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Trouble and Sons Pizzeria, Whitefish Bay, WI

Trouble and Sons Pizzeria

4.8
4.8
314 Reviews
$30 and under
Italian
From-scratch Italian fare, cocktails and wine in a rustic and welcoming atmosphere.
Reservations at troubleandsonspizzeria.com.
Curbside to-go not currently available.
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

9:00 PM


Booked 14 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

    Everything on our menu is available for catered events.

  • 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, Patio/Outdoor Dining, Takeout, Vegan, Wheelchair Access, Wine

Popular dishes

What 314 people are saying

Overall ratings and reviews

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

4.8
4.8 based on recent ratings
  • 4.8Food
  • 4.8Service
  • 4.7Ambience
  • 4.6Value

NoiseModerate

Loved For

  • Wisconsin

    Best Value

  • Wisconsin

    Kid Friendly

  • Wisconsin

    Neighborhood Gem

  • Wisconsin

    Italian

  • Milwaukee

    Best Overall

  • Milwaukee

    Best Value

  • Milwaukee

    Kid Friendly

  • Milwaukee

    Good for Groups

  • Milwaukee

    Neighborhood Gem

  • Milwaukee

    Italian

Sort by

Filters

  1. MB

    MarkB

    Milwaukee

    1 review

    vip
    5.0

    1 review

    Dined 6 days ago

    overall5food5service5ambience5
    So great to have this restaurant back.
  2. 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.
  3. FD

    FineDiner

    Milwaukee

    10 reviews

    vip
    5.0

    10 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.
  4. 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.
  5. ML

    MollyL

    Washington DC

    22 reviews

    vip
    5.0

    22 reviews

    Dined on July 9, 2022

    overall5food5service5ambience5
    Always fantastic service and food!
  6. 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.
  7. 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.
  8. T

    Trudy

    Milwaukee

    179 reviews

    vip
    5.0

    179 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!
  9. 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.
  10. OT

    OpenTable Diner

    Milwaukee

    12 reviews

    5.0

    12 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!
  11. F

    Foodie

    Milwaukee

    5 reviews

    5.0

    5 reviews

    Dined on June 4, 2022

    overall5food5service5ambience5
    Food and drinks were outstanding - garlic bread is a must have! The waitresses and waiters were exceptional, possibly the best service we’ve had!
  12. OT

    OpenTable Diner

    Philadelphia

    2 reviews

    vip
    5.0

    2 reviews

    Dined on June 3, 2022

    overall5food5service5ambience5
    We ate outside it was great. Good wine list.
  13. SF

    SteveF

    Milwaukee

    23 reviews

    5.0

    23 reviews

    Dined on June 2, 2022

    overall5food4service5ambience5
    Great service as always
  14. n

    nancym

    Milwaukee

    1 review

    5.0

    1 review

    Dined on May 31, 2022

    overall5food5service4ambience4
    The pizza was absolutely DELICIOUS but your glass of wine price was OUTRAGEOUS. I enjoyed going out for dinner and relaxing with a glass of wine, but next time I will think twice after paying $13.00 for one glass. That’s unacceptable.
  15. J

    Jenny

    1 review

    5.0

    1 review

    Dined on May 28, 2022

    overall5food5service5ambience5
    It was a very nice place we had multiple staff for our party of 8.
  16. OT

    OpenTable Diner

    Philadelphia

    3 reviews

    vip
    5.0

    3 reviews

    Dined on May 28, 2022

    overall5food5service5ambience5
    Great atmosphere, food and service. Love the owners.
  17. c

    candyman

    Milwaukee

    43 reviews

    vip
    5.0

    43 reviews

    Dined on May 27, 2022

    overall5food5service5ambience5
    Excellent food, service!
  18. k

    kimm

    1 review

    3.0

    1 review

    Dined on May 26, 2022

    overall3food1service4ambience4
    Very disappointed. Last time I went to restaurant it was prior to the pandemic and the food was good. Yesterday, I had a pizza and it was not good. The salad didn't enough dressing but the mozzarella stick was very good. I will not go back. 😞
  19. KS

    KimberlyS

    1 review

    5.0

    1 review

    Dined on May 20, 2022

    overall5food5service4ambience5
    Delicious! It was it first visit and won’t be the last. Garlic bread was absolutely amazing and worth the cost. Margarita pizza was very good, interesting with the pesto. Spaghetti and meatballs also good
  20. CG

    ClaudiaG

    Milwaukee

    42 reviews

    vip
    5.0

    42 reviews

    Dined on May 18, 2022

    overall5food5service5ambience5
    A group of us celebrated a family birthday. It was a wonderful event! The service was excellent! We ordered pizzas, salads and tiramisu. Everything was outstanding. We will definitely return!
  21. P

    Prontomac

    Washington DC

    406 reviews

    vip
    4.0

    406 reviews

    Dined on May 14, 2022

    overall4food4service4ambience5
    Large party well served by staff. Pizza very tasty. Garlic bread outstanding. Well managed restaurant
  22. P

    Phyre

    Milwaukee

    44 reviews

    5.0

    44 reviews

    Dined on May 11, 2022

    overall5food5service5ambience5
    It was nice being able to sit out on the patio and enjoy the food, ambiance, and service. I will definitely return to the restaurant, especially to try another pizza.
  23. OT

