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Your chance to tell me where to go - departing Montauk

3918 Views 34 Replies 15 Participants Last post by smackdaddy, Oct 15, 2009

Bene505

Discussion Starter · Sep 28, 2009 (Edited)

..sailing that is.

I've been working my butt off all summer and as a result have a ton of vacation to use. Even if i carry over 5 days like last year... even if I take every day my kids have off that I don't... I still have 5 extra days. I'm using 1 day to take my wife into the city on her birthday. That leaves 4 days for sailing, with perhaps any connecting weekend held in reserve (to prevent sailing back on a schedule).

Any ideas?

Should I go solo or invite others? Or should I do a "supervised solo" with DavidPM like a couple weeks ago. (That's a flying term where the instructor watches you from the ground.) David sits around and make comments about sail trim. Yes, the "DM3000" also make a good autopilot, except for that sail-trim comment feature that other autopilots don't have. He'll jump up only if I need help with something. I got the spinnaker up and tried out the Gale Sail on that trip. )

I also have 4 free nights at Brewers marinas, thanks to spending the winter with them. (Those free night expire this year.) Maybe a trip to the canyon with some fishing gear? How about a trip to the gulf stream if the weather is good. I could escort my friend who is heading to the Virgin Islands later this month. I could go back to Cuttyhunk (I really liked it there.) I could go direct to Nantucket. Whatever I do, I could vary the start date and the destination. This is a real opportunity that I usually don't have, and may never have again.

No guarantee that I'll actually follow any particular suggestion. And not really looking for a BFS this time -- more like relaxation, cruising, taking it easy -- looking for a Big Fun Sail.

If there's something out there that I'm missing, I'd like to hear it.

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AlanBrown

· #2 · Sep 28, 2009

Cuttyhunk - Cause you like it.
Newport - Cause its a cool place.
Block Island - Cause you gotta pass it on the way back to Montauk.

I sailed solo for years, but have come to enjoy having company. Seeing an awesome Bahamas sunset all by yourself, sucks. Last time that happened, when I picked up my girlfriend in Nassau to go cruising, I proposed. She accepted.

P.S. My original thought was Nantucket (cause I love it), but I wouldn't want to visit there on a tight schedule.

CalebD

· #3 · Sep 28, 2009

I would never presume to tell you where to go Bene505!
One thought comes to mind if you want a relaxing trip: circumnavigate Shelter Island in a leisurely fashion. It is close to home, the crowds of summer have diminished and the marina rates have gone down from their summer highs. Plenty of parks with sandy beaches to dinghy to if that is your thing. Sag Harbor and Greenport come to mind as port towns that might be fun for the wife and kids and a few harbors on Shelter Island itself. The Peconic Bays are pretty bodies of water too and there is decent fishing there and in Gardiner's Bay. This could be challenging from the perspective that there will always be some sand bank or beach you could run up on.
A slightly more challenging idea would be to sail the Atlantic down to NY Harbor. You would need at least another watch keeping 'machine' other then the DM3000 as it is over 100 nm. which you should be able to do in a 24 hour period if the wind was from the north. Few areas to duck into so night sailing is normally a must. There are Shinnecock, Fire Island and Jones Inlets which can be interesting to enter or leave on an ebb tide.
Another option, sail up to DavidPM's area and visit some of the harbors up there.
Whatever you choose, have fun.
CalebD

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smackdaddy

· #4 · Sep 28, 2009

Dude - just pop on over to Galveston. I'll bring you some beers. Easy breezy.

davidpm

· #5 · Sep 28, 2009 (Edited)

The DM3000 has been upgraded to the DM3500. It still has the annoying audio "sail-trim commentary" feature but it now includes the digital "solo" sailor picture and movie taking feature that most of our solo sailors have been requesting.

You have the ordering information.

Did you get your steering loosened up?

There are several nice marinas on this side of the sound. Westbrook is very nice and you have a free pass. Also I was recently at Bridgeport and while the town is not fancy the marina is first rate.

I have visited Bristol RI to see the Herreshoff Museum by land and I think it would be a nice trip by boat too.
They have their own dock and their boats are a short walk away in an enclosed building.
Herreshoff Marine Museum & America's Cup Hall of Fame

Entering unfamiliar harbors and getting into slips with a 50' boat is obviously doable but just as obvious you are significantly reducing your margin of safety. If you choose to do it or not depends on your definition of fun.

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chef2sail

· #6 · Sep 28, 2009 (Edited)

Day 1-Westbrooke: on our trip to the Sound this summer and would stop there again (Good restauirant in the Brewer Marina there), or stop at Essex

Day 2- Northport : Another quiet laid back town with a nice harbor and great people. We also stopped there

Day 3- Greenport- alfready been commented on by Caleb

Day 4- Sag Harbor

We are already planning our trip from next July from the Chesapeake. It looks like the probable ports of call once we hit the Sound and beyond are:

On the way..
Northport- one Day
Essex-one day
Newport-one day
Cuttyhunk-one day
Marthas Vineyard-two days

On the way back...
Block Island-two days
Clinton- one day
Huntington or Greenwich- one day

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Bene505

Discussion Starter · #7 · Sep 29, 2009 (Edited)

davidpm said:
The DM3000 has been upgraded to the DM3500. It still has the annoying audio "sail-trim commentary" feature but it now includes the digital "solo" sailor picture and movie taking feature that most of our solo sailors have been requesting. You have the ordering information.

