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Trouble and Sons Pizzeria, Whitefish Bay, WI

Trouble and Sons Pizzeria

4.6
4.6
344 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 13 times 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 344 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
  • 4.4Value

NoiseModerate

Loved For

  • Wisconsin

    Neighborhood gem

  • Wisconsin

    Italian

  • Milwaukee

    Best Service

  • Milwaukee

    Best Value

  • Milwaukee

    Neighborhood gem

  • Milwaukee

    Italian

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Filters

  1. D

    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 6 days agoI'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

  2. OT

    OpenTable Diner

    Milwaukee

    1 review

    3.0

    1 review

    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!
  3. DH

    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.
  4. M

    Mingus

    Coastal Georgia

    1 review

    5.0

    1 review

    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.
  5. OT

    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.
  6. JB

    JamesB

    Milwaukee

    50 reviews

    vip
    5.0

    50 reviews

    Dined on December 17, 2022

    overall5food5service5ambience5
    Good as usual 👍🏼
  7. c

    candyman

    Milwaukee

    49 reviews

    vip
    5.0

    49 reviews

    Dined on December 14, 2022

    overall5food5service5ambience5
    Everything was excellent!!
  8. MS

    MaryS

    Milwaukee

    1 review

    5.0

    1 review

    Dined on December 11, 2022

    overall5food5service5ambience5
    The food was great. The service attentive. The atmosphere lively.
  9. SM

    SusanM

    Milwaukee

    1 review

    5.0

    1 review

    Dined on December 10, 2022

    overall5food5service5ambience5
    This was our first visit. Great waitress , service and food!!
  10. JM

    JillM

    Milwaukee

    51 reviews

    vip
    3.0

    51 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.
  11. OT

    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.
  12. z

    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.
  13. c

    candyman

    Milwaukee

    49 reviews

    vip
    5.0

    49 reviews

    Dined on November 19, 2022

    overall5food5service5ambience5
    Excellent food and excellent service!!
  14. JH

    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.
  15. JG

    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!
  16. c

    candyman

    Milwaukee

    49 reviews

    vip
    5.0

    49 reviews

    Dined on November 16, 2022

    overall5food5service5ambience5
    Everything was excellent. A real gem!!!
  17. CM

    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.
  18. SL

    SarahL

    Milwaukee

    9 reviews

    5.0

    9 reviews

    Dined on November 13, 2022

    overall5food5service5ambience5
    Great food, excellent service, great ambience. We’ll definitely go again!
  19. OT

    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!
  20. C

    Carrie

    1 review

    5.0

    1 review

    Dined on November 10, 2022

    overall5food5service5ambience5
    The food was amazing!! Service was friendly and swift. Very personable!!!
  21. MG

    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.
  22. MK

    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!
  23. DB

    DuaneB

    Milwaukee

    5 reviews

    vip
    5.0

    5 reviews

    Dined on October 29, 2022

    overall5food5service5ambience5
    Best pizza in the Milwaukee area. I highly recommend it.
  24. d

    doccheesehead

    Milwaukee

    41 reviews

    vip
    5.0

    41 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!
  25. SL

    SarahL

    Milwaukee

    10 reviews

    5.0

    10 reviews

    Dined on October 15, 2022

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

    Trudy

    Milwaukee

    182 reviews

    vip
    5.0

    182 reviews

    Dined on October 15, 2022

    overall5food5service5ambience5
    Food was fabulous and so was the service! Ann Marie even greeted me when I got there and I hope I am spelling her name correctly! I totally enjoy this restaurant as well as her other place, Moxie! I was glad to see how busy it was, and I wish it was open later than 9 o’clock, but I am grateful that the restaurant is there for everyone to enjoy! I will definitely continue going there and eating their exceptional food!
  27. FD

