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He’s Built 400 Boats. The Cheap Used Sailboats He’d Buy in 2026
Sailing Zingaro

He’s Built 400 Boats. The Cheap Used Sailboats He’d Buy in 2026

A 40-year boatbuilder and former charter-fleet operator breaks down which cheap, used cruising sailboats are actually worth buying, and which ones will eat your savings and your dream. If you are shopping for a first bluewater boat on a budget, watch this before you wire a deposit. Kyle Jachney has...
The Best Affordable Sailboats Nobody Talks About (With Kyle Jachney) | Sailing Truth Show
Sailing Zingaro

The Best Affordable Sailboats Nobody Talks About (With Kyle Jachney) | Sailing Truth Show

Everyone chasing the cruising dream gets pointed at the same handful of "name" boats — and most of them are priced out of reach for a first-timer. So today Kyle Jachney and I are talking about the ones nobody puts on a list: the older, affordable fiberglass cruisers from the 70s and 80s th...
WE’RE BACK! Returning to our Boat After 6 Months | Sailing on a Whim Ep. 33
Sailing on a Whim

WE’RE BACK! Returning to our Boat After 6 Months | Sailing on a Whim Ep. 33

WE’RE BACK! Returning to our Boat After 6 Months | Sailing on a Whim Ep. 32 On this episode of Sailing on a Whim, we finally return to Whim after six months on the hard in Florida. Upon our arrival we are surprised to find lots of mold and a few bugs that have taken residence in our home. With lots...
How Many Quacks does it Take to Remove a Fuel Tank? | Sailing Soulianis – Ep. 63
Sailing Soulianis

How Many Quacks does it Take to Remove a Fuel Tank? | Sailing Soulianis – Ep. 63

When we smelled diesel in our cabin, we knew we had a problem. We just hoped it would turn out to be an easy fix… but how often does THAT happen? Finding the source our fuel leak leads us into another big boat project, forcing us to postpone our launch date, and requiring — as all new boat project...
Adventure to Little Harbour | Sailing on a Whim Ep. 26
Sailing on a Whim

Adventure to Little Harbour | Sailing on a Whim Ep. 26

On this episode of Sailing on a Whim, we welcome a guest on board to sail and explore the Abacos together to find new places and adventures. We head out to check out the mangroves, discover a shipwreck, and even venture into a cave. Of course, we spend some quality time on the beach and Lilly makes ...
Living the Bahamas Life | Sailing on a Whim Ep. 23
Sailing on a Whim

Living the Bahamas Life | Sailing on a Whim Ep. 23

On this episode of Sailing on a Whim, we start living the Bahamas life by taking advantage of everything the islands have to offer by diving, catching conch, and…pizza? Along the way we make some lifelong friends and acquire a vast amount of knowledge about living off the ocean by learning how to ca...
We Found Paradise | Sailing on a Whim Ep. 22
Sailing on a Whim

We Found Paradise | Sailing on a Whim Ep. 22

On this episode of Sailing on a Whim, we find paradise on an island in the Abacos of the Bahamas. Blue water, amazing people, and lots of new adventures. We never knew places like this really existed but we definitely found paradise! This crazy adventure started in early 2018 as we started research...
Liveaboards to Cruisers: Final Preparations | Sailing Soulianis – Ep. 19
Sailing Soulianis

Liveaboards to Cruisers: Final Preparations | Sailing Soulianis – Ep. 19

Just one week is left before we depart our home port of Racine, Wisconsin — for good!?! — and take off south down the river. The list of projects, errands, and to-dos is still a mile long. We need to buy anchor chain, install an anchor swivel, hook up plumbing to our secondary water tank, install s...
Drilling Holes & Laying Fiberglass: Installing a Windlass  | Sailing Soulianis – Ep. 18
Sailing Soulianis

Drilling Holes & Laying Fiberglass: Installing a Windlass | Sailing Soulianis – Ep. 18

Settle in… we’ve got our first 20+ min episode for you! The river trip is right around the corner, and our preparations start getting serious. The list of boat projects we want to complete (as discussed in Ep 15) before leaving Lake Michigan is LONG. If, hypothetically, we had to pick just one proje...
GOODBYE Marine Head & Holding Tank, HELLO Composting Toilet  | Sailing Soulianis – Ep. 17
Sailing Soulianis

GOODBYE Marine Head & Holding Tank, HELLO Composting Toilet | Sailing Soulianis – Ep. 17

A leaky marine head can be a very shitty situation. At one point during our shakedown cruise around Lake Michigan, (thanks to a combination of rollicking seas, a leaky hand pump, and plain ignorance) we ended up with toilet water where it SHOULDN’T be — outside the bowl. Thankfully it was mostly con...
Dinghy Outboards are Tricky Little Beasts  | Sailing Soulianis – Ep. 16
Sailing Soulianis

Dinghy Outboards are Tricky Little Beasts | Sailing Soulianis – Ep. 16

Back in our homeport of Racine, we start tackling the long list of projects we want to finish before leaving for our journey down “The Ditch.” Kirk researches the heck out of LED bulbs. He determines the warm Kakanuo bulb to be the best option — based on color cast, energy consumption and brightne...
Results of our Shakedown Sail | Sailing Soulianis – Ep. 15
Sailing Soulianis

Results of our Shakedown Sail | Sailing Soulianis – Ep. 15

That’s a wrap on our shakedown sail! In this episode, after sailing back across Lake Michigan to our home port of Racine, Wisconsin, and getting a little weird during the crossing (being alone on a boat definitely makes you go a little batty), we talk through everything we learned during our 3-week ...
Freshwater Surfing on Lake Michigan | Sailing Soulianis – Ep. 14
Sailing Soulianis

