp against the skyline and flags snapping in the wind, was something else entirely. A couple nearby tried to get a selfie with her in the background; they were giggling because their hair kept blowing into their faces. I still think about that view sometimes — city on one side, history on the other, water everywhere.

Step-by-step itinerary

Day 1 — Boston Harbor sightseeing cruise

• Board classic 1920s-style yacht
• Relax in indoor grand salon
• Enjoy views from outdoor deck
• Cruise around Inner Harbor Islands
• See Spectacle Island transformation
• Cruise by USS Constitution
• View historic boat from water

Top questions

Is there commentary during the Boston Harbor cruise?

The captain provides moderate commentary on main sights but it is not a fully narrated tour.

Can I buy drinks or snacks onboard?

Yes, there is a bar selling beverages and light snacks by credit card.

Are children allowed on this Boston Harbor sightseeing cruise?

Yes, children are welcome but must be accompanied by an adult.

Is there indoor seating available?

Yes, there is a climate-controlled main cabin with comfortable seating.

Will we see the USS Constitution during this cruise?

Yes, you will cruise by the USS Constitution for unique views from the water.

Is hotel pickup included?

No hotel pickup; you check in at the ticket booth before departure.

Do I need to bring ID for this cruise?

Yes, bring photo ID matching your reservation name for check-in.

What’s included

Your day includes your sightseeing cruise aboard Northern Lights with both indoor grand salon seating and outdoor deck access, moderate live commentary from your captain on key sights like Spectacle Island and USS Constitution, plus access to purchase drinks or snacks at the onboard bar before returning to shore at your own pace.