    FineDiner

    Milwaukee

    14 reviews

    vip
    5.0

    14 reviews

    Dined on October 8, 2022

    overall5food5service5ambience5
    We have dined at Moxie several times, the waitress mentioned about Trouble and Sons and told us both restaurants are the same owners. We went there for dinner one night and love the food, service is excellent and will definitely go back again.
  28. c

    candyman

    Milwaukee

    49 reviews

    vip
    5.0

    49 reviews

    Dined on October 8, 2022

    overall5food5service5ambience5
    Everything was excellent!!!
  29. SW

    SusanW

    Washington DC

    3 reviews

    5.0

    3 reviews

    Dined on October 8, 2022

    overall5food5service5ambience5
    Second time here in two weeks - food, service and atmosphere are outstanding! The calamari, bread and arancini starters are delicious. Calamari is perfectly cooked and tender. Enjoyed the double trouble pizza (with cauliflower crust - amazing!). Second visit had salmon with pasta - again, all wonderful and cooked perfectly. The staff are terrific. Great cocktails too. Such a gem of a place and so glad they are open again!
  30. MB

    MatthewB

    Milwaukee

    15 reviews

    5.0

    15 reviews

    Dined on October 7, 2022

    overall5food5service5ambience5
    A great dining experience as always. So happy they’ve reopened. It was very busy last night and that was wonderful to see.
  31. MB

    MarkB

    Milwaukee

    2 reviews

    vip
    5.0

    2 reviews

    Dined on September 30, 2022

    overall5food5service5ambience5
    So great to have this restaurant back.
  32. MS

    MaryS

    Milwaukee

    14 reviews

    2.0

    14 reviews

    Dined on July 30, 2022

    overall2food2service1ambience1
    Sorry the entire menu wasn’t available due to chef illness. But, we greatly admired how the staff adjusted and carried on. Good thoughts for his recovery.
  33. FD

    FineDiner

    Milwaukee

    14 reviews

    vip
    5.0

    14 reviews

    Dined on July 30, 2022

    overall5food5service5ambience5
    It was our first timer to have dinner at Trouble and sons Pizzeria, it was too bad that they didn't have the Chef, so they couldn't serve Entrees. As I don't eat meat so I ordered the Veggie Pizza which is delicious. Can't wait going back there again and try the other items on the menu.
  34. OT

    OpenTable Diner

    Milwaukee

    1 review

    5.0

    1 review

    Dined on July 13, 2022

    overall5food5service5ambience5
    Wonderful dinner with friends. We miss the “Moxi” pizza but the new offerings were wonderful.
  35. ML

    MollyL

    Washington DC

    22 reviews

    vip
    5.0

    22 reviews

    Dined on July 9, 2022

    overall5food5service5ambience5
    Always fantastic service and food!
  36. F

    Fred

    1 review

    2.0

    1 review

    Dined on July 9, 2022

    overall2food2service2ambience2
    Took 1.75 hrs to receive dinner. Pasta was flavorless. Kitchen staff put our orders after delivery orders. Wasn't waitresses fault at all. Food was nothing exciting.
  37. RK

    RobertK

    Milwaukee

    5 reviews

    5.0

    5 reviews

    Dined on July 7, 2022

    overall5food5service5ambience5
    The service was great. Our pizzas were delicious. Dinner outdoors was so enjoyable.
  38. T

    Trudy

    Milwaukee

    182 reviews

    vip
    5.0

    182 reviews

    Dined on June 24, 2022

    overall5food5service5ambience5
    Love trouble and sons and the food was fabulous! Dined with four other friends a couple of days prior to my birthday to celebrate and we had a great time. Service was Wonderful! I will be back!
  39. OT

    OpenTable Diner

    Milwaukee

    6 reviews

    5.0

    6 reviews

    Dined on June 19, 2022

    overall5food5service5ambience5
    Trouble and Sons never disappoints! The food, service, and ambiance are always top notch.
  40. OT

    OpenTable Diner

    Milwaukee

    13 reviews

    5.0

    13 reviews

    Dined on June 17, 2022

    overall5food5service5ambience5
    Great food! And great service! It was our first time here but I'm sure it won't it be our last!

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 344 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 13 times 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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