Bucket List

Oct 19, 2017
7,733
O'Day 19 Littleton, NH
I wasn't raised a trailersailor. I grew up with big boats in a home marina and sailing the Gulf coast of Florida and a big trip to Maine and back, with big ideas of sailing the World on a live aboard. Life moves on.
Since bringing home my Mariner 19 on her trailer, I've been working on a mental list of small boat trailer sailing destinations. I want to make the most of Dragonfly's trailerability.
My most ambitious plan is to trailer from Northern NH to the Southern tip of Florida and sail the 75 miles to Dry Tortugas. There are a growing list of sailing venues that I hope to get to: the Cranberry Islands in Maine, Matinicus, Block Island, the wild side of lake Winnepisauki, lake Champlain, the Finger Lakes and the Erie Canal to the Great Lakes. The list goes on and on.
What would you consider a good top 10 trailersailer sails? There is the Texas 200, Key Largo to Bimini, or just around the John Pennikamp reef for good snorkeling and a little fishing. Where would you like to go and what would you do when you while going there?

-Will (Dragonfly)
 
Jan 5, 2017
2,263
Beneteau First 38 Lyall Harbour Saturna Island
Maybe a little bit farther to drive but the best area in the world is the West Coast ( Puget Sound to Alaska). It offers everything from big cities to complete privacy.
 
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Jul 25, 2018
43
O'day 19 MK-II Weekender Narragansett Bay
Hey Will,
Since purchasing my 1983 O'day 19 Weekender last August I too have been thinking of all the trailer sailing possibilities. Even though I had crewed on a J29 quite a few years ago, the O'day 19 is my first sailboat. And as such my sailing horizons are limited to southern New England.

I do look forward your yours and others' bucket list suggestions however. Maybe I'll add a few of my own.
Cheers.
 
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Nov 26, 2012
1,653
Hunter 34 Berkeley
I love it. I live the SF Bay Area so I would definitely sail up into the estuary. There are 1200 miles of navigable waterways so a small boat like that would be perfect.
 
Oct 19, 2017
7,733
O'Day 19 Littleton, NH
Michael and Mark,
I seriously would like to sail the West coast, especially North. I've been to that coast by car and I can easily imagine the sailing being among the best in the World. I love sailing for the view and the sense of connection to the World that I get when hiking or camping or farming. There is a satisfaction in being self-reliant that sailing offers and gives me a sense of place that little else can give.
The PNW seems like it offers that like few places on Earth can offer to a sailor. I don't know the area well enough to even begin to talk about specific launch or destination sites. I imagine sailing under the Seattle skyline would be a one of a kind experience. San Francisco bay also looks like it would offer some unique experiences.
I once took a dinner cruise with my family and in-laws and we paused by the stadium on the edge of the bay and watched a couple of minutes of a baseball game. Pretty cool. From my little boat I wouldn't have the same view that the upper deck offered on that dinner cruise, but how profoundly unique such a perspective would be.

-Will (Dragonfly)
 
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Jun 2, 2004
3,390
Hunter 23.5 Fort Walton Yacht Club, Florida
Mine is an odd one
Columbus ,GA to Apalachicola, FL
Mostly because I've never heard of anyone doing it.
 
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Oct 19, 2017
7,733
O'Day 19 Littleton, NH
Mine is an odd one
Columbus ,GA to Apalachicola, FL
Mostly because I've never heard of anyone doing it.
That would be a very interesting sail, I think. That's the Chattahoochee river. Does that let out right in Apalach or is the a segment of coastal sailing?
That costline is some of the best part of Florida. The panhandle and Big Bend are beautiful. Great little side trips and eating in Apalachicola is some of my favorite.

