Eddie & Leanne · June 5–7, 2026 · Markham → Kingston
Drop your bags and head straight to Kingston's Lake Ontario waterfront pathway. It stretches past marinas, parks, and iconic limestone buildings — a perfect way to decompress after the drive and take in the city together before the big evening.
Kingston's iconic red trolleys take you through the city's historic limestone landmarks — from the 19th-century fort to the Kingston Penitentiary. A great way to get oriented to the city right after you arrive. Pick up from the same place as your cruise tickets: 248 Ontario St.
Tickets must be picked up in person at Waterfront Gifts & Apparel at 248 Ontario St — you cannot board without collecting them first. The cruise dock at Crawford Wharf (1 Brock St) is just a 2-minute walk from there.
Board the glass-topped Island Star and sail into the Admiralty Islands as the sun sets over the St. Lawrence. A three-course dinner is served at your table with live music and hosted commentary the entire cruise. You'll glide past Napoleon's Hat, Mandalay Mansion, and dozens of tiny cottage islands. One of the most romantic things to do in Ontario.
Kingston's crown jewel — a restored 1832 British fortress perched above Lake Ontario and the St. Lawrence. The Fort Henry Guard performs precision military drills, fife-and-drum music, and artillery demonstrations. The rampart views are stunning and the best vantage point in the entire city.
Wander Kingston's vibrant downtown after Fort Henry. Chez Piggy is the local favourite for a couple's lunch — eclectic seasonal menu, gorgeous courtyard patio, full of character. Alternatively, Union Restaurant has great sharing dishes and cocktails if you want something livelier.
Step inside Canada's oldest maximum-security prison, closed in 2013 after 178 years. The Standard Tour takes you through the cell blocks, segregation wing, shop dome, and recreation yard, led by retired corrections officers with real stories of riots, escapes, and daily life behind the walls.
Kingston's most celebrated restaurant. Waterfront dining with stunning Lake Ontario views, locally-sourced seasonal menus, and an exceptional wine list. Elegant without being stuffy — sophisticated, lakeside, and exactly right for a Saturday date night. Consistently rated the best meal in Kingston.
Wind the night down at Musiikki Café, a warm local gem with live music every single night of the week. Grab a craft beer or cocktail, find a cozy corner, and let the music take over. Low-key, intimate, and exactly right after a full day out together.
A slow, no-agenda Sunday morning walk along Kingston's Lake Ontario waterfront, ending at the Gord Downie Pier — named after Tragically Hip frontman Gord Downie, with sweeping views of the water and Kingston skyline. Completely free, zero schedule, and a genuinely beautiful way to close out the weekend.
Fuel up before hitting the 401. Princess Street has solid brunch spots for a proper sit-down with good coffee. On weekends, Springer Market Square often has a lively outdoor market worth a quick stroll through before you head out.
Head west on the 401 and let the weekend sink in together. Good time for a playlist and road snacks. The Big Apple in Colborne is right at the halfway point — a fun 20-minute stop for a slice of apple pie and a silly photo in front of the giant apple. Home by 4pm easily.