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Trouble and Sons Pizzeria, Whitefish Bay, WI

Trouble and Sons Pizzeria

4.6
4.6
359 Reviews
$30 and under
Italian
From-scratch Italian fare, cocktails and wine in a rustic and welcoming atmosphere.
Reservations at troubleandsonspizzeria.com.
Our Reservation Policies:
- Maximum reservation/table size on our PATIO is 6 guests.
- Maximum reservation/table size in our DINING ROOM is 10 guests.
- All guests must arrive within 15 minutes of reservation time.
- Payment with one check is required.
- A 20% gratuity may be added to parties of 6 or more.

Make a reservation

2 people

7:00 PM


Booked 1 time today

Additional information

  • Dining style

    Casual Dining

  • Cuisines

    Italian, Pizzeria

  • Hours of operation

    Dinner Tue, Wed 5:00 pm–8:00 pm Thu–Sat 5:00 pm–9:00 pm

  • Phone number

    (414) 800-5015

  • Payment options

    Discover, MasterCard, Visa

  • Dress code

    Casual Dress

  • Owned/operated by

    LGBTQ+, Women

  • Executive chef

    Chef Chris Feldmann

  • Catering

    Call our events and catering manager for information at 414-704-8970.

  • Private party facilities

    Call our events and catering manager for information at 414-704-8970.

  • Neighborhood

    Whitefish Bay

  • Cross street

    N Kent Avenue

  • Parking details

    Street Parking

  • Additional

    Bar/Lounge, Beer, Cocktails, Full Bar, Gluten-free Options, Indoor Fireplace, Patio/Outdoor Dining, Takeout, Vegan, Wheelchair Access, Wine

Popular dishes

What 359 people are saying

Overall ratings and reviews

Reviews can only be made by diners who have eaten at this restaurant

4.6
4.6 based on recent ratings
  • 4.5Food
  • 4.7Service
  • 4.7Ambience
  • 4.3Value

NoiseModerate

Loved For

  • Wisconsin

    Neighborhood gem

  • Milwaukee

    Neighborhood gem

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  1. OpenTable Diner

    Milwaukee

    2 reviews

    5.0

    2 reviews

    Dined on March 21, 2023

    overall5food5service5ambience5
    Great as always! Tried the potato pizza and it was delicious.
  2. NikkiG

    1 review

    5.0

    1 review

    Dined on March 21, 2023

    overall5food5service5ambience5
    Very friendly, efficient and attentive staff! The ambiance was lovely. Food was amazing. I had the chicken parmigiana and ate every bite.
  3. JohnZ

    Denver

    7 reviews

    vip
    5.0

    7 reviews

    Dined on March 17, 2023

    overall5food5service5ambience5
    We had a wonderful time!!! Excellent food, drinks and service. Very nice restaurant!!
  4. JenniferA

    1 review

    4.0

    1 review

    Dined on March 11, 2023

    overall4food5service5ambience5
    Sonya was very welcoming and a wonderful server even though end of night! Bartender made great drinks. Food was yummy!
  5. ARB1968

    Milwaukee

    128 reviews

    vip
    3.0

    128 reviews

    Dined on March 8, 2023

    overall3food3service4ambience4
    Second time here. Seemed pricey. We ordered the lasagna and lambrusco special, lasagna seemed watery, chicken parmesan, breading was bitter tasting, and eggplant parmesan.
  6. LindaH

    Milwaukee

    1 review

    5.0

    1 review

    Dined on March 7, 2023

    overall5food5service5ambience5
    had great service and great food. Fun time with friends on a Tuesday night! Would recommend! Very attentive staff right from the hostess to the server and bartender, even the owner! Thank you
  7. OpenTable Diner

    1 review

    4.0

    1 review

    Dined on March 3, 2023

    overall4food4service5ambience5
    Fish fry good but vey chintzy on coleslaw. Was served in a tiny ketchup cup! Why bother!
  8. AmandaG

    Milwaukee

    1 review

    5.0

    1 review

    Dined on March 3, 2023

    overall5food5service5ambience5
    The fish fry was outstanding. I could have eaten more than one portion of the Italian-inspired coleslaw.
  9. Mitch

