Antigua Sailing Week was invented to fill beds. That is not my cynicism talking. It is the regatta’s own history. In 1968 a group of friends, several of them hoteliers, started a race week to keep visitors on the island a little longer at the end of the winter season. Nearly sixty years later the problem has flipped. Now the hard part is finding a bed.
Antigua Sailing Week 2027 runs from 21 to 25 April 2027, with the Antigua Classic Yacht Regatta just before it from 14 to 19 April. If you are racing, crewing, chasing the fleet with a camera or flying in to cheer someone on, this is your guide to the dates, the new format, where to watch, and where to stay ashore without paying harbour prices for a room you only sleep in.
What is Antigua Sailing Week? It is the Caribbean regatta Antigua’s hoteliers started in 1968
Antigua Sailing Week is one of the Caribbean’s longest running regattas, first held in 1968 and based at English Harbour on Antigua’s south coast. The official history says the Antigua Hotel Association sponsored that first edition, from 8 to 15 June 1968, with boats from the United States, Canada and the Caribbean. People who were not racing watched from beach and verandah parties. Some paid a small fee for a spot on a boat.
The event is still owned by the Antigua and Barbuda Hotels and Tourism Association, and it still mixes serious racing with a week of island life ashore. What has changed is the shape of the racing itself, which I will come to in a moment.
When is Antigua Sailing Week 2027? It runs from 21 to 25 April 2027
Antigua Sailing Week 2027, the 58th edition, takes place from 21 to 25 April 2027, according to the organisers’ 2027 announcement. Entries are open now through Yachtscoring, with an early bird rate of US$12 per foot for entries paid by 31 October 2026.
If you are coming from overseas, plan to arrive at least two days early. Boats need preparing, crews need sleep after long flights, and the south coast gets busier by the day once April starts.
The Antigua Classic Yacht Regatta comes first, from 14 to 19 April 2027
The Antigua Classic Yacht Regatta runs from 14 to 19 April 2027 at Nelson’s Dockyard, so the two regattas fill most of April between them. The Classics are the older sibling in spirit. According to the regatta’s own story, in the 1960s the crews of classic charter yachts in English Harbour raced each other down to Guadeloupe at the end of the season, and that informal race became Sailing Week. By the late 1980s the classics were being outnumbered by modern racing boats, and their skippers started a regatta of their own.
If you can, stay for both. Two weeks in April on the south coast is the best boat watching in the Caribbean, and a two week stay is exactly where an apartment with a kitchen beats a hotel room.
The Antigua Sailing Week 2027 schedule follows a new loop around the island
Antigua Sailing Week now runs as a destination regatta, with point to point racing or a cruise in company that takes the fleet around Antigua and stops at a different anchorage each day, instead of racing round the cans off the south coast all week. The 2026 edition was the first in this format. Boats left English Harbour and stopped at Nonsuch Bay, Little Jumby Bay and Ffryes Beach before returning to Nelson’s Dockyard, with beach games, sunsets and a farewell party along the way.
For 2027 the organisers say the destinations are still to be announced. Check the official schedule on sailingweek.com before you book anything that depends on where the fleet will be on a given night. This matters for where you stay. If the fleet is on the east coast at Nonsuch Bay one evening and the west coast at Ffryes the next, a base in the middle of the island is closer to both than a room in English Harbour.
Is Antigua windy in April? Yes, and the steady trade winds are why the regattas sail then
Antigua is windy in April, because the island sits in the path of the northeasterly trade winds, which blow steadily through the dry season from December to April. That reliable breeze is the reason both the Classic Yacht Regatta and Sailing Week are held at the end of the season. April is also one of the drier months, which helps if you are watching from a headland all day.
Pack a proper hat and reef safe sun cream, and expect breezy evenings on the hills. The wind that makes the racing good also makes the lookouts cool after dark.
Racing or watching in April 2027? Apartments go early for regatta weeks. Check your dates or message us for a two week quote.
Where to watch Antigua Sailing Week from land is Shirley Heights or the forts above English Harbour
The best places to watch Antigua Sailing Week from land are Shirley Heights Lookout and the hiking trails out to the old forts and headlands around English and Falmouth Harbours, according to the event’s official vantage points page. It names Carpenters Rock, about 15 minutes along the headland from Galleon Beach, Fort Charlotte on the same hike, and the Middle Ground Trail from Nelson’s Dockyard out past Fort Berkeley to Pigeon Point.
- Shirley Heights Lookout. The organisers describe a Sailing Week breakfast there on the first race day, with local food and bush tea from 8 am to 11 am and a clear view of the start lines below.
- The fort trails. Both routes end at a beach, Galleon Beach or Pigeon Point, so you can swim when the boats have gone past.
- From the air or the water. The Chase the Race programme has offered helicopter flights and catamaran trips that follow the fleet.
One caution from me. That vantage points page was written for racing off the south coast. With the new loop format, some days the fleet will be on the far side of the island, so match your viewing plans to the 2027 schedule once it is out.
The whole area around English Harbour sits inside Nelson’s Dockyard National Park, a UNESCO World Heritage Site. Give yourself an afternoon on a non racing day just to walk the dockyard itself. It is often described as the only continuously working Georgian dockyard in the world, and it looks even better with a forest of masts in front of it.
