Your Best Area to be on a Sailboat

[RDW]

I will have 1-2 weeks this summer or fall to be anywhere on the water between Hamptom Virginia to Nova Scotia. Give me your best recommendation and why.

[waterworldly]

I vote for Long Island Sound. Plenty of great small harbors, easy sail to a new place each day, crossing back and forth across the sound is an easy sail, and if you want more excitement, you can use a mooring in most of the harbors on Long Island and take an easy train trip into NYC. Also, if you are more adventurous, you can take the canal to Cape Cod. Everything is so close that you can get a world of sailing without ever leaving the sound.

[callmecrazy]

Hampton Virginia. Easy access to the Bay, deep water, tons of boats and sailors, nice place to visit. Daysail on the bay, or weekend/cruise to just about anywhere South of Annapolis.

[Mark1977]

This is gonna be fun...Tall Ships | Waterfront Development
Might have an extra mooring for you too.

[mbianka]

I also recommend Long Island Sound. Lot's of anchorages within a few hours of each other. You could head to Mystic Connecticut, hangout in the Hamptons at 3 Mile Harbor, head over to Block Island, head up to Narrgansett Bay with a stop in Newport. Port Jefferson, Northport, Oyster Bay, Greenport, Shelter Island and Montauk are other stops you might consider. You often have a choice of docking, moorings or anchoring in many harbors.

[tartansail]

Depends on what you like. LI Sound gives you access to warm water, lots of harbors with towns and, in two weeks from the Eastern Sound, access to Martha's Vineyard and Nantucket.

If you like less crowds, anchoring out and lobstah, Maine is at the top of my list. We mostly sail from Penobscot Bay east to Schoodic Point. Enjoyable towns at each end in Camden, Castine and Northeast Harbor. Lots of working harbors in between. Plenty of quiet anchorages including too many to mention in Merchants' Row south of Deer Isle. The water is cold and the fog is a problem through July. However, the sailing is wonderful. We'll be there for a good part of August.

[Hud3]

September and October on the Chesapeake Bay are hard to beat!

[Rakuflames]

See -- I was going to say "cockpit!"

[jmackay]

+1 to Tartansail. IMHO LI Sound and north offers some of the best cruising you can find. You really can't go wrong. We go south for the winter but back north for the cruising.

[s/v Breakaway]

Chesapeake! 5000 miles of shoreline, everything from cities to quiet creeks.
Let us know what you decide.

[RDW]

So what is the prime time to be there? consider wind, weather, and events.
RDW

[s/v Breakaway]

As Hud3 says, September and October are great. Weather will be temperate and breezy. October has the huge Annapolis sailboat show, and various Bay events, like the Schooner Rendezvous in Cambridge on the Choptank River, plus beautiful fall foliage.

[deckofficer]

Originally Posted by waterworldly

I vote for Long Island Sound. Plenty of great small harbors, easy sail to a new place each day, crossing back and forth across the sound is an easy sail, and if you want more excitement, you can use a mooring in most of the harbors on Long Island and take an easy train trip into NYC. Also, if you are more adventurous, you can take the canal to Cape Cod. Everything is so close that you can get a world of sailing without ever leaving the sound.

Plus you can catch the US Tennis Open.

[mlydon]

The only problem with LI sound in summer is that there tend to be fairly light wind....definitely plan for EASTERN LI sound, Block Island, Fischer's Island, Mystic, etc.

I did Newport last summer, AbFab! Tons better than the sound.

Matt

[Ti' Punch]

I'm a Chesapeake Bay sailor, but if you are looking for a summer vacation I would go farther North. The last few summers on the bay have been brutally hot.