This blog post is overdue. When we were moving aboard a sailboat we would have loved to have had a checklist. Something that provided us with some direction from getting from house to boat.
This blog post doesn’t provide boating or financial advice. But, it summarizes a years’ worth of downsizing experience, and provides some details that I haven’t mentioned before in previous posts.
Moving Aboard a Sailboat: Comprehensive Planning
1. Medical Checklist
- visit a dentist well in advance of your departure date in case you require interventions such as a crown or filling
- visit an eye doctor and get your eyes tested
- visit family doctor and arrange for a years’ worth of medication
- visit specialists (such as allergists, for example. Discuss risks and possible emergency procedures.)
- visit a travel doctor to acquire medications for your ship’s medical chest
- take a medical training course
- carry copies of your prescriptions in case they are needed for border/customs
- research border protocols for carrying medications – certain substances may be prohibited
- plan to buy or build your own first aid kit
- arrange medical insurance
- arrange to extend your provincial health coverage before you leave the country (for Canadians)
2. Logistics Checklist
Offload Responsibilities Where Possible
- hire a babysitter or childcare provider
- hire a housecleaner
- hire window cleaners
Decide Whether to Rent or Sell Your Home
- engage with a real estate agent
- stage/clean interior for showings
- cut grass, landscape, etc.
- determine where you might live if you find yourself in limbo — between house and boat (we camped)
- If you decide to rent, hire a property manager to look after things while you are away
Sell Your Vehicle
- develop a plan to for your vehicle
- will you sell it yourself? Or, a dealer?
- can a friend sell it for you?
- where will you sell it? What country?
- research cross-border duties and taxes (if need be)
- arrange an online ad with AutoTrader or equivalent
- consider how you will manage after your vehicle is sold (taxis, friends, buses, bike, wagon, etc.)
Envision Your Final Weeks Before Moving Aboard a Sailboat
- Will you fly or drive to your boat?
- will you be staying in a hotel just prior to moving? Or, a campground?
Determine a Storage Plan
- Determine your storage plan (cost out, can things be stored with a friend or perhaps your own basement?)
- arrange for piano storage (if needed)
Prepare Friends and Family
- decide how and when to tell your kids
- decide how and when to tell your friends and family
Arrange Homeschooling
- Arrange homeschooling supplies
3. Legal & Paperwork Checklist
- Write note to school board re: intentions for homeschooling
- renew your passport (ensure you have at least six months validity remaining)
- arrange to forward your mail
- arrange electronic billing wherever possible
- update contact information with utility companies (if appropriate)
- give power of attorney to your lawyer (or someone you trust) to help streamline your affairs in your absence
- arrange a new bank account – for us that meant we opened a US bank account tom improve our exchange rates when we bought small items during our refit
- prepare yourself to cross a border as a cruiser (have on hand, boat registration documentation, as well as bank account or income information)
4. Downsizing Checklist
- Begin to sell your things immediately
- ship a pallet of things to your boat (for us, this was largely tools, and some homeschooling and kitchen supplies)
- Create four piles: those you plan to keep, to donate, to sell and to throw away
- keep creating the four piles to pare down. As the days progress you will become more ruthless
- take pictures of the books you treasure, and then get rid of them – few books these days are irreplaceable

- buy an industrial scanner – scan all paperwork, and store data online. Get rid of paper clutter, while keeping valuable documents like birth certificates
- then, sell your scanner
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