Here’s the cold, hard truth about sailboats: they are not an investment. They are a money pit and will require thousands of dollars in maintenance every year. Yet that doesn’t seem to stop people… and it surely didn’t stop us. There are thousands of boats available on the market, ranging from newly built to sunken project boats. Which is right for you will depend on what type of sailing you want to do and what you are capable of. The reason we decided to start sailing right out of college was because we didn’t want to wait until we retired in our 60s before we hopped on a boat. We wanted the energy to enjoy the lifestyle and the strength to actually survive the voyages. Your age shouldn’t stop you from starting to sail, but you should consider the type of sailing and boat that fits your situation. So, if you are looking to buy your new-to-you sailboat soon … or if you are fortunate enough to buy an actual new boat… this guide will help you decide what the right type of boat is for you.
The Different Types of Sailing
Forget the brand names of sailboats for a moment. What matters right now is understanding yourself and your capabilities. A beginner sailor isn’t going to start on a 60-foot yacht. If you do, you’ll find yourself stuck at the docks waiting for a crew that might never come, because a boat that size will definitely be too overwhelming to singlehand (handle the boat solo).
Choose the type of sailing you want to engage in or see yourself doing:
- Dinghy sailing
- Day sailing
- Racing
- Coastal cruising
- Living aboard
- Ocean crossing
Dinghy Sailing
This is by far the best way to get into sailing cheaply. If you live near a coast or bay, chances are there are sailing clubs nearby. In the San Francisco Bay, there are a few clubs that offer lessons for kids as well as clubs for adults, like the Cal Sailing Club in Berkeley. We went there during college because they offered a discounted membership rate.
Dinghies are typically less than 15 feet long and are used for short trips or learning how to sail. Most cruising yachts carry a dinghy to get from their anchorage to shore, but what we’re talking about here are sailing dinghies… popular for recreational sailing and racing in sheltered water.
We recommend starting here to get your feet wet. See if you even enjoy sailing before you buy one. You might also make some friends with the same idea as you!
Day Sailing
Day sailing refers to pleasure excursions that usually only last a day. You leave the docks, sail around a bit, and return the same day. We live in a marina on our sailboat, and this is by far the most common type of sailing we see from other similarly sized boats (20–40 feet).
What are the best boats for day sailing? Even though you’re only out for the day, you should always plan for the worst. My friend Bruce called me one day to help him move a boat he’d just bought in Sausalito. He needed help sailing it up the Bay and into a marina on the Napa River. We got on the boat and planned for a 4–6 hour sail, but nature and his engine had other plans. The engine gave out on us and we couldn’t get it started again. We were at the mercy of the tides, which decided to pull us out to sea instead of in the direction we needed to go. Our 4-hour sail turned into a disastrous 10-hour ordeal that ended with us getting rescued by the Coast Guard.
Even if you’re just heading out for the day, you should have a few days’ to a week’s worth of supplies on hand. You’ll also want a head… or at least somewhere to relieve yourself. A berth or somewhere to lie down for a bit doesn’t hurt either. You can always stretch out in the cockpit, but interior cabin space is a nice escape from the elements.
Racing
Racing sailors are a different breed. If day sailors are out for a leisurely Sunday drive, racers are the ones weaving through traffic at 90 miles an hour … and loving every second of it.
Sailboat racing ranges from casual beer-can races at your local yacht club to serious offshore competitions. Race boats are built for one thing: speed. They tend to be lighter, have taller rigs, and carry more sail area relative to their hull size. Creature comforts are usually sacrificed for performance… think bare interiors, stripped-down galleys, and spartan sleeping arrangements if there are any at all. These are not boats you want to live on. They are machines.
Popular racing designs include the J/24, one of the most raced one-design keelboats in the world, and the Beneteau First series for those who want performance without completely gutting the interior. If you’re getting into offshore racing, designs like the ULDB (Ultra Light Displacement Boat) or the IRC-rated offshore racers are worth looking into.