Where to stay for Antigua Sailing Week depends on your role in the regatta
Where to stay for Antigua Sailing Week depends on your role. Racing crews often sleep aboard, but owners, shore teams, families and spectators need a bed on land, and the rooms in English Harbour and Falmouth Harbour are the first to sell out and the most expensive during regatta weeks. A self catering apartment in central Antigua is about 20 minutes’ drive from Nelson’s Dockyard and usually a fraction of the harbour price.
| Where you stay | Distance to Nelson’s Dockyard | What it is like in regatta week |
|---|---|---|
| English Harbour and Falmouth Harbour | Walking distance | Right in the action, loud late into the night, booked months ahead |
| Jolly Harbour and the west coast | Around 30 to 40 minutes by car | Calm beaches, resort and villa prices, close to Ffryes Beach |
| St John’s | Around 30 minutes by car | Shops and the airport side of the island, no beach on the doorstep |
| Central Antigua (LambLion) | About 20 minutes by car | Quiet nights, a full kitchen and laundry, close to both coasts |
Drive times are approximate and grow on race days around English Harbour, so leave early. I have written a fuller island breakdown in where to stay in Antigua.
Staying ashore as a crew between boats or before delivery
Crew who arrive early to prepare a boat, or who are waiting on a delivery, need a real bed, a shower that works and a washing machine for salty kit. Every apartment at LambLion has free self service laundry, free Wi Fi and free parking, and the one bedroom twin apartments have two separate beds, which suits two crew sharing. If you are looking for a place on a boat, the official Sailing Week crew board is where skippers and sailors find each other.
Staying ashore as a family or a spectator
If you are here to watch a partner or a parent race, you want sleep, breakfast that is not a buffet, and a pool of options for the days you are not on a headland. The two bedroom apartments at LambLion sleep up to five with a full kitchen. On the days off, the beaches are around 15 minutes away and the rest of the island is open to you.
Staying on after the regatta
Plenty of sailors stay on for a week after the prize giving, when the island empties and the prices drop. That is when a self catering base really pays off. Our medium term apartments are set up for exactly that kind of slower stay, and if you are thinking even longer, read my guide to one month in Antigua.
Getting from central Antigua to English Harbour during Sailing Week takes about 20 minutes by car
Getting from LambLion in central Antigua to English Harbour during Sailing Week takes about 20 minutes by car, heading south through the villages to the coast. A hire car is the easiest way to do it, because you will want to move between the dockyard, the lookouts and the anchorages on your own schedule. Bring your home licence and budget for the temporary driving permit, which the Antigua and Barbuda Tourism Authority lists at EC$50.
If you plan to enjoy the evenings properly, do not drive. Book a taxi for the ride home, agree the fare before you get in, and ask Lionel and Lorilyn for a driver they trust. They have been helping guests get around the island for years.
A mast tree grows in the LambLion garden, and Lionel will tell you how it got there
A pair of tall, straight trees stands in the LambLion garden that Lionel Walker calls mast trees, grown from seeds a Grenadian guest brought when he lived in Antigua for a few years. I did not expect a sailing story on a garden walk. Lionel told it to me under the trees.
The nickname of these plants are mast, m a s t, mast or mast plant. The trunk of the tree stands so vertical, without having a lot of branches coming off of it, I think they use the trunk of this tree to make the mast of a ship.
Lionel Walker, co owner of LambLion
He planted the two at the same time. One grew bigger, the way two brothers do. Wherever their timber ended up in the old days, it is a good thing to stand under at the end of a race week, with a papaya from the next tree and nobody shouting about protests.
LambLion is family owned by Lionel and Lorilyn Walker, and it is Green Globe certified, with solar power, solar hot water and rainwater harvesting. That matters to sailors, who know better than most what plastic does to the sea. You can read how they run the place on the sustainability page, meet them properly in meet the family behind LambLion, or see my review on Hold The Throne.
What to do in Antigua on the days off the water during Sailing Week
The days off the water during Sailing Week are for the beaches, the dockyard, the market in St John’s and the music. Reggae in the Park, a mid regatta concert, has been an official Sailing Week event since 2010, held at the Nelson’s Dockyard Marina in recent years, so check whether it is on the 2027 programme.
- Walk Nelson’s Dockyard and the Dockyard Museum early, before the heat.
- Swim at Pigeon Point or Galleon Beach after a fort hike.
- Do a Friday or Saturday morning at the Public Market in St John’s, then stock the kitchen.
- Spend a slow morning in the LambLion garden picking what is ripe.
- Sunset at Shirley Heights on the Sunday.
April is also when the island’s sailing season peaks before summer. If you love the island’s event calendar, look at the Antigua Charter Yacht Show in December and Antigua Carnival in the summer too.
Those hoteliers in 1968 wanted sailors to stay a little longer. Do them the honour. Race hard, then give yourself a few quiet days in the middle of the island, where the only thing tacking is the breeze through the banana leaves.
Working the whole sailing season? Our page on yacht crew accommodation in Antigua covers longer stays for crews, brokers and contractors.
Book your Sailing Week base directly
Eleven self catering apartments about 20 minutes from Nelson’s Dockyard. Book two nights or more directly and get 15% off the nightly rate.