Long Island Sound is home to one of the densest concentrations of historic lighthouses on the East Coast — nineteen of them still standing along its shores, reefs, and rocky ledges, some dating back to the early 1800s. Most people driving along the coast never see more than one or two. Seeing them the way they were meant to be seen — from the water, at the pace of a boat instead of a car — is a different experience entirely.
This guide walks through where the lighthouses are, what makes each cluster worth seeing, and how a private lighthouse tour compares to trying to piece the trip together yourself.
Why See Long Island Sound’s Lighthouses By Boat
Almost every lighthouse on the Sound was built to be seen from open water, not from shore — which means the view you get from a car pullout or a beach parking lot is rarely the one the lighthouse keepers themselves saw every day. A few also sit on islands, rock ledges, or shoals that simply aren’t reachable on foot at all, like Execution Rocks or Stratford Shoal. If you want the full picture, a boat isn’t the scenic option — it’s the only option for several of these sites.
There’s also the history. These lighthouses have witnessed maritime disasters, hosted decades of keepers who lived in near-total isolation, and in several cases were automated only within the last 50 years. That kind of context lands very differently standing on deck a few hundred feet from the structure than it does reading a plaque on land.
The Lighthouses, Grouped by Region
A full Long Island Sound lighthouse tour typically moves through three general clusters, working east from the western end of the Sound.
Western Sound (New York and Connecticut) This stretch includes Execution Rocks Lighthouse — one of the Sound’s most striking and eerily-named landmarks — along with Stepping Stones Lighthouse, Sands Point Lighthouse, Great Captain Island Lighthouse, and Stamford Harbor Ledge Light. This is usually the starting stretch for tours departing from the New Rochelle or Port Washington area.
Central Sound (Long Island’s North Shore) Moving east along Long Island’s North Shore, this section includes Cold Spring Harbor Lighthouse, Huntington Harbor Lighthouse, Eaton’s Neck Lighthouse, and Old Field Point Lighthouse — a cluster of harbor lights that guided fishing and shipping traffic in and out of some of Long Island’s busiest historic ports.
Offshore Castles and Reefs (Central and Eastern Connecticut) The most dramatic stretch. This includes Stratford Shoal Middle Ground Lighthouse (built directly on a mid-Sound shoal), Penfield Reef Light, Peck Ledge Light, Sheffield Island Light, Greens Ledge Light, Black Rock Harbor/Fayerweather Island Light, Tongue Point Light, Stratford Point Light, Southwest Ledge Light, and Faulkner Island Light. Several of these sit on isolated rock outcroppings that look more like small fortresses than typical lighthouses — hence the “offshore castles” nickname among Sound regulars.
Seeing all nineteen in one outing is a full undertaking, which is why a well-run tour is usually spread across two days rather than rushed into a single afternoon.
What a Private Lighthouse Charter Gets You That a Public Tour Doesn’t
Most public sightseeing boats on the Sound run a single fixed route, at a fixed pace, past one or two lighthouses at most — they’re built for general sightseeing, not lighthouse enthusiasts. A private charter flips that: the boat, the pace, and the stops are built around the lighthouses specifically.
That matters most when you actually want to slow down. Getting a clean, unobstructed photo of Execution Rocks or lingering near Stratford Shoal to hear the keeper stories behind it isn’t something you can do if the boat is on a schedule built for forty other passengers. It’s the same logic that makes private sunset cruises worth the difference over a crowded public boat — control over the route and the pace changes the entire experience.
Monty’s Ark Adventures Long Island Sound Lighthouse Tour
Monty’s Ark Adventures runs a dedicated Long Island Sound Lighthouse Tour that covers all nineteen lighthouses across the western, central, and offshore clusters described above. A few practical details:
- Duration: Two full days (roughly 8 hours each), which gives enough time to actually slow down and appreciate the lighthouses that are worth really taking a look at, rather than cruising past all nineteen at speed.
- Group size: Capped at 6 passengers, so it stays a private, personal experience rather than a tour-boat crowd.
- Pricing: Starts at $1,500.
- Departure locations: Port Washington; Norwalk, CT: Pier 25 in Manhattan ($400 surcharge); and Jersey City, NJ ($400 surcharge)
- What’s included: Historical narration covering maritime disasters and keeper stories along the way, plus a customizable itinerary if there are specific lighthouses you want extra time at.
If two full days is more than you’re looking for, the itinerary can also be paired with a sunrise or sunset cruise for a shorter, more scenic version of the route — worth asking about when you book.
Planning Your Trip
A few things worth deciding before you book:
- How many lighthouses actually matter to you. If you’re a completist, the full two-day route covering all nineteen is the way to go. If you mainly want the western cluster (Execution Rocks, Stepping Stones) or the offshore castles (Stratford Shoal, Penfield Reef), a shorter custom route can usually be arranged.
- Your departure point. Port Washington is the standard, no-surcharge pickup point. If you’re coming from Manhattan or Jersey City, NJ, factor in the additional fee and travel time to get to the dock.
- Timing. Tours run Wednesday through Sunday, with specialty charters available given seven days’ notice — plan ahead if you’re targeting a specific date, especially during peak season.
- What you want out of it. History buffs will want extra time built in for the keeper stories and shipwreck history; photographers will want to prioritize golden-hour timing near the offshore lighthouses, where the light and the isolation make for the most dramatic shots.
For more on what to expect once you’re on board — what’s included, what to bring, and how the day is structured — our FAQ page covers the most common questions, and our photo gallery has real shots from past charters, including several of the lighthouses along this exact route.
See All 19 Lighthouses the Way They Were Meant to Be Seen
Nineteen historic lighthouses, three distinct stretches of the Sound, and a level of access you genuinely cannot get from the shoreline — a private lighthouse charter is the only way to see all of it properly, at a pace that actually lets you take it in.
Book the Long Island Sound Lighthouse Tour and reserve your dates before the Wednesday–Sunday summer schedule fills up.
Not sure whether the full two-day route or a shorter custom itinerary is the better fit for your group? Contact Captain Steve’s team and they’ll help you build the right route around the lighthouses that matter most to you.