-Will (Dragonfly)
 

Tom J

.
Sep 30, 2008
2,301
Catalina 310 Quincy, MA
My Dad always had a small motorboat on a trailer. We would drive to various ramps up and down the Massachusetts coast, and explore new waters. Our favorite trip was to launch at Falmouth and motor to Martha's Vineyard. We were so proud of ourselves for making an "ocean crossing"! I think to launch a small sailboat from Cape Cod and sail to the Vineyard and check out the beautiful harbors and towns there would be a worthwhile trip.
 
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Jun 2, 2004
3,390
Hunter 23.5 Fort Walton Yacht Club, Florida
That would be a very interesting sail, I think. That's the Chattahoochee river. Does that let out right in Apalach or is the a segment of coastal sailing?
That costline is some of the best part of Florida. The panhandle and Big Bend are beautiful. Great little side trips and eating in Apalachicola is some of my favorite.

-Will (Dragonfly)
Chattahoochee to the Apalachicola to Apalachicola
 
Jul 1, 2010
962
Catalina 350 Lake Huron
We live in the Fingerlakes region of NY so we've taken our Seaward 25 to many of the northern places you mentioned in your original post. Lake Champlain is one of our favorites and on the not to be missed list. So is Penobscot Bay, Mn. We've also been off the coast of RI. Never made it out to Block Island, but went out to Cuttyhunk and Martha's Vineyard. The northeast corner of Lake Ontario is another great place for cruising. And whatever you do, don't miss making a trip to the North Channel of Lake Huron. We've trailered out boat up there 3 times now, and will be back again.

We tend to overlook the places we live. We've had our boats on Cayuga Lake for years. Our only complaint with Cayuga and Seneca is they are long north-south lakes and most sails involve tacking out and downwind sailing back, or downwind sailing out and tacking back, so it does get old after a while. Also, not much in the way of anchorages to cruise to. The area is beautiful, though, with lots to do.

We've done parts of the Erie (Barge) canal back in our powerboat days. No interest doing it with a sailboat unless we needed to use it to get somewhere. Lot's of history, but I've had more fun traveling parts of it by bicycle.
 
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Sep 30, 2013
3,538
1988 Catalina 22 North Florida
I wasn't raised a trailersailor. I grew up with big boats in a home marina and sailing the Gulf coast of Florida and a big trip to Maine and back, with big ideas of sailing the World on a live aboard. Life moves on.
Since bringing home my Mariner 19 on her trailer, I've been working on a mental list of small boat trailer sailing destinations. I want to make the most of Dragonfly's trailerability.
My most ambitious plan is to trailer from Northern NH to the Southern tip of Florida and sail the 75 miles to Dry Tortugas. There are a growing list of sailing venues that I hope to get to: the Cranberry Islands in Maine, Matinicus, Block Island, the wild side of lake Winnepisauki, lake Champlain, the Finger Lakes and the Erie Canal to the Great Lakes. The list goes on and on.
What would you consider a good top 10 trailersailer sails? There is the Texas 200, Key Largo to Bimini, or just around the John Pennikamp reef for good snorkeling and a little fishing. Where would you like to go and what would you do when you while going there?

-Will (Dragonfly)
I'll take Bimini, if we ever got the vacation time. I'd want a month for that one, to insure weather windows.

The Tortugas were always number one on our list, but we finally scratched that itch last month, so it's off the list. Not something I would do twice, I don't think. The prevailing E winds make weather windows very rare. Easy to get there, hard to get back.
 
Oct 26, 2008
6,045
Catalina 320 Barnegat, NJ
the Erie Canal to the Great Lakes.

-Will (Dragonfly)
I don't see that trip as a good one for a trailer sailer. Why would you want your destination to be Lake Erie? With a canal trip in mind, I'd think the Trent-Severn Waterway in Ontario would be a better option. There are multiple lakes on the route, so you could raise your mast and sail during regular intervals along the canal system. Aside from that, you could start with 1,000 Islands at the east end of Lake Ontario and complete the journey in Georgian Bay on Lake Huron. If I were to make the Great Lakes my destination, I think I would be most willing to skip the western half of Lake Ontario and all of Lake Erie.

