$10K to $100K Sailboats — Which One Would YOU Buy?
If you’ve been watching the used sailboat market waiting for the perfect 2026 deal, this one’s for you. In this video, we break down five of the best budget sailboats you can buy — from a $10,000 weekend cruiser to a $100,000 liveaboard dream.
We’ll cover real-world prices, performance, what to watch for when buying, and which boats are the best value in each price bracket. Whether you’re looking for your first coastal cruiser or a full-time liveaboard, these boats prove you can still go sailing without spending a fortune.
⛵ Featured Sailboats:
💸 $10,000 – Hunter 27-2
💵 $25,000 – Sabre 32 / 34 / 36
💰 $50,000 – Catalina 34 / 36
💶 $75,000 – Beneteau Oceanis 33–38
💎 $100,000 – Cabo Rico 38 or Catalina 42 Mk II
In this episode:
👉 What makes these boats such great value in 2026
👉 Common issues to look out for when buying used
👉 How to avoid money pits and find a sail-ready boat
👉 The best starter sailboats, coastal cruisers, and liveaboards on a budget
If you’re shopping this winter, keep your eye on the listings — these are the boats worth pouncing on when the spring deals hit!
⚓ About Lady K Sailing
Our mission has always been to get more people sailing, more easily. Join the community, get access to group chat, direct messaging, and live consultations by becoming a Patron: https://patreon.com/LadyKSailing
#sailing #sailboats #cheapboats #budgetboats #affordablesailing #sailboatlife #sailboatsforsale #sailboatshopping #cheapboatsforsale #liveaboardlife #liveaboardsailboat #sailinglifestyle #boatingonabudget #usedsailboats #cruisingsailboats #coastalcruising #bluewaterboats #ladyksailing #catalina36 #hunter27 #beneteauoceanis #caborico38 #sabre34 #sailingcommunity #sailing2026 #sailboatmarket
Need a consult? Click here to drop a message: https://ladyksailing.com/consults/
Want to help support Lady K Sailing? Click here to become a Patron: http://www.patreon.com/ladyksailing
Or here to make a one time donation: http://www.ladyksailing.com/team-k
Follow Lady K on Facebook: https://www.facebook.com/ladyksailing
Or Instagram: https://www.instagram.com/ladyksailing/
If you’ve been watching the used sailboat market waiting for the perfect 2026 deal, this one’s for you. In this video, we break down five of the best budget sailboats you can buy — from a $10,000 weekend cruiser to a $100,000 liveaboard dream.
We’ll cover real-world prices, performance, what to watch for when buying, and which boats are the best value in each price bracket. Whether you’re looking for your first coastal cruiser or a full-time liveaboard, these boats prove you can still go sailing without spending a fortune.
⛵ Featured Sailboats:
💸 $10,000 – Hunter 27-2
💵 $25,000 – Sabre 32 / 34 / 36
💰 $50,000 – Catalina 34 / 36
💶 $75,000 – Beneteau Oceanis 33–38
💎 $100,000 – Cabo Rico 38 or Catalina 42 Mk II
In this episode:
👉 What makes these boats such great value in 2026
👉 Common issues to look out for when buying used
👉 How to avoid money pits and find a sail-ready boat
👉 The best starter sailboats, coastal cruisers, and liveaboards on a budget
If you’re shopping this winter, keep your eye on the listings — these are the boats worth pouncing on when the spring deals hit!
⚓ About Lady K Sailing
Our mission has always been to get more people sailing, more easily. Join the community, get access to group chat, direct messaging, and live consultations by becoming a Patron: https://patreon.com/LadyKSailing
#sailing #sailboats #cheapboats #budgetboats #affordablesailing #sailboatlife #sailboatsforsale #sailboatshopping #cheapboatsforsale #liveaboardlife #liveaboardsailboat #sailinglifestyle #boatingonabudget #usedsailboats #cruisingsailboats #coastalcruising #bluewaterboats #ladyksailing #catalina36 #hunter27 #beneteauoceanis #caborico38 #sabre34 #sailingcommunity #sailing2026 #sailboatmarket
Need a consult? Click here to drop a message: https://ladyksailing.com/consults/
Want to help support Lady K Sailing? Click here to become a Patron: http://www.patreon.com/ladyksailing
Or here to make a one time donation: http://www.ladyksailing.com/team-k
Follow Lady K on Facebook: https://www.facebook.com/ladyksailing
Or Instagram: https://www.instagram.com/ladyksailing/
Lady K Sailing
Sell everything, sail off into the sunset, and make videos to help other people join into the cruising life and explore this beautiful world. That's always been the mission of Lady K Sailing. I'm Tim and I set out from my days of PHRF sailboat racing on the Great Lakes to explore the world on my 1980 Hughes 35 foot sailboat - Lady K. I refit her extensively, traversed the Erie Canal, and made my way down to the beautiful blue waters. I made a video every Friday with some adventure clips and some "how to" segments to help you get your own boat and come join me. Since the big trip I am back on land refitting Lady K for another big adventure but in the meantime I am making the "Everything You Need to Know" videos and boat shopping videos to help more people enjoy the wonderful world of sailing.
