Sailboats cost a lot to maintain. Bottom Job every 5 years $3000 Constant Teak maintenance for exposed wood, Canvas, lines, too many maintenance items to list. Slip payments $200 - $600 + a month depending on length, it adds up. And just like the Jeep, they require an emergency fund. I miss the Days when my boat was small enough to fit on a trailer and dry storage was only $50/month. Jeeping and boating gets expensive. You pick your poisons, I guess.