No two first-time buyers are alike. One may be making their first forays into boating, while others only consider buying a boat after half a lifetime of sailing on board other people’s boats, possibly along with regular chartering in their own right. What makes a suitable first boat therefore differs enormously between different people.

Yachts today can be much easier to handle than in the past, with sail handling systems that can be operated by one person in the cockpit and efficient self-steering systems. In addition, yachts of the past 20 years or so are easier to manoeuvre than their forebears. The combination of these factors mean that larger boats than were previously viable can be considered for first ownership. This is particularly the case for those who already have plenty of experience crewing or chartering on larger boats.

Beneteau First 27.7: best first sailing yachts

Small, second-hand, inexpensive yachts such as this Beneteau First 27.7 are a great way to dip your toe into boat ownership (Photo: JM Liot/Groupe Finot).

Nevertheless, there’s also a sense in which a budget-priced boat can be an attractive option that allows you to get a feel for how much time you will actually use it, before investing in a larger vessel. In any case, often a first boat is only kept for around three years, during which time you may learn much more about the type of sailing you want to do, and the desirable attributes of a suitable boat for that kind of use. Starting with a low-cost boat is likely to minimise the total cost of changing to a different vessel for longer-term ownership.

Don’t confuse size with overall length – there are boats that try to cram too much into a certain hull length that are harder to manoeuvre than a boat a few feet longer that has a more hydrodynamically efficient keel and rudder.


Westerly Centaur

Westerly Centaur: best first sailing yachts

With over 2,000 examples built, the Westerly Centaur is a small bilge-keeler with standing headroom.

I’d have been reluctant to include this model a decade ago – at that time this venerable 26-footer attracted a unfathomable premium on the price, with the result that there were better boats available for the same money. However, since then prices have declined by almost half, even for good examples.

A large number were built – more than 2,400 – so there are plenty to choose from, and there’s a huge body of knowledge about solutions to common problems. As a result this is one of the most cost-effective ways to get a boat with full headroom in a pleasant and well lit interior. Downsides include staid performance and narrow sidedecks that make deck work more awkward than for more recent wider beam designs.

Another option is the Sabre 27, which has softer styling that has stood the test of time better. When new in many ways it was seen as a better boat than the Centaur, however production problems meant fewer were sold.

For more on twin-keelers, see: 8 of the best bilge-keel sailing yachts.


Red Fox 200E

Red Fox 200: best first sailing yachts

The unique Red Fox 200E. Floats in 20cm thanks to the lifting daggerboards and ballasted hull.

This is undoubtedly one of the best designed small boats around, with great sailing performance and a well laid out bijou interior. It’s an ideal choice for those looking for an economic low maintenance boat that will still leave time and budget for chartering in the sun. Alternatively, you can hook the trailer up to the back of the car and take the boat to the South of France or the Baltic for a week or two’s holiday.

The boats are a delight to sail, with many examples having twin rudders, which makes for positive control, even when well heeled. The two asymmetric daggerboards provide positive lift to windward, and yet don’t impinge on interior space (the hull is ballasted – there is no keel). Below decks the largely open plan layout has room for up to four people with sitting headroom and a small galley area. This is also one of the smallest boats to have the benefit of a separate heads compartment.


Beneteau First 27.7

Beneteau First 27.7: best first sailing yachts

Close-winded upwind with double-digit speeds available downwind – what's not to love? (Photo: JM Liot/Groupe Finot).

This is one of my favourite boats of this size – it’s a Finot design that offers enough accommodation for civilised weekending and longer periods on board, combined with safe, easy handling and excellent performance. As such it offers fun, safety and easy maintenance all in one package. The boat was offered with a choice of lifting and fin keels, both of which provide plenty of stability thanks to deep draught and a heavy bulb at the base of the foil, allied to plenty of form stability from the hull shape.

This is a boat whose relatively compact dimensions belies its speed potential. The combination of an efficient rig and underwater profile makes the 27.7 much more close-winded than most cruising yachts, while double-digit speeds are easily achieved downwind, without pushing hard. The accommodation layout includes an open-plan saloon/forepeak, a simple galley, small navigation station, plus an enclosed heads aft and a separate double quarter cabin.

For more great lifting keel options, see: 5 great lifting keel cruising yachts.


Sadler 32

Sadler 32: best first sailing yachts

The Sadler 32 is an expanded, slightly less austere update to the Contessa 32.

This is a proper yacht that will take you anywhere at a sensible price. While it lacks the multiple cabins and voluminous interiors of more recent designs, if you want a solid boat with respectable performance, vice-free handling and reasonable accommodation, there are few boats that offer more at a similar price. The design was conceived by David Sadler in the late 1970s as a more modern interpretation of the hugely successful Contessa 32. While it has all the hallmarks of the earlier boat, it has greater beam and freeboard that significantly increases internal volume and makes for a drier ride.

Accommodation is in a traditional layout with a vee berth that converts into a double in the forepeak and a heads compartment across the full width of the boat separating that area from the saloon. This has two decent settees that make good sea berths each side of a central table. There’s also a proper chart table, single quarter berth and a decent galley. Later boats, from around 1984/5 onwards, had a more sophisticated layout, with better use of the space and higher quality of finish.

For more inspiration and alternatives along these lines, see: 6 great family cruising yachts for £20k.


Jeanneau Sunshine 36

Jeanneau Sunshine 36: best first sailing yachts

The mid-1980s Jeanneau Sunshine 36 has three double cabins.

This mid-1980s design was one of the first performance cruisers of this size offered with a three double cabin layout, making it ideal for families that feel each child needs their own space on board. The saloon offers good seating space, while also providing both additional berths if required, as well as more enclosed stowage space than on many more recent designs. The downsides of the accommodation, however, are that there’s less feeling of space than with newer boats and the interior is somewhat darker.

For all-round cruising inspiration, see: Float free: cruising on your yacht or powerboat.

Written by: Rupert Holmes
Rupert Holmes has more than 70,000 miles of offshore cruising and racing experience, in waters ranging from the North Sea to the Southern Ocean and Cape Horn. He writes about all aspects of boat ownership and marine travel, including destinations, seamanship and maintenance, as well as undertaking regular new boat and gear tests. He currently sails around 5,000 miles per year and in the past couple of seasons has cruised from the UK to the Azores, as well as winning his class in the 2014 two-handed Round Britain and Ireland Race. He also owns two yachts, one based in the Mediterranean and the other in the UK.