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As others have mentioned your original plan seemed a bit much. Sailing out of NGBay I've been going to all the places you mentioned alternating them every few years for the last 12 or so during our 2 separate weeks of vacation every summer. My only real "advise" to you would be - Fuel Up !! Before my Nauticat I had a couple Catalinas that were decent sailers but of all those years I only actually got to stricly "sail" a couple times to those various destinations. The winds in this area are just not steady or predictable enough to plan a multi-hop "sailing" vacation in a limited time frame. I always ended up Motor Sailing so...... I bought a Motor Sailor. There were other reasons also, but I do my "sailing" weekends on the bay, for vacation destinations it's Motor Sailing 90 + percent of the time ;)
 

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I'd second the fool on the comparison of MV to WH. If you can maintain the 7kts or at least 6+ you should have no problem Newport to Vineyard Haven in a fairly long day.
 
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