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Discussion Starter #1
Hi Folks,

New to the forum here, so I apologize if I am posting in the wrong spot! I'm looking to charter a sailboat in the Boston, MA area, or close to it. I'd like to take my girlfriend for a weekend trip to Maine, or just up and down the coast. Any suggestions? As a poor Tall Ship sailor, I have the certifications and experience, but cost is always an issue.

Thanks!
 

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Learning the HARD way...
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Boston Harbor Sailing Club (Boston Sailing - Schools Lessons Certifications - Boston Harbor Sailing Club - Sailboat Racing Moorings Rentals Charters) charters some old (weary) Pearson / CAL / Albin boats. They have full electronics, but in my experience (2005-2007), you will want to clean their boat before you spend the night on it.

For a more expensive, and traditional, charter experience, contact Hope Swift Hope Swift, Charter Broker specializing in crewed and bareboat charters. Assuming that you want to go to Maine, you will want a boat on the north shore of Boston (Ipswich, Salem, or Winthrop MA). Otherwise, I suggest that you look at chartering on Buzzards or Narragansett Bay. Hope has charters there, as does Narragansett Sailing ()

August - October are the BEST times to sail in New England.

Have FUN!
 

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YIKES! I just looked at the prices...

If you're interested in chartering out of Providence, I'll give you a discreet-captained charter for 2 on my O'day 35, for the price of the Albin 28. PM me if interested.
 

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Discussion Starter #4
August - October are the BEST times to sail in New England.

Have FUN![/quote]



Thanks! I am leaning towards the Boston Harbor Sailing Club that you mentioned. Do you have any recommendations as to which vessel I should try to choose? I think we will have 4 guests aboard, counting myself. Would the Cal 33 or Pearson 31 be suffiecient space wise? I might just go with the Cal 39.....
 

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You really can't go to Maine in a weekend unless you charter a Cigarette. Not a lot of short term options, Swift Yachts is a good resource, but is not likely to brokero less than a full week, the Boston Harbor Sailing Club boats are available short term but are pretty beaten up, so maybe roll the dice and try https://boatbound.co/boat-rentals?near=Boston,+MA.
 

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If you're looking to sail with 6 aboard, the Cal 39 (All is Lost boat) or the Pearson 36 would be good choices... The Cal 33 or the Pearson 34 (assuming that Kaching-Kaching is still in the fleet) would be fine for a total crew of 4.
 

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You really can't go to Maine in a weekend unless you charter a Cigarette. Not a lot of short term options, Swift Yachts is a good resource, but is not likely to brokero less than a full week, the Boston Harbor Sailing Club boats are available short term but are pretty beaten up, so maybe roll the dice and try https://boatbound.co/boat-rentals?near=Boston,+MA.
I mis-read the OP... I thought that you were looking for a week, not a weekend!

I TOTALLY agree with SF's post. Fuggedabout Maine.

Do-able on a sailboat from Boston would be Scituate to Plymouth and back, or P-Town and back.
 

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Discussion Starter #8
Thanks for all the great information guys!

Just to clarify-you don't think it's possible to go from boston to York Maine in a 3 day trip? I believe it's only around 70 NM.....
 

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Plan on 5kts and 8hr days. I'm not saying that it can't be done, but I assume that your guests would like to enjoy the trip, rather than make a delivery.

Also, because of the prevailing winds, it is far easier to get to Maine from Boston, than get to Boston from Maine.
 

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Day Sailing trips from Boston on a 40 ft sailboat well equipped
NOT leaving at first light and ending end late afternoon to enjoy evening at restaurant on land

Sailing North : Gloucester 1 day
Sailing South : Provincetown Or entrance to Canal

Forget A trip to Maine in a WE Not realistic
 

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Discussion Starter #12
So-Final question....

What would you folks recommend for a romantic weekend? We actually just visited P-town last week-Not saying its out of the question, but maybe a better option? Perhaps Wellfleet?

I'm planning on leaving early friday morning, and hope to return Sunday evening-Obviously weather dependent. My original hope was York Maine, or perhaps kittery, but that looks like its out of the question. Maybe Portsmouth however?