    Milwaukee

    1 review

    5.0

    1 review

    Dined on February 25, 2023

    overall5food5service5ambience5
    The food is very good, the service is friendly, and the drinks are delicious. Great for a fancier pizza might or a date!
  10. Connie

    Milwaukee

    15 reviews

    5.0

    15 reviews

    Dined on February 19, 2023

    overall5food5service5ambience4
    Food was very good. Everyone was satisfied with their meals. Restaurant was busy, but we had a large table to accommodate our group. Service was excellent and we had a lovely evening. Not the quietest, but tolerable.
  11. OpenTable Diner

    Jackson Hole

    1 review

    5.0

    1 review

    Dined on February 18, 2023

    overall5food5service5ambience5
    It’s awesome and bartenders Ron and Mike keep us coming back.
  12. ElizabethG

    1 review

    5.0

    1 review

    Dined on February 16, 2023

    overall5food5service5ambience5
    Food was delicious and beautifully presented. Everything was fresh and seasoned to perfection.
  13. Lana

    Milwaukee

    36 reviews

    vip
    4.0

    36 reviews

    Dined on February 15, 2023

    overall4food5service4ambience4
    The food was excellent-we had deep-fried eggplant (it came with a white sauce that we didn’t care for. Next time, we will ask for marinara) and a pizza. The service was very good. The cocktails were so over-priced. Nice place. We will definitely return.
  14. MollyL

    Washington DC

    25 reviews

    vip
    5.0

    25 reviews

    Dined on February 12, 2023

    overall5food5service5ambience5
    Delicious food. Attentive service. Always a good time!
  15. SarahL

    Milwaukee

    10 reviews

    5.0

    10 reviews

    Dined on February 12, 2023

    overall5food5service5ambience5
    The food was excellent and the service was great. I had the Family Roots Entree, which is sautéd vegetables, pasta and a sun dried tomato pesto sauce. Everything was cooked perfectly. I highly recommend Trouble and Sons and the Family Roots Entree.
  16. Disappointed

    1 review

    4.0

    1 review

    Dined on January 26, 2023

    overall4food2service4ambience3
    The waitress over-sold the lasagna special on a Thursday night. We later found it the lasagna was the Wednesday night special and we were served a left-over dish.

    Trouble and Sons PizzeriaResponded on January 28, 2023I'm sorry to hear that you weren't able to try our lasagna Thursday night! To address your concern, yes, we did make and serve a lasagna special on Wednesday. However, because it's a guest favorite that we are bringing back, we decided to run the special again on Thursday, so more guests would have a chance to try it. Unfortunately, we ran out before the end of the night. In any case, we appreciate your patronage and hope we will see you again at Trouble and Sons. Tamela, Owner

  17. OpenTable Diner

    Milwaukee

    2 reviews

    3.0

    2 reviews

    Dined on January 11, 2023

    overall3food5service3ambience5
    We ordered the eggplant appetizer and it was delicious. The custom pizza we ordered was also really good, however a bit pricey. The salty pear martini was also delicious. Wait staff was very friendly and accomodating to our special requests, however service was slow. Will definitely go back!
  18. DavidH

    Milwaukee

    1 review

    3.0

    1 review

    Dined on January 8, 2023

    overall3food3service4ambience5
    Always love the vibe at T&S. Kitchen got crunched at 6PM so service (bar and food) was slow. Eggplant parm was overdone (maybe sat around under the heat lamp too long) and veggie pizza was bland (compared to the truffle fries). Cocktail and wine were excellent, however, and our waitress did a very nice job.
  19. Mingus

    Coastal Georgia

    2 reviews

    5.0

    2 reviews

    Dined on January 6, 2023

    overall5food4service5ambience5
    We had a very enjoyable evening. The restaurant was busy but not crowded. Tables were spaced comfortably apart. They had music on but you could easily hear the person across from you speaking. The entrees were delicious and reasonably priced. The staff was very friendly, attentive, prompt and not hovering. It is nice to see a restaurant where young children are welcome with their families for a great dining experience.
  20. OpenTable Diner

