In the summer of 2007 I set off to kayak around the whole of the Irish coastline, a distance of 1,000 miles. The challenges of the trip included 20ft-high Atlantic rollers, stretches of cliffs lasting for miles and no landing place, and paddling for seven hours or more to get from headland to headland or across Ireland's largest bays. Added to this, I did it during some of the worst weather on record. Not only did it rain incessantly from June to September, there were times when high winds pinned me ashore, sometimes for days on end.

These random strandings sometimes meant camping on remote peninsulas in a tiny, damp tent until the weather eased. But often I managed to make it to the shelter of remote villages, harbours or island communities and was able to find entertainment, warmth and welcome company in bars.

Rather than being frustrated by the vagaries of the weather and the long hold-ups I reverted to past habits and borrowed guitars to play in come-all-ye sessions or added my tales – looking around to find a shark as long as the kayak following me when off the Mayo coast, being caught in a gale and dragged out to sea in Dundalk Bay – to the stories told along counters over slowly sipped pints.

I finally completed the circuit of the world's 20th largest island in mid-September. It took me two and a half months to struggle round the first 500 miles from Mizen Head in the south to Ireland's most northerly point, Malin Head. But it took only two and a half weeks to paddle the second 500 from Malin down the east coast back to the Mizen. Either the weather was four times better in the second half of the circumnavigation, or I was four times fitter. Or, as someone else pointed out, perhaps there were four times fewer pubs to distract me.

The Jolly Roger, Sherkin Island, Roaringwater Bay, Co Cork

Photograph: Jasper Winn

You'll need to kayak out to the Jolly, or at least take the ferry from Baltimore, but once on the island you're in paradise. Ramble the fuchsia lined lanes, swim from Silver Strand or visit the ruins of the old abbey. Then head to the Jolly for a drink and very likely an informal music session. There are regular gigs from mainland bands and with its crosswords, games and fire it's just as – or even more – welcoming in the winter. I know this because I've spent several months over past winters on the island and the Jolly was the antidote to gales and rain.

• +353 (0)28 20379, facebook.com/thejollyrogerpub

Dick Mack's, Green Street, Dingle, Co Kerry

Dingle specialises in the traditional shop-bar … or is it bar-shop? Depends on whether you need a drink or to buy something. Dick Mack's is barely a leather-work workshop nowadays, though the tools, cutting board and bits and pieces are still there, but it is the best place for wildly creative talk about local myths, Fungi the dolphin, the time that Ryan's Daughter was filmed on the peninsula and the state of the world. Though it has few formal music sessions it's the kind of place where musicians on the way to gigs or winding down after playing strike up for the hell of it. Don't miss the handprints of famous visitors, Dolly Parton among them, pressed into the pavement at the door. My sea kayak circumnavigation of Ireland stalled here for several weeks and I spent many evenings with a borrowed guitar banging out old tunes.

• dickmacks.homestead.com

Gus O'Connor's, Doolin, Co Clare

Doolin is jumping off point for ferries out to the Aran Islands but it's long been known that there's as good or better traditional music here than on the mainland. The 150-year-old O'Connor's attracts a mix of tourists and Irish for the nightly sessions and though there's often a ballad with a "toorrah-loora, wack-for-me-diddly, tiggiddy-tiggidy-tora" chorus for anyone to join in with, the emphasis is on jigs and reels. Accordions, flutes and, invariably, fiddles ring the changes and keep toes tapping. And don't miss the local mussels in garlic with crusty bread.

• +353 (0)65 7074168, gusoconnorsdoolin.com

The Community Centre, Inishturk, Co Mayo

Inishturk island. Photograph: Alamy

Lying seven miles off-shore from the Mayo coast, Inishturk is one of Ireland's remotest inhabited islands, and the local community centre reflects that. Much more than a bar, it's where islanders and visitors come for a chat and often a late night dance to live traditional music. The 70 or so locals see plenty of visitors through the summer, especially when the harbour fills with boats for the July sailing regatta, but in winter the ferry can be delayed for days in poor weather. Not a bad place to get stranded at all, though, and when it's clear it has one of the best views from any pub, from high up on the island's coast.

