Best Sailboats to Retire On

Best Sailboats to Retire On | Life of Sailing

Last Updated by

Daniel Wade

December 28, 2023

Retiring on a sailboat is a great way to save money and explore the world, especially if you pick the right kind of vessel.

The best sailboats to retire on are the Nordic 40, the Pearson 422, the Catalina 38, the Gulfstar 44, the Island packet 35, the Catalina 30, and the Cabo Rico 38. These sailboats are spacious and seaworthy, making them ideal for retirement and cruising.

In this article, we will cover seven of the best sailboats for retirement and long-range cruising. All of these are liveaboard-ready boats, and they feature plenty of room and creature comforts. Additionally, we'll go over the characteristics that make a sailboat ideal for retirement, along with some things you may want to avoid.

We sourced the information for this article from sailboat guides and manufacturer specifications to make sure we provide the most accurate details possible. Additionally, we drop the experiences of retirees who live and cruise aboard sailboats.


Table of contents

What Makes an Ideal Retirement Sailboat?

There are several qualities that set the best retirement sailboats apart from the rest. These characteristics make living aboard a sailboat both safe and comfortable. That said, the last thing you want to do is get stuck with a boat you're not happy in.

So at the end of the day, it's essential to climb aboard and see for yourself. Based on what retirees in the sailing community have determined, here are the qualities that make a sailboat ideal for retirement.

Size and Overall Length

When it comes to retiring on a sailboat, bigger is usually better. This is especially true if you're retiring as a couple. Larger sailboats can make a world of difference in comfort and ease of mobility.

Sailboats with a greater length and wider beam have spacious hallways, ample storage space, large bathrooms and showers, and comfortable berths. Additionally, larger sailboats have kitchens that are suitable for full-time living.

Technology and Electronics

A sailboat doesn't have to feel like a spaceship to meet modern standards, but certain electronics can make life aboard much easier. Air conditioning, automatic temperature control, stereo systems, and a modern navigation system are major benefits when living aboard.

Additionally, modern lighting and ample 120-volt outlets are necessary for the 21st century. These systems are unnecessarily complex, and many of them operate just like they do in a regular home.


Safety is a key factor, especially on cruising sailboats. If you plan to retire on the sailboat, it's best to ensure your vessel has the latest safety equipment. This includes everything needed to meet Coast Guard standards. Perhaps a life raft or locator beacon could also provide peace of mind while cruising.

Cabin Comfort

Comfort is another important factor to consider. When you examine the floor plan, is it spacious enough for you? Is there enough room in the bathroom, and is it easy to move around? This is why it's essential to see the boat in person.


Everybody's price range is different. The most important factor when it comes to pricing is value. Are you getting the boat you need, and is it worth what you pay? These factors are subjective, but it's important to weigh the pros and cons along with the overall price.


The condition of the boat is one of the most important factors. Retirees especially should find vessels in the best condition unless they're willing to spend time and money restoring the boat.

Top 7 Best Sailboats for Retiring

We considered all of the factors above and chose seven of the best new and used sailboats to retire on. All of these vessels were constructed with high-quality materials, and they're all available either new or used on the American market.

1. Nordic 40


The Nordic 40 is not the most common sailboat on the used market, but it's certainly one of the best in terms of capability, ease of handling, and cabin comfort. The Nordic 40 has a reputation in the industry for being a fine vessel, and it is adored by the vast majority of its owners.

Interior spaces are spacious and feature wide hallways, large seats, and a master bedroom upfront. It has plenty of room to move around in the head as well, which is unusual for vessels with standard floor plans.

The Nordic 40 wasn't produced in great quantities. However, it can be found on the used market from time to time. If you're interested in doing any offshore sailing during retirement, it's definitely worth investigating the Nordic 40 and checking one out if it pops up on the market.

2. Pearson 422


If space is what you're after, look no further than the Pearson 422. The sailboat is an absolute monster compared to similar-looking cruising boats, and it has one of the most spacious interiors in its class.

The Pearson 422 has cabins fore-and-aft, along with a large master head, a smaller head up front, multiple seating areas, and a full galley. Unlike most sailboats, where the forward V-berth is the finest accommodation, the Pearson 422 has a large after-cabin with a big bed and a walk-in shower.

The Pearson 422 is also a true offshore cruiser. It's a single-mast monohull design, which will be easy to handle if you've sailed on a typical sloop in the past. It's large enough to handle rough weather in almost any conditions, and it has a virtually unlimited range.

The Pearson 422 comes equipped with a large 50+ horsepower inboard engine (typically diesel) which is plenty powerful enough to move it around when sailing is not ideal, and it's quite easy to steer for its size.

