Chester Waterfront Homes Tour — See the Billionaire Estates by Boat
Chester's Best-Kept Secrets, Revealed
Chester has long been a haven for the ultra-wealthy — but the most spectacular estates are completely invisible from the road. The only way to see them is from the water. This narrated boat tour takes you along Chester's legendary waterfront, past billionaire mansions, private islands, and hidden coves that most visitors never know exist.
What You'll See
A narrated cruise past Chester's most impressive waterfront properties
Grand Historic Estates
Century-old summer homes built by American and Canadian industrialists — stunning architecture hidden from public roads.
Modern Showpieces
Contemporary waterfront mansions with private docks, infinity pools, and designs you have to see to believe.
Private Island Properties
Entire islands owned by some of North America's wealthiest families — accessible only by water.
Chester Yacht Club
Home of Chester Race Week, one of the largest sailing regattas in North America. A landmark of the harbour.
Hidden Coves & Coastline
Tucked-away beaches, rocky points, and scenic coves that most visitors never know exist.
Tour Details
This tour departs from the Chester Yacht Club area. Timing is flexible — contact us to arrange a departure that works for your group. Private charters are also available.
The Perfect Pairing
Make a day of it. Combine your Chester Homes Tour with dinner at one of Chester's iconic waterfront restaurants — the Rope Loft or the Seaside Shanty — both steps from the harbour. Or pair it with our Oak Island Tour for a full afternoon on the water.
