The Road to Havana


When Trump recently rolled back Obama’s initiatives to open lines of trade and communication with Cuba, he dashed many American’s dreams of visiting. For fifty years this fair land has been a tropical destination for everyone but America. Canadians love its close proximity – just 90 miles from Key West, Cuba is an easy three-hour flight from Toronto.

I’ve been enthralled with Cuba since my 20’s, since Buena Vista Social Club. I loved hearing my great aunt’s stories of her pre-Castro cruise trips to Havana, where she’d scour the flea markets for cool jewellery. I didn’t have the option to visit until becoming a citizen of Canada. I love a beach vacation, but I was especially interested in seeing Havana. In planning my first Cuban adventure I relied on the knowledge of my travel companion and frequent Cuba visitor from Travelful Life. We decided on the Melia Varadero, a popular beach resort along Cuba’s Hicacos Peninsula.

Varadero to Havana
If you’re staying in Varadero, you’re close enough for a day trip to Havana. Take a bus from your resort if you like the group tours, but I recommend hiring an English-speaking driver to take you for a private tour in a vintage car. (You can opt for the round trip drive and a self-guided tour.) Either way, agree to a fee in advance.

En route to Havana, do make a pit stop at Puente de Bacunayagua, located an hour outside of Varadero. Here you can stretch your legs, take some scenic photos (see video below) and enjoy one of their famous pina coladas. It’s also a good place to ogle classic cars if that’s your thing. (It’s totally my thing.)

In Havana we saw the most visible impact of Cuba’s political isolation. Decrepit infrastructure. Buildings falling down or halted in mid-construction. Kids hustling tourists in the street for money. But the beauty, the raw beauty of the streets, the music and the people was inspiring. There is an infectious joy to Havana, so slow down and dig in.


Hemingway legend is all over this city, the most famous being the Floridita where he drank 16 daiquiris with no sugar and double rum. While crowded and overpriced, you can at least revel in the air conditioning. Take a stroll along the Malecon, or scoot over to the Christ of Havana sculpture for a little perspective on life (he stands 15 meters tall).

No Logos
When I’m not vacationing, I spend a lot of time reading or talking about brand marketing. From that perspective it was jarring not to see Coca-Cola or Walmart everywhere. But I’m thrilled to have visited before U.S. corporations take root in Cuba. Some may mourn the end of an innocence when the (inevitable) American commercialization hits, but the Cuban people deserve more than an oppressive life in a 1950’s time capsule. In the meantime we can embrace them.

Well, we can. Sorry, America.

Downtime at the Drake Devonshire


Photo courtesy the Drake Devonshire

(This post was updated May 2017.)

The Drake Hotel often gets credited with helping draw people to an emerging West Queen West, that downtown Toronto strip of Queen just east of Dufferin. And deservingly so. Upon opening in 2004 it not only ushered in a new kind of boutique hotel experience, it set the stage for hipster lifestyle before hipsters even existed.

Less than a decade later the brand expanded to the financial district with a restaurant called Drake One Fifty. Last fall they did it again, this time in Prince Edward County – specifically Wellington, Ontario – with the Drake Devonshire. The brand’s extension into a lakefront inn has been done beautifully.

“The Drake Devonshire flirts with the luxury summer camp in English country house style.” ~ Paris Vogue

Prince Edward County offers a bounty of things to do in the summer – beaches, cycling, wine tasting, antiquing. But even if you don’t leave the hotel, your time at “Drake by the Lake” won’t be dull. The Drake brand is rooted in design, art, music and culinary excellence. There is always something happening.


photo by John Cullen | Travel + Leisure


As with the original Drake, the Devonshire’s guest rooms and suites come in all shapes and sizes. The rooms have been meticulously designed and outfitted with custom furniture and millwork, mixed with antiques and vintage pieces, and feature original artwork. Some even boast balconies that overlook the Lake and the property.

Fish Fry Friday

photo courtesy of Drake Devonshire


I met Matthew DeMille, Devonshire head chef, a man who brings plenty of big city experience and a wealth of knowledge on the local area. Everything is a nod to PEC. His ‘farm and lake to table’ philosophy extends all the way to featured wines from the region’s many wineries. There’s nothing precious about Drake’s food, not with special events like the Good Friday Fish Fry or a Terroir Run Pasta Party, but it aims to please. Don’t overlook their well-stocked beer list and cocktail program which is always ahead of the trend.


Here’s another thing Drake fans will recognize. The Devonshire features a rotating exhibit of work regularly with a new show installed every couple of months, as well as an ongoing Artist-in-Residence program. Even the guest rooms are an exhibition unto themselves.


Devonshire’s weekly calendar listings include open mic nights, live music performances and events like flow yoga. And since hipsters have babies too, they offer kid-friendly, mid-afternoon Highchair Hangouts for parents and little ones.

Room reservations and other Drake Devonshire information available here.