Freshwater Surfing on Lake Michigan | Sailing Soulianis – Ep. 14

Freshwater surfing! Kirk’s beyond stoked to get a chance to surf Lake Michigan. After leaving Charlevoix, we snuck into Leland just before a cold front moved in. The front brought strong winds that ended up sticking around for three days, which prevented us from being able to leave, but on the fli...
Summer in Michigan is Downright Lovely | Sailing Soulianis – Ep. 13
Sailing Soulianis

Summer in Michigan is Downright Lovely | Sailing Soulianis – Ep. 13

Summer in Michigan is magic, because it’s so fleeting. It usually arrives sometime in June, and by the time you’ve attended a family get together and a wedding or two, it’s already August, and you’re wondering where the heck the time went… If you’re like most, you manage to squeeze in a week of vac...
Sailing to Charlevoix: A Childhood Dream ACHIEVED! | Sailing Soulianis – Ep. 12
Sailing Soulianis

Sailing to Charlevoix: A Childhood Dream ACHIEVED! | Sailing Soulianis – Ep. 12

Every summer as Kirk was growing up, his family would visit Charlevoix, a quaint vacation town located on a skinny isthmus between Round Lake and Lake Michigan. Round Lake was a boating mecca; all sorts of craft paraded across its waters, waiting for the fuel dock, or a city marina slip, heading t...
Cruising the West Coast of Michigan | Sailing Soulianis – Ep. 11
Sailing Soulianis

Cruising the West Coast of Michigan | Sailing Soulianis – Ep. 11

Our shakedown cruise is officially underway! After crossing Lake Michigan with Kirk’s dad, we arrive in Pentwater, MI where we meet up with the rest of Kirk’s family. It’s our first of many ports of call along Michigan’s west coast we visit over the next few weeks. Pentwater ends up being one of ou...
Solar to the Rescue! | Review of Suaoki Solar Panel + Power Station
Sailing Soulianis

Solar to the Rescue! | Review of Suaoki Solar Panel + Power Station

Products in this Review Suaoki 150Wh Portable Power Station Suaoki 100W Solar Panel Charger -- Just when we thought we didn’t need any more solar… When designing our boat’s new battery and solar system, we had hired a contractor to build a bimini — on which we planned to mount most of our sol...
The LAKE MICHIGAN Crossing | Sailing Soulianis – Ep. 10
Sailing Soulianis

The LAKE MICHIGAN Crossing | Sailing Soulianis – Ep. 10

It’s our FIRST OVERNIGHT PASSAGE! We set sail across Lake Michigan, leaving in the middle of the night to ride the fading winds of a storm. Kirk’s dad arrives just before midnight to join us for the trip. The sail starts out with 15+ knts on the nose, and 5’ waves which drop to a couple feet by the...
Preparing for our Shakedown Sail | Sailing Soulianis – Ep. 9
Sailing Soulianis

Preparing for our Shakedown Sail | Sailing Soulianis – Ep. 9

Products in this video: Tea Kettle - Manual Food Processor - We bought the boat, daysailed the boat, and have taken our first overnight trip to Milwaukee. Now we’re planning to sail up and down the west coast of Michigan, during which we want to spend some time at anchor. This multi-week trip wil...
First Sail on our Tartan 37 | Sailing Soulianis – Ep. 8
Sailing Soulianis

First Sail on our Tartan 37 | Sailing Soulianis – Ep. 8

Until now, family and friends have always sailed with us on our Tartan 37, but this time we sail her by ourselves, up to Milwaukee and back. Leaving the dock at our marina in Racine is tricky. The dock is on the Root River (which frequently floods and drains), and is situated only a couple hundred ...
Moving Aboard our Sailboat & Freedom Party | Sailing Soulianis – Ep. 7
Sailing Soulianis

Moving Aboard our Sailboat & Freedom Party | Sailing Soulianis – Ep. 7

The Tartan 37 is ours, and it’s time to celebrate! With the 4th of July arriving just days after we close on the boat, we decide it’s rather fitting to pop some bubbly and celebrate our own new-found freedom… from land! The hardest part of moving aboard is figuring out where to put our stuff. Fortu...
WE BUY A TARTAN 37 SAILBOAT | Sailing Soulianis – Ep. 6
Sailing Soulianis

WE BUY A TARTAN 37 SAILBOAT | Sailing Soulianis – Ep. 6

WE FINALLY BUY A SAILBOAT. It feels like we’ve been searching for a boat forever! In this episode we finally buy a boat, a beautiful Tartan 37. Before we find the Tartan, we look at two other options in the Milwaukee area: a Pearson 38 and a Southerly 35. The Pearson had been left on the hard for a...
Leaving the Beach for a Boat | Sailing Soulianis – Ep. 1
Sailing Soulianis

Leaving the Beach for a Boat | Sailing Soulianis – Ep. 1

We show you a slice of our San Diego lives, and talk about why we decided to leave our beach cottage in California — for life aboard a sailboat. Our search for the right sailboat took years: We researched thousands of sailboats online, saw hundreds in person. We made some crazy decisions, like dri...
Boat #5: 1981 Tartan 37
HaveWindWillTravel.com

Boat #5: 1981 Tartan 37

This is a real treat for you here guys. This is our buddy, Mike (the beekeeper's) boat who was our neighbor at the shipyard, so you get to see some before and after footage from his ongoing restoration of this beautiful Tartan that unfortunately sank at the dock, as well as a mast climb and a ...
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