Did you get your steering loosened up?

There are several nice marinas on this side of the sound. Westbrook is very nice and you have a free pass. Also I was recently at Bridgeport and while the town is not fancy the marina is first rate.

I have visited Bristol RI to see the Herreshoff Museum by land and I think it would be a nice trip by boat too.
They have their own dock and their boats are a short walk away in an enclosed building.
Herreshoff Marine Museum & America's Cup Hall of Fame

Entering unfamiliar harbors and getting into slips with a 50' boat is obviously doable but just as obvious you are significantly reducing your margin of safety. If you choose to do it or not depends on your definition of fun.

I forgot about the (waterproof) photo capability of the DM3500! It seems everything has an embedded camera these days, how could I forget? THE DM3500 IS WELCOME ON OUR BOAT ANYTIME.

I should probably list the places I've been. I'd like to do something new, I think:

Sag Harbor
Sherter Island -- except the harbor on the north side
Block Island
Cuttyhunk
Tarpaulin Cove (on the way from Cuttyhunk to Mystic)
Mystic (joined, membership now expired)
Port Jefferson
Edgartown, Martha's Vineyard
Newport (with BillyRuff'n)
Woods Hole (with BillyRuff'n)
Cape Cod Canal (with BillyRuff'n)
Provincetown (with BillyRuff'n)

EDIT: We bought our boat near Annapolis, so there was also our sail up from there. We didn't leave the boat so there were no shore excursions. Adding these to the list though:

Upper Chesapeak
C&D Canal
Delaware Bay
Cape May (overnighted there for a wicked storm that went through)
Up the Jersey coast
Along the Long Island coast

That's it! Looking at this list, I should really get out more.

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Bene505

Discussion Starter · #8 · Sep 29, 2009

I'm a bit fearful of a long ocean trip, evne though I know (with proper precautions) it is safe, so maybe I should do something that requires sailing at night or should go out XX miles and come back.

I do like beautiful places and this could serve as a scouting expedition for when my family can join me.

Generally, some easy skill building would be good.

NaviGsr

· #9 · Sep 29, 2009 (Edited)

Block Island is pretty great this time of year. Locals and sailors only it seems. Also, moorings are only $20!

Westbrook is nice but seems pretty dead right now. NY harbor will require a lot of motoring.

Why not go up to Southern MA. Buzzards bay/woods hole and of course hit up Newport and the Vineyard!

and take me with you!

JohnRPollard

· #10 · Sep 29, 2009

Bene505 said:
...I do like beautiful places and this could serve as a scouting expedition for when my family can join me...

Along those lines, have you been to Hamburg Cove yet?

SOUNDBOUNDER

· #11 · Sep 29, 2009

NaviGsr said:
Block Island is pretty great this time of year. Locals and sailors only it seems. Also, moorings are only $20!

Westbrook is nice but seems pretty dead right now. NY harbor will require a lot of motoring.

Why not go up to Southern MA. Buzzards bay/woods hole and of course hit up Newport and the Vineyard!

and take me with you!

Even in the summer months, I am not a big fan of Clinton or Westbrook. Along that stretch of CT, I would choose Thimble Islands, Milford, or maybe Guilford.

aferlazzo

· #12 · Sep 29, 2009

If you have not yet been to Block or Newport, I would spend the entire 4 days visiting one or both. Both places are a lot of fun and just great cruising destinations.

danielgoldberg

· #13 · Sep 29, 2009

Hey there Brad!

Bene505 said:
I forgot about the (waterproof) photo capability of the DM3500! It seems everything has an embedded camera these days, how could I forget? THE DM3500 IS WELCOME ON OUR BOAT ANYTIME.

I should probably list the places I've been. I'd like to do something new, I think:
Sag Harbor
Sherter Island -- except the harbor on the north side
Block Island
Cuttyhunk
Tarpaulin Cove (on the way from Cuttyhunk to Mystic)
Mystic (joined, membership now expired)
Port Jefferson
Edgartown, Martha's Vineyard
Newport (with BillyRuff'n)
Woods Hole (with BillyRuff'n)
Cape Cod Canal (with BillyRuff'n)
Provincetown (with BillyRuff'n)
That's it! Looking at this list, I should really get out more.

Hope all is well. We didn't do the greatest job of spending time with you on that cruise this summer. Sorry about that. Hope you guys had fun though. You seemed to have had a good time at our cocktail party on that Cabo Rico 42 (Confresi's Child). We'll have to do better next time. By the way, how did you make out with your transmission?

