Trouble and Sons Pizzeria

Name: Trouble and Sons Pizzeria
Address: 133 E Silver Spring Dr, Whitefish Bay, WI, United States, 53217
Telephone: (414) 800-5015
Price range: $30 and under
Rating: 4.6

4.6

344 Reviews

$30 and under

Italian

Top Tags:

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

Party Size

2 people

DateTime

Feb 3, 2023

7:00 PM

Booked 13 times today

Order delivery or takeout

Takeout

(414) 800-5015

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
Website
http://troubleandsonspizzeria.com/
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.

Location
133 E Silver Spring Dr, Whitefish Bay, WI 53217
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

Featured in

Popular dishes

Buttermilk Calamari$16.00
Hand-cut calamari, lightly seasoned and fried, served with marinara and Calabrian pepper aioli
Eggplant$14.00
Fresh, hand-cut eggplant, deep-fried, served with lemon basil aioli and marinara
Arancini$14.00
House-made parmesan risotto breaded and stuffed with mozzarella cheese, served with marinara
Tomato Caprese$14.00
Sliced heirloom tomatoes, fresh mozzarella and basil, balsamic glaze
Garlic Bread$8.00
Mini loaf of warm garlic bread topped with parmesan cheese, served with marinara
Meatballs$14.00
Homemade meatballs served with marinara and crostini
Pallini di Pasta$12.00
Baked balls of dough topped with mozzarella cheese, made-in-house garlic butter, and parmesan cheese
Parmesan Truffle Fries$11.00
Thinly sliced Yukon Gold potatoes, tossed in a blend of spices, cheese, and truffle oil

Sandwiches

Served with soup or salad (house or Caesar)

Stromboli$18.00
WFB Art Festival favorite! Pocket filled with cheese and pepperoni
Chicken or Eggplant Parmesan$20.00
Lightly breaded and deep-fried, topped with mozzarella, marinara, and onion jam

Salads

All salads are served with toasted crostini. Chicken* $7 | shrimp* $9 | anchovies* (2oz) $6 | portabella mushroom cap $6 | salmon* $14

Antipasto*$18.00
Olives, feta, provolone, shaved parmesan, pepperoncini peppers, red onions, cherry tomatoes, pepperoni, prosciutto, salami tossed in a fresh herb vinaigrette
Grilled Italian Wedge*$19.00
Crisp romaine lettuce wedge, prosciutto, sliced pepperoncini, cherry tomato, red onion, shaved parmesan, sherry Dijon vinaigrette drizzle
The Strawberry Goat$16.00
Fresh baby spinach, sliced strawberries, spicy pecans, shaved red onions, crumbled goat cheese, strawberry balsamic (vegan available)
Caesar$12.00
Romaine, shaved parmesan, garlic butter croutons tossed in Caesar dressing

For the Kiddos

Pasta$6.00
Choice of spaghetti, penne or linguini tossed with butter, marinara or alfredo

More Great Stuff

Soup
- Cup$4.00
- Bowl$6.00
Side Roasted Root Vegetables$9.00
Sliced Bread$5.00
Side House Salad$7.00
Side Caesar$7.00
Side Truffle Fries$7.00

