6 Factors to Consider When Buying a Sailboat in 2025

Having spent more than 15 years immersed in the world of boats, I’ve witnessed firsthand how the sailboat buying landscape has evolved. A decade ago, the market was much simpler. Most buyers made their decisions almost entirely based on intuition and passion, often chasing a romanticized dream of sailing, while rarely considering the long-term costs, maintenance challenges, or suitability of the boat.

I made the same “classic mistake” myself when buying my very first sailboat. I fell in love with the appearance of a Used Monohull sailboat and purchased it without hesitation. At the time, I did almost no research and gave little thought to whether it truly suited my sailing plans. Fortunately, that boat turned out to be relatively reliable and carried me steadily through my novice stage. But looking back years later, I know that “good fortune” was more a matter of luck than reasoned choice. Many buyers who act on impulse the way I did could easily end up with a completely different outcome—owning an unsuitable boat that brings endless problems and expenses.

That first secondhand monohull I bought marked the beginning of my realization: choosing the right boat isn’t just the start of a dream, it’s a discipline that requires both experience and rational decision-making. That’s why I’m writing down the lessons I’ve learned over the years—to share them with future buyers. Think of this article as advice from a friend, only this friend has inspected hundreds of boats and seen nearly every mistake imaginable.

If you’re a complete beginner, I suggest first reading “2025 Beginner's Guide: 7 Key Points to Know When Choosing the Right Boat” to get familiar with the different kinds of boats. For now, here are six key factors to consider when buying a sailboat.

 

Table of Contents

1. What’s your sailing dream?

2. What type of sailboat suits your needs?

3. What size of sailboat is right for you?

4. Sailing purpose and conditions

5. Building a cost checklist

6. Planning for the future

 

1.What’s Your Sailing Dream?

Before buying a sailboat, ask yourself the most important question: Why do you want one?

Over the years, I’ve met buyers with vastly different goals. Some want to do weekend coastal cruising with family and friends, hopping from marina to marina. Others dream of living aboard long-term, turning a sailboat into a floating home. And then there are the true adventurers, whose vision is to cross oceans on bluewater voyages.

Your goal determines everything. The best path is to clarify your dream or need first, then decide what type and size of boat fits. Different answers will lead you to very different choices—and that’s the beauty of sailing.

 

2.What Type of Sailboat Suits Your Needs?

The type of sailboat should align with your intended use. When I first entered the sailing world purely out of passion, I too wanted a high-performance yacht.

According to Grand View Research’s Sailboat Market Size, Share & Trends Analysis Report, the market is broadly divided into monohulls and multihulls. In 2023, monohulls accounted for 59.2% of the global market, and from 2024 to 2030 they are projected to grow at a compound annual rate of 4.4%. Historically, monohulls have been the first choice for most sailors.

Here’s a breakdown:

Monohulls The most common type, and the first step for many sailors. Known for their stable sailing experience, straightforward design, and relatively lower purchase cost. My first boat was a 30-foot monohull, perfect for weekend trips along the Florida coast—easy to handle without feeling overwhelming. For beginners, small monohulls are the best entry point to learn sailing skills in a manageable environment.

That said, there are more advanced options. Reinforced bluewater monohulls are well-suited for transoceanic or round-the-world voyages, with designs that emphasize durability and safety in rough seas.

Catamarans If comfort and stability matter most, a catamaran is an excellent choice. With two hulls, they heel less than monohulls—ideal for those prone to seasickness. I’ve helped clients find liveaboard catamarans, and they consistently value the wide deck space, abundant storage, and overall comfort. Larger catamarans over 40 feet often come with full kitchens, spacious saloons, and even private cabins—perfect for family cruising or long stays on the water.

Trimarans Trimarans are more niche, often associated with racing. Lighter and faster than traditional monohulls or catamarans, they combine speed with remarkable stability thanks to their wide beam. I’ve had the thrill of sailing a high-performance racing trimaran—the spray flying and the adrenaline pumping at full speed is unforgettable. But they demand more skill and higher maintenance, better suited for seasoned sailors or racing enthusiasts. As world-class sailor Franck Cammas once said in an interview with Sail-World, these boats can cover nearly 600 miles in 24 hours, an impressive feat.

 

3.What Size of Sailboat Is Right for You?

Once you know your intended use, the next big decision is size. Bigger isn’t always better—size affects carrying capacity, handling, and ongoing costs.

I once met a young couple in Barcelona determined to buy a 45-foot yacht because they had seen one on Instagram. But when I asked about their actual plans, it turned out they only wanted to cruise the Balearic Islands on weekends. For them, a 30-foot boat was more than enough—far easier to maintain and much less costly.

Here’s a rough guide:

• Small sailboats (20–30 feet): Ideal for beginners or solo sailors. Easy to handle, budget-friendly, and a great learning platform.

