Downeast Yachts Downeast 38 Cutter
The purpose-built passagemaker of the under-$30K market, and the easiest big cutter to sail alone.

Best for: The 6'4"+ sailor who wants a heavy, forgiving boat for a solo Hawaii crossing and back.
The good
- Cutter rig with two Furlex furlers splits the sail plan into small pieces one person can handle.
- D/L 357, Comfort Ratio 35, CSF 1.76: a long-keel hull that carries stores and tracks under a windvane.
- This listing has the solo kit: electric windlass with 300 ft of chain, davits, 2,000 W inverter, five AGMs, radar mast.
The bad
- 7.2-knot hull speed makes it the slowest of the tall-headroom picks; plan on 16+ days.
- 50 gal of water is light for a 19,500 lb boat; carry jerry cans or fit a watermaker.
- Long-keel boats back into a slip like a shopping cart. Irrelevant at sea, annoying in a marina.
Of 140 boats under $30K on the West Coast, this is the one that was drawn to do the job you are asking of it. A sister ship lists 6'5" headroom and the seller says full standing headroom throughout. Survey the 1978 hull and the chainplates, re-rig if the wire is over ten years old, and go.