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25 Sailboats Under 40′

By Cruising World Staff
Updated: March 25, 2014

Catalina 275 Sport

“This is a complete package; it’s a good sailing boat and well-thought-out. It’s definitely ready for prime time,” says Boat of the Year judge Ed Sherman. Click here to read why the Catalina 275 Sport won Best Pocket Cruiser in 2014.

Beneteau First 30

As they approached the First 30 to conduct their dockside evaluation during the boat show, the BOTY judges may have been just a little skeptical of this performance-oriented 30-footer’s cruisability. But that skepticism turned into appreciation as soon as they stepped below, and they were downright enamored with how the boat sailed. Click here to read why the Beneteau First 30 won Best Small Cruiser, 20 feet and Under in 2011.

The Presto 30 is an innovative, well-built, good looking cruising boat that satisfied its stated design brief as well as any other boat the judges looked at, though it’s not what you might expect from an average cruising boat. Cruising World judges also noted that this easy-to-handle boat may attract new sailors to the sport so they can learn the ropes and then trade up to another model, an approach that’s important to the health of the entire industry. Click here to read how the Presto 30 won the Cruising Spirit Award in 2011.

Catalina 309

“I think that for the purpose it was put on the water, to be able to walk down, jump aboard, and simply go enjoy it on a weekend, the boat not only hit the price in terms of value but also hit the mark in terms of use,” remarked judge Alvah Simon, a world voyager. Click to read why the Catalina 309 won Domestic Boat of the Year for 2007 .

The J/95’s retractable centerboard and dual rudders make it possible to sail in just 3 feet of water. During our dockside visit, designer Rod Johnstone told us that he wanted to build a comfortable coastal cruiser that could keep people sailing by providing “high performance in shallow water,” and the J/95 did exactly what Rod said it would. Click here to read how it won Best Weekender and Domestic Boat of the Year for 2010.

Catalina 315

This nifty pocket cruiser raises the Catalina quality bar with more comfort and better performance. It’s the little things that make this boat special, including the tall rig, the wide cockpit, the large anchor locker, the sprit for the asymmetric kite, and the clever use of space below. Click here to read how the Catalina 315 won Best Inshore Cruiser for 2013.

The Delphia 33 is a boat that’s maximized every inch of available space, and the overall fit and finish, from the joiner work to the systems installation to the structural integrity of the boat, is well done. Click here to read why the Delphia 33 won Import Boat of the Year in 2008.

“With this introductory cruiser, Hunter is trying to bring people up through its ranks and into cruising from trailer-sailers and smaller boats,” said Alvah Simon. “And the company has done that with a 33-footer that has quality and affordability but is still manageable and unintimidating.” Click here to read why the Hunter e33 won Best Compact Cruiser for 2012.

C&C 101

The 33-foot C&C 101 boasts thoroughly modern lines and a nice turn of speed but also features a fine layout belowdecks, with cherry furniture and a teak cabin sole. Click here to read why the C&C 101 won Domestic Boat of the Year and Best Performance Cruiser in 2013.

This dual-purpose cruiser is both easy to handle and zippy on the racecourse. Click here to read why the X-34 won Best Racer-Cruiser for 2009.

Beneteau 34

This affordable performance cruiser is a blast to sail, with details often lacking on more expensive boats. Click here to read a boat review of the Beneteau 34. Click here to read why the Beneteau 34 won the award for Best Value in 2009.

Tartan 3400

The Tartan 3400, with double cabins fore and aft, was still sufficiently nimble and distinctive to cop the 2006 Boat of the Year award for Best Production Cruiser from 31 to 36 Feet. Click here to read more.

The BOTY judges found lots on which to agree as they proclaimed the Najad 355 to be the Best Small Cruiser of 2008: great sails, solid motion through the water, practical interior, well-laid-out deck. Click here to read more.

Catalina 355

Two themes—consideration and principles—epitomize the Catalina 355. Click here to read why it won Domestic Boat of the Year in 2011.

Sabre Spirit

Andrew Burton found the 36-foot Sabre Spirit boat not only easily handled and fast but also a sheer delight to sail; no wonder it won the Judges’ Choice Award in Cruising World’s 2008 Boat of the Year contest. Click here to read more .

Island Packet Estero

Comfortable surroundings are easily driven by a fully self-tending and roller-furling rig on the 36-foot Island Packet Estero. Click here to read why it won Best Midsize Cruiser Under 40 feet in 2010.

Hallberg-Rassy 37

Like the Swedes who manufacture it, the Hallberg-Rassy 37 is a hardy sailer. The boat’s seakindly performance gives the assurance that it can take you anywhere, and once you get aboard, that’s exactly where you’ll want to go. Click here to read why it won Import Boat of the Year in 2006.

Malö 37 Classic

This purpose-built craft is a dream to steer and a delight to the eyes. Click here to read how it won Import Boat of the Year for 2009. Click here to read a full boat review.

Catalina 375

Solid construction and thoughtful amenities make life onboard this boat more comfortable. Click here to read why the Catalina 375 won Best All-Purpose Cruiser, 30 to 40 Feet in 2009.

Jeanneau Sun Odyssey 379

This midsize offering from Jeanneau has a modern look and is ready for sea. Click here to read why it won Domestic Boat of the Year and Best Midsize Cruiser for 2012.

“This very responsive sailboat scoots along quite nicely, I think as well as anything we sailed in this fleet,” says Boat of the Year judge Mark Schrader. Click here to read why the Dehler 38 won Best Cruising Sailboat Under 38 Feet in 2014.

Better-than-expected performance, good design ideas, and follow-through in their execution led to the Hunter 38 winning Best Production Cruiser Under 40 feet for 2005. Click here to read more.

Who says a cruising cat under 40 feet isn’t big enough for comfortable accommodations? The 38’s hulls are narrow where they meet the water for performance purposes but flare out to create ample interior space. Click here to read why the Leopard 38 won Import Boat of the Year in 2010.

Seawind 1160

This 38-foot cat will appeal to cruisers who want a well-built boat that can sail away in a hurry. Click here to read why the Seawind 1160 won Best Multihull Cruiser and Most Innovative Boat for 2007.

“The company is mixing traditional aesthetics with modern gear–from the carbon rudder to tweakers on the jib tracks, and it works really well,” said Boat of the Year judge Steve Callahan of the Sabre 386. Click here to read why it was named Domestic Boat of the Year for 2005.

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