I've lived on a boat since April 2014 - a 22 meter classic Turkish gulet - based out of Fethiye, Turkey. We offer luxury cruise vacations for families and small groups during the tourist season (May through September), sailing the Mediterranean coast of Greece and Turkey with guests from all over the world, so the boat is comfortably outfitted, much like a floating boutique hotel and restaurant.
Except for a few days every winter, the climate in this area is very forgiving for boat life.

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Things to know if you plan to live on a boat
Living on a boat isn't like living in a house, even if you never leave the harbour. The boat is constantly in motion, so things break more than they do in a house. Pipes (or more accurately, hoses) leak, tanks split, wiring corrodes, diesel lines (to power your engine and generator) clog, etc. So you need skills to do repairs on your own, or the funds to pay someone to do them on your behalf. (In my experience, boat repairs cost at least double what I'd pay for the same service on land.)
Boats are subject to a lot of "rules" - maritime laws, national / federal laws, local / municipal laws and harbour / marina policies - which you need to know and understand. The rules influence where you can keep the boat, how long you can remain in place, where and when you can do repairs, the requirements for safety inspections, the qualifications of the person(s) responsible for the boat, etc. While most of the rules are obviously safety-related, some seem arbitrary (and therefore, silly). Ignore them at your peril!

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Insurance costs and coverage are different for boats than they are for regular homes. You may need to do some shopping around to find a policy that covers your unique circumstances.
Being able to read and predict the weather is a must for boat living. Expect the odd sleepless night keeping watch during storms. A loose line or shifting anchor needs to be tended to immediately to avoid damage to your own boat, or those around you. And you must monitor the boats around you. Don't assume that other owners (or their crew) know what they're doing.
You'll need to make make arrangements for someone to care for your boat if you go away for an extended period. Unlike a house-sitter who simply collects the newspaper and waters the plants during your absence, a competent boat-sitter needs to understand the boat's systems and be able to handle the boat in an emergency.

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The boat and all systems require routine maintenance to remain seaworthy and safe. A small leak can turn into a big problem in no time at all. (Even boats in the harbour can sink! RIP M/S Edith...) You'll need to budget appropriately, and also make arrangements for somewhere to live (and store your belongings) when your boat is in dry dock.
What's different when you live on a boat?
- There's constant motion, even when the boat is anchored. I love the feeling (and am NOT prone to seasickness), but it takes time to get used to. You quickly learn to adjust - but the occasionally unpredictable motion can add complexity to even the most routine of activities (e.g., shaving, showering or brushing your teeth).
- The constant motion also impacts decorating choices and housekeeping. Wall hangings are firmly screwed in place, furniture is built-in or otherwise attached. Appliances are bolted in place. Anything breakable is stored in wardrobes, lockers, etc. (There's a reason that people say "getting things ship shape" when they tidy-up!)
- The combination of constant motion and sea water means things break - A LOT. Sometimes, the impact is minor - a broken glass. Sometimes, the impact is moderate - a broken toilet or air conditioner unit. Sometimes the impact is major - losing a propeller.
- Repairs always seem to cost more than they do on land. (In our area, some servicemen seem to believe that owning a boat = being rich, which couldn't be farther from the truth!)
- "Going out" requires more planning when you're on a boat, especially when you're at sea. I'm not able to operate the dinghy (I have very limited vision), so have to rely on my husband or a crew member to to take me ashore if I want to leave the boat. And, someone always has to "stay home" as our insurance requires that the boat be attended by qualified personnel at all times - even when we're in harbour.
- Storage space is at a premium - no attic, no basement. We prioritize storage: #1. safety supplies, spare parts, and tools; #2. food and drink; #3. stuff required to operate the business - cleaning supplies, bed linens, towels, etc.; and finally, #4. personal belongings. (All of my personal belongings fit into two suitcases.)
- Telephone and Wi-Fi reception are unpredictable. We use VHF radio and walkie talkies to supplement communications when trying to "stay in touch", especially when travelling in foreign waters.
- Fresh water, while not scarce, is never wasted. We fill out tanks at every opportunity. Likewise, dirty tanks are emptied whenever we're in harbour.
- We stock up on most provisions when we're in harbour, but also purchase perishables from "floating markets" that visit bays and coves popular for summer cruising. Garbage collection is similar. We drop off trash in harbour bins; "garbage boats" collect from us when we're at sea.

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I love boat life and see it as part of my lifestyle for the next few years, but living on a boat is definitely not for everyone!