The 5 Best Sailing Regattas In The World

Paul Stockdale Author Avatar
Written by Paul Stockdale | February 18, 2023

A sailing regatta is a series of boat races that take place on the water. Regattas can be organized by yacht clubs, sailing organizations or other entities and can vary in size and scope from local races to national or international events.

The races in a regatta typically involve a number of boats sailing around a set course marked by buoys or other markers with the goal of completing the course in the shortest amount of time possible

The 5 best sailing regattas in the world are:

  1. Barcolana Regatta
  2. Kiel Regatta
  3. Cowes Week
  4. Sydney Harbor Regatta
  5. Les Voiles de St. Tropez

These sailing regattas are well organized, offer ideal sailing conditions, and are located in beautiful locations with many tourist attractions.

1. Barcolana Regatta

Top Sailing Regatta Barcolana Regatta

The first top sailing regatta in the world is the Barcolana Regatta, also known as "Barcolana Week" or "The Barcolana". The Barcolana Regatta is hosted in the Gulf Of Trieste in Italy. We rate the Barcolana Regatta 9.9/10 as a sailing regatta.

The Barcolana Regatta is held annually on the second Sunday in October. The event lasts for 10 days.

According to the Guinness World Records, the Barcolana Regatta is the largest sailing race in the world with over 25,000 sailors in 3,500 boats entering and over 300,000 spectators visiting during the regatta week.

The Barcolana Regatta is operated by the Societá Velica di Barcola e Grignano (Sailing company of Barcola and Grignano) which is the local yacht club in the area. The regatta has been held since 1969.

The winner of the Barcolana Regatta is the sailor that sets the fastest time over the race distance. The Barcolana Regatta course is 13 nautical miles (15 miles) in length with 4 fixed buoys forming a square shape route in the sea.

Barcolana Regatta Sailing Route

The sailing route starts between the Miramare Castle and the headquarters of the Sailing Company of Barcola and Grignano and the finish line is in the stretch of sea in front of Piazza Unità of Italy in Trieste.

Most sailors complete the Barcolana Regatta sailing route in under 2 hours.

Barcolana Regatta Side Events

While the regatta itself takes place on the second Sunday of October, there are 12 side events that take place in the lead-up to the finale.

The 12 side events that occur during the Barcelona Regatta are:

  • Barcolana Young: This is the beginning event that opens the regatta. The Barcolana Young is for sailors under the age of 14. It includes six competitive and pre-competitive sailing races
  • Barcolana Swims: This is a swimming event where both amateur and professional open-water swimmers of all ages can compete. The swimming event
  • Barcolana Maxi-Trofeo Portopiccolo: This is a side event race for boats over 53 feet (16m) long
  • Barcolana For The Community: This is a side event at San Giusto Basin of a whole day dedicated to sailing and solidarity for charities and organizations fostering the social integration of people with disabilities
  • Barcolana Sea Chef: This is a charity event at the Barcolana Regatta whereby award-winning chefs accompanied by a skipper will compete in a race. Once the race is over, they will cook for a charity dinner
  • Go To Barcolana: This event will turn the crews' journey to Trieste along Italy's Adriatic Coast into an engaging and one-of-a-kind race arriving just in time for Barcolana. The starting line will be in Ravenna and the finishing line will be located in the Gulf of Trieste for this pre-race event.
  • Regatta For LNI Boat Owners: This event is for LNI boat owners and for the different vessels of the LNI boat that are in Trieste
  • Barcolana Classic: This is a boat parade of vintage vessels that takes place during Barcolana week
  • Barcolana By Night: This is a race that occurs during sunset and at night for Ufo28, Meteor and Melges 24 owners
  • Go To Barcolana From Slovenia: This is a race whereby sailors from the eastern Adriatic coast travel to Trieste for the main Sunday regatta
  • Barcolana Fun: This is an event for adrenaline lovers that includes special watercraft (foil, kitesurfing, windsurfing)
  • Barcolana One Design: This is an event for sailors that own a One Design boat to compete in a race before the main event on Sunday

There are festivals and exhibitions during the Barcolana week too for the regatta spectators to enjoy.

How To Participate In The Barcolana Regatta

To participate in the Barcelona Regatta, sailors will need to register online with the regatta organizers on their website.

The price to enter the regatta as a participant is €110 ($116). Spectators can come to the Barcolana Regatta free of charge.

Barcolana Regatta Weather

For spectators and participants at the Barcolana Regatta, the weather conditions in October for the regatta event can range from 68°F (20°C) and 55.4°F (13°C) air temperature.