• No contact details

McGowan's, Easkey, Co Sligo

The big Atlantic rollers meeting the shallowing seabed at Easkey have created one of Europe's newest surfing hotspots, with big waves to challenge the very best boarders. But the small rivers and streams behind the town have long been the haunt of game fishermen in pursuit of salmon. Surfers and line slingers meet up in McGowan's, a pub which took me straight back to my youth in the 70s. A pool table, boxes of Tayto crisps and regular low-key music sessions that might mix children still mastering the fiddle, banjo or "box" (accordion) with two or even three older generations. Nothing fancy here, but a warm welcome and great conversation. And don't miss the pottery next door – another McGowan is the craftswoman turning out gloriously glazed bowls, tea mugs and the like. I carried the porridge bowl I bought there round the rest of Ireland, and still use it today.

• No contact details

Farran's, Malin Head, Co Donegal

Ireland's most northerly pub, and one of the friendliest. I spent a number of long days here waiting for winds to die so I could continue round Malin Head. There was always easy, rolling conversation, a shared crossword passed back and forth along the counter and plenty of opinions – mainly pessimistic, and correct – about the weather. A brisk walk out to the tip of the head itself is a great observatory for spotting gannets, shearwaters, skuas and other sea birds, and occasionally migrating whales. In the mythology of modern Ireland, Farran's is one of the rare pubs where you'll get a "perfect" pint. I'm not usually a stout drinker, but still had to try a couple, and they were pretty fine.

• No contact details

Fullerton Arms, Ballintoy, Co Antrim

Location, location, location. This stretch of coast is home to the Giant's Causeway, and the Carrick-A-Rede rope bridge – which is just that; a rope bridge over a dizzying sea channel separating a tiny island from the cliffs. The Bushmills Distillery is just up the road, too, making the Fullerton Arms a perfect end of day target after doing "the circuit". It's just above Ballintoy's picture-perfect harbour which on a sunny day feels like a tiny Mediterranean cove, though far less so in grey and blustery weather; I was there on a good day and have warm memories. The Fullerton doesn't miss many tricks; there's accommodation and a restaurant as well as live music in the evenings, which is always cheering after a long day.

• + 44 (0)28 2076 9613, fullertonarms.com. Rooms from £35pp pn

The Bloody Stream, Howth, Co Dublin

Howth, on the north side of Dublin Bay, is joined to the mainland by so thin and brittle a stalk of land it's almost an island. And rather a posh one at that, home to the Howth Sailing Club and U2's drummer Larry Mullen, not to mention WB Yeats in times gone by. But the Bloody Stream is a welcome and welcoming pub, right next to the Dart station if you're coming from Dublin rather than arriving by kayak. The flagstone floors, open fire and jumble of bygones are a great setting for seafood dishes and live music – not just traditional sessions but blues and jazz as well. And for those rare days of sun and balmy breezes there's a Mediterranean garden.

• +353 (0)1 839 5076, thebloodystream.com

Rockett's of The Metal Man, Westown, Tramore, Co Waterford

This pub is named after the "metal man", a dashing figure in 19th-century sailor's outfit who stands atop one of three warning pillars erected by Lloyd's of London high on the cliffs above this treacherous stretch of coast. I spotted him from far out at sea and was drawn in to take a closer look – rather defeating the purpose of the warning. Rockett's speciality is traditional dishes, and particularly crubeens, pigs' trotters boiled into a gloriously rich and gelatinous finger-food. This is the kind of rib-sticking bar food that was popular before more fancy stuff came along and is still perfect after a day walking the cliffs or on the water.

• +353 (0)51 381 496

Mary Ann's, Castletownshend, Co Cork

Photograph: Alamy

I started and finished my circumnavigation of Ireland in Castlehaven, and knew Mary Ann's from years before. And so have many others; it's not unusual for people to drive from Dublin to eat from the Egon Ronay award-winning bar and restaurant menus, and it's a byword for seafood (particularly lobster) among visiting yacht crews. But it's also a busy bar, especially in the summer regatta and sailing season. Winters are kept lively through wine tasting evenings and openings at the attached art gallery. No better place to end – or start – a long trip, however you're travelling.

•+353 (0)28 36146, westcorkweek.com/maryanns

• Paddle: A long way around Ireland by Jasper Winn (published by Sort of Books, £8.99)