I would use this to get around: Flashy convertible. You’ll need a vehicle to get from Kelowna to all the other hotspots in the Okanagan Valley, so you may as well make a splash. This is exactly the kind of place where brightly coloured cruisers are widely accepted, if not outright expected.
I would stay here: A cute little guesthouse in one of the smaller towns like Summerland, Peachland, Naramata or Oliver. We got a great vacation rental in Summerland using airbnb.com and I’d highly recommend doing the same. You’ll meet locals who can give you advice on which wineries to hit and which ones to miss, the best Greek food in town and their favourite spot to catch the sunset over Okanagan Lake. Summerland was sleepy and quiet like us, but still central to busier and bustlier places like Kelowna and Penticton.
I would eat here: The Cobblestone Wine Bar at the Heritage Inn in Naramata has a nice patio and great lunch menu. We started our afternoon wine tour right here with some carb loading in the sun and a few sample flights to, you know, whet our pallet or something. Theo’s is a great spot in Penticton for Greek food and more wine, and I’d get sushi from Just Delicious Bistro in Summerland, if only because I like the name.
I would drink here: EVERYWHERE. On a boat, tubing down the canal, at the beach, on a patio, in the bathtub, you name it. While many of these options are (probably) not 100% legal, it’s easy to get crafty with your choice of container and chill with adult beverage in hand. I honestly can’t imagine doing it any other way.
I would do this: I’ll start by stating the obvious, which is to check out some of the best wineries in all The Land. (The Land = Canada) Top hits: Mission Hill Winery (West Kelowna), Hillside (Naramata), Road 13 and Hester Creek (Oliver). Next most-obvious choice is to get yourself the sexiest speedboat you can afford and tear around Okanagan Lake all day. Dockside Marine in Peachland showed us a real good time. Coyote Cruises out of Penticton rents tubes and runs shuttles that allow for an afternoon of lazy floating on the canal between Okanagan Lake and Skaha. Speaking of Skaha, some of BCs best rock climbing and mountain bike trails can be found in this little hard core haven. Otherwise, day hikes and beaches abound and there is no shortage of patios to contemplate your spectacular life choices.
I wouldn’t do this: Stay by the airport in Kelowna. It’s a good option for the night before your flight, I suppose, but it puts you as far away as possible from the good stuff and right in the thick of stuff like parking lots and gas stations. Downtown Kelowna is worth a wander, but I’d limit my time in the city if I were you.