### Pilotage Plan: City Island, NY to Stony Brook, NY#### Route OverviewThis delightful route takes you from the personality-rich City Island, NY, across the beautiful Long Island Sound, ultimately landing you at Stony Brook, NY. This journey offers a fusion of stunning coastal views, interesting stops for leisure, and notable navigation challenges, making it a rewarding trip for intermediate to experienced boaters.#### Start Point: City Island, NYAs you kick off your adventure from City Island (Coordinates: 40.8406666667, -73.7883333333), take a moment to soak in the artisanal charm of this quaint community, filled with galleries, seafood restaurants, and captivating views of the harbor. Before setting off, ensure your vessel is well-equipped and that you have filed a float plan. The city is generally safe for boating, but it never hurts to be prudently prepared.### Navigational Considerations#### Channel and Routes1. **Navigating East from City Island:** As you exit City Island, steer carefully into the Eastchester Bay, being mindful of the shallow areas, particularly near the shorelines. The Eastchester Bay is well-marked with navigation aids, but keeping a watchful eye on your chart is essential.2. **Crossing Long Island Sound:** Once you clear the bay, head southeast towards Long Island Sound. The sound is a major navigational waterway, but stay within the designated channels marked by buoys and be vigilant for larger vessels, especially ferries and cargo traffic.3. **Closer to Stony Brook:** As you approach Stony Brook, you will navigate through the Port Jefferson Harbor. The inlet can be busy with recreational and commercial traffic, so proceed at a safe speed and always yield to vessels navigating in or out of the harbor.### Points of Interest and Shelter Bays Along The Way- **Manhasset Bay (on your way to Port Jefferson):** This is a fantastic place to seek shelter if the weather worsens. It’s well-equipped with marinas and facilities. You can anchor at several points, allowing for a leisurely stop to explore or dine.- **Port Jefferson:** A charming village, perfect for a midday stop, where you’ll find restaurants, shops, and a vibrant waterfront area. It's also an excellent place to refuel or replenish supplies if needed.- **Bays and Inlets:** Points like Huntington Bay and Northport, positioned along your route, offer additional shelter if the wind picks up. Both are scenic spots with facilities for a break, offering the chance to have a swim or a picnic.### Safety ConsiderationsAs you voyage, ensure your vessel is compliant with all local regulations, including maintaining proper safety gear, such as life jackets, fire extinguishers, and a functional Marine VHF radio. Before departure, check the local weather forecasts; if conditions look unfavorable, it’s wise to postpone or adjust your journey.Finally, stay alert to changing weather patterns while at sea, particularly in the Long Island Sound. Fog can roll in quickly, so having radar and a good GPS system, like **Savvy Navvy**, can significantly enhance your navigational safety.### ConclusionThis route from City Island to Stony Brook combines a touch of adventure with the stability of navigational aids, ensuring that boater safety remains paramount. It’s ideal for those with a sense of exploration, yet it suits those looking for a relaxing day on the water as well, thanks to the varied points of interest you'll encounter along your journey. Enjoy the magnificent views, embrace the nautical spirit, and always respect the power of nature while on the water!