3. Catalina 38


Great liveaboard sailboats don't have to break the bank, and the Catalina 38 is the sailboat that just might fit the bill. These boats were produced in great numbers, and their spacious interiors and excellent handling capabilities characteristics make them a good choice for the cruising retiree or couple.

The Catalina 38 features everything you've come to expect in a sailboat cabin 30-foot boat, with eight extra feet to spare. There's plenty of room to move around inside of the cabin, and the galley is larger than what you'd expect to find on a boat of this size. It's also highly affordable on the used market.

Additionally, this vessel was produced with multiple interior layouts. Much of the Interior furnishings are made of high-quality wood, and a little bit of effort and varnish can make it look premium. The Catalina 38 is known for its seaworthiness and ease of handling. It's a sloop and uses the highly manageable and easy to operate Bermuda rig.

4. Gulfstar 44


The Gulfstar 44 is an excellent cruiser inside and out. It's an after cabin sailboat, which means it has a portion of the interior space behind the cockpit. The cockpit itself is toward the stern of the sailboat, and all the controls are exactly where you'd expect to find them.

And while the Gulfstar 44 is attractive on the outside, but where it really shines is down below in the cabin. This is one of the most spacious sailboats in its class, and it includes excellent interior amenities for both the primary owners and their passengers.

The Gulfstar 44 features a full U-shaped galley across from a large sitting area with a table. There's an additional sitting area across on the starboard side and plenty of space to move around. The after-cabin has a master bedroom and a private head, which is ideal for a cruising couple.

The berthing area up front is enclosed, and it's almost a mirror of the after bedroom. It also features a private head with a shower in the bathroom. The sailing characteristics of the Gulfstar 44 ideal for coastal and blue water cruising.

The center cockpit is well protected, and the vessel's high freeboard makes it dry and comfortable even in rougher weather. The standard Bermuda rig is easy to handle, and a large genoa makes it efficient and light winds.

5. Island Packet 35


The Island Packet 35 is a beamy and capable cruising sailboat that also makes a great liveaboard. It's perfect for retirees because it's easy to handle and relatively new, meaning there are more of them on the market in good condition.

Though pricier than some similarly sized boats, the Island Packet 35 holds its value well and makes an excellent investment. Most of these vessels have already taken their depreciation hit and only go up in value, assuming they are well maintained.

The cabin is roomy and features a wide central area, which is easy to move around in. It features two spacious berths, a large galley, two comfortable places to sit, and a large head with a separate shower. There are also hanging lockers and plenty of room for storing clothing.

It features a forward and after cabin, which makes it a great boat for accommodating guests. The Island Packet 35 has a long full keel with an additional swing Keel for stability. This makes it an excellent cruising boat with blue water handling capabilities.

6. Catalina 30


Are you looking for something small and capable? The Catalina 30 is a go-to for liveaboards due to its economical price, stiff and stable handling characteristics, spacious cabin, and long standing reputation.

The Catalina 30 is one of the most widely produced sailboats ever, and dozens are available on the used market at any given time. This 30-foot sloop has made almost every voyage that you can imagine, and it serves as a comfortable home for liveaboards all over the world.

The majority of the Catalina 30s on the market were built between the 1970s and 1980s. Despite their average age, most of them are in excellent condition. Parts are widely available, and they make a great boat to restore. It's a well-built and thoughtfully designed vessel that makes a great liveaboard sailboat for retirees.

The cabin of the Catalina 30 features everything you'd expect, including a galley, large table, spacious forward berth, and a head with shower. Though not as roomy as the Island packet 35 or the Catalina 38; it's perfectly acceptable for one or two adults and possibly a guest.

7. Cabo Rico 38


The Cabo Rico 38 is one of the most thoughtfully designed sailboats in its class. It makes an excellent home as well as an offshore cruising vessel, as it was designed for extended bluewater voyages. The Cabo Rico 38 is certainly a large boat, and it features everything you'd expect in a vessel nearly twice the length of the average coastal cruiser.

The Cabo Rico 38 has a full-keel and a thousand feet of sail area. It's a cutter rig, which makes it unique among the boats on this list. The vessel is ideal for a cruising couple that intends to make longer voyages or one that just prefers a more spacious interior and superior rough weather handling capabilities.

The cabin of the Cabo Rico 38 is large and laid out in a standard sailboat configuration. One could compare it to a scaled-up Catalina 30, which is practical and familiar to most sailors. It features a spacious forward berth that comes in two configurations: one square and one triangular. Both versions feature a large head with a shower at the sink, along with a full galley and several sitting areas in the center of the cabin.

Best Sailboats to Retire On
Daniel Wade

Daniel Wade

I've personally had thousands of questions about sailing and sailboats over the years. As I learn and experience sailing, and the community, I share the answers that work and make sense to me, here on Life of Sailing.

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