1. Ranger 26

Conceived as a way to bridge the gap between a safe, comfortable, family cruiser and a competitive racer, Gary Mull’s Ranger 26 does exactly as it was designed to. Undeniably fast, (one won the 1970 IOR North American Half-Ton Cup) the boat sails as well as it looks. However speed isn’t the Ranger’s only strong-suit, with over 7 feet of cockpit there’s plenty of room for socializing after an evening of racing. The Ranger 26 sports a nice balance of freeboard and cabin height ensuring that a handsome profile wasn’t sacrificed for standing headroom.

2. Hunter 27

The Hunter 27 perfect encompasses the pocket cruiser ideal. Even if you don’t want a big boat, you can still have big boat amenities. With the generously spacious layout, wheel steering and a walkthrough transom the Hunter feels much larger than 27 feet. Step below deck and any doubts you had that the Hunter was secretly a big boat will be gone. The amenities below are endless; a full galley including stove, microwave and cooler, head with full shower, several berths and not to mention a saloon with seating for 6. The Hunter 27 has reset the benchmark for 27-footers.

3. Contessa 26

When the Contessa 26 was released in 1965, it immediately proved itself to be a strong, seaworthy vessel. The Contessa has continued to prove itself throughout its lifetime, being the boat of choice for two solo circumnavigations under the age of 21. While upwind performance leaves some wanting, the boat is sturdy and can carry full sail in up to 20 knots of breeze. Suited more for single-handing, the Contessa lacks standing headroom and the accommodations are sparse. Nonetheless, the Contessa 26 performs well as a daysailer with guests aboard.

4. Andrews 28

Open and airy below deck, the Andrews 28 doesn’t sacrifice comfort for speed. Designed by Alan Andrews, the Southern California naval architect renowned for his light, fast raceboats, this 28-footer will certainly appeal to the cruiser who also enjoys a little club racing. Sporting a total of 6 berths, a galley, head and nav area, you might forget you are on a boat small enough to be easily trailered. The retractable keel allows the Andrews 28 to be easily launched and hauled and ensures it’s as comfortable as a daysailer as it is a racer.

5. S2 8.6

S2 8.6 photo on sailboatdata.com

Much like its older sibling, the S2 8.6 still holds its contemporary style, despite its 1983 introduction. Like all other S2 Yachts, the 8.6 is recognized for the quality craftsmanship that allows the boat to hold up today.The S2 8.6 is a very comfortable and easily managed coastal cruiser and club racer. It’s relatively stiff, its helm feels balanced, and it tracks well. On most points of sail, it compares favorably with other boats of similar size and type.

6. S2 9.2

Within a wide field of well-designed and competitive racer/cruisers of the 1970s, the S2 9.2 stands out, mainly because it wears its age very well. Unlike most boats from this time, the S2 9.2 is not tailored to fit the trending fashion or rating rules of the day. Without a scoop transom and boarding steps or skinny portlights below the sheer, it looks modern, while performing as well as it looks. Sturdy and solid in heavy breeze, the S2 9.2 can be just as suited to racing as it is cruising, often giving younger boats a run for their money.

7. Islander Bahama 28

On top of being a real eye-catcher, the Islander Bahama 28, with its 5-foot-6-inch draft and 3,300 pounds of ballast, sails beautifully, tracks well, and responds quickly to the helm. Inspired by the International Offshore Rule, it is unusually wide, offering stability in breeze without sacrificing the sheer and lines that make it so attractive. Below deck, the Islander Bahama 28 comes standard with plenty of berths and storage space and a galley complete with stove, icebox and sink.

8. Newport 27

Debuted in 1971 in California, the Newport 27 was an instant success on the local racing scene. For a modest 27-footer, the Newport 27 has an unusually spacious interrior with over 6 feet of standing headroom. With 4 berths, a table, nav station, head and galley the Newport 27 has all the amenities you might find in a much bigger boat, all in a compact package. While quick in light air, the drawback of the tiller steering becomes apparent with increasing breeze and weather helm often leading to shortening sail early.

9. Cape Dory 28

While the sleek lines and the teak accents of the Cape Dory 28 may grab the eye, it is the performance of the boat that make it unique. The Cape Dory comes with all amenities that you might need available, including a V-berth, 2 settees, and a head. Safe, sound and comfortable as a cruiser it is still capable of speed. Quick in light wind and sturdy and capable in heavy air, it is off the wind where the Cape Dory 28 shines with a balanced helm and the ability to cut through chop and still tack perfectly.

While the sleek lines and the teak accents of the Cape Dory 28 may grab the eye, it is the performance of the boat that make it unique. The Cape Dory comes with all amenities that you might need available, including a V-berth, 2 settees, and a head. Safe, sound and comfortable as a cruiser it is still capable of speed. Quick in light wind and sturdy and capable in heavy air, it is off the wind where the Cape Dory 28 shines with a balanced helm and the ability to cut through chop and still tack perfectly.

10. Balboa 26

First splashed in 1969, the Balboa 26 continues to enjoy a strong following among budget-minded cruisers. Built sturdy and heavy, all of the boat’s stress points are reinforced. The spacious cockpit comfortably seats 4 and is self bailing, ensuring that sailors stay dry. While only 26 feet, the Balboa still has room for a double berth, galley with stove and freshwater pump, and an optional marine head or V-berth. The Balboa has the ability to sleep five, though the most comfortable number is two or three. Under sail, the Balboa is fast and maneuverable, but may prove a handful in heavy breeze as weather helm increases.

11. Etap 28s

The Etap 28 just might be the most unusual and innovative boat in our lineup. With a contemporary profile topside and an inviting floor plan below, it earns points for both style and comfort. The most innovative feature however is not one you can see as Etap uses a double hull construction method to render the ship virtually unsinkable. Despite boasting 6 berths, a galley and a nav area, it won’t feel crowded below deck. The space is enhanced by the numerous ports and hatches that adorn the saloon.