Here is the obvious idea -- dump the Excursion and pick up a Yaris or some other small car.  Put the savings towards Marina fees and you are ready for fun on the water!

I believe that one can blue-water cruise on ANY boat.  It comes down to making prudent decisions about weather and one's own abilities.  There are many examples of people successfully making long passages on small boats.  The real difference is comfort and style.  The Contessa is a long way from an IMOCA 60 racing yacht but both can cross oceans.  And the boat to traverse the North-West passage is likely not the best boat for the Caribbean. 

Go sailing.  Crew for others.  Daysail.  Overnight.  Try Racing.  Help maintain someone else's boat (polish anyone?) and see if you like the work.  Sail different boats.  Have some adventures.  Want to try a longer trip?  -- charter a boat for a holiday.  Don't rule out going to smaller open boats or even sea kayaks.  Sail alone.  Sail with your family -- their enthusiasm (or lack) will be important in your decisions. 

The goal is to decide what kind of cruising you want to do -- long trips, short trips, an hour here and there?  Once you've done that, choosing the boat is easy.

I once lived a 20 minute walk from a yacht club.  Our neighbour had a busy family so each evening after dinner he would walk down to hang out on his boat.  Sometimes he sailed and sometimes he didn't but the whole experience was Zen.  Don't rule out sailing close to home in Philadelphia if it means you get to sail more often.

The best boat is the boat you use.  Make it as easy as possible to do what you want to do.

Just as quick side note- the EXCURSION (the car whose name must be always written in capital letters) with a 6.0L Diesel is a "land-boat". That is-  you spend so much money on repairs it makes a boat seem cheap.

You pretty well figured out what I'd want to do- have a true blue water cruiser  that I can trailer to beat marina fees.

There are few other factors which make sailing attractive- freedom to go mostly anywhere you want.

Thank you again.

The reason a trailer for one's boat is desirable is that the trailer can extend one's cruising range given a limited period of time.  My friend's Contessa was towed from Ontario down to Florida for a three-week adventure in the Bahamas.  Another friend of mine sailed his boat down the St. Lawrence River (with the current and the prevailing winds) and then used a trailer to bring the boat home again -- the trailer made it possible to travel further and concentrate on the enjoyable parts of his trip.

The Contessa appeals to many because it is perceived to be the cheapest proven boat for a trans-Atlantic.  Very few people actually make the trip but they are drawn to the possibility.  It is a bit like your truck.  It appeals because it can go almost anywhere 4WD can go, but in practice, many Excursions never leave the pavement. 

My suggestion then is that you you should visit your goals for your sailing this season.  Because your budget restricts you, be objective and decide what boat do you really need. 

By far the best way to lower the cost of ownership is to not own at all.  There are LOTS of people looking for crew.  Their boats are often in prime areas and, in time, a friend may allow you to 'borrow' their boat.  If you have not yet sailed a Contessa, crewing is a superb way to learn the boat.

What kind of sailing do you want to do?  Picnic sailing, blasting around in big winds, racing, coastal camping trips, trans-Atlantic?  The Chesapeake is renowned as a sailing destination and you need go no further for years of adventure of all kinds.

Are you intending to sail alone or with a group?  All the time or mostly alone? 

Let's say your time is cheap and you are committed to owning a trailerable boat.  As you've learned from these posts, the Contessa is not an optimal trailer-boat.
While not pretty, a Macgregor 26 is a practical trailerable boat -- and with a 50hp outboard it can cover a lot of distance quickly when the wind dies.  I know a fellow who has a center-boarder Sirius 21 which he has towed and cruised all over Canada and the US. 

You can go smaller too.  There are books describing some great trips in small open boats such as Wayfarers and Lightnings.  Sailing Raids have become trendy in the last few years -- basically open boat sailing from point-to-point with camping at each end.  The smaller the boat the easier it is to launch, rig and maintain.  And smaller boats cost less too!

Here is the best news of all:  regardless of the boat, your choice is not permanent -- you can quickly sell the boat and get a different one which better suits your objectives.

You have many options and I do not doubt that the members here will be happy to weigh-in with great ideas.  Contessa owners are a friendly and supportive group.  Tell us what you need!

Cheers!

Christopher

Reducing the costs of ownership is extremely important and the biggest cost that I immediately perceive is getting the boat in and out of the water.

Thank you for the suggestions.

I'm open to any ideas.

The Contessa 26 is light enough that it can be kept on a trailer and hoisted into and out of the water like the racers do with their J boats.

If your sailing club has a hoist, that can cut cost of ownership by a large margin.

My 1984 C 26 #320 is below the 6,000 lb. weight limit for the hoist at our club and it goes in and out easily.

Also, where are you located?

The next question is what sort of sailing do you want to do?  Daysailing smaller boats is less costly and can be lots of fun too.  A Wayfarer or a Lightning can be easily towed and quickly set up for sailing.  Also, many marinas and yacht clubs have dry-sailing areas where you can leave your mast up but not pay the full expense of a wet berth. 

Something else  to consider is renting/chartering.  In one of your posts you mentioned towing the boat, setting it up for a couple of weeks and then towing it home again.  Bareboat chartering can give you the same usage pattern.  And the bonuses are that you will sail in preferred destinations such as the Caribbean, you will be saiiing larger and more modern boats, and you'll have more space for spouse/family/friends (which can reduce the cost),

Some yacht clubs drysail larger boats too, such as Sharks and Tanzer 22s.  Again you'll need a boat and a trailer.

MIT be an option worth considering?

Marina slip fees in my area are very high in the amount of around $4,000 per year...and that's for some back-water marina too.

It would be nice if it were otherwise.

Do you folks have any suggestions or ideas?

Do you know what exact steps are required for foreign purchase and importation of a boat from Canada to the US?

What should be avoided if possible?

Can a Contessa 26 be classified as a "yacht" under US Coast Guard regulations/rules? I think, though not sure, I read someone in the US doing that.

Thank you