Re: Trip to Block Island...
Rob is right. Block can be a zoo this time of year on weekends. Can be done, especially if you are willing to have a long dinghy ride, but you will be on drag alert. Not just yours, but everyone around you. High winds are obviously concerning, but no wind can be worse. You really need a sweet spot. Moderate winds with a weekend that is forecast to be a washout to keep people away, but turns out nice afterall.
Getting from the upper bay to Block should be no problem. I don't know why, but I often have this mental picture of it being a short open ocean run from Point Judith to Block and it is. However, you are actually exposed to open water from Beavertail at the bottom of Jamestown (Conanicut Island), making the open water portion twice as long.
If you haven't head out that way much, the swell just south of Beavertail is usually higher than what you'll find in open water. I must be due to the ocean funneling up the Bay.
From Warwick, it must be approx 30 miles all in. Nice trip, you should be sure to get it in eventually. Literally, the place become a no brainer on the weekend following Labor Day.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.