In order to go cruising, most of us require a sailboat with a head, a galley, and bunks. The boat, likely a 30-footer and more often a 40-footer, will have electronics for navigation and entertainment, refrigeration if the trip is longer than a coastal hop, an engine for light wind, and, depending on our appetites for food and fun, perhaps a genset to power our toys and appliances.
To go sailing, however, all we really need is a hull, mast, rudder, and sail. To experience the pure joy of sheeting in and scooting off across a lake, bay, or even the open ocean, there’s nothing better than a small sailboat. You can literally reach out and touch the water as it flows past. You instantly feel every puff of breeze and sense every change in trim.
Some of the boats in this list are new designs, others are time-tested models from small sailboat manufacturers, but every one is easy to rig, simple to sail, and looks like a whole lot of fun either for a solo outing on a breezy afternoon or to keep family and friends entertained throughout your entire sailing season. This list is made up of all types of sailboats, and if you're looking for a list of some of the best small sailboats for beginners, you'll find exactly that here.
Any one of these boats could be labeled as a trailerable sailboat, daysailer, or even a weekender sailboat. Enjoy browsing!

Marblehead 22 Daysailer

Catalina 22 Sport

Hunter 22

BayRaider from Swallow Boats
$28,900, (904) 234-8779, www.swallowboats.comBayRaider

West Wight Potter P 19

NorseBoat 17.5
$19,000, (902) 659-2790, www.norseboat.comNorseBoat

Montgomery 17


Sun Cat from Com-Pac
$19,800, (727) 443-4408, www.com-pacyachts.comSun Cat

Catalina 16.5

Hobie 16

Hunter 15
$6,900/$9,500 (boat-show prices for the 15 and 18 includes trailers), (386) 462-3077, www.huntermarine.comHunter

Super Snark
$970, (800) 247-6275, www.meyersboat.comSuper Snark

Norseboat 21.5
$36,000 (starting), 902-659-2790, www.norseboat.comNorseboat

Flying Scot
$17,300 (includes trailer), 800-864-7208, www.flyingscot.comFlying Scot

RS Venture
$14,900, 203-259-7808, www.rssailing.comRS Sailing

Topaz Taz
$2,900 (includes main and jib), 410-286-1960, www.topazsailboats.comTopaz

WindRider WRTango
$3,000, 612-338-2170, www.windrider.comWindRider