Trouble and Sons Pizzeria

4.8
203 Reviews
$30 and under
Italian
Curbside To-Go AND In-House Dining:
Delicious pizza and classic Italian pasta dishes, cocktails and wine.
Call 414-800-5015 or order online or make a reservation at www.troubleandsonspizzeria.com.

Support Trouble and Sons Pizzeria during COVID-19

Safety precautions

Cleaning & Sanitizing
  • Surfaces sanitized between seatings
  • Common areas deep cleaned daily
  • Digital, disposable or sanitized menu provided
  • Sanitizer or wipes provided for customers
  • Contactless payment available
  • Sealed or wrapped utensils used
Physical Distancing
  • Limited number of seated diners
  • Distancing maintained in common areas
  • Extra space between tables
Protective Equipment
  • Waitstaff wear masks
  • Diners must wear masks unless eating or drinking
Screening
  • Sick staff prohibited in the workplace
  • Staff temperature check required
What 203 people are saying
Overall ratings and reviews
Reviews can only be made by diners who have eaten at this restaurant
4.8based on recent ratings
4.7
food
4.8
service
4.7
ambience
4.6
value
Noise · Moderate
100% of people would recommend it to a friend
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SW
SteveW
Milwaukee
11 reviews
Dined 4 days ago
Overall4food5service4ambience4

It was a pleasant visit. The staff was very friendly and the owner followed up after our meal to ensure our satisfaction. The food was delicious and came out in a timely manner. We will come back again.

CM
CM5321
1 review
Dined on May 1, 2021
Overall5food5service5ambience5

We celebrated our ten year anniversary here and it was made very special by everyone working!
Drinks and food are always delicious here!

h
honest
Milwaukee
13 reviews
Dined on April 11, 2021
Overall5food5service5ambience5

This was our first dining experience since last summer after being vaccinated. We brought our 90 yr old mother and had a delicious roasted veggie pizza with a hand tossed crust and house salad. Tables were spread out, limited guests, and the staff wore masks. We appreciated the Covid precautions and felt safe to eat there. The staff is always fun and friendly. Will be back again!

T
vipTrouble
Chicago
21 reviews
Dined on April 9, 2021
Overall5food4service5ambience5

delicious food and ward and friendly service. Great spot

CJ
CJF1
Chicago
3 reviews
Dined on April 2, 2021
Overall3food3service5ambience4

Service was great but disappointed they no longer have a thin crust pizza option. The pizza is now just mediocre. I’ve had better frozen pizzas.

JZ
JaneZ
Milwaukee
1 review
Dined on March 12, 2021
Overall5food5service5ambience5

As always their food is considently well prepared and delicious! We also love the blues playing in the background. Great neighborhood treasure.

SF
SarahF
Milwaukee
2 reviews
Dined on March 6, 2021
Overall5food5service5ambience4

Great service and great food, very pleasant hosts. We always enjoy going there and are happy it's open for at least partial indoor dining again.

JG
JonG
Milwaukee
1 review
Dined on February 27, 2021
Overall5food5service5ambience5

Always love this place, good food, good service, warm atmosphere!

6
vip6406nb
Milwaukee
13 reviews
Dined on February 20, 2021
Overall5food5service5ambience5

It's one of our favorite places hands down. There is nothing negative to report. Go and enjoy!

T
vipTrudy
Milwaukee
160 reviews
Dined on February 12, 2021
Overall5food5service5ambience5

Food was fabulous and so is the service! So glad to see they are open!

MK
vipMKEtraveler
Milwaukee
38 reviews
Dined on November 7, 2020
Overall4food4service5ambience4

Excellent food and a pleasant setting. The staff was great and we thoroughly enjoyed our meal. Jane

OT
OpenTable Diner
Milwaukee
1 review
Dined on November 5, 2020
Overall5food5service5ambience5

Great experience! Would go back there

SL
SaraLynn
1 review
Dined on October 18, 2020
Overall5food5service5ambience5

We love this place. We ate outside on a cool night and they surrounded us with heaters and it was lovely. Excellent food and service as well!

A
vipAnnie
Tampa
54 reviews
Dined on October 17, 2020
Overall3food3service4ambience4

We were disappointed they only had one type of crust for pizza this time. We ordered pizza, mozzarella sticks and eggplant parmesan. (Previously, I had ordered eggplant appetizer). The pizza crust lacked crispiness and was OK overall. The mozzarella sticks were not greasy at all - a hit with husband. I was disappointed with the eggplant parmesan. The eggplant was sliced thin and actually hard (overcooked?) and lacked flavor. The cheese on top was a tiny sprinkle. I will stick with my homemade eggplant parmesan.
Hoping Trouble and Sons can step up their game again - we had 2 great visits this summer, but this one was a complete disappointment. Maybe it was an off day.

