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Anniversaries and date nights: a black car makes the evening

A date night by black car is an evening with no parking, no driving after the wine and no phone at 11 p.m. — a bar, a table, a view, and a car that waits on the corner the restaurant's door faces. Here is the evening from the chauffeurs who drive it, from the first anniversary's dinner to the fiftieth's drive along the lake.

Weddings, proms & celebrations · · 9 min read

The date night, in one paragraph

An anniversary or a date night by black car is a three-act evening — a bar (the Four Seasons' d|bar, the Ritz's DEQ, Bar Raval, the Park Hyatt's Writers Room), a dinner (the fine dining article's tasting rooms, Canoe's 54th floor, the CN Tower's 360, Scaramouche's hill, a neighbourhood room), and a nightcap or a view (the Library Bar, a rooftop, the Bluffs at sunset, the waterfront's promenade, the Christmas lights in December, the fall colours in October) — on the hourly with the chauffeur waiting at each door, or the dinner alone on two transfers; the theatre or a concert as the second act (the theatre district article, the concert article); the hotel night in the city for a 905 couple (the Toronto luxury hotels guide); the flowers and the champagne in the car (the champagne under a licensed stretch's rules, the flowers in any vehicle); the surprise the chauffeur keeps; the babysitter's curfew as the return's fixed point; and the milestones — the first anniversary's dinner, the tenth's hotel night, the fiftieth's drive — each with its own evening. The proposal planning article covers the date night that becomes one.

The date night is the black car's most private booking — two people, an evening, and a car whose whole purpose is that neither of them drives, parks, checks a phone or waits on a corner — and the chauffeurs who drive them have learned its shape: the bar at 6:30, the table at 7:30, the nightcap or the view at 10:30, the home or the hotel at midnight, and the small things (the flowers on the seat, the champagne in a licensed stretch, the route past the lake, the surprise kept from the passenger who does not know where the evening ends). This guide covers the three-act evening and its rooms, the drives that make an evening, the theatre and the concert as the second act, the hotel night, the flowers and the champagne, the surprise, the babysitter's curfew, the hourly versus two transfers, the seasons' evenings, the milestones, the 905 couple's night in the city, and a worked anniversary.

A couple stepping from a black sedan outside a Yorkville restaurant on an evening out
A couple stepping from a black sedan outside a Yorkville restaurant on an evening out

The three-act evening

Act one, the bar (6:30): d|bar at the Four Seasons (the Four Seasons article's porte-cochère), the DEQ terrace at the Ritz (the Wellington driveway), Bar Raval on College (College's curb off-peak), the Writers Room at the Park Hyatt (the Hazelton and Park Hyatt article's lay-by), the Library Bar at the Royal York, Civil Liberties on Bloor — a drink, forty-five minutes, the chauffeur on the corner. Act two, the dinner (7:30): the fine dining article's rooms and their corners — Alo's Spadina, Edulis's Niagara Street, Canoe's Wellington, Scaramouche's Benvenuto driveway (the view from the hill), Don Alfonso's Westin, the 360 at the CN Tower (the CN Tower loop article's Bremner) — or a neighbourhood room the couple loves (the Yorkville guide's, the Beaches and Leslieville guide's, the Bloor West and High Park guide's). Act three, the nightcap or the view (10:30): a rooftop (the Thompson's, the Broadview's), a hotel bar, or a drive — below. The hourly holds the three acts and the hourly vs point-to-point article says it beats three transfers by the second.

The drives that make an evening

The evening's third act can be a drive rather than a room: the Scarborough Bluffs at sunset (the Scarborough guide's Bluffer's Park and the Rosetta McClain Gardens' lookout — twenty minutes from downtown along Kingston Road, the lake and the cliffs, the car waiting), the waterfront (the Harbourfront guide's promenade from the Music Garden to Sugar Beach, a walk with the car following to the next cross street), the Christmas lights (the Christmas Market and holiday events article's two-hour light drive through the Beaches, Kingston Road and Forest Hill), the fall colours (the fall colours article's Don Valley and the Humber's ravines in October, or the Caledon hills an hour north), the Humber Bay's skyline view (the Etobicoke guide's Humber Bay Park at night, the city across the water), High Park's cherry blossoms (the Bloor West and High Park guide's fortnight in May, at dusk when the crowd has gone), and the Toronto Islands' last ferry (the Islands article's skyline from the water). A chauffeur who is told "somewhere with a view after dinner" has a list.