2. Kiel Regatta

Top Sailing Regatta Kiel Regatta

The second-best sailing regatta in the world is the Kiel Regatta also known as "Kiel Week". The Kiel Regatta is hosted in Kiel city in northern Germany. We rate the Kiel Regatta 9.8/10 as a sailing regatta.

The Kiel Regatta is held annually for one week with its conclusion on the last Sunday in June. The event lasts for 7 days.

Approximately 4,500 participants in 1,500 boats enter the Kiel Regatta every year with over 3,000,000 people visiting Kiel city for the Kiel Regatta.

The Kiel Regatta is operated by Kiel Yacht Club, North German Regatta Club and Club Seglerhaus am Wannsee. The regatta has been held since 1870.

The Kiel Regatta consists of three main classes which are the Olympic Classes, International Classes, and Keelboats.

Kiel Regatta Side Events

During the Kiel Regatta, there are a number of side events that participants and spectators of the regatta can enjoy.

The side events that occur during the Kiel Regatta are:

  • Concerts: There are over 300 concerts from various bands with live music throughout the week of the regatta that spectators can enjoy
  • Windjammer Parade: The parade takes place on the Saturday before the finale on Sunday. It proceeds northeast and passes the lighthouse Friedrichsort. It is a great sailing parade to watch the tall ships as a spectator
  • Kids Painting & Puppet Shows: There are kids painting activities and puppet shows performed by theatres for children to enjoy at the regatta
  • Gewaltig Leise Comedy Shows: There are multiple comedy shows during the regatta that adults can enjoy
  • Fireworks Show: There is a music themed firework show that families can enjoy while visiting the Kiel Regatta

How To Participate In The Kiel Regatta

To participate in the Kiel Regatta, sailors will need to register online with the Kiel Regatta organizers on their website.

The price to enter the Kiel regatta as a participant is between €300 ($318) and €175 ($185) depending on the boat class entered. Spectators can come to the Kiel Regatta free of charge.

Kiel Regatta Weather

For spectators and participants at the Kiel Regatta, the weather conditions in June for the regatta event can range from 69.8°F (21°C) and 53.6°F (12°C) air temperature.

3. Cowes Week

Top Sailing Regatta Cowes Week

The third top sailing regatta in the world is Cowes Regatta, also known as "Cowes Week". Cowes Week is hosted in Cowes on the Isle of Wight. We rate Cowes Week 9.5/10 as a sailing regatta.

Cowes Week is held annually on the last week in July. The event lasts for 7 days.

According to Cowes Week, Cowes Regatta will see 5,000 competitors and 60,000 spectators over the entire week of the regatta.

Cowes Week is operated by Cowes Week Ltd. The regatta has been held since 1826.

The winner of the Cowes Week is the sailor that sets the fastest time over the race distance.

The best place to watch this regatta as a spectator is the area between the Castle of the Royal Yacht Squadron and the cannons. There is a Cowes Week App whereby spectators can watch live tv streaming and replays.

The Cowes Regatta divides up the boat classes into two group which are the white group and the black group.

Cowes Week Side Events

The side events that occur during the Cowes Week are:

  • Spectator Boat Tour: For £15 ($38), spectators can spend 1 hour on a boat watching the regatta up close
  • Family Day: Family Day at Cowes Week takes place on the first Sunday of the regatta. It is a day of family fun and children can do activities like gymnastics and acrobatics and enjoy a dinosaur show at the Regatta Village on Cowes Parade
  • Clubhouse Crew Bar: There is a nearby bar with a beer tent and decked garden with plenty of seating and a view across the harbor. The bar is also host to a string of bands that play live music after 8pm
  • Live Music: There is live music, food and drinks at nearby Cowes Yacht Haven and Northwood House

How To Participate In Cowes Week

To participate in Cowes Week, sailors will need to register online with the Cowes Week organizers on their website.

The price to enter the regatta as a participant ranges from £84 ($101) to £305 ($368) for a daily entry at the regatta and between £339 ($409) and £1,217 ($1,470) for the whole regatta. The prices vary based on the class entered.

Spectators can come to Cowes Week free of charge.

Cowes Week Weather

For spectators and participants at Cowes Week, the weather conditions at the end of July for the regatta event can range from 68°F (20°C) and 56°F (13°C) air temperature.

4. Sydney Harbor Regatta

Top Sailing Regatta Sydney Harbor Regatta

The fourth top sailing regatta in the world is the Sydney Harbor Regatta. The Sydney Harbor Regatta is hosted in Sydney's Middle Harbor Yacht Club, Mosman. We rate the Sydney Harbor Regatta 9.2/10 as a sailing regatta.

The Sydney Harbor Regatta is held annually on the first weekend in March. The events lasts for 2 days.

According to the Middle Harbor Yacht Club, the Sydney Harbor Regatta will see 190 keelboats race across 19 divisions.