    OpenTable Diner

    Chicago

    3 reviews

    3.0

    3 reviews

    Dined on May 10, 2022

    overall3food3service3ambience3
    Just okay. That’s all I can say.
  24. K

    Keri

    Milwaukee

    6 reviews

    vip
    5.0

    6 reviews

    Dined on May 7, 2022

    overall5food5service5ambience5
    Best garlic bread in town. Excellent service and staff
  25. WW

    WendyW

    Milwaukee

    3 reviews

    5.0

    3 reviews

    Dined on May 5, 2022

    overall5food5service5ambience5
    The best food I have had in a long long time - wait staff and owners wonderful!
  26. SW

    SantiagoWalker

    Milwaukee

    4 reviews

    5.0

    4 reviews

    Dined on April 28, 2022

    overall5food5service5ambience4
    We went expecting great food, and we enjoyed a selection of food that was even better. And the staff, of all responsibility levels, including: table cleaning and resetting, taking orders and delivering, food preparation, welcoming; was great!!!! And our food was beyond our expectations!!!
  27. f

    foodlover

    New York Area

    19 reviews

    5.0

    19 reviews

    Dined on April 28, 2022

    overall5food5service5ambience4
    this was my first time at Trouble and Sons, and I was very impressed with the great food and friendly, efficient service. A larger group can always be a bit of a challenge, bt our server was right on. The calamari appetizer was great - lightly breaded and seasoned. A unique and delicious take on garlic bread. The pizzas were also very good with a not quite thin crust and generous toppings. Definitely a place I'll return to!
  28. OT

    OpenTable Diner

    Milwaukee

    6 reviews

    4.0

    6 reviews

    Dined on March 12, 2022

    overall4food5service4ambience5
    Birthday dinner. Easy to set up reservations. Great server, Jessie. Yummy food once again! Garlic bread is to die for!!
  29. SF

    StevenF

    Washington DC

    1 review

    5.0

    1 review

    Dined on March 12, 2022

    overall5food4service5ambience4
    Excellent and friendly service. Delicious pizza. One of my favorite places.
  30. LA

    LilaA

    Milwaukee

    5 reviews

    5.0

    5 reviews

    Dined on March 12, 2022

    overall5food5service5ambience5
    Amazing ! Great waiter incredible food!
  31. OT

    OpenTable Diner

    Chicago

    8 reviews

    5.0

    8 reviews

    Dined on March 11, 2022

    overall5food5service5ambience5
    It was our first time. The ambience was great!! Lobster ravioli was great. Pizza was very good!! Loved my Caesar salad too! Chardonnay was excellent!
  32. MP

    MeredithP

    Orlando

    7 reviews

    5.0

    7 reviews

    Dined on March 4, 2022

    overall5food5service5ambience5
    Everything fantastic as always. It was my friends birthday and they took amazing care of us. We all got pasta - I got the lobster ravioli with vodka sauce (so yummy) and the wine our server suggested to go with it was super good. We got drinks and an app at Moxie first and then dinner at Trouble. Awesome WFB evening!!
  33. JB

    JamesB

    Milwaukee

    48 reviews

    vip
    5.0

    48 reviews

    Dined on March 4, 2022

    overall5food5service5ambience5
    Everything was excellent as always. The staff, food and atmosphere are what keep us coming back time and time again.
  34. JP

    JPJS

    London

    1 review

    5.0

    1 review

    Dined on February 26, 2022

    overall5food5service5ambience5
    Very professional staff, nice wine menu and delicious food!
  35. R

    Rich

    Milwaukee

    1 review

    5.0

    1 review

    Dined on February 19, 2022

    overall5food5service5ambience5
    Great spot. Friendly and helpful staff. Great food.
  36. OT

    OpenTable Diner

    1 review

    5.0

    1 review

    Dined on February 18, 2022

    overall5food5service5ambience5
    Our waitress was great and the food was delicious!! Would highly recommend.
  37. MH

    MichaelH

    Milwaukee

    12 reviews

    vip
    5.0

    12 reviews

    Dined on February 16, 2022

    overall5food5service5ambience4
    Salmon Pesto Pasta, Eggplant Parm, and Shrimp Diavolo we’re all delicious as was Mediterranean salad!
  38. CN

    ChloeN

    Milwaukee

    22 reviews

    vip
    5.0

    22 reviews

    Dined on February 13, 2022

    overall5food5service5ambience5
    Food is always excellent and service impeccable. Great place!
  39. KB

    KeithB

    Milwaukee

    4 reviews

    5.0

    4 reviews

    Dined on February 12, 2022

    overall5food5service5ambience5
    What a wonderful evening. We were in our first round of drinks when we learned of our new great niece being born at 4:30 this afternoon. From Tricia the server, to the bartender, to the owner, they all celebrated with us. They were kind enough to bring us 2 glasses of Champagne to celebrate our new great niece. The food, drinks and service were wonderful. We'll be back. Wonderful place
  40. a

    allisoncs19

    1 review

    5.0

    1 review

    Dined on February 6, 2022

    overall5food5service5ambience5
    The food was great, and it came out relatively quickly. The decorations were very nice, and the waiters and waitresses we very helpful and considerate.

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 4.8 stars by 314 OpenTable diners.

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

Make a reservation

2 people

9:00 PM


Booked 14 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, Patio/Outdoor Dining, Takeout, Vegan, Wheelchair Access, Wine

  • Phone number

    (414) 800-5015

  • Catering

    Everything on our menu is available for catered events.

  • Private party facilities

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

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