The theatre and the concert as the second act

The dinner at 5:30 and the show at 8 — the theatre district article's Mirvish theatres and their side streets, the Four Seasons Centre's opera and ballet with the University lay-by, Roy Thomson Hall's and Massey Hall's concerts (the concert article), Koerner Hall's chamber music, a summer night at the Budweiser Stage — and the nightcap after; the chauffeur knows the show's running time, waits on the side street from ten minutes before the curtain-down, and the date night's three acts become four with the hourly holding them.

A couple looking at the Toronto skyline from a lakeside lookout at dusk with a black car behind
A couple looking at the Toronto skyline from a lakeside lookout at dusk with a black car behind

The hotel night in the city

A couple from Oakville, Markham or Whitby whose anniversary is a night in the city — the Four Seasons, the Hazelton, the Ritz, the Shangri-La, the St. Regis, the Park Hyatt, the Broadview, the Drake (the Toronto luxury hotels guide's doors) — books the car from home to the hotel's porte-cochère at 4, the evening's three acts from the hotel, and the drive home after breakfast; the cities pages cover the routes, the 407 article's toll road the Friday afternoon's shortcut from Markham, and the hotel's bell staff the bags and the flowers the chauffeur brought. The visiting clients itinerary article's hospitality pattern is the couple's own, at home.

The flowers and the champagne

The flowers on the back seat when the passenger is collected — a bouquet the booker had delivered to dispatch that afternoon, or one the chauffeur collected from a florist on the route (the Yorkville guide's and the midtown guide's florists) — are the date night's easiest gesture and any vehicle carries them; the champagne is the stag and bachelorette article's rule — a licensed stretch or a licensed limousine only, iced, with two glasses, and the stretch limo page says which vehicles carry the licence; a couple in a sedan toasts at the table. The in-car amenities article covers the water, the tissues and the phone charger every vehicle carries, and the music the passenger chooses.

The surprise

Half of date nights are surprises — one partner books, the other is told "be ready at 6" — and the chauffeur keeps it: the destination is not on the confirmation the surprised partner sees (the booker's phone gets the itinerary; the passenger's gets "your chauffeur is [name], arriving 6"), the chauffeur says "good evening" and nothing about where, the flowers are on the seat, and the route is the booker's; a surprise that is a proposal is the proposal planning article's, with the ring in the booker's pocket and the photographer at the lookout. The privacy and discretion article's standard covers a surprise as it covers a board's secret.

The babysitter's curfew

A couple with children has a fixed point the chauffeur plans around — the babysitter's midnight, the grandparents' 11 — and the evening's third act ends at the corner at 11:15 for a 11:45 home; the hourly's end is set at booking and a text at 10:45 ("last drink, home by 11:45") keeps it; the child seats article covers the car seats that stay in the family's own car and not in the date night's.

The hourly versus two transfers

The dinner alone — the home to the restaurant's corner, the corner to the home — is two transfers and the hourly vs point-to-point article says so; the moment the bar before or the nightcap after is added, the hourly's four or five hours beat three transfers, the chauffeur's waiting is included, and the coats stay in the car; the how much does a black car cost article works both and the engine quotes them for the date. A couple in Yorkville dining at Sotto Sotto walks two minutes and a chauffeur says so; a couple in Leslieville dining at Scaramouche books the hourly.

The seasons' evenings

Spring: High Park's blossoms at dusk, the patios' first evenings, a Blue Jays afternoon game as the first act (the Rogers Centre guide). Summer: the waterfront's promenade, the Islands' last ferry, a Budweiser Stage concert, the Bluffs at a 9 p.m. sunset, the Caribbean Carnival's fete for a couple who dance. Fall: the fall colours drive, the TIFF screening, the Nuit Blanche walk, a Leafs game (the Leafs article). Winter: the Christmas lights drive, the Nutcracker, the skating at Nathan Phillips Square, the New Year's Eve dinner, a January hotel night when the city is quiet and the winter driving article's chauffeur drives the snow. Valentine's Day (February 14 — the rooms and the fleet booked three weeks ahead, the how early to book article's peak logic) is the date night's own holiday.

The milestones

The first anniversary: the restaurant of the first date, or the wedding's venue's room (the wedding venues article), the same chauffeur if the wedding's was ours. The tenth: the hotel night in the city, the tasting menu, the drive to the lookout. The twenty-fifth: the family's dinner in a private room (the fine dining article's chef's tables) with the children's cars, and the couple's car alone after. The fiftieth: the drive — the neighbourhood the couple married in, the church, the first apartment, the lake — on an afternoon hourly with the accessible service article's vehicle if it is needed, an early dinner, and the family waiting at home; the chauffeurs who drive fiftieths say they are the evenings they remember.