• Medium sailboats (30–40 feet): A balanced option for broader cruising or sailing with a small family or group. Offers comfort while still manageable in operation and upkeep.

• Large sailboats (40+ feet): Best for long-distance voyaging, liveaboard lifestyles, or larger crews. They provide space and luxury but demand more expertise, effort, and expense. I’ve sailed on a 50-foot yacht—it felt like a luxury apartment on the water, but safely managing it required significant skill and dedication.

My advice: be realistic. Choose a boat that matches your actual sailing plans, not just what looks glamorous on social media.

 

4.Sailing Purpose and Conditions

Where and how you plan to sail greatly impacts the kind of boat you should buy.

For exploring coastal waters, a shallow-draft monohull is ideal—you’ll have access to coves, bays, and protected harbors. Friends of mine in the Caribbean and Mediterranean love such boats because they can easily navigate narrow areas.

For offshore cruising, catamarans often make more sense, thanks to their comfort and space.

Don’t forget to consider environment and climate:

• Saltwater is highly corrosive, requiring specific materials, design, and more regular maintenance.

• Freshwater, on the other hand, causes less wear on hulls.

 

5.Building a Cost Checklist

The purchase price is just the beginning. Many additional expenses can quickly add up, so planning ahead is essential.

Prices range widely—from a few thousand dollars for a small used boat to several million for a large custom yacht. Beyond the purchase, ongoing costs include:

• Insurance: Varies by boat type, size, cruising region, and coverage level. Coastal cruising policies differ from bluewater ones. In 2025, premiums continue to rise due to higher repair costs and extreme weather claims. For those unfamiliar with insurance, I recommend reading The 2025 Used Yacht Insurance Guide—it covers saving strategies and more.

• Dockage and marina fees: In prime harbors, slip fees can rival apartment rents. Costs depend on slip size, location, and included utilities. Long-term contracts may increase annually.

• Fuel and energy: Even sailboats rely on engines for docking, maneuvering, and emergencies. Generators, heaters, and appliances add to consumption. With 2025’s rising energy costs, this is a significant budget item, especially for larger engines or hybrid systems.

• Safety equipment maintenance: According to the Maintenance Requirements for Life-Saving Appliances issued by the International Maritime Organization (IMO), the maintenance and inspection of life-saving appliances on board ships should comply with international regulations, and life rafts, EPIRBs, flares, fire extinguishers and life jackets need to be regularly inspected, serviced and replaced. These are mandatory and neglecting to update them may result in the lapse of insurance or fines.

• Routine maintenance: Includes hull cleaning, antifouling, sail repairs, engine servicing, and rigging checks. Costs vary by boat size, material (fiberglass, aluminum, steel), and whether you DIY or hire professionals.

 

6.Planning for the Future

Your needs will likely change over time. Buying a sailboat isn’t just about the present—it’s about anticipating future shifts.

A couple might start with a small boat, but as their family grows, they’ll want more space and amenities. Choosing a versatile boat with upgrade potential helps reduce the hassle of trading up later.

Resale value is another key factor. Some brands hold value better thanks to quality or bluewater reputation. Research the resale trends before buying. Well-kept classics often maintain strong market prices, while others depreciate quickly.

Upgrades and customization are also worth considering. You might want to enhance comfort, add new tech, or boost performance over time. Before buying, ask yourself: “Where do I want my sailing life to be in five years?” Then choose a boat that can either get you started or evolve with your plans.

 

Conclusion

Buying a sailboat in 2025 is both exciting and daunting. It’s a major decision that requires considering everything from purpose and size to costs and long-term plans.

The romance of the sea is real, but so are the responsibilities and expenses. Over the past 15 years, I’ve inspected countless boats and advised countless people as they pursued their dreams. The happiest sailors aren’t those with the most expensive yachts—they’re the ones who made wise choices and kept their passion for the sea alive. That’s my wish for you as well.

 

Author:

Michael Andrews has 15 years of hands-on experience in the marine industry. He is a certified Senior Marine Surveyor by the Society of American Marine Surveyors (SAMS®) and an active participant in international boat shows and industry conferences. Over the years, he has inspected and evaluated hundreds of sailboats, from small entry-level monohulls to luxury catamarans and high-performance trimarans, across a variety of sailing environments. His achievements include winning the Rolex World Sailor of the Year Award in 2018 and receiving recognition from the International Maritime Organization (IMO) Maritime Safety Committee (MSC). His professional work has taken him to more than 30 of the world’s leading yacht harbors across North America, Europe, and Asia.

Disclaimer:

This article is for reference only, intended to share the author’s personal experience and views on sailboat buying and sailing. While the author has extensive professional expertise, readers should conduct their own research and consult qualified professionals before making any purchase, financial, legal, or safety decisions. Buying a sailboat involves risks—including costs, maintenance, insurance, and navigation safety—that should be carefully evaluated.