Planning Your Sailboat Liveaboard Lifestyle: An Ocean Sailor's Risk Analysis

Key Takeaways

Transitioning to the Sailboat Liveaboard Lifestyle requires more than just boat preparation—it demands a rigorous, honest assessment of personal, financial, and emotional risks. A formal, expert approach, such as a SWOT analysis and subsequent risk register, is the key to identifying potential show-stoppers (like running out of money or relationship strain) before they force you back ashore.

Wise sailors know that confronting and mitigating the 'what ifs' is what transforms a dream into a sustainable reality.

Making the Leap: From the Tamar to the Tropics
Systematic Risk Assessment: The Sailor's SWOT Analysis
Mitigation Strategies: Turning Threats into Confidence
Financial Sustainability: The Offshore Sailor's Budget
Summing Up
Frequently Asked Questions (FAQ)

Making the Leap: From the Tamar to the Tropics

The NIKE approach would be to "Just do it!" but for us, a lifestyle change of this magnitude deserved considerable thought and planning.

Afterall, Mary and I lived a perfectly comfortable life. We owned a small house in Devon (UK), had two well-paid jobs and our sailboat, Alacazam, sat right there on a deep-water mooring on the River Tamar and the open sea was just a couple of miles down river. It was a not-unattractive status quo.

But we both had long agreed that wall-to-wall grafting no longer represented a sensible utilisation of the rest of our working lives. Having spent five years building a suitable boat for long-distance cruising, it was time to get on with it. The children had flown the nest, the cats had departed this life, and the boat was paid for. The green light glowed enticingly.

Even so, I had lingering doubts; it was my partner (now my wife) Mary’s resolute approach that made it happen. Had it been left to me, we'd still have been spinning the same treadmill. I was subconsciously reluctant to voluntarily cut off the income stream, perhaps not the risk-taker I thought I was. I knew the period of indecision was over when my boss called to tell me that Mary had handed in my notice.

Property Strategy and Destination Decisions

A crucial part of our planning revolved around the house. We thought long and hard about selling and investing the proceeds, but finally decided it would be prudent to hang on to it for the medium term at least. We preferred the hassle of letting the property to finding ourselves out of the rising UK property market if our new life was curtailed for any reason.

As for destination, Mary reasoned that if we were going to cross an ocean, we ought to do it before we got too old. Our destination was settled for us when we picked up a whole portfolio of second-hand Caribbean charts for a very reasonable sum. The Caribbean it was to be.

Systematic Risk Assessment: The Sailor's SWOT Analysis

Buoyed up by the prospect of a carefree life in the sun, we had initially failed to objectively consider the downside. Our familiarity with project management techniques prompted us to look at the decision through a SWOT (Strengths, Weaknesses, Opportunities and Threats) Analysis lens. While the strengths and opportunities were immediately apparent, it was the weaknesses and threats that represented the risks and required rigorous identification and rationalisation.

The resulting list evolved into a risk register, specifically focusing on events that would fundamentally affect the sustainability of the Sailboat Liveaboard Lifestyle, rather than just general sailing risks.

Risk Event	Probability of Occurrence	Impact on Lifestyle
Incapacitating injury or illness	Low	High
One or both find working insecurity untenable	Low	Low
Total loss of the boat	Low	High
Bad tenant damages home or doesn't pay rent	Low	Medium
Out-of-pocket expense budget exceeded	Medium	High
Boat unsuitable for long-distance sailing	Low	Medium
Family issue at home requires return to UK	Low	Medium
Personal relationship strain from close proximity	Low	Medium
Initial enjoyment palls, becomes boring	Medium	High

This systematic approach, combining probability and impact, allowed us to categorise the severity of each risk and focus our energy on mitigation.

Severity Category	Probability	Impact
Category 1 Risk (Show-Stopper)	High	High
Category 2 Risk	High	Medium
Category 3 Risk	Medium	Medium
Category 4 Risk	Low	High
Category 5 Risk	Low	Medium
Category 6 Risk (Inconsequential)	Low	Low

Mitigation Strategies: Turning Threats into Confidence

No risks fell into the critical Category 1 (High Probability/High Impact), which was a major relief. This meant all threats were manageable through proactive planning.

Category 2 Risk	Category 3 Risk	Category 4 Risk	Category 5 Risk
Initial enjoyment palls	Budget is exceeded	Incapacitating injury/illness	Bad tenant/rent issue
		Relationship strain	Family issue requires return
		Boat unsuitable	Insecurity becomes untenable
		Total loss of the boat

We examined each risk in turn, considering how to reduce its probability and mitigate its impact:

Initial enjoyment palls, becomes mundane and boring: This requires flexibility. Be prepared to change pace, take up short-term work, or move cruising grounds to reignite the sense of adventure.

Out-of-pocket expense budget exceeded: We established a significant contingency fund and remained prepared to seek employment if necessary.

Incapacitating injury or illness:* We sought expert advice for inoculations and a comprehensive medical kit, and, crucially, obtained health, sickness and personal accident insurance that covers medical evacuation (medevac).

