Grosse Pointe Date Night
8 stops · about 4 hours · Updated October 12, 2026
Build a date night in Grosse Pointe, MI around dinner, a cocktail and something sweet, with dessert pickup planned before the evening begins. Dirty Dog Jazz Cafe pairs upscale, eclectic cooking with live music, dark-wood decor and leather seats in an intimate dining room. Bucci offers another intimate dinner setting, with seasonal Italian cooking from an open kitchen and a changing wine list. For a casual start, Licavoli's Market & Pizzeria serves stone oven-fired pizza, subs and calzones, with counter-service dining and takeout.
Follow dinner with barrel-aged cocktails at Sidecar Slider Bar in Grosse Pointe, MI, where bar games and sports viewing are part of the casual setting. The Charlevoix offers cocktails, elevated bar food and a cozy neighborhood atmosphere. Side Street Diner provides a quieter alternative with an on-site bar, beer, wine and desserts; it closes at 8 p.m. Monday through Friday and 3 p.m. on weekends.
For the sweet finish, collect handmade baked goods from Classics From Scratch before its daily 4 p.m. closing, or European pastries from Josef's European Pastry Shop, open until 6 p.m. Tuesday through Saturday. Dinner reservations are recommended at both Dirty Dog Jazz Cafe and Bucci.
Dinner
evening
Stop 1
Dirty Dog Jazz Cafe
4.6(798)Grosse Pointe Farms
Dirty Dog Jazz Cafe combines upscale, eclectic cuisine with live music in an intimate dining room furnished with dark wood and leather seats.
Stop 2
Licavoli's Market & Pizzeria
4.6(654)Grosse Pointe Woods
Licavoli's Market & Pizzeria offers a casual dinner with stone oven-fired pizza, subs and calzones, plus counter-service dining and takeout.
Stop 3
Bucci
4.6(254)Grosse Pointe Woods
Bucci brings seasonal Italian cooking from an open kitchen to an intimate dining room, with a changing wine list and dinner reservations.
Cocktails
evening
Stop 4
Side Street Diner
4.6(908)Grosse Pointe
Side Street Diner offers a casual, cozy and quiet setting with an on-site bar, beer, wine, coffee and desserts.
Stop 5
Sidecar Slider Bar - Grosse Pointe
4.6(452)Grosse Pointe
Stop 6
The Charlevoix
4.6(405)Grosse Pointe Park
The Charlevoix pairs cocktails with elevated bar food in a casual, cozy neighborhood setting, with outdoor seating and happy-hour food and drinks.
Something sweet
night
Stop 7
Classics From Scratch
5.0(45)Grosse Pointe
Classics From Scratch makes baked goods by hand using family recipes dating to the 1920s, with delivery and takeout available.
Stop 8
Josef's European Pastry Shop
4.6(665)Grosse Pointe Woods
Josef's European Pastry Shop specializes in European pastries, bread and custom-designed cakes, with coffee and takeout available at the long-running bakery.