    Milwaukee

    2 reviews

    3.0

    2 reviews

    Dined on December 23, 2022

    overall3food2service3ambience4
    Mediocre. This place used to be much better. I’m not sure if the pizza recipe has changed but it’s not very good. The sauce has no flavor, the toppings were gross- I ordered onions and bell peppers on my pizza and o got huge pieces of both, not really appetizing to have two-three inch pieces of onion on a slice of pizza. Service was ok, they were attentive but we started off in the wrong foot when our party of 11 turned to a party of 10. The waitress made it clear that they “accommodated” our request and seemed frustrated that one person didn’t come. She then told us she was taking away one of the tables that they had pushed together, so it could be used by other customers. Fine, except that it was completely unnecessary to act so put out that one person didn’t come. Also, the restaurant was virtually empty the entire time we were there, so was it really necessary to do a table change/disrupt our group to move a table away? We had also decided last minute (morning of) to make the reservation for dinner that night. We were unable to book a table large enough for our group online, but the restaurant wasn’t open to talk to anyone. So, we made two reservations for a table of 5 and a table of 6. We called and left a message and explained the situation and asked if they could seat us all together at one table, or even put us at two tables near each other. They called us back later when they opened and told us they’d have to put us at tables on opposite ends of the restaurant. It felt like they didn’t want us to come, honestly. We told them that would be ok- and then got there and found they had pushed tables together to make an 11 top. So, I don’t get why they told us one thing, then did something else, and the restaurant wasn’t crowded at all, so what’s all the fuss about? Overall, not a great experience, won’t be back.
  21. JamesB

    Milwaukee

    50 reviews

    vip
    5.0

    50 reviews

    Dined on December 17, 2022

    overall5food5service5ambience5
    Good as usual 👍🏼
  22. candyman

    Milwaukee

    51 reviews

    vip
    5.0

    51 reviews

    Dined on December 14, 2022

    overall5food5service5ambience5
    Everything was excellent!!
  23. MaryS

    Milwaukee

    2 reviews

    5.0

    2 reviews

    Dined on December 11, 2022

    overall5food5service5ambience5
    The food was great. The service attentive. The atmosphere lively.
  24. SusanM

    Milwaukee

    1 review

    5.0

    1 review

    Dined on December 10, 2022

    overall5food5service5ambience5
    This was our first visit. Great waitress , service and food!!
  25. JillM

    Milwaukee

    54 reviews

    vip
    3.0

    54 reviews

    Dined on December 3, 2022

    overall3food3service5ambience4
    Service excellent. Eggplant fabulous but smaller portion than used to for $. Pizza just okay. Crust tasteless. Nice atmosphere.
  26. OpenTable Diner

    Milwaukee

    30 reviews

    vip
    4.0

    30 reviews

    Dined on November 26, 2022

    overall4food3service4ambience4
    T&S has been one of our go-to restaurants for awhile now, really good food, value and service. I was a bit disappointed in the eggplant parmigiana this trip which was a bit bland. I’m hoping it was just a one-off in the kitchen. Service as always was excellent.
  27. z726beth

    Milwaukee

    151 reviews

    vip
    5.0

    151 reviews

    Dined on November 23, 2022

    overall5food5service5ambience5
    Their pizza is great - absolutely is all it's cracked up to be. Also highly recommend the grilled italian wedge salad. We will go back.
  28. candyman

    Milwaukee

    51 reviews

    vip
    5.0

    51 reviews

    Dined on November 19, 2022

    overall5food5service5ambience5
    Excellent food and excellent service!!
  29. JudyH

    Milwaukee

    2 reviews

    5.0

    2 reviews

    Dined on November 18, 2022

    overall5food5service5ambience5
    Had an enjoyable dinner. Service was great. Food was excellent. Would recommend eating there.
  30. JulieG

    Milwaukee

    1 review

    vip
    5.0

    1 review

    Dined on November 17, 2022

    overall5food5service5ambience5
    We, again, enjoyed our experience! So glad to have them in WFB!
  31. candyman

    Milwaukee

    51 reviews

    vip
    5.0

    51 reviews

    Dined on November 16, 2022

    overall5food5service5ambience5
    Everything was excellent. A real gem!!!
  32. ClaireM