I wouldn't make that trip with a trailer sailer, but I would love to do that trip with our Starwind. If I were to really spend the time, I would sail from Barnegat up the Hudson, drop the mast and take the canal to Lake Champlain, raise the mast and spend time on Lake Champlain, then drop mast again for Richelieu waterway to St. Lawrence River, put mast up again and explore the area between Quebec City to 1000 Islands, drop mast for Trent-Severn Waterway and then raise the mast for Georgian Bay to Traverse City or Marquette. There would need to be a winter lay-over for sure somewhere along the way. But as my fantasy develops, I would sell my little boat at end of season and buy a larger boat for the next season on the Great Lakes. I would have to circle Lake Superior and explore all of northern Lake Michigan, including Grand Traverse Bay and Green Bay and islands in between. Then, I would need to make up my mind to layover another winter and reverse course to the east coast, or maybe a better option would be to head south via Lake Michigan and the Mississippi River network.

Sailing Soulianis have posted their latest video from the Mississippi River on their Tartan 37. I'm very interested in their trip!
 
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Sumner

.
Jan 31, 2009
5,254
Macgregor & Endeavour 26S and 37 Utah's Canyon Country

Lake Powell, UT. Not the best lake for sailing with the canyons and finicky winds but it can be done. A year and a half ago with Dottie aboard I finally finished sailing the 150 mile length of the lake. So maybe a fair amount of motoring for those who don't have the time to sail it but...

... some of the most unforgettable scenery on the planet. In the past there has been a group of trailer sailors out of San Diego that have made the trip as a group with others joining them. Some have quite small boats and camp ashore each night. More about it in our trip reports below,

Sumner
==========================================================================
1300 miles to The Bahamas and Back in the Mac...
Endeavour 37 Mods...

MacGregor 26-S Mods...http://purplesagetradingpost.com/sumner/endeavour-main/endeavour-index.html
Mac Trips to Utah, Idaho, Wyoming, Canada, Florida, Bahamas
 
Jul 29, 2010
1,392
Macgregor 76 V-25 #928 Lake Mead, Nevada
On St. Martin's, Sailed and got to steer, Stars and Stripes, 12 meter Dennis Conner won the America's Cup in. OH BOY!
 
Jul 7, 2004
8,402
Hunter 30T Cheney, KS
Like Sumner mentions in his post. Sometimes the best part of a trailer sailor is being able to beach it.
We never trailered our Mac 26S anywhere, but the 18" of draft came in handy when the reservoir got low.
 
Oct 19, 2017
7,733
O'Day 19 Littleton, NH
On a Mariner 19?
Yes. I may not be the best sailor, but I am a confident sailor. :)
Of course, I would need to do a little customization for extended travel and livability. The Mariner is MORC certified. I just have to be careful not to defeat her self-righting rating.

-Will (Dragonfly)
 
Oct 19, 2017
7,733
O'Day 19 Littleton, NH
Scott,
I get your point about the canal sailing. I just think it would be an interesting experience to travel on the canals to get between bodies of water.
Your trip into Lake Champlain and on to the Saint Laurence would be very interesting to. Montreal would be a great stop on the way to Nova Scotia, by boat.

-Will (Dragonfly)
 
Aug 16, 2018
82
Newport 30-mkIII Baltimore
My Dad always had a small motorboat on a trailer. We would drive to various ramps up and down the Massachusetts coast, and explore new waters. Our favorite trip was to launch at Falmouth and motor to Martha's Vineyard. We were so proud of ourselves for making an "ocean crossing"! I think to launch a small sailboat from Cape Cod and sail to the Vineyard and check out the beautiful harbors and towns there would be a worthwhile trip.
I've never even been there, but Martha's Vineyard is on my trailer bucket list, for some reason.. :) Looks like such a cool place to sail to/around at. With a 6-7 hr drive each way it would have to be a pretty long trip though, week or more
 
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