Tony Bennett famously sang that he left his heart in San Francisco. A cliché, yes, but we—and the 16 million tourists who flock here annually—totally get it. Between riding historic trolley cars, wandering the labyrinth streets of Chinatown and playing peekaboo with the Golden Gate Bridge through a gauzy layer of fog, the city’s charms remain forever alluring.

But rather than surrender your heart to San Francisco, why not reclaim your ticker and make it beat even faster by biking and hiking the city’s steep hills, or paddling its picturesque bay? Trust us: San Francisco’s attractions look even better when you work for them. 

Day One 

Morning Leave your retro digs at Hotel Vertigo and walk to Flour & Co. for a satisfying breakfast of homemade muesli. From there, hop on a cable car and ride it down Hyde Street to Blazing Saddles Bike Rentals & Tours, just up from Hyde Street Pier. Saddle up on a rental bicycle and join a guided tour—or choose the self-guided option. Pedal past the million-dollar homes along Marina Boulevard and through Crissy Field, part of the Golden Gate National Recreation Area, to the iconic Golden Gate Bridge. Stick to the bike lane and ride across the city’s most-photographed landmark, but be sure to take in the stunning views of Alcatraz, the city skyline and the frothy bay below.

Afternoon Coast in to sunny Sausalito, a tourist town known for its boutiques, restaurants and consistently better weather than San Fran. Make your first stop the ferry terminal to secure your (and your bike’s) passage back downtown. Next, find a spot on the patio at Salsalito Taco Shop and settle in for some Baja-style fish tacos before hopping on the return ferry. Tip: Plan this 13-kilometre bike trip during the week to avoid the throngs of weekend cyclists.

Evening Dive in to the city’s cocktail history on a Union Square Craft Cocktail Tour with Avital Tours. You’ll explore speakeasy-style taverns and posh hotel bars on the search for the best Poquito Picante or Pisco Punch, San Francisco’s signature drink. To prevent all that booze from going to your head, fill up on a delicious, steaming bowl of ramen from Katana-ya afterward—it’s worth the wait.


Day Two 

Morning Take it easy on an Urban Safari, an off-the-wall tour where you don goofy field hats while exploring San Francisco and viewing its native species (humans) from the comfort of a modified zebra-striped Ford. Highlights include a stop at the Palace of Fine Arts Theatre, set adjacent to a lovely lagoon on the eastern edge of the Presidio, and lunch at Harvest Ranch Market. 

Afternoon Tackle a few of San Francisco’s 43 hills with Urban Hiker, a hiking outfit that explores the hidden stairways and paths that wind up the city’s steep topography. Starting from local landmark The Castro Theatre, climb 282 metres to the top of Twin Peaks, then descend through a eucalyptus forest and give your legs a final workout stepping down the crumbling Pemberton Place Stairs (210 in all).

Evening From the Castro District, ride a refurbished antique trolley down Market Street, get off at Gough, and walk three blocks to rustic-yet-refined Rich Table. Open your palate to the restaurant’s unusual flavour combinations.

Day Three 

Morning Start your day at the bustling Ferry Building Marketplace, a locavore’s delight with vendors selling everything from fresh artisan bread to locally made honey. Fill up on a bowl of Broken Farro Porridge at Il Cane Rosso before boarding a ferry back to Sausalito. Once there, it’s a quick cab ride to Sea Trek Kayak and Stand Up Paddling Centre for a guided paddle to the underbelly of the Golden Gate Bridge. Along the way, spot harbour porpoises and seals cavorting in the bay, admire sprawling hillside homes and come to understand why only one prisoner ever successfully escaped from Alcatraz (or so legend has it) by swimming through the choppy water to the fog-shrouded city across the bay.

Evening After a much-needed nap, make your way to the Mission District for dinner at Foreign Cinema, a restaurant that serves Californian and Mediterranean-inspired cuisine in a converted theatre space. For dessert, try the chevre cheesecake—it’s so rich and creamy, you may just leave your heart in San Francisco after all.

Getting There: WestJet flies to San Francisco twice a day from Calgary and Vancouver starting May 3, 2015.