Where to Go on Vacation in October?

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GorillaToast

GorillaToast

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Sep 2, 2011
1,041
Hunter 27 Cherubini Alum Creek State Park
Ive got a couple of weeks vacation I can take in late October, and I'd like to spend it scouting possible places to sail and liveaboard when I retire in a few years. I'm wanting to spend my retirement years sailing New England in the summers and SC or FL in the winters.

Other than Annapolis or Chesapeake, does anyone have any thoughts?
 
gpdno

gpdno

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May 16, 2011
144
Watkins 27 Venice
I'm down in Venice, Fl. Gulf coast 1.5 hrs south of Tampa. My wife and I love it here. Five minute drive from the house to the beach or boat. Only takes about 10-15 minutes to motor from my slip to the ocean.
 
GorillaToast

GorillaToast

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Sep 2, 2011
1,041
Hunter 27 Cherubini Alum Creek State Park
Sounds great, but I'll be going to Orlando for the PGA show at the end of January, and I'm going to try and take a couple of ASA courses while I'm down there. For now, I'm looking for something in New England.
 
W

Winkfish

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Jul 28, 2010
914
Boston Whaler Montauk New Orleans
Can't help with New England, but we've gone down to the Florida Keys for 4 years now on family vacations. It's very nice; we love it. Very much a Caribbean island flavor. There are others on the forum who live in that general area and can probably give much more info on it.
 
R

Rob19574

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Feb 4, 2005
524
Catalina C-30 Mattituck, NY
If you want to check out New England then you should try Newport, RI and from there venture out to Block Island, Long Island (east end), Martha's Vineyard and Nantucket. You can take Ferry's around from Island to Island to scout around.
 
T

t37224

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Aug 15, 2012
2
Tartan 37 Mark Twain Lake
New England - try Buzzard's Bay - Newport - Woods Hole - Natucket Sound. Farther north, many great places in Maine. Penobscot Bay gives you Camden, Castine, Bucks Harbor, Southwest Harbor, Winter Harbor, Frenchboro, and tons of beautiful sailing and scenic views in between. Lots of great anchorages too - Seal Cove, Pulpit Harbor, ect. Lobster pots a-plenty but don't let them scare you off!

I know you said "Other than Annapolis and the Chesapeake" but anyone else might want to give Annapolis and vicinity a try during the first week in October. It's boat show time! Best boat show there is - and we've been to most of them.

If anyone does do the show, make sure you stop by the Good Old Boat magazine booth. We'll be there much of the time.
 
Bob J.

Bob J.

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Apr 14, 2009
775
Sabre 28 NH
If you really want to sail New England, go to Maine.
Sorry guys, RI/CT doesn't cut it :)
 
robertsapp

robertsapp

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May 28, 2009
764
Hunter 376 Pensacola, FL
A vacation in October? Forget New England - go to Fantasy Fest in Key West.
 
GorillaToast

GorillaToast

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Sep 2, 2011
1,041
Hunter 27 Cherubini Alum Creek State Park
robertsapp said:
A vacation in October? Forget New England - go to Fantasy Fest in Key West.
Click to expand
Thanks all for your suggestions to go to FL in October, but as I stated in myOP, I'll be going to FL in late Jan.

I'm not concerned about cold weather. I come from Oh, so I'm used to it. Anyway, after the hot, hot summer we had in the Midwest, I'll welcome cooler temps.

Btw, I'm not taking my boat, nor planning to charter one. Just looking at marinas, and towns for a base for sailing Maine in spring/summer.
 
All U Get

All U Get

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Oct 2, 2008
3,811
Pearson/ 530 Strafford, NH
After Labor Day the boating gets easier in Maine and NH cause most of days are a bit chilly. A lot of boats get hauled by Columbus Day or head south. We're planning to be away from Maine by the end of Sept. more or less keeping an eye on weather. Need a PM?
All U Get
 
Chris Patterson

Chris Patterson

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Oct 17, 2011
2,809
Ericson 29 Southport..
Bill, you don't wanna move up north with all them durn yankees, do you?
Oh, wait a minute, Ohio is up north, isn't it. Never mind...

(My wife's gonna kill me).
 
GorillaToast

GorillaToast

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Sep 2, 2011
1,041
Hunter 27 Cherubini Alum Creek State Park
t37224 said:
I know you said "Other than Annapolis and the Chesapeake" but anyone else might want to give Annapolis and vicinity a try during the first week in October. It's boat show time! Best boat show there is - and we've been to most of them.

If anyone does do the show, make sure you stop by the Good Old Boat magazine booth. We'll be there much of the time.
Click to expand
Unfortunately, my boss will be on vacation the first two weeks of October, so I'll have to miss the boat show.

It looks like Chesapeake will be my best bet. At least there's lots of marinas to look at, and I have a guide book.
 
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