Personal relationship strain: We tackled this by completing a number of longish shakedown cruises together before setting off. There’s no better way to test a relationship than navigating heavy weather together in close quarters.

Boat would prove to be unsuitable for long-distance sailing: As with relationship strain, this requires practical experience. Testing the vessel thoroughly on those long shakedown cruises allows you to identify necessary modifications to ensure your boat is truly ready for Bluewater Sailing.

Total loss of the boat: This relies on regular inspection, using accurate weather websites, maintaining a constant lookout, and insuring with a reputable marine insurance company.

Bad tenant would damage home, or not pay rent: We selected a professional letting agent with great care and ensured we had robust landlord insurance.

* Some people would say we took this to extremes, as we actually considered what we do if one of us died on passage. We both agreed that the prospect of having a decomposing corpse aboard for a week or more would be discouraging at best, so after logging the incident and taking appropriate photographs, the body would have to go over the side. Even so, the survivor would have some explaining to do with the authorities on arrival in the Caribbean.

Financial Sustainability: The Offshore Sailor's Budget

For the experienced ocean sailor, the financial burn rate is a well-known concern. Sustaining the Sailboat Liveaboard Lifestyle hinges on a multi-layered financial defence:

The Cruising Fund: Your primary liquid assets for routine expenses. Always budget generously; plan for a 20% buffer on top of your estimated annual spend.

The Maintenance Fund: A separate account dedicated to high-cost cyclical items like sail replacement, rigging renewal, and haul-out fees etc.

The Contingency/Emergency Fund: An untouched account for serious life events (e.g., medical bills, urgent flights home, or non-insurable boat damage). This is your ultimate safety net against the Category 3 Risk (Budget exceeded).

Knowing you can earn money is also a vital psychological and financial safeguard. We kept our network of employment contacts alive and were prepared to mix sailing with some form of work if the Category 5 risk of finding the insecurity of a non-working environment untenable, became a reality.

Summing Up

The decision to adopt the Sailboat Liveaboard Lifestyle is exciting, but for those contemplating long-term offshore cruising, excitement is no substitute for methodical preparation. This risk analysis approach, drawn from our project management experience, was the single most effective way to convince ourselves that we had properly considered this seismic shift.

Prospective liveaboard sailors soon get to realise that the greatest threats come not from the sea, but from unmanaged lifestyle risks. By identifying and mitigating potential 'show-stoppers'—especially those related to relationships, finances, and long-term satisfaction—we moved from a state of lingering doubt to one of clear, firm confidence.

The essence of preparing for a successful Sailboat Liveaboard Lifestyle is moving from a subjective dream to an objective plan. This rigorous process gives you the clear conscience and increased resilience required to sustain the life you've chosen, allowing you to press the 'go' button and truly enjoy the adventure when it begins.

Placeit 3D First Time Atlantic Crossing (RHC)

The forefoing tells the story of our preparation for moving aboard Alacazam and 'living the dream', which we wrestled with some 25 years ago. How tempus flugit...

So this is probably a good time to re-introduce you to Mary's eBook, a 'warts-and-all' account of our subsequent east-to-west Atlantic Crossing, which we embarked upon all those years ago.

Somewhat predictably perhaps, most of the warts are mine.

Take a look at it here...

This article was written by Dick McClary, RYA Yachtmaster and author of the RYA publications 'Offshore Sailing' and 'Fishing Afloat', member of The Yachting Journalists Association (YJA), and erstwhile member of the Ocean Cruising Club (OCC).

Frequently Asked Questions (FAQ)

Q1: What is the single most common reason the Sailboat Liveaboard Lifestyle fails?

A: The most common reasons are not boat-related, but personal: relationship strain due to prolonged close proximity, and the cruising budget being exceeded. Addressing these through shakedown cruises and robust financial planning is key.

Q2: Should I sell my house before starting the Sailboat Liveaboard Lifestyle?

A: Generally, no. Most experienced sailors advise against selling, preferring to let the property. This strategy provides a stable income stream, a place to return to if cruising is curtailed, and retains your position in the property market.

Q3: How much money should I allocate to a contingency fund for cruising?

A: A strong contingency fund should cover at least six months of your budgeted annual cruising expenses, or the cost of an urgent flight home plus three months of expenses, whichever is greater. This fund must be kept separate and untouched.

Q4: How do I mitigate the Category 4 risk of relationship strain?

A: The most effective mitigation is spending a significant amount of prolonged time aboard together—at least several weeks—on shakedown cruises before cutting the lines. This exposes potential pressure points in a controlled setting.

Q5: What technical steps protect my property (the Category 5 risk)?

A: Mitigating a bad tenant involves three main steps: carefully selecting a professional letting agent, obtaining the highest level of comprehensive landlord insurance, and setting aside a buffer to cover potential rent voids.

Q6: What insurance is most critical for long-term liveaboards?

A: You need three types: comprehensive marine insurance (hull, third party), health/personal accident insurance that explicitly covers you internationally and includes medical evacuation (medevac), and landlord insurance if you are renting out a property.