The Sydney Harbor Regatta is operated by the Middle Harbor Yacht Club which is the local yacht club in the area. The regatta has been held since 2005.

The winner of the Sydney Harbor Regatta is the sailor that sets the fastest time over the race distance.

Sydney Harbor Regatta Sailing Route

The sailing route consists of 7 course areas throughout Sydney Harbor and offshore near Sydney Heads.

Most sailors complete the Sydney Harbor Regatta sailing route in approximately 1 hour and 40 minutes.

Sydney Harbor Regatta Side Events

The side events that occur during the Sydney Harbor Regatta are:

  • Prize Giving Ceremony: This is a ceremony that takes place at the end of the regatta to present winners with their trophies
  • Yacht Club House Party: There is a party at the yacht club with food and drinks for everyone to enjoy
  • Beach Party: On the Saturday evening of the regatta weekend, there is a beach party for everyone to enjoy

How To Participate In The Sydney Harbor Regatta

To participate in the Sydney Harbor Regatta, sailors will need to register online with the Sydney Harbor Regatta organizers on their website.

The price to enter the regatta as a participant is $440 for the weekend or $220 for one day. Spectators can come to the Sydney Harbor Regatta free of charge.

Sydney Harbor Regatta Weather

For spectators and participants at the Sydney Harbor Regatta, the weather conditions in March for the regatta event can range from 77°F (25°C) and 64.4°F (18°C) air temperature.

5. Les Voiles de St. Tropez

Top Sailing Regatta Les Voiles de St. Tropez

The fifth-best sailing regatta in the world is the Les Voiles de St. Tropez. The Les Voiles de St. Tropez Regatta is hosted in the bay of Saint Tropez, France. We rate the Les Voiles de St. Tropez 9.2/10 as a sailing regatta.

The Les Voiles de St. Tropez regatta is held annually on the last week in September. The event lasts for 9 days.

Approximately 250 maxi, modern and classic yachts will participate in the regatta.

The Les Voiles de St. Tropez is operated by Société Nautique de Saint-Tropez. The regatta has been held since 1981.

Les Voiles de St. Tropez Side Events

During the Les Voiles de St. Tropez, there are a number of side events that participants and spectators of the regatta can enjoy.

The side events that occur during the Les Voiles de St. Tropez are:

  • Challenge Day: The organizers of the Les Voiles de St. Tropez regatta will set a challenge day course for sailors to participate in
  • Bowls Competition: There is a bowls competition on the Wednesday of the regatta where crews can participate in the competition
  • Crew Parade: This is a parade whereby spectators can see the boat's parade. It starts at the regatta village and ends at the far end of the harbor. A group of musicians lead the parade while crews behind dance and sing

How To Participate In The Les Voiles de St. Tropez

To participate in the Les Voiles de St. Tropez, sailors will need to register online with the Les Voiles de St. Tropez organizers on their website.

The price to enter the Les Voiles de St. Tropez as a participant is €3,600 ($3,821). Spectators can come to the Les Voiles de St. Tropez free of charge.

Les Voiles de St. Tropez Weather

For spectators and participants at the Les Voiles de St. Tropez, the weather conditions in September for the regatta event can range from 69.8°F (21°C) and 51.8°F (11°C) air temperature.

Best Sailing Regattas In The World Summary

Rating Regatta Best For When Is It On?
9.9/10 Barcolana Regatta Great for spectators seeing 3,500 boats Annually, 2nd Sunday in October
9.8/10 Kiel Regatta Great for festivals and fun Annually, last week in June
9.5/10 Cowes Week Great for family regatta with lots of kids activities Annually, last week in July
9.2/10 Sydney Harbor Regatta Great for keelboat lovers Annually, first weekend in March
9/10 Les Voiles de St. Tropez Great for regatta crew as there are plenty of crew activities to enjoy Annually, last week in September

Frequently Asked Questions

Below are the most commonly asked questions about the top sailing regattas in the world.

What Is The Cheapest Top Regatta To Participate In?

The cheapest top regatta to participate in is the Barcolana Regatta which costs €110 ($116).

What Is The Most Expensive Top Regatta To Participate In?

The most expensive top regatta to participate in is the Les Voiles de St. Tropez which costs €3,600 ($3,821).

What Is The Best Sailing Regatta In The World For Spectators?

The best sailing regatta in the world for spectators is the Barcolana Regatta with 3,500 boats for spectators to see.

What Is The Shortest Top Regatta Event In The World?

The shortest top regatta event in the world is the Sydney Harbor Regatta which lasts 2 days.

What Is The Longest Top Regatta Event In The World?

The longest top regatta event in the world is the Barcolana Regatta which lasts 10 days.