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BarryL 04-20-2011 05:06 PM

Looking for a Sailing Area
Hi Guys,

I am looking to my friends at Sailnet for some advice.

Each August four of us get together and sail somewhere. First year it was in Cape Cod on a Pearson 30. Year two was LA, where we were on a Hunter 46 and sailed to Catalina Island. Last year we were on my boat (O'day 35) and sailed the Long Island Sound.

We are out of friends with suitable boats, so we are thinking of chartering somewhere. I have read lots of good things about the great lakes, but being far away from there I haven't paid that much attention. We are looking for a sailing area with a number of destinations for 4 days sailing. We like to sail for a few hours (4-8), arrive somewhere and swim, explore, whatever. We mix between cooking on board and eating in restaurants. An ideal place would allow for a day at anchor and then a day in a marina.

So, if you have suggestions for a destination like that, where we could rent a monohull in the 32-38' range, I would love to hear it. We usually go in August, but could do a trip in late July. We are spread all over the country, so we need a place near a major airport as well.

Or, if you want to join the adventure, and have a boat big enough for five, please let me know. We are all adults, share expenses and like to have fun.

Thanks for any information you can provide.


CalebD 04-20-2011 05:59 PM


Have you looked into the Chesapeake?
In the mid-Chessy I know there are boat charter places in Annapolis and Rock Hall, MD.
The only problem is the timing as July and August tend to be not so windy (like the LIS).

Minnewaska 04-20-2011 06:50 PM

Chessy is a good idea. Maine has limitless destinations, but swimming isn't the highlight. Narragansett Bay (RI) has a couple of charter outfits and you can do the Elizabethan islands, Martha's Vineyard, Nantucket and Block Island in a week. Chop it in half for only 4 days. Newport to Cuttyhunk to Martha's Vineyard to Block Island and back, maybe.

I've heard good things about this outfit. I'm told they are extremely diligent with their boats and expect the same from their clients. That's a fair trade in my book.

Sailing Charters, Newport, Rhode Island

chef2sail 04-20-2011 08:15 PM

Barry...come to the Chesapeake. Great anchorages and towns all around. It is after all where the country was really first settled so some of the towns date almost back to John Smith time.

Many of the towns are like the NE towns along the Sound and in Conn and RI. There is a good charter company in Rock Hall which would have a larger boat like you have chartered before and its bnot an arm and a leg.

I am also sure many of the Sailnetters down here would like to meet or help. You and I almost met our last trip to LI in Port Jeff.

Feel free to PM for more info


Cruiser2B 04-20-2011 08:42 PM

i dont think you could go wrong with the Ches bay, my wife and I are planning to sail around Delmarva penisula this oct. looks like a great trip. I would think that the Maine coast would be beautiful to sail too.

mgiguere 04-20-2011 08:54 PM

We love and sail the Chesapeake Bay year round, but you do not want to plan a cruise down here in July or is just too hot and often no wind. Believe me, the Bay has fantastic cruising, many harbors, etc, but the prime sailing season down here is spring and fall. I would highly recommend Maine. It's probably one of the best cruising grounds in the world. The negative with Maine is the potential for fog...especially in late July/August. Cape Cod and the islands are also great, but very busy in summer after July 4th. You could probably get a great deal in the British Virgin Islands since it's off-season. The weather and winds would be good and the cruising is outstanding. As a final alternative (that I'm familiar with), you could cruise from Boston, MA to Portland, Maine...many great cruising stops in between without risking the fog of Maine (further down east) and avoid the crowds of Cape Cod. Great stops along the way from/to Boston would be Scituate, Marblehead, Salem, Rockport, Portsmouth NH, and Portland among many others.

Anyway, just a few ideas. If you advanced you vacation time to May-June or Sept-October, then the Chesapeake Bay would be fantastic and you could attend the Annapolis Boat Show in early October at the same time (Columbus Day weekend), definitely not in the summer IMHO.

CalebD 04-20-2011 09:08 PM

While the Chessy does not need a hard sell I've got to say that Dave's sailing area (back yard) is nothing like the LI Sound. It is a lot bigger with great anchorages all over. It is also a lot shallower (in terms of water depths) and much more unspoiled then a lot of LI Sound's bays and harbors, especially the eastern shore. Anchoring out is usually easy and there are marinas for when you want accommodations and a restaurant instead of home cooking.
The light airs of summer (July/August) would also be a good time for using a spinnaker or asym. There is much less current in the Chessy then the LI Sound and if you are going to run aground somewhere it would be in the Chessy where the bottom is shallow but mostly sand or soft mud. Recent charts and common sense will help keep you from grounding though.
If you like seeing Ospreys and Bald Eagles among the throng of other shore birds you will enjoy the Chessy. I've seen sting rays mating and dolphins are sometimes seen in the southern Bay near the mouth of the ocean; I have not seen this yet though.
For the past 3 or 4 years I've had the privilege of being able to get down to a friends 32' sailboat for 2 long weekends each year. I always enjoy it and get to see new anchorages and places nearly every visit. I grew up sailing on the LI Sound and still love it but the Chessy is a special place.
Hope you like crabs (the kind you can eat that is).

Joesaila 04-20-2011 09:18 PM

Boston Harba and the islands and north
Seriously this is nice cruising grounds. Shouldn't be too difficult to rent in this area either. Hingham bay is nice with lots of good ancorages. We do a couple of trips yearly to Rockport and anchor outsid the harbor and enjoy the restaurants, ice cream and really great 'new' Shalin Liu Performance center. You can check their schedule, reserve tickets and pick from chamber, folk to blues music and view your boat at anchor while listening to it all. Between Boston and Rockport is Salem, nice area and great sail grounds! Come on summer!

PaulinVictoria 04-20-2011 09:29 PM

You can always come up this way, San Juans, Gulf Islands. Nice sailing, nice scenery, lots of places to gunkhole, lots of marinas.

newpbs 04-20-2011 09:54 PM

Apostle Islands
Since you are specifically interested in the great lakes, you should look into the
Apostle Islands. They are located in Lake Superior. I have never made it into Lake Superior myself but I've heard wonderful things about the islands.

Superior Charters & Yacht Sales :: Lake Superior Apostle Islands Sailing Charters and Yacht Sales

The other destination to consider is the North Channel. My brothers and I were there last summer. Incredible anchorages and pristine islands. I am not aware of and people specifically chartering boats there but I'm sure someone must.

August would be a good time of year for either of these destinations.

Good Luck


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