In terms of a short cruise this time of year, keep in mind that you'll be cold, particularly at night, and particularly if you go east from Montauk. That said, give some thought to heading up Narragansett Bay. I see you've been to Newport (though it's not really possible to spend too much time in Newport, IMHO), but how about Bristol and Wickford? Both are nice towns with an active and inviting waterfront. Plus, if you get bored for whatever reason, you are a hop, skip and a jump to Newport where you can live it up a little. The beauty of that entire area is that it might be a touch warmer up the bay, and you can get there in one day's sail from Montauk (a day there, hang for two days, then a day home).

Now, you also mentioned sailing in or to the Carribbean, and if it were me, I'd take that option.

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billyruffn

· #14 · Sep 30, 2009

Brad,

BR is currently scheduled to leave Portsmouth, RI on Thursday and head into LI Sound and East River on our way south to the Chesapeake. Would be most pleased to meet you somewhere along the track and race you to New York with a case of beer to the winner!

Screw the cruise, let's race!

Bene505

Discussion Starter · #15 · Sep 30, 2009

billyruffn said:
Brad,

BR is currently scheduled to leave Portsmouth, RI on Thursday and head into LI Sound and East River on our way south to the Chesapeake. Would be most pleased to meet you somewhere along the track and race you to New York with a case of beer to the winner!

Screw the cruise, let's race!

Very tempting. I could possibly put a few extra bolts in your engine bilge. I didn't do it the first time, but I like the idea.

Not sure I'd race a steel boat that's twice my weight. I wouldn't want to make you mad, simply put. (And you might throw off my compass when I pass you.

Actually I have a family event to go to this weekend. Have a great sail BR.

Bene505

Discussion Starter · #16 · Sep 30, 2009 (Edited)

danielgoldberg said:
Hope all is well. We didn't do the greatest job of spending time with you on that cruise this summer. Sorry about that. Hope you guys had fun though. You seemed to have had a good time at our cocktail party on that Cabo Rico 42 (Confresi's Child). We'll have to do better next time. By the way, how did you make out with your transmission?

In terms of a short cruise this time of year, keep in mind that you'll be cold, particularly at night, and particularly if you go east from Montauk. That said, give some thought to heading up Narragansett Bay. I see you've been to Newport (though it's not really possible to spend too much time in Newport, IMHO), but how about Bristol and Wickford? Both are nice towns with an active and inviting waterfront. Plus, if you get bored for whatever reason, you are a hop, skip and a jump to Newport where you can live it up a little. The beauty of that entire area is that it might be a touch warmer up the bay, and you can get there in one day's sail from Montauk (a day there, hang for two days, then a day home).

Now, you also mentioned sailing in or to the Carribbean, and if it were me, I'd take that option.

Daniel,

Thanks for the suggestions. We had an excellent time at that party. What were those drinks called? Painkillers or something like that? They were excellent.

It was actually a lost prop. Brewers is reimbursing us, once I get around to putting the receipts together. They serviced the prop and put it back on only 2 weeks before.

We had fun exploring MV, once we figured out it was only the prop. I still have my sights on Nantucket though. Eventually. And your Bermuda trip in a year or two.

Regards,
Brad

danielgoldberg

· #17 · Sep 30, 2009 (Edited)

Bene505 said:
Daniel,

Thanks for the suggestions. We had an excellent time at that party. What were those drinks called? Painkillers or something like that? They were excellent.

It was actually a lost prop. Brewers is reimbursing us, once I get around to putting the receipts together. They serviced the prop and put it back on only 2 weeks before.

We had fun exploring MV, once we figured out it was only the prop. I still have my sights on Nantucket though. Eventually. And your Bermuda trip in a year or two.

Regards,
Brad

A lost prop!!!! All at the same time that's excellent and much better than a blown tranny, yet also incredibly infuriating as it impaired a vacation. At least Brewer's is stepping up for the replacement value.

I can't remember what Ken and Miriam were making that night. Probably Dark 'n' Stormies, but who knows.

Nantucket still will be there whenever you manage to get out, so don't sweat it. Talk soon.

G

· #18 · Sep 30, 2009

Head South

Bene505

Discussion Starter · #19 · Sep 30, 2009

stpetersburgsailor said:
Head South

Yes but then I may not come back. Most people will not see that as a problem, but it's not time for a permanent migration.

I'd love to move our boat south and bring the family (and me) down for vacations. Could I find a cheap mooring and visit for a couple weeks during the winter? Is that doable on a tight budget?

I'd bet I could find some people willing to make the trip too. (The DM3000 is invaluable and already offering to help, I just don't know what to tell him yet.) On the other hand I still have work to do on the keel - when the air is dry, like it is in the fall up here.

How about it. Is there a place to keep a boat through the winter, knowing I'm only going to be around for a few weeks? Somewhere south enough to be warm?

AlanBrown

· #20 · Sep 30, 2009

Brad,

Up on Log Bay Island, Lake George, NY, the recipe for a Painkiller is as follows:

1/3 Southern Comfort
1/3 Blackberry brandy
1/3 Anisette

They were so strong that we only drank them out of shot glasses, while offering a toast to our drinking partner.

My thanks to Jim Ringer, m/v Painkiller, for teaching me the secrets of his drink.

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