Living Aboard a Boat: How to Know When You’re Ready

Embracing the call of the open sea and making the life-altering shift to living aboard a sailboat isn’t just about following a to-do checklist. Preparation and knowledge are crucial, but at some point you must cast aside the list and take that daring plunge into the unknown. The question is: How do I know when I am ready to take on this adventure?


You Can Overcome Your Checklist Obsession

It’s tempting to obsess over every item on your “sailboat dream” checklist, but don’t let the list be a barrier to achieving your dream. Overthinking can stall your journey before it begins. Laugh it off with a hearty “LOL” and take a leap of faith! 
You know you are ready when you can accept that things will not be “list-perfect”.

Ignore the Noise

The internet is flooded with opinions from so-called “experts.” (like us? LOL) They can provide useful insights…we certainly aim to do so. But don’t let their chatter cloud your judgment. Trust your instincts and your partner’s. You know you are ready when you can make these decisions and not second guess yourself:

  • Have confidence in your boat and equipment – is the boat and equipment in good condition?
  • Feel confident in boat handling, anchoring, docking, maintenance – do seaschool / engine course.
  • Know what you want in a boat. Choose 5 things you cannot live without and 5 things that would be a deal breaker – the things that matter are anchor, engine, sails, solar, lithium, refrigeration, dinghy, washer, aircon, etc.

Communication is Key

Discuss openly with your partner what about your expectations, limitations, and boundaries are. It’s essential to be on the same page. A well-thought-out safety net or a backup plan can ease any anxieties. You are ready when you can discuss a plan to:

  • Commit to a timeline.
  • Purchase a boat that is affordable fitting within a sensible budget. Don’t over capitalize. Your exit strategy is important to being sensitive about both partner’s abilities, sensibilities, and limitations.

Shared Commitment

This adventure isn’t solely your partner’s responsibility. 

To make it work and worth it, you both must be equally invested. Without mutual dedication, resentment may creep in and that’s not what you’re setting sail for. You are ready when you embrace:

Sailing is a team activity. Be prepared to be fully involved and invested in a good and happy outcome. You cannot be a passenger. I know because I made this mistake when Stephen and I first set sail relying on him completely. It was tough on both of us. Competence gives you confidence. Are you ready to:

  • Stand watches and sail at night with no stopping for days – takes endurance.
  • Fix the boat.
  • Handle the sails.
  • Anchor.
  • Tie a line.

Embrace Uncertainty

Feeling unsure is natural when embarking on such a significant life change. Remember, no one masters everything instantly. Practice and experience will be your best teachers. Be flexible and adaptable. Be a “can-do” person because this is sometimes really hard, physically and mentally! Be prepared and creative. Prepare as much as you can, but accept that everything is a challenge.

Compromise onboard and be flexible ready to “tack” in life and in sailing. Don’t let small things freak you out. Avoid blaming the boat, your partner, the island, etc. as the blame game will sink your dream.

Make sure that the sacrifice is worth it for you. Is this a rewarding alternative for giving up some things to gain others? The smallest “irritation” on a boat can become an insurmountable obstacle if you are not happy with your choices. Consider:

  • Can you significantly pare down on “stuff”
  • Do you understand and accept the limitations of onboard refrigeration and storage?
  • Can you comfortably adhere to a budget? Modern, intricate boat systems can unexpectedly inflate expenses. And many components can only be repaired by an experienced hand, so you’ll need to differentiate between essentials and luxuries.
  • Are you okay with sailing overnight and standing watches?
  • Are you OK with missing out on family and friends’ events and in-person visits?
  • Consider your connectivity needs. Do you need to work while onboard? Can your budget accommodate a Starlink or Iridium-Go plan or will local options suffice?

Second Chances

It’s perfectly fine to make mistakes along the way. If you find that you’ve sailed off course, there’s no shame in turning back and giving it another shot. Sometimes, the second try is the charm. If not…well, it may take a third try.

In the end, the sea beckons with its promise of adventure and freedom. So, whether you’re a seasoned sailor or a newbie, remember that sometimes, it’s the bold, unplanned leaps that lead to the most rewarding journeys. Bon voyage! 🌊⛵

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