Entrées

Served with soup or salad (house or Caesar). Gluten-free pasta available

Sicilian Steak$48.00
Char-broiled 8oz NY Strip topped with toasted breadcrumbs, herbs, fried capers, garlic confit, compound butter; served with roasted tomatoes and house-made parmesan truffle fries
Shrimp Fra Diavolo*$22.00
Gulf shrimp, fresh basil, minced garlic, red pepper flakes, tossed in angel hair pasta and a spicy red sauce
Tuscan Salmon*$27.00
Grilled salmon topped with roasted tomatoes and onions over angel hair pasta with charred asparagus, basil and Tuscan sauce
Stuffed Portabella$24.00
Balsamic marinated portabella mushroom caps stuffed with parmesan risotto, drizzled with a balsamic reduction and julienne cut vegetables (vegan available)
Family Roots$25.00
Sauteed carrots, sweet potatoes, shallots, green beans, garlic confit, tossed with penne pasta and sundried tomato pesto sauce with pine nut garnish
Rosemary Chicken*$25.00
Chicken marinated in fresh rosemary and garlic, lightly breaded and baked. Served with parmesan risotto and mushroom ragout
Chicken* or Eggplant Parmesan$22.00
Lightly breaded and deep-fried, topped with mozzarella and marinara over linguini in a light cream sauce
Chicken Pesto Linguini*$26.00
Chicken topped with house made pesto and fresh mozzarella over linguine in a white wine cream sauce with asparagus, sundried tomatoes and shallots
Spaghetti and Meatballs*$20.00
Two house made meatballs, marinara, parmesan

Pizza

Toppings: Andouille Sausage, Italian Sausage, Pepperoni, Anchovies, Artichokes, Banana Peppers, Basil, Black Olives, Tomatoes, Mushrooms, Red Bell Peppers, Onions, Roasted Garlic, Spinach, Fresh Mozzarella. Other Popular Toppings: Shrimp $9, Chicken $9, Anchovies $6, Vegan Cheese 10 inch $5, 12 inch $5, 16 inch $9

Cheese
- 12" Hand-Tossed$16.00
- 16" Hand-Tossed$20.00
- 10" Cauliflower Crust (Gluten Free)$17.00

House Pizzas

Sorry, no topping substitutions on House Pizzas. Sorry, no half/half on specialty Pizzas

Pizza Margherita*
pesto base, roasted tomatoes, fresh mozzarella, fresh basil
- 12" Hand-Tossed$22.00
- 16" Hand-Tossed$27.00
- 10" Cauliflower Crust (Gluten Free)$23.00
MKE Classic
Italian sausage, mushrooms, onions, mozzarella
- 12" Hand-Tossed$22.00
- 16" Hand-Tossed$28.00
- 10" Cauliflower Crust (Gluten Free)$23.00
The Bella Potato*
pesto base, Yukon Gold sliced potatoes, onion, prosciutto, fresh mozzarella cheese
- 12" Hand-Tossed$20.00
- 16" Hand-Tossed$24.00
- 10" Cauliflower Crust (Gluten Free)$21.00
WFB Veggie
truffle ricotta base, roasted tomatoes, red peppers, mushrooms, artichokes, garlic, mozzarella
- 12" Hand-Tossed$23.00
- 16" Hand-Tossed$28.00
- 10" Cauliflower Crust (Gluten Free)$24.00
Double Trouble
Italian sausage, andouille sausage, pepperoni, banana peppers, mushrooms, mozzarella
- 12" Hand-Tossed$24.00
- 16" Hand-Tossed$29.00
- 10" Cauliflower Crust (Gluten Free)$25.00
House Special
prosciutto, fresh basil, banana peppers, onions, mozzarella
- 12" Hand-Tossed$22.00
- 16" Hand-Tossed$28.00
- 10" Cauliflower Crust (Gluten Free)$23.00

Custom Pizzas

Toppings: Andouille Sausage, Italian Sausage, Pepperoni, Anchovies, Artichokes, Banana Peppers, Basil, Black Olives, Tomatoes, Mushrooms, Red Bell Peppers, Onions, Roasted Garlic, Spinach, Fresh Mozzarella. Other Popular Toppings: Shrimp $9, Chicken $6, Anchovies $6, Vegan Cheese 10 inch $5, 12 inch $5, 16 inch $9

Custom Pizzas
- 12" Hand-Tossed$16.00
- 16" Hand-Tossed$20.00
- 10" Cauliflower Crust (Gluten Free)$17.00

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

Noise • Moderate

Loved For

Wisconsin
Neighborhood gem
Wisconsin
Italian
Milwaukee
Best Service
Milwaukee
Best Value
Milwaukee
Neighborhood gem
Milwaukee
Italian

