A thought -
Our latest sailbaot is quite livable, and cost well under 20K with upgrades and parts to get it back in shape. It's quite seaworthy from what we can tell, and we're getting geared up to cruise the gulf of mexico and maybe a great loop.
My dad's nordhavn cost him over 700K without fees and taxes. I remember when he bought it, and I got to glance at the papers before I almost fell out of the chair. He spends about $7500 annually on
fuel to cruise south california , baja mexico and over to hawaii. so far this year, I've spent $184.33 on
fuel. I can keep the few receipts in my logbook.
I haven't put thousands of miles on my sailboats yet, but I can guarantee you I can cruise for just as many miles as he can, just slower and nearly for free.
I have about a 30-40 gallon tank for a 25 horsepower motor and I use it about 10% of my time saiing. He has about 1500 gallons and uses the twin diesels constantly unless in port, then usually a generator is running in absence of shore power leads.
My wife and I were your age when we started "fun adventures" like what you're planning on doing about 10 years ago. We've searched for our own boat, and lived aboard the Nordhavn too. Now we're on sailboats and are very happy, much more so than a power boat / passagemaker.
We have a house too, but we could very easily live aboard the 28 footer if we had to and lived in an area that would be proper.
Initially I thought space and comfort would be a premium, so we bought a Beneteau 323 which was like a floating cavern, and it would be big enough for either one of us to single hand. Now that we've been out sailing and learning, we re-addressed what we like in a sailboat and now we have a little lancer 28 which is PERFECT for us.
I wish I could have seen what I needed beforehand and it would have saved me thousands of dollars on fees, surveys, and a stressful $150,000 loan I wouldn't be able to pay with just my retirement pension if I wanted to cruise too. If we had to manage a business, I'd keep the bene, otherwise we both really enjoy our Lancer 28 (and anyone here can tell you I have an affair with it, Andrea calls it my mistress) and it cost more than a hundred thousand dollars less after a complete restoration adn refit, with all modern electronics
rigging, sails and anything else we found needed to be re-done. It's really a new boat with an old hull and mast.
So, certainly $50K is very do-able for a cruising boat. Heck, 30K would exceed what we've sunk into the Lancer so far and it is perfect for us now, and is heavy/stable enough to take to the sea, and if we crash it, no problem; we didn't loose our shirts too much. insurance is less than $250.00 A YEAR for full replacement cost on everything we've put into it. It was 6 times that on the Bene, and required by the mortgage broker.
A note about our Beneteau - when I used to singlehand it, I used to get flat nervous because there was just so much money at stake each time I cast off. I can relax with the Lancer and learn learn learn, not to mention enjoy sailing without a care in the world and having a f-ing great time.
Sail to enjoy it, not to show off or worry. Have fun with your best friend as much as you can before kids come and the game changes. Do what makes you happy and you're reap the benefits ten fold.
Read up on "Modern Cruising Under Sail" and "Singlehanded Sailing" as well as "Storm Tactics" the you'll have a great clarity on what you NEED to get your task done, rather than what you'll think you need. Also grab an Annapollis (sp?) Guide to Seamanship manual and a Duttons Navagation book.
Hope that helps you in your search!