Beginner looking for advice to get into sailing full time

Hi all,

My partner and I are on the hunt for our next adventure. Currently, we move seasonally between working at a ski resort and a whitewater outfitter on the west coast. We’re itching for something completely different and are seriously considering buying a sailboat next summer (after getting some experience working for a charter company on Lake Tahoe with friends this summer) and living on it during the summers. Our hope is to spend next summer sailing the Maine coast, learning the ropes and seeing if we truly love it, with the dream of bigger trips down the line.

For context: we have a solid amount of savings and are realistic about spending a signifant chunk of money on a boat and any repairs, and I have a flexible and well paying marketing job in the ski industry. We’re very used to small spaces and limited creature comforts (we've lived in an 18' trailer for the past 2 years and a van before that). That said, we both have minimal sailing and ocean experience, which definitely makes me a bit apprehensive to even dive into this journey, in case we are being naive or may not enjoy this lifestyle.

For those who’ve sailed full-time — what do you wish you knew before you started? Any advice for beginners? Are we in over our heads dreaming of living on a boat full time and eventually sailing around the world, or is this a reasonable leap if we approach it thoughtfully? I’m eager to chase this dream, but would really value a gut check and honest insight from people who’ve done it. Thank you in advance!