Monday, August 2 is a holiday in Ontario (the Civic Holiday), so it's a long weekend on the Toronto side too. Build the Monday in: it's the day people remember. It's also Toronto Caribbean Carnival weekend, with the Grand Parade on the Saturday: the city is full, loud and delicious, so book rooms and flights early.
I'm turning 40 back home in Canada, and I want the people I actually like in one city for five days. Here's the whole plan, in the open. Come to all of it, or come to the parts you want.
This is not a wedding. There is no head table and no seating chart. Every time slot below tells you two things: where I'll be, and what else is going on if that's not your thing.
Every block says exactly where I'll be. Shadow me all five days and you'll never have to ask. Peel off whenever you want and nobody's feelings get hurt.
Late riser, early sleeper, don't drink, can't walk far, travelling with a four-year-old. There's something in every block that works for you.
Friday evening: dinner at the top of the CN Tower. That's the one. Everything else on this page is a suggestion.
Five days across, times down the side. Red means I need a headcount for it, or it's a hard time you should not miss. Dashed means an open block — show up and do your own thing. Meals are marked with a fork. Tap anything to jump to the detail.
Swipe the board→
For a few meals and one afternoon there are two good options, and I'd rather go where the crowd is. Tap one in each. You can change your mind right up to the day.
Everything except Niagara is within a short, flat walk of the hotel. Maps open in your phone.
Where most of us are staying, a block from the CN Tower and five minutes from Union Station. Group rate and booking link coming.
The birthday dinner. Revolving floor, the whole skyline, observation deck and glass floor included. The date is open for us; the contract gets signed once the headcount settles.
The Jays watch party. Which room we take depends on how many of you tick the box, so tick the box. Five minutes' walk from the hotel, kids welcome, mocktails in the fridge.
The coach drops and collects here. Level ground at the edge of the Horseshoe Falls, with washrooms, a restaurant and free loaner wheelchairs.
No ticket, no registry, no deposit. I need three numbers: how many for the Friday dinner, how many seats on the Saturday coach, and how many for the Sunday watch party. Tick what you're in for, and change it any time; this page remembers you.
— people on the list so far.
Thursday, July 29 through Monday, August 2, 2027. My birthday is the Friday, and the birthday dinner at 360, the restaurant at the top of the CN Tower, is that evening. Thursday and Monday are quiet days for whoever's around.
If you can only do part of it, Friday through Sunday is the core. If you can stretch it, stay through Monday — Monday flights are usually cheaper and calmer than Sunday night ones, and the Monday crowd always has the best time.
No, and I mean that. This whole page is built so you can dip in and out. Every block lists where I'll be plus at least one alternative. Skip a day, skip an afternoon, show up for one dinner.
The single thing I'd genuinely love you at is Friday evening. Everything else is a menu.
A valid passport — you're leaving the country, even if it's only a two-and-a-half hour flight. If yours is expiring in 2027, renew it early in the year, because renewal times get ugly in spring.
Direct flights run from Orlando, Tampa, Miami, Fort Lauderdale and Jacksonville into Toronto Pearson. From Pearson, the UP Express train gets you downtown in 25 minutes for about $12, which is faster and cheaper than a cab.
Late July in Toronto is hot and humid, usually high twenties Celsius, which is low eighties for you. It's a Florida summer with better hair days.
Not at all — plenty of you are twenty minutes away. Come for the blocks you want and sleep in your own bed.
That said, at least one of you should consider a room for the Friday night, because the people who stay at the hotel are the people still talking at one in the morning.
Parking downtown is expensive and the hotel charges for it. If you're coming in just for Friday, GO Transit into Union Station is a five-minute walk from everything.
Friday's party is on me — the room and the food are covered, and you don't need to bring anything. I mean that about gifts too.
You cover your own flights or gas, your hotel room, and your own meals on the other days. I'm negotiating a group rate at the hotel and the booking link will land here once it's signed.
Saturday's coach to Niagara is a shared cost, and I'll post the per-person number here as soon as I have real quotes. Attractions in Niagara you pay for yourself, and there's plenty to do there that's free.
No. Roughly a third of the plan happens before six in the evening, and several people coming don't drink at all — you won't be the only one.
The Friday venue has a real non-alcoholic menu, not just soda water and a lime, and it's one of the reasons it's on the shortlist. Nobody is going to hand you a drink or ask you why you're not having one.
Saturday's casinos are an option for whoever wants them, not a plan. My parents aren't going anywhere near them, and there's a whole day of Niagara that has nothing to do with gambling or drinking.
Yes, and I hope you do. The aquarium, the islands, Niagara and the butterfly conservatory are all built for them, and 360 at the CN Tower has a kids' menu. High chairs are limited, so tell me if you need one.
The only thing that's genuinely off-limits is the casinos, which are 19 and over just to walk in.
They were on my mind the entire time I built this. Everything downtown is flat and within a short walk, Friday dinner is an elevator ride rather than a climb, the Sunday watch party space has to be step-free or it doesn't get booked, and the Niagara stop is Table Rock, which is level ground right at the falls with washrooms and a restaurant on site.
There's a rest window written into Friday afternoon, and no day requires more than about twenty minutes of walking at a stretch.
If someone needs a wheelchair, a walker, or a lift-equipped seat on the coach, tell me early — accessible coaches have to be booked months ahead, not the week before.
I am. I'm an independent advisor working under OutsideAgents.com, registered in Florida, and cruises are my thing.
So if you want help with this trip — flights, a room, insurance, or a few extra days somewhere on either end — ask me. It costs you nothing, it's the same price you'd pay booking it yourself, and I'd rather it went through me than a search engine.
One rule I have to follow: I can't take your money directly. You'll always pay the hotel, the airline or the supplier yourself. Anyone telling you to send a travel payment to a person instead of a company is doing it wrong.
It got measured and it didn't survive. The Jays are away in New York that weekend, and getting a busload of us there is eleven to thirteen hours each way once you add a border crossing. It would have eaten two days of the trip.
So we're watching it together on the Sunday afternoon at Steam Whistle Brewing instead, in the Roundhouse under the CN Tower, five minutes from the hotel. If you genuinely want to be at that game, fly down and go — I'll help you book it, and I'll see you back here Monday.
Two reasons. It's the Civic Holiday long weekend, and it's the Toronto Caribbean Carnival, the biggest Caribbean festival in North America. The Grand Parade is on our Saturday, July 31, along Lake Shore Boulevard at Exhibition Place, about a million people, from mid-morning to evening. Lake Shore West and a few Gardiner ramps close from midnight Friday to Sunday morning, which is why the Niagara coach leaves from the east side of downtown on time.
What it means for you: book your room and flights early, and if a meal vote doesn't grab you, there is Caribbean food everywhere that weekend, including the free Island Soul festival at Harbourfront Centre six minutes from the hotel. If you'd rather do the parade than Niagara, that's a perfectly good Saturday; take the 509 streetcar from Union, or walk the waterfront west.
Most of you have my number or my email. Ask me anything, including the awkward stuff — money, mobility, dietary, family logistics. I'd much rather sort it in March than in July.