One of the things I like most about travelling is planning ahead. In fact, I can humbly say that my personalized maps and itineraries are famous among my friends. Planning a trip is an art–one I believe I’ve come to master and that requires the right balance between rest and adventure; between scoring that elusive restaurant reso and leaving room for spontaneous discoveries. Prince Edward County, set on expansive Lake Ontario–just two hours from Toronto and four from Montreal, embraces both mindsets. But still, it doesn’t hurt to come prepared. Thankfully, I’ve done all the work for you, with a four-day itinerary that maps out everything you should do and eat to experience the County at its very best.

Day 1

First things first, cocktails 

You likely already have a few hours of driving under your belt by the time you reach the County. Which is why, after exiting the 401, I recommend heading straight to the Drake Devonshire for lunch. Very few things say “we have arrived” more than the hot spot’s bright yellow parasols, mid-afternoon cocktails, and relaxing ambient wave sounds.

Some will swim and some will nap

Next, consider heading to your accommodation for a stretch and a nap. Better yet, you could do the same at Wellington Beach, a stony stretch of land that’s free on weekdays and open until 9:00 pm every night.

Time for dinner

After you’ve frolicked in the sun and water, head to nearby Lakeside Motel for dinner. The waterfront deck may be new, but it’s already a classic for casual fare and not-so-casual sunset views–the perfect way to end your first day.

Day 2

But first, coffee

Start your day with a light breakfast of coffee and pastries at PECish Baking Co. in Milford or Beacon Bike + Brew in Picton, then waste no time getting to Sandbanks Provincial Park. Make sure to reserve your daily access beforehand and remember that the earlier you get there, the better: not only to take advantage of the scenery for as long as you possibly can, but also to avoid long lineups at the entrance. The Dunes might be the most famous area of the park, but it’s The Outlet’s long stretches of sand that really do it for me.

Snack game strong

You might never want to leave the beach, but if the snacks you thoughtfully packed aren’t doing the trick anymore and you get a hankering for something more substantial to eat, you could do a lot worse than Firebird’s fire-roasted chicken and garlic butter buns at Lighthall Vineyard, or a platter of oysters and a generous portion of fish ‘n’ chips at Sand and Pearl. Wait, who am I kidding? You could hardly do better than that.

More oysters? Aw, shucks. Don’t mind if I do. 

Speaking of which, Kinsip House of Fine Spirits, in the heart of Bloomfield, is now serving oysters and cocktails every Friday from 2:00 pm ‘till sunset. In the team’s own words, “the view is killer and the cocktails are banging”. Make of that what you will, but I know what I’m doing with that intel.

Old-fashioned movie night

If you’ve still got it in you after another day of pure County fun, wrap up the night with a double feature under the stars at the Mustang Drive-In, a movie theatre that’s been around since the ‘50s. Best of all, there’s a snack bar for all your late-night cravings.

Day 3

Two-take Drake

Day 3 already! Phew. I hope you took a couple days off work, because you still got a lot to get to. For brunch, consider heading back to the Drake Devonshire. The menu is varied (and tempting) enough to justify repeated visits, and that view– you just won’t get enough of. Don’t forget to sneak in a subtle Instagram photo sesh before saying goodbye (or more accurately: “see you next year!”).

Cheers to that

Dedicate your afternoon to cider and wine tasting. Now, it would be impossible to list the bounty of cider houses and vineyards worth the detour in Prince Edward, but I like to start off light at Loch Mór with a sampling of sparkling dry cider, best enjoyed out in the orchard. Next, I’m most likely to hit up Morandin for a glass of rosé, Hinterland for some bubbly, Trail Estate for the best orange wines in the County (or is that country?), and Long Dog for gorgeous bottles of red to store away for the winter.

Did someone say snack time?

You didn’t think I’d let you drink all day without getting some food in you, did you? Out on the wine route, you’ll find J.K. Farm, where chef Jamie Kennedy is dedicating his considerable cooking dexterity to churning out the most delightful fries in the area. Meanwhile, at Grange Winery, mobile cocktail bar Old Salt is serving up creative drinks and dogs avec classe.

Fire, fire, tell me who will score a table tonight

I’d never ask you to choose between fries and hot dogs, but make sure you leave enough room for dinner, because you won’t want to miss this one. Let’s just say it’s a good thing the region’s vineyards all close around 5:00 pm, ’cause you’ll need to arrive early in the evening to score a table at Flame + Smith, “a sustainably minded restaurant that embraces the exciting art of wood-fire cooking” and surely one of the most popular eating destinations in the County.

Day 4

Out on the town

It’s our final day out here together, but that won’t keep us from making the most out of the time we’ve got. Indulge in a good ol’ diner breakfast of eggs and sausages or fluffy pancakes at The Vic Drive-In before deciding how you’re going to spend your last few hours. You could stroll through town one last time, lingering in curated boutiques like Kokito and Scandiskin or antique shops like the straightforwardly named Dead People’s Stuff. Or why not do…

One more round ‘fore we go

Check out a couple more cider and brew houses to stock up on your favourite local libations. FieldBird Farm and Cider, The County Cider Company, Slake Brewery, and Parsons Brewing Co. all come highly recommended.

Do we really have to leave?

No one would judge you for making a final pit stop at Bloomfield Public House for Judy’s Fried Chicken. After all, you’ve got a long road ahead of you. If you’re not hungry right then and there, but still want to take a piece of County living home with you, your final stop (I mean it) should be My Pies for sweet or savoury baked goods (or both).

There’s more

Of course there’s more. There’s always more. Guess you’ll just have to start planning next year’s trip. Or hey, maybe you could call in sick tomorrow…

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