No visit to Antigua is complete without taking in the sunset atop Shirley Heights Lookout at its weekly Sunday sundowner party. The view from Shirley Heights is without a doubt the most famous, most photographed, most celebrated vista gracing Antigua. Immediately below, English and Falmouth Harbours clutch their bays. On clear days you can see Guadeloupe to the south and Montserrat with it's still active volcano to the south west.
It does get busy, so expect a crowd and while there might be a couple locals sprinkled in here and there, it's mostly visitors. Around 7ish, the tunes crank up with either some reggae classics, some pumping soca, or even live a steelpan band.
Smoke from a collection of barbecues compete with the music to fill the air and stimulate your senses. Expect chicken and ribs slathered in local flavors, plus burgers for the less adventurous. I did have some trouble getting grilled fish on my last visit, but once I found some, it was charred to perfection.
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Come Ashore for Some Fun During Sailing Week
Antigua Sailing Week is about more than what happens out on the waters surrounding the island. Some of the hottest action actually occurs on terra firma.
In 2013, after a day rocking on the water under the sun, watching boats of all shape and size skim back and forth along the Antigua coast, I was super psyched to be climbing the rise to Shirley Heights just after sunset. Locals were strolling up the hill and in the distance music was thumping out of the darkness.
Our destination was a concert with Mr' Lova Lova himself, Shaggy. It seemed like half the island had come out, plus practically every Sailing Week visitor. The atmosphere was light, the English Harbour Rum was flowing, and the Wadadli's were tinkling.
In the end, I couldn't tell you what was more special about my Sailing Week day, the sailing or the Shaggy.
Shirley Heights is less a fort to explore and more of a sprawling military complex. Named after Sir Thomas Shirley, governor of the Leeward Islands and credited with strengthening Antigua's defenses in 1781, Shirley Heights was Britain's last stronghold in the Americas, along with Barbados, after they'd lost every other colony in the new world.
In those tumultuous times, Shirley Heights' formidable fortifications protected Antigua's large sugar-producing estates and the all-important dockyard where war ships and trading vessels docked, restocked, and left to sail the Caribbean for Britain's interests.
Today, the majority of the complex has long crumbled away, but it's definitely worth the visit. The main lookout is now a restaurant hosting a large weekly sunset party on Sunday as well as concerts, but beyond that history buffs walking these walls can come in contact with Antigua's rich history.
As far as I could tell, all of Antigua heads to Shirley Heights on a Sunday evening, and its no surprise why. An open air party atop a hill where the views are beautiful and the rum flows freely - the best night of my trip.
Around 5 o'clock I caught a taxi from my hotel. By that point it was already getting busy, with cars and minivans lining the side of the road - the excited atmosphere is probably worth getting there even earlier for.
Peruse the craft stands with a rum cocktail, grab some barbecue and settle down on the hill edge.
At the risk of sounding clichéd, the view is simply breathtaking - the island and its peripheral rocks spread out before you, the harbour lights blinking below, and of course the glorious pinky orange of the dusk sky.
The excitement builds as the sun gets lower and lower, cameras abound, and the flash of green as the sun disappears gets the party started.
As the guests move away from the cliff edge, the music gets louder and the dancing gets more and more energetic; the initial nervous divide between cautious tourists and locals disappears and soon the whole hilltop is dancing at singing at full volume to reggae classics.