OT
OpenTable Diner
Milwaukee
9 reviews
Dined on October 3, 2020
Overall5food5service5ambience5

Excellent service and food!

MI
MImi
Milwaukee
4 reviews
Dined on September 25, 2020
Overall5food5service5ambience5

Food is always fantastic at Trouble and Sons! We sat outside and felt very safe with our socially distant seating. Service was great as well!

PB
vipPattiB
Milwaukee
6 reviews
Dined on September 2, 2020
Overall5food5service5ambience5

Great food

WL
vipWineLuvr
Milwaukee
22 reviews
Dined on September 2, 2020
Overall5food5service5ambience5

As usual, the food and ambiance was top notch. The staff are so attentive and friendly. My two friends and l all had pasta dishes and everyone raved about the quality and taste.
I will definitely return.

A
vipAnnie
Tampa
54 reviews
Dined on August 28, 2020
Overall5food5service5ambience5

Excellent service! Super food - we had the Double Trouble pizza (tons of meat and fantastic sausage!), eggplant appetizer, garlic bread (addictive!) and cauliflower crust pizza with brussels and chicken. The tiramisu, for dessert, was also delicious! We left filled up and happy :)

JO
vipJoyceO
Tampa
13 reviews
Dined on August 20, 2020
Overall5food5service5ambience5

Trouble in Sons is providing very safe service during the pandemic. My husband and I dined in the secluded back area and felt very comfortable. Many folks were seated on the outdoor patio area. The food here is amazing! We always get the roasted vegetable salad and one of their wonderful pizzas. You have to get a 16 inch so you have leftovers to take home!

S
vipSlow
Milwaukee
14 reviews
Dined on August 8, 2020
Overall4food4service4ambience4

Outdoor seating was nice.

WL
vipWineLuvr
Milwaukee
23 reviews
Dined on July 29, 2020
Overall5food5service5ambience5

This is one of my favorite places. The owner/manager is always very welcoming and truly glad to see you. It has a very relaxed atmosphere. The food is always wonderful. My favorites are a shrimp and pasta in mildly spicy tomato sauce. The last time I had their "Double Trouble"pizza and was impressed by the volume of toppings. Our server, Tim, was personable, attentive and thorough. I highly recommend this establishment.

JO
vipJoyceO
Tampa
14 reviews
Dined on July 18, 2020
Overall5food5service5ambience5

We had a nice secluded table in an alcove. Wonderful service and exceptional meal!

GA
GinaA
Milwaukee
4 reviews
Dined on July 12, 2020
Overall5food5service5ambience5

Awesome as usual!!! Garlic bread to die for with yummy meatballs and salad.
Of course, cool, refreshing, minty, Mojito's...

6
vip6406nb
Milwaukee
14 reviews
Dined on July 10, 2020
Overall5food5service5ambience5

Excellent as always. They treat us special and we keep coming back.

F
Finngirl
Milwaukee
2 reviews
Dined on July 9, 2020
Overall5food5service4ambience5

We sat outside but had to go in due to a storm. Excellent eggplant parm with quite large helpings so I had lunch the next day . Wonderful cosmopolitan !!

KG
vipKristinG
San Francisco
1 review
Dined on July 1, 2020
Overall5food5service5ambience5

Great service. Great food. Pizzas are delicious! Crispy crust and fresh ingredients. We frequently dine here.

WL
vipWineLuvr
Milwaukee
23 reviews
Dined on June 19, 2020
Overall5food5service5ambience5

Wonderful food - - fantastic staff. They went above and beyond to make sure we had a wonderful evening. Will definitely return

d
vipdinegal
Milwaukee
5 reviews
Dined on June 13, 2020
Overall5food5service5ambience5

Great Experience! The staff is taking the new Covid19 guidelines very seriously. We will definitely be going back!

WT
WayT
Milwaukee
3 reviews
Dined on June 12, 2020
Overall5food5service5ambience5

The owners from our perspective have the top two restaurants in the Bay. Consequently, we try to frequent them. Trouble however, we asked our server Tim to check with the kitchen if we could get it, & we did. We supplemented that with a 12” pizza. The other party with us had the lobster ravioli which they have had before, & to no ones surprise everything was excellent with leftovers to take home.

MP
MikePicks
Milwaukee
11 reviews
Dined on June 4, 2020
Overall4food4service4ambience4

Patio seating on a lovely day with great food and beverages was a nice way to emerge from social distancing due to Covid-19. Nothing beats fresh air, good company, and tasty food.