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Lady K Sailing Lastest Videos
$10K to $100K Sailboats — Which One Would YOU Buy?
If you’ve been watching the used sailboat market waiting for the perfect 2026 deal, this one’s for you. In this video, we break down five of the best budget sailboats you can buy — from a $10,000 weekend cruiser to a $100,000 liveaboard dream. We’...
Sailing Is Way Scarier Than You Think – Ep 353 – Lady K Sailing
Sailing looks calm, romantic, and free — until it isn’t. In this video, we explore the real-life disasters and accidents that show just how fast things can go wrong at sea — from the 1979 Fastnet Race tragedy to the Cheeki Rafiki and Sydney to Hobart...
Valiant 40 Sailboat | The Legendary Bluewater Cruiser Changed Offshore Sailing Ep 352 Lady K Sailing
The Valiant 40 sailboat is one of the most iconic offshore cruisers ever built. Designed by Bob Perry in the 1970s, this legendary 40-foot yacht combined speed, comfort, and safety in a way no production cruiser had before. In this video, we take a deep d...
Do NOT Buy – Prout 34 Bluewater Catamaran – Ep 351 – Lady K Sailing
Looking for a proven bluewater catamaran that won’t break the bank? Meet the Prout 34 Catamaran, a legendary British cruising multihull designed for serious passagemaking. In this video, we take a closer look at the history, design, layout, and sailing p...
Westsail 32 Shipmaster Review | The Legendary Bluewater Cruiser Explained – ep 350 Lady K Sailing
Thinking about buying a Westsail 32 Shipmaster? In this video, we take a deep dive into one of the most iconic bluewater cruising sailboats ever built. The Westsail 32 earned its reputation as a rugged, heavy-displacement cutter that’s carried sailors sa...
Best 30ft Sailboat to Buy? Catalina 30 Walkthrough & Review – Ep 349 – Lady K Sailing
Thinking about buying a 30 foot sailboat? The Catalina 30 is one of the most popular and best-selling cruising sailboats of all time — and for good reason. In this video, we dive into why the Catalina 30 is considered the best 30 foot sailboat to buy and...
Lost at Sea: The Story of Sailor Jay Caunter & His Sabre 34 Venture – Ep 348 – Lady K Sailing
This is the story of sailor Jay Caunter, a man who set out aboard his Sabre 34 sailboat Venture in search of freedom and the call of the sea. Sadly, Jay was lost at sea, leaving behind both mystery and memory. In this video, we honor his journey, explore h...
Fountaine Pajot 80 | The Ultimate Luxury Sailing Catamaran Superyacht – Ep 347 – Lady K Sailing
The Fountaine Pajot 80 isn’t just a sailboat—it’s a floating luxury resort that can cross oceans in style. In this video, we dive into everything that makes the FP 80 one of the most impressive luxury sailing catamarans on the market today. From its ...
TOP 3 TINY Sailboats You Can Live On! – Ep 346 Lady K Sailing
Dreaming of living on a sailboat but don’t want (or need) a massive yacht? In this video, we explore the top three tiny sailboats you can actually live on. These compact cruisers prove that you don’t need a big boat to enjoy the freedom of life on the ...
How Much Solar is Too Much on a Sailboat? ⚡️ (Sailboat Solar Power Explained) Ep 345 Lady K Sailing
Thinking about adding more solar panels to your sailboat? At what point does it go from smart energy management… to a floating solar farm? In this video, we break down the truth about sailboat solar power: how much solar you really need, when it becomes ...
Why Sailboats Don’t Tip Over (and Other Sailing Questions Answered!) – ep 344 – Lady K Sailing
Ever wondered why sailboats don’t just fall over in the wind? 🌊⛵ In this video, we answer some of the most common sailing questions: Why sailboats don’t tip over Do sailboats sink? Why sailboats are “slow” compared to powerboats Is sailing...
