The Best Regattas To Check Out

Docking out for another day-sail cruise. Feeling the wind in your hair, the sun warming your face and the sprinkle of saltwater cooling it down again

A few deep breaths.Filling your lungs with the fresh air of the sea while pointing your bow straight to the horizon will reward you with a sense of freedom and calmness that you just can’t get ashore.

However, this is only one aspect of sailing.Although rewarding, you may eventually get curious to figure out what the next step is. 


For that step, we highly recommend trying out one of the many legendary regattas situated allover the world. Maybe you have already participated in your sailing club's annual weekend race.

Maybe you have even participated in a few of the larger races in your region. But truthfully, these will be no comparison to a fashioned international regatta.

Imagine for instance a starting line filled with so many boats that you are not able to see the horizon regardless of which way you are looking.

imagine sailing in historic waters where the most famous stories of sailboat racing has unfolded in years past. Or just imagine,that you are battling it out with your competitors in the closest race you could ever think possible.

Where the smallest decision can make the difference between winning and losing.

If you find yourself intrigued, read on. We have carefully measured and weighed all of the best regattas out there.

Boiled a long list down into a select few to assemble a shortlist of our absolute favorites. 

So what are you waiting for. Sign up immediately. Or actually. Maybe you should actually go through the list first. Here goes.


Best Regattas

Barcolana Regatta,Italy


Located in the Gulf of Trieste and held annually on the second Sunday of October, the regatta is by far one of the most popular in the world.

Around 2500 boats from all over the world, ranging from professional world-class crews in super-yachts to recreational racing crews in regular sailboats will gather on the starting line.

And this number is growing year by year. 

It is open for anyone to join, so all you need is to fill in a simple registration form and get our boat to Trieste. Once there, you are good to go. 

The regatta is held by the local yacht club - Societá Velica di Barcola e Grignano but over the years the sailing event has turned into somewhat of a festival. 250.000 spectators annually means that the entire city has become involved and sailings no longer the sole attraction.

Over 10 days, the Barcelona Regatta will offer experiences within culture, art, mystique and much more.

The race itself will be the pinnacle of the event and will be held on the final Sunday of the festival. It is a simple race course of 13 nautical miles around 4 fixed buoys forming a square in the sea.

Boats will be grouped into divisions based on their size and there will be prizes and honor to fight for in every division. 

However, the overall fastest time is the most prestigious and attracts some of the finest sailboats and crews to battle for the glory.


Kiel Week, Germany

regatta germany

This regatta takes place just outside the city of Kiel in the Northern part of Germany and is held annually in the final week of June.

The regatta itself is only a part of the city festival which attracts around 3,5 million visitors per year - which arguably makes it the largest summer festival in Europe.

There is plenty of activities in the streets. Music playing, dancing, carnivals, arts, comedians and fairs is just a small slice of what awaits you aside from the sailing.

The regatta itself has several entry points. You can participate either in a dinghy, a keel-boat for offshore racing or a keel-boat for class-based racing.

For dinghies, the week will be split in two halves. The first half will schedule races for non-Olympic dinghies, while the second half will be exclusively for Olympic dinghies and a few selected keel boats.

Even though it is not permitted to partake in the racing, we will definitely recommend being around as a spectator to watch the creme of the crop in Olympic sailing do what they do best. 

The offshore racing offers a variety of challenges, you can do the regular Kiel Cup which is normally the race that will attract most participants.

Then, if you wish to opt in for the challenge, you can register for either the single-hand or the double-hand race. For these races you will have only yourself or 1 other crew member,respectively.

These races are becoming increasingly popular, but you seriously need to make sure that you have what it takes to sign up.


Cowes Week, United Kingdom

cowes regattas

Definitely one of those regattas where you will feel the breath of history when heading towards the starting line.

The regatta has been held every year since 1826 in the storied waters of the Solent - stretching from the south of England to the Isle of Wight.

These waters are known for its strong breeze and currents, ensuring that even skillful and experienced sailors will be pushed to their limits.

It is typically held in the last week of July, where around 1.000 boats will take part in the racing. There will be 1 start per day for all boats. Some will be class-based while others will be based on handicap-systems - so no matter what sailboat you have, you will be able to get some great racing in.

The races will mainly be based on race courses put in place by the race committee, however the final race will be offshore and will send the entire fleet around the Isle of Wight.

There will be several different trophies to aim for. Most prestigious is the Cowes Overall Winner Trophy, the Duke of Edinburgh Triple Crown Trophy and the Triple Crown Island Challenge Trophy. 

Registration is open to everyone so all you need is to sign up. From then on, all you have to do to secure your very own page in the history books of sailing, is to beat the very best sailors in the world. What are you waiting for?


Chicago to Mackinac,USA

chicago regatta

Also known as “The Mac”, this is the longest annual fresh water race in the world. From the Chicago Lighthouse the race will take you 289 nautical miles to Mackinac Island.