C
vipCeeng
Milwaukee
156 reviews
Dined on March 5, 2020
Overall5food5service5ambience4

I was taken to our table that had a small chalk board welcoming our party, really nice touch. Our server asked if I’d like anything until my guest came. He had wonderful recommendations. It was a great evening of good wine, great garlic bread, super Caesar salad, and delicious pasta carbonara which our server suggested. We were never rushed, checked on often, and treated like family. Our first visit and we will be back. Thank you!

n
vipnona
Milwaukee
57 reviews
Dined on February 23, 2020
Overall4food4service4ambience4

We enjoyed our meal at Trouble and Sons. We intended to order a pizza when we went there, and it was very good. We also discovered a wider range of Italian entrees on the menu, all of which sounded delicious, so we will probably try one of those next time.

OT
OpenTable Diner
1 review
Dined on February 22, 2020
Overall5food5service5ambience5

Great service

OT
vipOpenTable Diner
Milwaukee
12 reviews
Dined on February 15, 2020
Overall5food5service5ambience5

The server was excellent. The food was delicious!!!

OT
OpenTable Diner
1 review
Dined on February 14, 2020
Overall5food5service5ambience5

This was an overall great experience.

OT
OpenTable Diner
1 review
Dined on February 14, 2020
Overall5food5service4ambience5

Our 2nd visit here! Everything very good except coffee was barely warm. We had finished dessert and were fine with not waiting for new pot to be brewed. This will not deter us from returning! Our food was very good :)

LL
LisaL
San Francisco
5 reviews
Dined on February 14, 2020
Overall4food4service5ambience4

Myself, son, daughter and granddaughter went to Trouble & Sons for the first time in Valentine’s Day. In hindsight, maybe not the best time to go, but we really enjoyed it! We had a bit of a wait for our 6:30 reservation, but were able to sit on a sofa and have a glass of wine. The only downside is there are a lot of tables in a small room, so there is a lot of movement. We were near the bar, which also contributed to the activity. We had the toasted ravioli and mozzarella sticks for starters—both good! My daughter and granddaughter are major meat eaters, so got the Double Trouble with thin crust. My son got the classic sausage, and I was in a risk-taking mood so got the Hawaiian with a hand tossed crust. It was delicious! Gordon Ramsey is wrong about pineapple on pizza. It was not at all overpowering. We all liked our pizza very much and there was plenty to take home—the portion sizes are good. We split a chocolate/vanilla panna cotta for dessert. I really liked it, though my daughter was not fond of the vanilla portion, as she said it did not have much vanilla flavor. The service was very good and it was a pleasant evening—we all agreed we would be back!

D
Domnitz13
Milwaukee
6 reviews
Dined on February 14, 2020
Overall5food4service5ambience5

I brought my Daughter Lucy here for Valentine’s Day. They had a small plaque on the table, it read “Ari & Special Guest”. I had written on the open table reservation that it was a “Daddy / Daughter” Valentine’s Day dinner. It was a nice touch. The meal was very nice, the service was wonderful. Having one of the owners stop by was a highlight. Our only disappointing moment was a non molten lava cake that Lucy had been looking forward to enjoying. But these things happen and won’t keep me from returning. The restaurant is beautiful and has a great feel. It’s kid friendly but doesn’t promote the idea that it’s a place for kids to run wild. I love the spacing and thoughtfulness of the decor and the casual yet attentive nature of the service staff. There is a wonderful glow of intentional hospitality throughout the restaurant. Friendly bar staff, recommendations without pressure and a feeling that you are valued as a guest. I really enjoyed this restaurantC this was my second time her and I’ll be back soon.

WT
WayT
Milwaukee
4 reviews
Dined on February 12, 2020
Overall5food5service5ambience4

Love the owner & what she & her partner have done for the Whitefish Bay dining experience. They have added two superior restaurants(Moxies & Trouble & Sons) to the area. Both restaurants have excellent food & bar service. In addition the one owner is hands on to insure customers are happy with their experience. She also helps the staff in bringing food to customers & whatever else needs to be done. Pizza is the specialty of Trouble & Sons. The soup & appetizers are excellent as well.

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 203 OpenTable diners.

Trouble and Sons Pizzeria does offer gift cards which you can purchase here https://troubleandsonspizzeria.com/gift-card-shop/.

Yes, you can generally book this restaurant by choosing the date, time and party size on OpenTable. Due to local restrictions, this restaurant may not be accepting reservations at the moment.