Boston to Toronto, Yacht delivery of an Island Gypsy 32′ Trawler

Island Gypsy Trawler












“Captain Ed delivered my boat from Boston to Toronto.  He did it on schedule and in a very professional manner, keeping me informed of his progress every step of the way.  I had intended to bring the boat home myself but life happens, and I contacted Ed with very short notice.  Despite several scheduling issues he worked with me and rearranged his own schedule to make the delivery happen.  He was very up front about his fees and costs; there were no surprises; and at the end of the day I couldn’t be happier with his services.  Would recommend him to any of my boating friends.”
Ralph Bush, Toronto
Island Gypsy 32′ Trawler


Back on the water conducting a yacht delivery from Boston to Toronto. Flew out of from Toronto Island Billy Bishop airport on a Porter Airlines flight, landed in Boston in an hour, both are island airports. It was a very interesting flight, flying from one harbour to another. As soon as we landed it was lunch on the pier in Boston, lobster roll! Then we quickly got the groceries done, hydration packed in ice box! Ready to roll in the morning!


The little trawler “Style” an Island Gypsy 32 footer we are delivering from Boston to Toronto! Some more pics of this 40 year old trawler. She sports a 150hp diesel, almost 5,000 hours on it! Very fuel efficient. This boat is a beauty. Purchased for about $40,000 USD by the owner, I would consider one of these myself, and have it nicely restored! This boat was a pleasure to be on and drive. She cruises comfortably at 7-8 knots. With a heavy breeze aft, we had her surfing 10-12 knots.

Near zero visibility, foggy 6am morning start. Fired up the radar! We don’t stop for anything!


We left Boston the first morning, we made it down the coast on a beautiful sunny day, then through the Cape Cod Canal. Apparently sometimes they have to close the canal for whales that are transiting through the canal. Before sunset we made it to the little town of Onset Massachusetts! Cape Cod, USA!

We enjoyed a locally caught grilled and fried haddock, we shared 1/2 each. We actually met the guy on dock who caught it in the morning! The next day we passed by “Cuttyhunk” and “Martha’s Vineyard”. Been here before with my own boat Black Diamond.

Running since 8am. We are long past Newport, RI. Going 24 hours a day now until NYC expect to arrive tomorrow early morning. Was a tad rough. But manageable. Wind shifted to following seas early afternoon and then smooth sailing to NYC. During this overnight transit of Long Island Sound, with following seas, is where we were able to get her to surf at 10-12 knots, making excellent time! 

We passed a very large floating barge, actually a prison, an addition to Riker’s Island prison. Expression is, “You earned yourself a life long cruise”

Without a mast, we were able to take a little short cut, avoiding Hell’s gate and taking north on the Harlem River. Where the Harlem River meets the Hudson River, you’ll find Columbia University. We needed to ask for a swing bridge opening that commuter trains use. We radioed ch 13, and within a couple of minutes the bridge was open and we were in the Hudson north of the George Washington Bridge, effectively saving us 1/2 a day rounding lower Manhattan. (Dont attemp with a sailboat, lowest bridge is 24 feet.)
After a 33 hour non-stop run from the Cape Code Canal, through Long Island Sound, up the Harlem River and part of the way up the Hudson, we’ll spend the night in what was the first capital city of New York state, Kingston NY, now a lovely little maritime town with a rich history.
Continuing north, soon we were in the Erie Canal Locks and making progress completed 12 locks our 2nd day out, and 1/3 of locks done!
Not bad from Boston in 5 days! We pulled a couple of all nighters, and long 12-16 hour days. Overnight one shot across Lake Ontario, and pulled into the Etobicoke Yacht Club in Toronto, with the owner waiting at the dock at 6am!

s/v Black Diamond

With almost 30,000 Nautical miles of experience and 1,800+ sea days and nights on the water. (1,800 sea days is like 5 years on the water, 365 days a year!) I am an RYA Skipper and ICC International Competent Captain, currently working on my RYA Yacht Master with a Commercial endorsement for a 200 ton vessel. My qualifications include; MED A2 Emergency Safety at Sea, Helicopter Rescue, Life raft deployment and use, Offshore Rescue and Fire Fighting at Sea, etc, STCW Code A-VI/1-3, Canadian Equivalent Marine First Aid and CPR/AED. I am an Open Water Certified diver and completed various CYA & Canadian Power and Sail Squadron certifications which include Power/Sailboat handling, Seamanship Sail, Piloting/charting, CYA Coastal Navigation, GPS Navigation, Extended Offshore Cruising, VHF Radio operation license and a Toronto Harbour License. I am now providing skippered charters and yacht deliveries globally, including crew positions for offshore passages. However, my specialities are the Bahamas, US East Coast, The Great Lakes, Welland Canal, Erie Canal and the Adriatic Sea, Croatia, looking to add Greece. Feel free to contact me at [email protected]

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