For about 10 years or so, I’ve wanted to sail around the world.

Some of the first ‘lessons’ I ever took in the craft were over summer break in my late teens. My Dad thought it’d be fun to rent some Sunfish and mess around on the lake. Turns out we needed more instruction than we originally thought, but we were able to get out there 5 or 6 times mess around and make it back to the beach or more or less one piece.

I was hooked, not so much on the actual act of Sailing, which still terrified me due to lack of any skills or instinct whatsoever, but in the possibilities that means of travel can bring the salty dog that tames it.

A quick search on youtube brings you no less than double digit thousands of videos of ill-advised sailors throwing caution (sometimes) to the wind and exploring all over this beautiful planet. Some on fancy drool-inducing yachts, but even more on what I’d call ‘Craigslist Specials’. Just making it work, and cobbling their noble vessel together with all the duct tape and zip ties they can carry.

If you want to travel around the world on a powerboat. You’re going to need some serious engines, maintain them, and you better learn how to operate them safely. Then just buy tens of thousands in fuel and you’re on your way!

In a sailboat, you can learn how to use the wind in a weekend, and even something as cheap as a $10,000 hunk could get you from Florida all the way through the Caribbean islands. Note, that’s not advisable or comfortable, or even safe… but it’s possible.

With a few cables, and some old sails, you can get pretty much anywhere you want… if you have the time that is. And that’s the beauty of it. What’s the hurry? The journey is the destination, baby. Especially if that journey only costs you about 30 bucks in gas to get across an entire ocean.

The dream is clear to see. You wake up to a stunning sunrise (or in my case 9AM sun streaming into the cabin), and sip your coffee in your boats cockpit while gently bobbing in turquois carribean waters.

Maybe you do some work, or maybe you make some breakfast, plop down a map (chart) and plan out the days adventure. Exploring caves in the national park you’re parked in front of, hopping over to another island, meeting up with some newly made sailing friends who just cruised in the the area… and on and on.

And if you’re fortunate to have a girlfriend who loves both you and the sea, then the picture is pretty much made. Certainly no complaints about your lady lounging in bikinis day after day.

I don’t think I have to do much more selling her to convince you that a winter bobbing around the Caribbean is a very solid dream to have and make happen.

Alas, but dreams cost money my friend. At least this one certainly does at first blush.

What’s Required

So how do we accomplish this goal, of say 1 season (8~ish months) sailing and exploring the Caribbean? And more importanty, how do we do it if we’re not fabulously wealthy or have trust funds (damn you, Mom and Dad) to cash in?

  • We need a boat that’s safe and comfortable (that we can afford)
  • We need to know what the heck we’re doing on it.
  • We need enough time to achieve both of the above.

The first is a matter of budget and research. The second is a matter of practice and some formal training, and the third is really just a function of how much I want to sacrifice and prioritize this.

The Timeline and Route

Timing wise, next ‘Winter’ would be ideal, setting sail by November through April/May pending the storm seasons and how far we actually make it.

I’m not big on planning a ‘route’, so lets just say we go ‘down’ as far as we make it. At the end of the season, will be a decision to store the boat, try and sell ‘in-place’, or boogie it all the way back up to Florida to finish out the adventure. I suppose there’s always the possibility that we get hooked on the life and want to carry on, through Panama/central america as well.

A Reasonable Budget for the Caribbean

This is where things get interesting. From my research and knowledge of boats, you have everythign available from the bareboans shit pile at 15k all the way up through a beautiful newish-production boat at 120k+.

That’s a pretty damn big variance, so to help zero in I think it’s important to establish exactly what need to have first. Then it’ll simply be a matter of researching boats with that filter criteria and getting an average cost idea.

I’ve made a detailed spreadsheet for this (shocking, I know), but we can list out some of the big must-haves in terms of boat and hardware.


I don’t see us surviving on anything smaller than a 36 foot boat. I know couples have traveled the world on 30 feet and less (and love to tell you about how economical and great it is), but there’s no way my introverted sel would be able to survive all of that close quarters confinement.

Living Space

We need a big and comfortable bed (Queen is ideal), and a properly size bathroom ideally with a separate shower to keep my girlfriend sane.

Boat Gear and Accessories

Good sails, stronge anchor setup, a dignhy, a Bimini (sun/rain cover for the cockpit), autopilot, and AIS Radar/VHF Radios are all essentials to safe and efficient cruising life. All have a dollar amount (if yo uwere to buy them new), but the real value is in being able to find a boat for sale that already has them included.

Starklink and Electrical

To be discussed later, but it’s pretty much guaranteed that we will both be working our way through this adventure. The budget may allow for some less ‘frantic’ working on my end, but I know Erin will want to (and should) keep her day job. That means we’ll be relying on the wonders of Elon Musk’s Starlink to keep us connected to the money-making world.

Fortunately, I’ve already tested this out rigorously on a boat. So I know that with enough battery/solar power (and a gas generator for backup), we’ll have no real trouble.

Some form of Air Conditioning

This goes at the bottomo of the list for it’s not truly an ‘essential’. Though I’ll know I’ll be glad I sprung for it on those brutally hot middays when my lady is stuck onboard working and fans won’t cut it.

Water Maker

Another very overlooked and very worthwhile accessory on a cruising boat is a water maker. The alternative? Lug giant jugs of water back forth in your Dinghy to shore to fill up (hopefully) nearby your boat. Plenty of people do it, we will not be among them.

And on and on forever

You can really get crazy with fancy boat gear and creature comforts and blow as much of your budget as you want. But these above are the absolute essentials to safe and comfortable cruising. I’m hoping that the ability to do some work along the way offsets some of the additional costs.

Go Now – Go With What You’ve Got

My favorite saying in the sailors world is ‘Time and tide wait for no one’. Ay, it’s true. The online sailing forums/groups are chocked full of retirees who are perpetually waiting for the time to be ‘right’ to set off for the horizon. They are waiting on more cash, to have their boat setup just right, to retire from the job they couldn’t care less about with ‘enough in savings’.

Sometimes waiting and being strategic is the prudent thing. Hell, this whole series of articles is about waiting for the ‘time to be right’. But, with one key difference. I want to use these articles to set a firmer timeline, and actually identify what it takes to make a dream like this happen. The skills, the cash, all of it.

Fortunately, I’ve been building the sailing skills necessary for the last several years with pretty intense focus (another article on this soon for those that are curious).

As for the budget part of the equation. My approach to this is simple.

  1. Figure out what we want/need (already done in this article)
  2. Perform some rough ‘boat research’ to see what’s out there that has what we need (next article)
  3. Add in some buffer costs, and then simply tally it all up.

That will get my ‘target number’ needed to buy the boat and set off. It likely will be higher than what I have in the bank right now… so that’s where the planning comes in and the ultimate question. Will a little over 1 year be enough time for me to close the gap between what I have, and what I need?

Time will tell.

Coming Up Next

My idea was to write a series on each of the biggest components in order ot make this kind of trip happen by next winter, 2024. Following articles will include:

  • The Boat – Research, budgets, and buying decisions
  • The Skills – how the f*ck do you learn to sail and navigate safely (and all the other things?)
  • The Plan – Where to go, when, what to do when you get there?
  • The Budget – What will it all cost at the end of the day (and how to make the cash needed)?
  • The Why – Romance of the sea, philosophy of living alternative kinds of lifestyles, and all the existential reflections needed for such and undertaking.

Stay tuned my land-loving friends, things about to get interesting.