Date ideas in Toronto: 19 ideas from the islands to Casa Loma

• Budgetfree to medium
• Best forfirst date
• Time1 to 2 hours
• WhereOld Town, east of downtown

The old Gooderham and Worts distillery is now a pedestrian-only maze of cobblestone lanes and red-brick Victorian buildings full of galleries, small shops, cafés and restaurants. It looks great in every season, and because there are no cars, you can stroll and talk without dodging traffic. It's one of those places where a 20 minute coffee can quietly turn into dinner.

Tip: Agree on one exact meeting point beforehand, since the lanes look alike and it's easy to miss each other. If it rains, the covered courtyards and galleries still work.

• Budgetlow
• Best forfirst date, foodies
• Time1 to 2 hours
• WhereKensington Market, west of Spadina

Kensington Market isn't a single market but a small neighborhood of narrow streets, vintage shops, bakeries, cheese shops and food counters from all over the world. It's colorful, a little chaotic and very Toronto. Sharing a few snacks from different places takes the pressure off a sit-down dinner and gives you plenty to compare.

Tip: Walk south afterwards and cross Queen Street West to find Graffiti Alley, a lane packed with murals that changes all the time. On some summer Sundays the market streets close to cars, which makes it even more fun.

• Budgetlow to medium
• Best forfirst or second date, daytime
• WhereFront Street East, Old Town

St. Lawrence Market has been at the heart of Toronto's food life since the 1800s. The main hall is full of bakers, butchers, cheesemongers and lunch counters, and it's where many locals send visitors for their first peameal bacon sandwich, a Toronto classic. It's lively, cheap and casual, so it's a good format for a daytime first date.

Tip: Buy one thing each without telling the other, then swap. Saturdays are busiest, so a weekday lunch is calmer. The Distillery District is a short walk east if you want to keep going.

• Budgetlow
• Best forromantic, summer
• Timehalf a day
• WhereJack Layton Ferry Terminal, foot of Bay Street

The Toronto Islands are a chain of small islands just across the harbor, and they feel like a holiday 15 minutes from downtown. There are no cars, just paths, beaches, little cottages and lake views. Ward's Island is the quietest part: walk the boardwalk along the lakeshore, then head to the harbor side as the sun goes down. The view back to the skyline from here is the one on every Toronto postcard.

Tip: Pack a picnic and a blanket, since food options on the islands are limited. On hot summer weekends the ferry lines can get long, so go early or on a weekday evening. Centre Island and Hanlan's Point are reachable by other ferries from the same terminal.

• Budgetfree
• Best forfirst date, cheap
• Time1 hour
• WhereQueens Quay West, Harbourfront

This small park on the waterfront was designed together with the cellist Yo-Yo Ma and is based on Bach's first Suite for unaccompanied cello. Each part of the garden stands for one movement of the music, from a swirling riverscape to a grassy amphitheater. It's quiet, unusual and right by the lake, a lovely place for a slow walk and a conversation.

Tip: Play the suite quietly on your phone as you walk from section to section. In summer, the garden usually hosts free concerts, so check the Harbourfront Centre program. Afterwards, follow Queens Quay along the water for a drink.

• Budgetfree
• Best foractive, day date
• Timehalf a day
• WhereBluffer's Park, Scarborough

On the eastern edge of the city, pale cliffs rise high above Lake Ontario. Bluffer's Park at the bottom has a beach, a marina and paths where the cliffs tower over you. It's the kind of view people don't expect from Toronto, and it makes a good date for a couple who likes to get out of the downtown bubble.

Tip: Getting there takes a while by transit, so make a day of it and bring snacks. Stay on the marked paths and don't climb on or near the cliff edges, as the bluffs are fragile and erode.

• Budgetfree
• Best forromantic, evening
• Time1 hour
• WhereBroadview Avenue, Riverdale

The hill in Riverdale Park East faces west across the Don Valley, and at sunset the whole downtown skyline turns gold and then sparkles. It's a local favorite rather than a tourist spot, which makes it feel like a small secret. Afterwards, walk up Broadview to the Danforth, Toronto's Greektown, for something to eat.

Tip: Bring a blanket and something warm to drink. Arrive a little before sunset to grab a spot on the slope, especially on warm summer evenings.

• Budgetmedium
• Best forspecial occasion, third date
• Time2 to 3 hours
• WhereCasa Loma, Midtown

Casa Loma is a real castle in the middle of a residential neighborhood, built in the early 1900s for the financier Sir Henry Pellatt. You can explore towers, a long underground tunnel, secret passages and terraced gardens with views over the city. It's a little over the top, which is exactly why it works as a date.

Tip: Climb the towers first while you still have energy. In the warmer months the gardens are the prettiest part. The castle also hosts seasonal events, so check what's on before you book.

• Budgetsplurge
• Best foradventurous couples, anniversary
• Timeabout 1.5 hours
• WhereCN Tower, downtown

EdgeWalk is a hands-free walk on a ledge around the very top of the CN Tower's main pod, more than 350 meters above the ground, attached to an overhead rail. You lean back over the city on purpose. It's expensive and absolutely not for everyone, but if both of you love a thrill, you'll talk about it for years.

Tip: EdgeWalk usually runs only in the warmer months and depends on the weather, so book ahead and have a backup plan. For a calmer version, the glass floor on the observation level gives you the vertigo without the harness.