Sort by

Filters

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
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!
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.
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.
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.
JB
JamesB
Milwaukee
50 reviews
vip
5.0
50 reviews
Dined on December 17, 2022
overall5food5service5ambience5
Good as usual 👍🏼
c
candyman
Milwaukee
49 reviews
vip
5.0
49 reviews
Dined on December 14, 2022
overall5food5service5ambience5
Everything was excellent!!
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.
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!!
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.
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.
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.
c
candyman
Milwaukee
49 reviews
vip
5.0
49 reviews
Dined on November 19, 2022
overall5food5service5ambience5
Excellent food and excellent service!!
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.
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!
c
candyman
Milwaukee
49 reviews
vip
5.0
49 reviews
Dined on November 16, 2022
overall5food5service5ambience5
Everything was excellent. A real gem!!!
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.
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!
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!
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!!!
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.
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!
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.
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!
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.
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!
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.
c
candyman
Milwaukee
49 reviews
vip
5.0
49 reviews
Dined on October 8, 2022
overall5food5service5ambience5
Everything was excellent!!!
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!
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.
MB
MarkB
Milwaukee
2 reviews
vip
5.0
2 reviews
Dined on September 30, 2022
overall5food5service5ambience5
So great to have this restaurant back.
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.
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.
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.
ML
MollyL
Washington DC
22 reviews
vip
5.0
22 reviews
Dined on July 9, 2022
overall5food5service5ambience5
Always fantastic service and food!
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.
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.
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!
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.
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

Party Size

2 people

DateTime

Feb 3, 2023

7:00 PM

Booked 13 times today

Order delivery or takeout

Takeout

(414) 800-5015

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

Website
http://troubleandsonspizzeria.com/
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.

Trouble and Sons Pizzeria

Make a reservation

Order delivery or takeout

Takeout

Additional information

The Best Cheap Eats in Milwaukee

The Best Pizza in Milwaukee

Women-Owned and -Operated Restaurants to Support in Wisconsin

Eggplant

Custom Pizzas

Pasta

Starters

Buttermilk Calamari$16.00

Eggplant$14.00

Arancini$14.00

Tomato Caprese$14.00

Garlic Bread$8.00

Meatballs$14.00

Pallini di Pasta$12.00

Parmesan Truffle Fries$11.00

Sandwiches

Stromboli$18.00

Chicken or Eggplant Parmesan$20.00

Salads

Antipasto*$18.00

Grilled Italian Wedge*$19.00

The Strawberry Goat$16.00

Caesar$12.00

For the Kiddos

Pasta$6.00

More Great Stuff

Soup

Side Roasted Root Vegetables$9.00

Sliced Bread$5.00

Side House Salad$7.00

Side Caesar$7.00

Side Truffle Fries$7.00

Entrées

Sicilian Steak$48.00

Shrimp Fra Diavolo*$22.00

Tuscan Salmon*$27.00

Stuffed Portabella$24.00

Family Roots$25.00

Rosemary Chicken*$25.00

Chicken* or Eggplant Parmesan$22.00

Chicken Pesto Linguini*$26.00

Spaghetti and Meatballs*$20.00

Pizza

Cheese

House Pizzas

Pizza Margherita*

MKE Classic

The Bella Potato*

WFB Veggie

Double Trouble

House Special

Custom Pizzas

Custom Pizzas

Overall ratings and reviews

Loved For

Sort by

Filters

Cleaning & sanitizing

Physical distancing

Screening

FAQs

Does Trouble and Sons Pizzeria offer delivery through OpenTable or takeout?

How is Trouble and Sons Pizzeria restaurant rated?

Is Trouble and Sons Pizzeria currently accepting reservations?

Make a reservation

Order delivery or takeout

Takeout

Additional information

Featured in

The Best Cheap Eats in Milwaukee

The Best Pizza in Milwaukee

Women-Owned and -Operated Restaurants to Support in Wisconsin