Racing is an incredible way to build skills quickly and meet serious sailors. Just know going in that it is competitive, sometimes expensive, and absolutely addictive.
Coastal Cruising
Coastal cruising is the sweet spot for a lot of sailors… and honestly, where most people find their groove. You’re not just circling the bay for an afternoon, but you’re not crossing an ocean either. You’re hopping from port to port, anchoring in quiet coves, and waking up somewhere new every few days.
Coastal cruisers typically stay within range of land, rarely venturing more than 20–50 miles offshore. Think sailing down the Pacific Coast, exploring the Sea of Cortez, or threading your way through the islands of the Pacific Northwest. It’s adventurous enough to feel like an expedition but forgiving enough that if something breaks, help isn’t too far away.
The boats that shine here are the ones that balance seaworthiness, comfort, and ease of handling. You want a boat that can take a punch if the weather turns but is still comfortable enough to spend a week aboard without losing your mind. Boats in the 28–45 foot range tend to hit that sweet spot. Popular choices among coastal cruisers include the Catalina 30, the Jeanneau Sun Odyssey series, and the ever-dependable Hunter 33.
Storage matters. So does a reliable engine, because coastal passages often involve tight marina approaches, unpredictable currents, and anchorages where you’ll want confidence in your iron sail. A functional galley, decent berths, and a proper head go from “nice to have” to non-negotiable when you’re spending real time aboard.
Live Aboard
Living aboard is a lifestyle choice. It’s waking up to the sound of water lapping against the hull, knowing that your home can untie its lines and sail away at any moment. That’s the dream, anyway. The reality involves a lot of boat maintenance, creative storage solutions, and explaining to people on land why you don’t have a “real address.”
We live this life. On a 28-foot sailboat with our two dogs, every square inch counts. It teaches you to be resourceful, to prioritize what actually matters, and to let go of a lot of stuff.
Liveaboard boats need to be livable first and sailing machines second. You want solid systems: reliable electrical, good ventilation, a functional galley that doesn’t make cooking feel like a punishment, and enough berth space that you’re not sleeping in a pretzel. Tankage matters too… water and fuel storage become part of your daily routine in a way that weekend sailors never think about.
The best liveaboard boats tend to be full-keel or fin-keel designs with beamy, stable hulls and generous interior volume. Boats like the Pacific Seacraft 37, the Island Packet 35, and the classic Westsail 32 are cult favorites among the liveaboard crowd for good reason. They’re sturdy, comfortable, and built to be lived in.
Ocean Crossing
This is the deep end of the pool. Ocean crossing sailors are a rare and sometimes slightly unhinged group of people who look at a chart, find the nearest continent a few thousand miles away, and think, “Yeah, let’s go.”
Crossing an ocean… whether it’s a transatlantic passage, a Pacific crossing from California to Hawaii, or a circumnavigation… demands a different level of preparation, seamanship, and boat. There is no calling the Coast Guard when you’re 1,000 miles from land. You are on your own, and your boat had better be up to the task.
Blue-water passage-making boats need to be built tough. Heavy displacement or moderate displacement hulls with proven offshore track records, redundant systems, serious sail inventories, watermakers, SSB radios, life rafts, and EPIRBs are not optional. The interior needs to be designed for offshore sailing, with sea berths that keep you from being thrown across the cabin when things get rough and a galley that can be operated safely in a seaway.
The names that come up time and again in blue-water cruising circles include the Valiant 40, the Hallberg-Rassy series, the Hans Christian 33, and the legendary Westsail 32. For those who want newer designs, the Outbound 46 and Amel 50 are considered among the finest offshore passage makers on the market today.
Make no mistake… ocean crossings are not for the faint of heart or the underprepared. But for those who do the work, learn the skills, and put in the sea miles, there is nothing in the world quite like watching a sunrise from the middle of the Pacific Ocean, knowing you sailed there yourself.
No matter where you start, every mile you sail teaches you something. Start small, build your skills, and let the sea tell you where you belong. Where do you see yourself sailing? Comment below 🙂
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