    Milwaukee

    10 reviews

    3.0

    10 reviews

    Dined on November 15, 2022

    overall3food3service3ambience4
    It took quite a while to get our order but it was so good. Loved the pizza.
  33. SarahL

    Milwaukee

    11 reviews

    5.0

    11 reviews

    Dined on November 13, 2022

    overall5food5service5ambience5
    Great food, excellent service, great ambience. We’ll definitely go again!
  34. OpenTable Diner

    1 review

    5.0

    1 review

    Dined on November 11, 2022

    overall5food5service5ambience5
    The service was amazing and so was the food. We’ll definitely be back!
  35. Carrie

    1 review

    5.0

    1 review

    Dined on November 10, 2022

    overall5food5service5ambience5
    The food was amazing!! Service was friendly and swift. Very personable!!!
  36. MG123

    Milwaukee

    7 reviews

    vip
    3.0

    7 reviews

    Dined on November 4, 2022

    overall3food2service4ambience3
    Food was not as good as it used to be.
  37. MKEretiredgirl64

    Milwaukee

    12 reviews

    5.0

    12 reviews

    Dined on October 29, 2022

    overall5food5service5ambience5
    Always love going to Trouble! So glad they are open again!
  38. DuaneB

    Milwaukee

    6 reviews

    vip
    5.0

    6 reviews

    Dined on October 29, 2022

    overall5food5service5ambience5
    Best pizza in the Milwaukee area. I highly recommend it.
  39. doccheesehead

    Milwaukee

    42 reviews

    vip
    5.0

    42 reviews

    Dined on October 29, 2022

    overall5food5service5ambience5
    First time back with new menu. Same welcoming vibe. Pallini Di pasta app (bread, cheese, olive oil) is outstanding. Double trouble pizza still awesome. Tuscan salmon has great flavors with very tasty pasta. Waitstaff, including Shannon and Tonieh are fantastic as always!
  40. SarahL

    Milwaukee

    11 reviews

    5.0

    11 reviews

    Dined on October 15, 2022

    overall5food5service5ambience5
    Excellent menu, food, service, and ambiance. We will definitely go again.

Safety precautions

  • Cleaning & sanitizing

    • Surfaces sanitized between seatings
    • Digital, disposable or sanitized menu provided
    • Sealed or wrapped utensils used
    • Common areas deep-cleaned daily
  • Physical distancing

    • Limited number of seated diners
    • Distancing maintained in common areas
    • Extra space between tables
  • Screening

    • Sick staff prohibited in the workplace

FAQs

Trouble and Sons Pizzeria offers takeout which you can order by calling the restaurant at (414) 800-5015.

Trouble and Sons Pizzeria is rated 4.6 stars by 359 OpenTable diners.

Yes, you can generally book this restaurant by choosing the date, time and party size on OpenTable.

Make a reservation

2 people

7:00 PM


Booked 1 time today
Google Map for Trouble and Sons Pizzeria

133 E Silver Spring Dr, Whitefish Bay, WI 53217

Additional information

  • Cross street

    N Kent Avenue

  • Neighborhood

    Whitefish Bay

  • Hours of operation

    Dinner Tue, Wed 5:00 pm–8:00 pm Thu–Sat 5:00 pm–9:00 pm

  • Cuisines

    Italian, Pizzeria

  • Dining style

    Casual Dining

  • Dress code

    Casual Dress

  • Parking details

    Street Parking

  • Payment options

    Discover, MasterCard, Visa

  • Owned/operated by

    LGBTQ+, Women

  • Executive chef

    Chef Chris Feldmann

  • Additional

    Bar/Lounge, Beer, Cocktails, Full Bar, Gluten-free Options, Indoor Fireplace, Patio/Outdoor Dining, Takeout, Vegan, Wheelchair Access, Wine

  • Phone number

    (414) 800-5015

  • Catering

    Call our events and catering manager for information at 414-704-8970.

  • Private party facilities

    Call our events and catering manager for information at 414-704-8970.

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  • Terms of Use
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  • Do Not Sell or Share My Personal Information
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