⚓ Annapolis Sailboat Show 2025 Full Tour, Boats, Gear & Sailing Inspiration! ⚓ Ep 343 Lady K Sailing
Join us as we explore the 2025 Annapolis Sailboat Show, the largest in-water sailboat show in North America! From sleek new cruising yachts to cutting-edge multihulls, performance racing sailboats, and the latest marine gear, we take you inside the docks t...
How SAILBOAT Brands Got Their Names – Ep 342 – Lady K Sailing
Lady K For Sale: https://www.sailboatlistings.com/view/109515 Apply to film boat tours: https://ladyksailing.com/apply/ Ever wonder how Beneteau got the name Beneteau? Or Hunter? Catalina? Pearson? This week, we look at how each major boat manufacturer w...
Lagoon 410 for $190,000! What’s the Catch? Ep 341 – Lady K Sailing
This week we're catamaran shopping and looking at a Lagoon 410 in Florida. The Lagoon might be the perfect family catamaran but the price of this sailboat is a bit cheap. What's going on with this catamaran for sale in Florida? This week we dive into a tou...
3 STEPS, So easy you can SKIP ONE! Ep 340 – Lady K Sailing
Learnign to sail in three easy steps that are so beginner and simple you can actually skip one and learn to sail a small sailboat in two simple steps. Learning how to sail doesn't have to be difficult. Let me know in the comments if this video helped you l...
EASY YouTube HOW TO MAKE SAILING VIDEOS – Ep 339 – Lady K Sailing
Last week we talked about making YouTube videos for sailing and a lot of you were interested in the DIY process of actually making a video from start to finish, how to make money and edit videos. So today, we take a tour of the life of a sailing youtube. T...
HOW TO CHECK SAILING WEATHER – Ep 337 – Lady K Sailing
Sailing safely is key and having a sail plan is critical to a good sailing day. I use Windfinder to see the wind and waves and plan my sailing trip to make sure I know what to expect, have a back up plan, and bail out points. Choosing how much wind is too...
FIVE CRITICAL Lessons to Learn BEFORE you Set Sail – Ep 336 – Lady K Sailing
Dream of sailing off into the sunset? Living on a sailboat can be an exciting life but also hard. Here are five lessons I've learned along the way to help you be successful in quiting land life and living on a sailboat. Want to help support Lady K Sailing...
Gemini 105MC Review: The Affordable Cruising Catamaran That Actually Delivers! Ep 335 Lady K Sailing
Looking for a smart, budget-friendly catamaran that’s actually comfortable, capable, and fun to sail? Meet the Gemini 105MC—one of the most popular American-built catamarans ever made! In this video, we dive deep into what makes this 34-foot catamaran ...
BAGGYWRINKLE? NEED to KNOW Sailing Words – Ep 334 – Lady K Sailing
Learing how to sail can be hard, but learning the ridiculous vocabulary makes sailing scary! Today we cover some of the need to know words you need to learn if you're going to be learning how to sail. Learn how to use the TELL TALES to TRIM a sail, which s...
The INSANE PRICE of a Beneteau Sense 50! – Ep 333 – Lady K Sailing
Why Is the Beneteau Sense 50 So Expensive? Used Sailboat Prices Explained In this video, we dive into the world of the Beneteau Sense 50, a luxury cruising sailboat that still commands a steep price tag—even when it's over a decade old. What makes this ...
Learn to SAIL for FREE! Or Find Good Crew Here! Ep 332 – Lady K Sailing
Are you interested in learning how to sail for free? Or looking for crew for your sailboat for free? Join us on crewfinder for the east coast or the Great Lakes so learn to sail, teach people how to sail, or get help sailing your sailboat! East coast crew...
TOP 3 Small Sailboats You Can Sail AROUND THE WORLD! Ep 331 – Lady K sailing
This week we look at the top three small sailboats you can sail around the world. What makes a good off the grid liveaboard sailboat? What do you NEED to have on a sailboat to live on, sail alone solo, from roller furling to sailboat toilets to sailboat en...
Sabre 38’s Cored Hull – Excellent sailboat, or one to stay away from? – Lady K Sailing – ep 330
Join us for an in-depth look at the Sabre 38 sailboat, a timeless cruiser-racer known for its quality craftsmanship, solid performance, and enduring appeal. In this video, we take you on a full tour above and below deck, explore its sailing characteristics...
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