Are there Any hidden gems on the cape that I could reach? Suggestions?

Thanks guys!
 

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A romantic weekend for 6?!?! :confused:


I suggest that you travel from Boston to Scituate, spend the night, then to Plymouth, spend the night, and finally back to Boston. The romance is up to you... and your guests...
 

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Thanks! I am leaning towards the Boston Harbor Sailing Club that you mentioned. Do you have any recommendations as to which vessel I should try to choose? I think we will have 4 guests aboard, counting myself. Would the Cal 33 or Pearson 31 be suffiecient space wise? I might just go with the Cal 39.....
I moor with them and know most of the staff well. I've been on their Cal 39 and I've been out on their Pearson 31 (briefly) and thought they were in pretty good condition actually. Though I agree it looks like the Pearson 26 fleet is aging (haven't been on one though)

Why not aim for the Pearson 36 or Cal 39? They only have one of each (I'm fairly certain) so you might not get the one you want for the particular weekend.
 

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So-Final question....

What would you folks recommend for a romantic weekend? We actually just visited P-town last week-Not saying its out of the question, but maybe a better option? Perhaps Wellfleet?

I'm planning on leaving early friday morning, and hope to return Sunday evening-Obviously weather dependent. My original hope was York Maine, or perhaps kittery, but that looks like its out of the question. Maybe Portsmouth however?

Are there Any hidden gems on the cape that I could reach? Suggestions?

Thanks guys!
How early friday morning? A stretch would be a long day to Provincetown (50nm) for the first night, then divide the return with a stop in Scituate (nice little harbor).

Hidden Gems? Not that I know of. The bay side of the cape actually has surprisingly few harbors. Wellfleet is no closer than Provincetown so I don't see it being worth the stop.

North you could do a long day to the isle of shoals or Portsmouth (~50/60nm) and breakup the return with Newburyport, Gloucester, or Marblehead.

Both of those are a lot of sailing for a weekend though, and not a lot of time at any of the destinations. If you wanted to be less ambitious a night at/on one of the Boston harbor islands is a decent option as well.
 

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Another suggestion since you asked about a "gem" on the cape. BHSC also has boats in Westport, which is on Buzzards Bay. They have a Pearson 36, a Cal33 and maybe one other boat down there. Westport itself is quaint and beautiful, but there are many other destinations that can be done in a day or less, including Cuttyhunk and other Elizabeth islands.
 

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To the south you've got Situation, Plymouth or Provincetown as good places to go with the cruising sailboat. The "harbor or refuge" at the end of the canal is not particularly scenic. Situate is easy in, easy out, Plymouth is a long way in to the bay, P-town sounds like you've been there, probably the best of the 3 for scenic cape harbor on the bay side.

I'd probably go north if I was you. Consider Rockport, it maybe hard to find a place to stay in this tiny harbor, but you can anchor in Sandy Bay just north if the wind has a W in it. Don't do it if the wind has an E in it.

On the way back, you could consider Marblehead.

Both these stops although not Maine we give you a classic New England feeling, scenic, stuff to do ashore, and not too far so you'll have time to look around.

Another choice would be drive to Maine and charter up there.
 

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Other options if you go North are Salem and Gloucester. Gloucester has public moorings and a launch service run by the harbor master. Salem has a water taxi to take you to shore.
 

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Another suggestion since you asked about a "gem" on the cape. BHSC also has boats in Westport, which is on Buzzards Bay. They have a Pearson 36, a Cal33 and maybe one other boat down there. Westport itself is quaint and beautiful, but there are many other destinations that can be done in a day or less, including Cuttyhunk and other Elizabeth islands.
Agree on Westport. The Westport Vineyards Winery is just 6 miles from Tripps boatyard. And, if you don't like wine, the Buzzards Bay Brewery is about another mile. Just don't tell anyone about it - OK? It has a lot of charm, and I would really hate to see it further "developed" to bring in a few more millionaires.

The only drawbacks to Westport are: the long slog up the entrance channel (no where near as long as Plymouth, however), and that you can't get there without a car. In Boston, you can fly in, take the water taxi from the airport to Rowe's Wharf, and you are right at the BHSC dock!
 
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