The 905 couple's night in the city

A couple from Oakville, Burlington, Mississauga, Vaughan, Markham, Richmond Hill, Pickering, Ajax or Whitby (the cities pages) whose date night is the city: the car from home at 5:30 (the QEW, the 401, the 407 — the rush hour article's Friday), the three acts downtown, and the drive home at midnight with the chauffeur on the empty highway while the couple sit in the back — or the hotel night; the long-distance vs flying article's arithmetic does not apply (it is forty minutes), but the Niagara wine tour article's day and the Prince Edward County article's weekend are the date nights that leave the city.

A worked anniversary

A couple from Leaside, their tenth, a Saturday in October. 4:00 p.m.: the Leaside home to the Hazelton's forecourt in an S-Class — the bags, and the flowers the husband had dispatch collect from a Yorkville florist on the seat (the surprise: she knew about the dinner, not the hotel). 6:30: the Hazelton to the Park Hyatt's Writers Room — a four-minute drive the chauffeur suggested walking; they walked. 7:30: the Park Hyatt's lay-by to Scaramouche — the Benvenuto's driveway on the hill, the city below. 10:20: collected in the driveway; the fall colours drive — Avenue Road north, the Nordheimer ravine's edge, Bayview through the Don Valley in the dark with the leaves in the headlights, the Brick Works, and back to Yorkville by 11. 11:05: the Hazelton. Sunday 11: brunch on Yorkville Avenue; noon: Leaside. Six hours on the Saturday's hourly, one surprise kept, one drive in the dark, and a chauffeur who was asked for the twentieth.

Date night quick reference

ActOptionsThe car
The bar (6:30)dbar, DEQ, Bar Raval, the Writers Room, the Library Bar, Civil LibertiesThe hotel's door or the corner; 45 min
The dinner (7:30)The tasting rooms; Canoe; the 360; Scaramouche; a neighbourhood roomThe room's corner; 2–3 h
The view / nightcap (10:30)A rooftop; a hotel bar; the Bluffs; the waterfront; the lights; the colours; Humber BayA drive on the hourly
The second act (alternative)The theatre, the opera, a concertThe side street at the curtain-down
The hotel nightFour Seasons, Hazelton, Ritz, Shangri-La, St. Regis, Park Hyatt, Broadview, DrakeHome → porte-cochère at 4; home after breakfast
Flowers / champagneFlowers in any vehicle; champagne in a licensed stretch onlyCollected from a florist on the route
The surpriseThe destination on the booker's phone onlyThe chauffeur says nothing
The curfewThe babysitter's midnightThe hourly's end set at booking
Hourly vs transfersDinner alone: two transfers; with a bar or a nightcap: the hourly—
Milestones1st: the first date's room; 10th: the hotel night; 25th: the private room; 50th: the drive—

Booking the evening

The hourly chauffeur page books the three acts; the engine takes the surprise's itinerary on the booker's side only; the fine dining article names the rooms and their corners; the stretch limo page the champagne's vehicle. Book Valentine's and the December Saturdays three weeks ahead.

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FAQ

Questions we are asked

How does a surprise date night work?

The booker's phone gets the itinerary; the surprised partner's gets only the chauffeur's name and the pickup time; the chauffeur says 'good evening' and nothing about where; the flowers are on the seat; and a surprise that is a proposal has the photographer waiting at the lookout.

Can we have champagne in the car?

In a licensed stretch limousine, yes — iced, with two glasses; not in a sedan or an SUV under Ontario's law, where the toast waits for the table. Flowers ride in any vehicle, collected from a florist on the route.

Where is a good view after dinner?

The Scarborough Bluffs' lookouts at sunset, the waterfront's promenade with the car following, Humber Bay Park's skyline at night, High Park's cherry trees at dusk in May, the Don Valley's fall colours in October, the Christmas lights in December — a chauffeur told 'somewhere with a view' has the list.

Is the hourly worth it for a date night?

For a bar, the dinner and a nightcap or a drive — yes, by the second stop, with the waiting included and the coats in the car; for the dinner alone, two transfers, and a couple in Yorkville dining two minutes away walks.

What do you do for a fiftieth anniversary?

The drive — the neighbourhood the couple married in, the church, the first apartment, the lake — on an afternoon hourly with an accessible vehicle if it is needed, an early dinner, and the family waiting at home; the chauffeurs say they are the evenings they remember.

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