The race attracts an attendance of around 350 boats. Among these some of the biggest names in sailing. Dating all the way back to 1898, this is another one of those regattas that is shrouded in history and “The Mackinac Trophy” is regarded as one of the most prestigious to claim in US sailing.

This attracts participants from all over the country as well as overseas.

The race is characterized by the tricky winds of Lake Michigan offering significant changes in wind speed as well as direction and provides many opportunities for gain sand losses.

As an extra bonus,participants can aim to enter the legendary and exclusive “Island Goat Sailing Society”. Membership is awarded upon completion of 25 “Macs”, and is currently including around 275 members.


Sydney Harbor Regatta, Australia

sailing regatta

Sydney Harbor is by itself a unique location for sailing. The Olympic waters from 2000 is unique due to its proximity to the city center and to the skyline of Sydney -particularly the iconic opera house is famous within this spectacular setting.

Thus, after the idea of having a regatta to bring all of the sailboats in the region together materialized into its very first edition in 2005, the race quickly grew.

These years around 200 entries are expected in a large variety of classes.

The most popular classes will have their own starts with fleet sizes between 10 and 25 boats. Other classes will be mixed together based on their boat length and sail size - among many other factors.

Participating boats will range between ‘state of the art’ racing yachts such as TP52 and Farr 40 all the way to small recreational sailboats. The mild breeze of Sydney Harbor means that most sailors will be able to handle their boats during the racing.

The tricky winds of Sydney Harbor will be a different story though. Recognized worldwide as any tacticians worst nightmare their will be plenty of overtaking lanes available.And similarly, leading a race here, you will not feel secure until you pass the finish lane. 


Les Voiles deSaint-Tropez, France

sailboat regatta

This is likely to be the most beautiful and extravagant regatta on this list. 300 sailboats - mixing stunning classical sailing vessels, elite racers and modern super-yachts - will line up to battle it out in the waters off the picturesque coastline of Saint-Tropez.

Perhaps the most famous coastal village of the French Riviera.The racing will be conducted over a full week of sailing stretching from late September into October.

Racing will mainly be inshore racing but finishing off with an offshore race up along the coast.

Aside from the racing itself, the main attraction of this regatta is to spend the evenings enjoying the french seafood cuisine with some fine wine and then walk along the harbor to take in the sight of the most beautiful sailing crafts ever made from all different eras.

Sailboats from former editions of the America’s Cup will be present along with 100 plus feet modern luxury sailboats.

The racing will mostly be in mild to moderate sea breeze conditions. However, the area is known for having many calm days which could result in postponement and cancelled races. Fortunately, this is not the worst area for this to happen, as you will have even more time to wander around and admire the sight of your competition. 


Regattas as a spectator

Above is the select few of our preferred regattas. However, many deserves to be mentioned. Among these, The Middle Sea Regatta (Malta), The St. Maarten Heineken Regatta (St.Maarten), The Dartmouth Royal Regatta (United Kingdom), King’s Cup (Thailand),Copa Del Rey (Spain), Færder Sailing Week (Norway), Hamilton Island Race Week(Australia).

Honestly, the list could go on and on from there in terms of regattas worth attending. Alternatively, you should as a sailing fan also consider to visit some regattas - not to attend - but to be a spectator. 


America’s Cup & Louis Vuitton Cup

sailing regattas

This is in-arguably the most prestigious regatta in sailing. The winner of the America’s Cup will bring home the oldest trophy in sports - The Auld Mug - that is dating all the way back to 1857.

The America’s Cup itself is a match race consisting of just two boats battling it out in a series of races. The winner will claim the trophy along with the responsibilities and rights to hold the next Cup.

This means that the design of the boat, the format of the racing and the location of the Cup will vary from Cup to Cup. Normally, there will be 4 to 5 years in between Cups and in order to find out who is allowed to challenge the champion,a regatta known as the Louis Vuitton Cup is held.

The format of this Cup will depend heavily on how the America’s Cup is set up - and will be agreed upon by those syndicates that has chosen to enter. 

The competition is famous for continuously pushing the boundaries of what sailing is - and what sailing can become - and there will be no other regatta in the world that will be able to attract the same kind of buzz and attention as this one. Being on location as a spectator will be truly… well.. spectacular.   


Volvo Ocean Race

volvo ocean race

The only regatta that even comes close to the America’s Cup in terms of attention. It is an entirely different race though.

It is an offshore race which over 6 months will take the competitors all the way around the world during 9 stages. The race mixes the adventurous aspect of sailing with a racing competition, setting the stage for some amazing stories to unfold.

Visiting the race at the start-harbor, during a stopover or at the end of the race will be a great experience regardless what you choose. You will be able to get quite close to the boats and perhaps even get onboard to have a look.

The crews are very forthcoming for sailing fans and you will be able to get a good understanding of what challenges are involved -and what life is like - when trying to race sailboats around the world.

You may also want to learn of some great places to sail. Make sure to check out our recommended places to see on your next sailing trip.