• Budgetmedium
• Best forrainy day, second date
• Time2 hours
• WhereDundas Street West, Grange Park

The Art Gallery of Ontario is one of the largest art museums in North America, and its building, redesigned by Frank Gehry, is worth the visit on its own. Walk the long wooden Galleria Italia, climb the twisting staircase and look for the large Canadian collection, including the painters of the Group of Seven. There's more than enough for an afternoon, so choose a few rooms and take your time.

Tip: Each pick a painting the other person would "definitely hang above the couch" and explain why. Grange Park behind the gallery is nice for a short walk if the rain stops.

• Budgetmedium
• Best forrainy day, curious couples
• Time2 hours
• WhereBloor Street West, Queen's Park

The Royal Ontario Museum mixes natural history and world cultures, from dinosaur skeletons to ancient Egypt. Its jagged glass and aluminum extension, known as the Crystal, juts out over Bloor Street and is a landmark in itself. It's an easy date because there's always something to wonder about, laugh about or argue over.

Tip: Challenge each other to find the strangest object in the museum within 30 minutes. Yorkville, with its cafés, is right next door for afterwards.

• Budgetlow
• Best forrainy day, quirky
• Time1 to 1.5 hours
• WhereBloor Street West, near St. George

A whole museum about shoes sounds niche until you're in it. The collection covers footwear from around the world and across centuries, from ancient sandals to celebrity boots, in a building that is itself shaped a bit like a shoebox. It's small enough for an hour and surprising enough to give you conversation for the rest of the day.

Tip: Combine it with the ROM, which is just a few minutes' walk east along Bloor. Guess which era each pair is from before you read the label.

• Budgetfree
• Best forrainy day, cheap, winter
• Time1 hour
• WhereAllan Gardens, Garden District

The Allan Gardens Conservatory is a set of historic greenhouses downtown, with a domed Palm House from 1910 at its heart. Inside you'll find tropical plants, orchids, cacti and seasonal flower shows, and it's warm and green even in January. Entry is free, which makes it one of the best low-key dates in the city.

Tip: Go on a cold or grey day for the full effect of stepping into the heat. The Palm House reopened after a long restoration, so check the City of Toronto website for current details.

• Budgetlow to medium
• Best forsecond date, music lovers
• WhereQueen Street West, near Osgoode

The Rex Hotel Jazz and Blues Bar on Queen Street West has been one of Toronto's best-known jazz rooms for decades, with live music almost every night of the week. It's relaxed, a bit worn in the best way and full of people who are there for the music. The sets give you a natural rhythm: listen, talk in the breaks, decide if you stay for another.

Tip: Check the schedule online and arrive early for a good table on weekends. Queen West is great for a late walk afterwards.

• Budgetmedium
• Best forsummer, sports fans
• Time3 hours
• WhereRogers Centre, next to the CN Tower

A baseball game is one of the best dates for talkers: the pace is slow, there's plenty of time between the action and the crowd does the cheering for you. The Rogers Centre has a retractable roof, so the game goes on even when the weather doesn't cooperate. Hot dogs and a shared bag of peanuts are part of the deal.

Tip: If one of you doesn't know the rules, let the other explain them. It's an easy way to see how your date teaches, jokes and handles a little confusion.

• Budgetfree
• Best forspring, romantic
• Time2 hours
• WhereHigh Park, west end

High Park is one of Toronto's biggest parks, with trails, a pond and woodland. In spring, its cherry trees, many of them a gift from Japan, bloom for a short window and turn the area near Grenadier Pond pink. It's beautiful, but also very popular, so the best version of this date is early in the morning.

Tip: Bloom times change every year, so watch for updates in late April and early May. Afterwards, walk down to Roncesvalles Village for brunch.

• Budgetfree
• Best forfall, outdoors
• Timehalf a day
• WhereBayview Avenue, Don Valley

An old brick factory in the Don Valley has been turned into a community space with gardens, wetlands and trails around the former quarry. In October the ravines around it glow red and orange, and on Saturdays there's usually a farmers market. It's a reminder that Toronto has a whole network of green valleys running through it.

Tip: Bring good shoes for the trails and a coffee from the market. You can link it with a walk through the Don Valley ravine paths if you're both up for more.

• Budgetfree
• Best forfall, night owls
• Timeone long night
• Whereall over the city

Nuit Blanche is a free, all-night contemporary art event that usually takes place on a Saturday in early October, from evening until sunrise. Installations, light shows and performances pop up across the city, and the streets are full of people wandering from one to the next. It's a date with built-in adventure and plenty of excuses to stay out late.

Tip: Pick one area instead of trying to see everything, and bring layers because October nights get cold. Watching the sunrise together at the end is the bonus round.

• Budgetfree to low
• Best forwinter, playful
• WhereNathan Phillips Square, City Hall

In winter, the reflecting pool in front of City Hall turns into an outdoor rink under the arches, right next to the big Toronto sign. Skating is free if you bring your own skates, and rentals are usually available. Down by the lake, the Natrel Rink at Harbourfront is another lovely option. In December, the Distillery District usually hosts a Christmas market with lights and warm drinks, which makes a perfect second stop.

Tip: Skating is the best excuse to hold hands that winter has to offer. If one of you is a beginner, say so early and laugh about it. Warm up afterwards in the PATH, the underground walkway network, or in a café nearby.