This "date" is basically a modified version of the Vineyard Wine Hike that I do.  I'm giving away trade secrets for your benefit! If you'd prefer more guidance, get a few other friends together and benefit from my expertise in local food and wine!  Or please consider sending visiting friends and family my way for this tour.  

Start by taking the S-Bahn or U-Bahn to Unterturkheim (depending on what's fastest for you).  Exit the station heading towards the hills and walk to Weinmanufaktur Unterturkheim where you can taste excellent wine for free (although they don't mind if you buy!)  during business hours.  

If you're athletic, walk up into the vineyards using the map provided from the Stuttgart Tourist Information Center about the Unterturkheim "Weinwanderweg". If you don't feel like walking up Stuttgart's second-highest hill, consider taking the 62 bus just outside the winery to "Rotenberg".

*insider tip: Check the website of Weinhof Zaiss to see if their besenwirtschaft in the vineyards above Unterturkheim is open!  (Spring and early Fall usually with a festival in mid-summer)

Once in Rotenberg, hike up to the Grabkappelle (Royal Grave Chapel) to witness this moment to the eternal love of King Wilhelm I to his Queen, Katerina of Russia.  There is English-language information available at the ticketbooth if you ask.  Then enjoy the magnificent views over Stuttgart-Ost. 

Walk down the other side of the hill to the charming village of Uhlbach, where locals have been growing wine for over 800 years!  Thursday through Sunday you can visit the Weinbau - Stuttgart's wine museum in a 700 year old building!  There is also a tasting room where you can purchase small glasses of wine, and the staff generally speaks English.  (Ask for Jurgen if he is there, he is delightful!)  

Uhlbach may be small but it has many great dining options.  In the fall and spring the besen of Weingut Currle is open, but the traditional restaurants are excellent as well.  Gasthaus Ochsen has the best real wienerschnitzel I've ever had, whereas Weinstube Loewen offers up consistently great food in a charming atmosphere year round, but their pumpkin menu in the fall is particularly fantastic.  Both restaurants have lovely outdoor seating areas in nice weather.  If you'd like a Besen experience but the local besen are closed, the "Trollinger Besen" is a restaurant that serves typical Besen food and atmosphere but is open year round.  

insider tip: if you happen to be in Uhlbach on a Sunday, the beautifully restored 600 year old church is open to the public.  The painted wood inside is well worth the effort if you make it in their two hour window from 14:00-16:00.

Monday through Saturday you can also taste more wine at the Collegium Wirtemberg winery's outpost in Uhlbach as well.  They also have an outlet in the vineyards above Unterturkheim.  Both locations are delightful and they regularly have wine tasting events with music and art to enjoy.

From Uhlbach it's an easy walk through residential neighborhoods down to Oberturkheim, or you can climb back into the vineyards for a more scenic hike if you prefer.  And you can also catch the bus directly from the main square in Uhlbach back to Oberturkheim, where you can catch an S-Bahn.