PEEKSKILL BOAT TOUR FIELD GUIDE
Hudson Highlands at Dusk: A 1.5‑Hour Sunset Cruise from Peekskill aboard the Evening Star
A 1.5-hour evening cruise departing Peekskill on the restored US Coast Guard buoy tender Evening Star, offering sunset views of Bear Mountain Bridge and other Hudson Highlands landmarks.
Hudson Highlands at Dusk: A 1.5‑Hour Sunset Cruise from Peekskill aboard the Evening Star.
Adventure brief
Hudson Highlands at Dusk: A 1.5‑Hour Sunset Cruise from Peekskill aboard the Evening Star
Board the Evening Star, a restored former U.S. Coast Guard buoy tender converted into a classic 36-passenger tour boat, for a 1.5-hour sunset cruise that departs from the Peekskill waterfront and runs north toward Bear Mountain Bridge before returning past Jones Point, Iona Island, Bear Mountain and Anthony’s Nose—a concise outing often recommended for date nights or cocktails with friends.
Hovering on the edge between urban energy and natural grandeur, Peekskill, New York, opens a gateway to the rugged beauty of the Hudson Highlands. The New York Boat Company invites adventurers and romantics alike aboard the Evening Star, a former US Coast Guard buoy tender transformed into a 36-passenger vessel. This 1.5-hour Sunset Cruise offers a unique vantage point from the water to witness the Hudson Highlands’ rugged cliffs, iconic landmarks, and winding river bends painted in golden hues.
Departing from Riverfront Green Park on Peekskill’s waterfront, the Evening Star cruises north along the Hudson River, cruising past scenic highlights like Jones Point and Iona Island. The boat then approaches the Bear Mountain Bridge, an engineering marvel that anchors this legendary stretch of river. The route continues past Anthony’s Nose, a steep rocky peak named for its distinctive profile, before looping back. The interplay of water, rock faces, and forested ridges defines this stretch of the Highlands, presenting one of the region’s most striking natural backdrops.
The Hudson Highlands region has long attracted visitors with its mix of wilderness and history—home to Revolutionary War sites and a biologically diverse ecosystem. The cruise offers a rare perspective on these elements, blending calm waters with dramatic landscapes as the sun dips below the horizon.
New York Boat Company’s Sunset Cruise holds a special place in the local outdoor scene thanks to its combination of accessibility, atmosphere, and insightful narration by knowledgeable crew members. Whether you’re sharing a quiet moment with a partner or unwinding with friends over cocktails, the Evening Star sets the tone for a memorable evening. This trip transcends a simple boat ride; it’s an immersive passage through the historic and scenic heart of the Hudson River Valley.
Route Schematic
Route & Stops
The cruise runs north from Peekskill to the Bear Mountain Bridge and back, passing a handful of Hudson Highlands waypoints along the way.
Peekskill Waterfront (Departure)
Boarding point for the Evening Star; the cruise departs from Peekskill and begins the northbound leg.
Jones Point & Iona Island (River Passage)
The boat passes Jones Point and Iona Island on the northbound or return leg, offering close views of these Hudson River landmarks.
Bear Mountain Bridge (Turnaround)
The cruise reaches the Bear Mountain Bridge area—an endpoint of the northbound leg—before turning to retrace the route back to Peekskill.
Bear Mountain & Anthony’s Nose (Return Passage)
On the return leg passengers pass Bear Mountain and Anthony’s Nose, key visual highlights of the Hudson Highlands corridor.
The Evening Star is configured as a 36-passenger tour boat; passenger limits are a factor in booking and capacity is fixed by the vessel configuration.
What the day feels like
What to Expect
After boarding at the Peekskill waterfront, the Evening Star departs on a 1.5-hour loop up the Hudson: the vessel heads north toward Bear Mountain Bridge, then returns past a sequence of river landmarks—Jones Point, Iona Island, Bear Mountain and Anthony’s Nose—while passengers relax aboard the restored former Coast Guard buoy tender.
THE LANDSCAPE
Sunset through the Hudson Highlands
The cruise delivers a short, focused passage through the Hudson Highlands at dusk, positioning passengers to watch the river and ridge-lines as the boat moves toward and away from the Bear Mountain Bridge.
THE ROUTE
Views of Bear Mountain Bridge and regional landmarks
The 1.5-hour run takes the Evening Star north to the Bear Mountain Bridge and returns while passing notable points including Jones Point, Iona Island, Bear Mountain and Anthony’s Nose.
THE BOAT
An intimate, historic Coast Guard vessel
Guests ride aboard the Evening Star, a restored former U.S. Coast Guard buoy tender configured as an intimate 36-passenger tour boat that frames the outing as a compact, social cruise.
Suitability
Who it's for
Who this cruise suits—and who should look elsewhere.
Practical planner
Details to review before reserving
The cruise lasts 1.5 hours.
Departure is from the Peekskill waterfront; the outing runs aboard the Evening Star, a restored former U.S. Coast Guard buoy tender.
The tour boat is configured for 36 passengers.
Check operator guidance for recommendations on clothing or items to bring.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is the Sunset Cruise?
The cruise runs 1.5 hours.
Where does the boat depart from?
Departures are from the Peekskill waterfront.
What vessel is used for the cruise?
The cruise is aboard the Evening Star, a restored former U.S. Coast Guard buoy tender configured as a 36-passenger tour boat.
What landmarks will we pass?
The route passes Jones Point, Iona Island, Bear Mountain, Anthony’s Nose and reaches the Bear Mountain Bridge area before returning to Peekskill.
Is the cruise suitable for a date night?
Yes—the outing is described as ideal for date nights or cocktails with friends.
How many passengers does the boat hold?
The Evening Star is configured for 36 passengers.
How this guide was prepared
This field guide is synthesized using verified supplier specifications, route descriptions, and destination data. Some booking links may generate affiliate revenue for ADV Guides.
- Verified: 2026-09-05T19:27:50.553Z
Some booking links may generate revenue for ADV Guides or The Adventure Collective.
Availability, pricing, schedules and operating details can change.
Trip details and contextual sources were reviewed by ADV Guides Editorial.