Best Time of Year to Learn to Sail (Cost & Weather)

Finding the best time of year to learn to sail can be crucial depending on your budget and penchant for volatile weather. Throughout the year, more and more people are learning how to sail whether on lakes, bays, seas, or oceans. However, there are certain locations around the world that should probably be avoided if you want to stay relatively safe out on the water.

So when is the best time of year to learn to sail? The most common sailing season months span between March and September. There are sailing schools that open earlier in the season starting in February, sailing schools that close later in October, and sailing schools that are open year-round.

If you’ve got an itch to learn to sail then you can rest assured that you’ll be able to find a time of year to learn to sail that fits your schedule. Late Spring, all of Summer, and early Autumn are great times to go sailing most anywhere above the equator and there are certainly still options on the table for Winter.

Best Time of Year to Learn to Sail

By far the best time of the year to go sailing is between the months of March and September. During these times, you’ll find virtually every sailing school open for business. As a matter of fact, many of them will already have a lot of bookings set up when it comes to sailing courses and sailboat charters.

Before you decide to learn to sail, it’s a good idea to understand your own budget before exploring too far into the subject. Depending on the sailing school, you’ll be able to get a discount on their normal rates if you choose to book early in advance. If the sailing schools know you’re going to come and you’re well out, they know it’s a good idea to lock in the purchase with an enticing discount.

If you end up finding a sailing school that offers sailing courses during the time of year you’re interested in, you’ll want to reach out to them as soon as possible. Many sailing schools book up fast once the weather starts getting nice out, so booking a spot early is a smart move.

Depending on the time of year and location, you might experience harsh weather or underwhelming weather. For example, if you choose to learn to sail in the Black Sea toward the bitter end of the season, you’ll be experiencing some intense weather. However, if you choose to learn to sail in the Caribbean at the same time, you’ll likely have pleasant enough weather with some light to modest winds.

It all really comes down to the type of experience you’re looking for and how much you’re willing to spend. The prime times of sailing for many people are, unsurprisingly, during the Summer. Regardless of where you are in the world, Summertime is going to be the most pleasant time to go sailing but it’ll cost you.

Again, if you want to assure you’ll have a spot in a sailing course while potentially being able to save a bit of cash, book your sailing courses as early as possible. However, some schools will even let you put down a non-refundable deposit to reserve your spot on a sailboat. This, of course, is a fraction of the cost you’d pay to reserve the spot outright and gives you the flexibility to alter your plans.

Learn to Sail for Cheap During Early or Late Season

It is certainly the case that some schools will charge less during the bordering months of the sailing season compared to the interior Summer months. While there are many people who want to learn to sail, the vast majority of them (and probably you as well) would prefer to learn to sail during the Summer.

Sailing in the Summer is one of the pleasant experiences someone can have. Having the sun out while cruising along with good breezes is difficult to beat. There’s certainly no better time to hit the water and have a relaxing time on your sailboat, especially if you’re able to get a decent tan.

With the popularity of the Summer months being what they are, it would make sense that sailing during those times is the most expensive. As a matter of fact, that is definitely the case for some sailing schools. Depending on the time of year, they’ll charge more or less so they can attract students during months that are less popular.

For the most part, if you’re sailing in the months outside of July and August you could potentially get a discount rate. For example, if you were to pay $600 for a six-day live-aboard sailing course during July and August, you might expect to get a 5% discount where you only pay $570 during June or September. If you chose the same course during the months of May or October, you might expect to get a 10% discount totally only $540 for the course. For the months of March, April, and November, over 15% off resulting in a $500 price tag wouldn’t be unreasonable.

If you find a sailing school you really like but they’re overall expensive and don’t seem to offer discounts for the bordering months, try contacting them to see if they off special deals for certain bookings that occur in those months. More likely than not, they’ll be willing to find a sweet spot where both of you win.

Finding Sailing Schools Open Year-Round

Believe it or not, there are sailing schools that operate all year-round. Whether you’re in the Northeast of the United States, in the Caribbean, or off the coasts of Thailand, there are sailing schools that offer courses for all levels so you have the opportunity to learn to sail anytime.

It makes sense that places with fantastic weather also have sailing schools that don’t close due to their season changing. They have the luxury to stay open no matter the season, so it’s unlikely they’ll be giving discounts depending on the season. Some of the best places to sail when it comes to beautiful weather include the Caribbean, the Canary Islands, Southern Spain, Southern Portugal, and Thailand.

Not every school has the luxury of having amazing weather year-round, but that doesn’t stop some sailing schools. There are a number of sailing schools open during the off-season, including in west-coast USA, east-coast USA, United Kingdom, and the Mediterranean. These locations don’t necessarily have the best weather all year-round, but they surely have some dedicated sailing schools that are ready for students.

Take a Sailing Holiday

If you’re just starting out learning how to sail, there’s no better way to get out and learn than participating in a learn to sail holiday adventure. This is one of the best ways for people to learn to sail because it mixes in vacation and a life-changing experience all in one.

Learn to sail holidays generally last 5-7 days and include a mix of theoretical and practical education. If you pay attention and build up enough miles while on the water, you might be able to move your way up in the certification ladder, which means you could eventually attain a sailing certificate.

Most sailing schools will offer some version of sailing holidays, so you’ll definitely have plenty of options to choose from. The best time of year to learn to sail really depends on you, but, again, you’ll want to shoot for between March and September if you’re looking to have a nice sailing holiday.

Whenever I’ve gone on a sailing holiday, I always choose to go on the bordering season months so I could save a bit of cash. The main reason for this, apart from simply saving money, is because I generally like to go abroad which means the flight isn’t going to be cheap. As I mentioned before, the time of the season can really make a difference in cost, so choose wisely and have fun!