Boat Guide

Best Cruising Sailboats Under 40 Feet

best cruising sailboats under 40 feet

Get to know the best cruising sailboats under 40 feet. In this article, we’ll give you a rundown of the top sailboats perfect for cruising through the Caribbean or any other body of water.

Cruising Sailboat

If you’ve ever dreamed of living aboard a sailboat, then a cruising sailboat would be your best bet. To illustrate, there’s truly nothing like the experience of having to captain a ship, with windswept hair as the speed of your boat picks up. In addition, just imagine ending everyday by watching the sun set on the horizon. Sounds like an ideal vacation, right?

The challenge offered by life on the sea, be it short term or long term, is enough of an enticement for many a people. Below, we’ve put together a list of the best cruising sailboats under 40 feet, which you should check out if you also want to get a taste of the sailing life.

Best Cruising Sailboat under 40 feet

The cruising sailboats we’ve identified below are based on their cost, performance, design, and durability. They range from the famous models to some you may find a bit obscure. However, all of them have unique traits that make them a cut above the rest.

1. Allied Seawind II

best cruising sailboat under 40 feet
image by Howard Hering and Dave Robertson

The Allied Seawind II is a fiberglass boat with a cult-like following. This 32-foot sailboat is an improvement of the initial Seawind, which was the first fiberglass hull boat to circumnavigate the globe. Its long, straight keel allows for directional stability, windward ability, and easy maneuverability while at sea.

Moreover, the Seawind II is comfortable enough for a small crew. Despite its size, its interiors were designed so that the occupants would not feel confined. Below deck, there’s enough headroom to accommodate people who are 6-foot tall. There’s also a ton of storage and counter space.  If you’d like to take a look at its original brochure, click here. On the other hand, if you want to jump right on an Allied Seawind II, you can rent one here.

2. Westsail 32

cruising sailboat
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Next is the Westsail 32, which is an oldie but a goodie. This beloved sailboat is 32 feet and has a fiberglass hull. During the 1970s, it was one of the reasons why cruising trickled into mainstream consciousness. While it might not be the most agile sailboat, the Westsail 32 is built for cruising through long distances.  In truth, it has been used for a number of circumnavigations.

What’s more, it has marvelous interiors below deck which make for very livable spaces. In fact, it includes a port side dinette, starboard sette, galley, opposing settes, and centerline table. As the saying goes, it’s not how fast you get to your destination that counts, but the journey towards it. If you had to take extended trips on water, the Westsail 32 is a great way to do it leisurely.

3. Andrews 28

best cruising sailboats under 40 feet
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Thirdly, we have to mention the Andrews 28. If we had to describe this sailboat in three words, we’d use quick, compact, and affordable. This particular sailboat pulls double duty as it can function as either a sporty cruiser or coastal cruiser. At 28 feet long, the Andrews 28 might seem small to you. However, its interiors are still comfortable enough to occupy. As a matter of fact, it’s so roomy that you don’t have to hunch over when you go below deck. That is to say, as long as you’re no taller than 5 feet and 10 inches.

To illustrate its interiors some more, this sailboat has a saloon with padded seats as well as storage cubbies. Moreover, it has a counter, sink, and stove. For most people, the Andrews 28 might not cut it. However, for those who have a need for speed and enjoy weekend trips at the same time, the Andrews 28 is an ideal cruising sailboat.

Contessa 26

cruising sailboat under 40 feet
image by

Another cruising sailboat we have to highlight is the Contessa 26. Classic Boat Magazine has dubbed it an Affordable Classic, and we can tell you that there’s really nothing quite like it. This fiberglass sailboat is 25 feet and 6 inches long. It has its roots in the famous cabin yacht Nordic Folkboat. Throughout history, there have been many accounts of the feat this sailboat has accomplished, be it racing or circumnavigating-wise. As a testament to its durability, there are still a number of Contessa 26’s in use today.

Similar to the Andrews 28, the Contessa 26 may also be used for racing, as it is fast, dependable, and well balanced. On top of that, this cruising sailboat is also capable of taking you on a trip around the world. Although the Contessa 26 is relatively small, it has spacious interiors with a large cockpit that can accommodate guests.

Tartan 3700

best cruising sailboat under 40 feet
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Lastly, one of the best cruising sailboats under 40 feet is the Tartan 3700. This cruising sailboat is 37 feet long and it sets the bar high for sailboats’ design and performance being that it’s able to balance speed, comfort, and style. What’s more, the Tartan 3700 embodies luxury in a sailboat that’s under 40 feet. To illustrate, the headroom below deck is more than 6 feet. This means, no need to crouch whenever you head down. Moreover, they have cabins and staterooms which can sleep 4 to 6 people comfortably.  

If you were looking to sail across the globe with your family in comfort, then this sailboat will definitely deliver. This is backed up by the many accolades it has garnered through the years. For example, in 2000, the Tartan 3700 was crowned Best Midsize Cruiser by Cruising World. It also made into Sail Magazine’s list of Top 10 boats.


As you can see, the best cruising sailboats under 40 feet do not necessarily cost an arm and a leg. Because of the popularity of sailing and how it has continued to gain high regard throughout the years, there is a wide selection of cruising sailboats that are relatively affordable. The few we mentioned above are just a few good examples.

Lena Horner
the authorLena Horner
Lena Horner is a LA Galaxy fan who does freelance writing and marketing. A graduate of UCLA with a degree in Marketing, she enjoys the outdoor. Lena enjoys the outdoor and is constantly convincing her partner to live in an RV fulltime.

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