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Romantic Spots to Include in Your Date Night – Lakeshore to Lake Country

I don’t know about you, but the past few years have really slowed our “going out” game. If we do, we usually take advantage of curbside services or take out options and I’ve rarely seen the inside of a restaurant establishment. With Valentine’s day rapidly approaching - we’re only a month away! - I’ve been feeling the urge to get out shake things up with a romantic date night. The restaurant landscape looks vastly different than it did 2 years ago, so I decided to do some research and find a few of the most romantic spots to include in your date night, spanning from the lakeshore out to Lake Country! Maybe I’ll see you out.


Let’s start with hotels! Honestly, most of my favorite restaurant experiences are establishments that are a part of a hotel. They really know how to cater to your needs and set the mood, so naturally I wanted to include a number of hotel dining options on this list.


Located in Wauwatosa right by Mayfair Mall, you’ll find Renaissance Milwaukee West. A fairly recent addition to the area, the sleek and modern interiors set you up perfectly for an upscale yet laid back date night. Eldr+Rime offers cocktails and dining, as well as their “Hygge Time” happy hour, which you can take advantage of inside, out on the patio, or if it’s winter, a luxe stuga experience - that means “cabin” in Swedish!

The Outsider

I will never turn down a night at a Kimpton Hotel - hello, wine happy hours - and one of my favorite Milwaukee spots is on the rooftop of the Journeyman Hotel - The Outsider! Boasting beautiful 9th floor views of the city, day or night, the scene of your date is sure to be set. You can enjoy small bites and cocktails while taking in all that Downtown has to offer! Hungry afterwards? Step downstairs to Tre Rivali for some Mediterranean fare while you’re at it!

I.d. Delafield

Out in Lake Country at the Delafield Hotel, you’ll find I.d. This restaurant is a shared plate dining experience serving upscale American fare and cocktails in a sophisticated, rustic-chic atmosphere. Cozy up with your honey and get ready to share a sensational evening together - this is actually where Paul and I have reservations for our Valentine’s date this year and I cannot wait!

The Dark Room

Everyone’s favorite Milwaukee hotel (myself, included) is the Saint Kate, who are we kidding? They’ve got so many great dining options, but my absolute favorite is their hidden dining room, The Dark Room, where you can enjoy a secluded, romantic evening together. The entrance is hidden by a bookcase with steamy art pieces and luxe décor inside, the mystique alone is going to set your date off right!

Blu Bar & Lounge

The Pfister Hotel in Milwaukee is absolutely the grandest of them all, and no bar tops their rooftop establishment, Blu. Located on the 23rd floor, this martini bar provides unparalleled views of Downtown Milwaukee and lady Lake Michigan - and of course delicious cocktails, starters, and desserts. They even have live music on Fridays and Saturdays to set that date night mood just right.

Ash Hearth & Bar

Some of my favorite vibes in Milwaukee are served at the Iron Horse Hotel. Their restaurant, Ash, features a seasonal American menu that specializes in the use of fire and smoke to enhance the flavor in all of their meats and veggies that will be sure to bring the heat to your date night experience!


Hotel Metro in downtown Milwaukee recently updated their entire establishment, including their inhouse dining. Oggie’s brings you delicious global inspired tastes with a Midwest twist made with local and seasonal ingredients so whether you’re enjoying a breakfast or dinner date, you’re covered. Their chic and modern décor provides the perfect atmosphere for an upscale romantic dining experience together!

Stella Van Buren

The Westin in Downtown Milwaukee brings you the airy, spacious, chic establishment that is Stella Van Buren. They’ve got you covered for every meal of the day (and all of the in between). Grab a cocktail and sit by the fire, take advantage of their new patio, or snuggle side by side in a booth and indulge in the upscale Italian-American fare and craft cocktails that they offer.


Not every great restaurant is inside a hotel - no, these establishments stand alone, and stand out! I’ve gathered a few new and a few old favorites, including a couple that I’ve just discovered in my research that I can’t wait to try out. Read on to find the perfect spot to set your date night right!


If you’re looking for an intimate, cozy Italian meal, look no further than Onesto. One of my favorite downtown restaurants to indulge in, Onesto offers a romantic atmosphere with handmade pastas. They’ve also been named the best Italian restaurant in Milwaukee!

Firefly Tosa

Aesthetic? 100. Menu? 1,000. Grab your honey and head to Firefly at Wauwatosa if you’re into a modern twist on classic comforts with a dash of creativity. The ambiance is set and ready for you to come share some love!

Cooper’s Hawk

Cooper’s Hawk Winery is located outside of Brookfield Square Mall and is one of my very favorite places to wind down. From build your own wine flights to delicious flatbreads and menu items, I would go here every night if I could. The lights are low and the mood for date night is so very right!

Le Reve

If there is one thing I love in this world, it’s French food. Paris is the city of love and you can get a little slice of it right here in Wauwatosa. Decadent brunches and dinners, plus an artful bakery case are the perfect indulgences for your next date!

Artisan 179

If you’re looking for a lake view while you dine, you’ll want to experience Artisan 179 in Pewaukee! Their modern global cuisine is freshly prepared from scratch and the restaurant strives to share their passion for craft, food, art, and music - all of the makings of a perfect date!

Belfrē Kitchen

Fun fact, one of the oldest existing buildings on its original foundation in Delafield is home to my next pick, Belfrē Kitchen. Today, they’re bringing local to life by sourcing their ingredients from farmers in their own backyard. With a “come as you are” attitude, you’re welcome in any outfit and sure to have a fantastic meal with your date while you’re at it.

Movida at Hotel Madrid

If you’re thinking about adding a little Spanish zest to your date night, look no further than Movida at Hotel Madrid in Milwaukee. Tapas, Paella, outdoor dining, special themed events - this place has it all and is sure to bring the heat to your next date. In addition to their special Con Amor menu for Valentine’s Day, you can look forward to Bar Far Far Away, their Star Wars themed pop up, too!


One of the restaurant’s on On Milwaukee’s Restaurant Bucket List is Buckley’s, a chic spot close to the lakefront offering brunch and dinner options. The goal of the Buckley’s team is to provide an enjoyable dining experience in a comfortable atmosphere, what more can you ask for when you’re planning your next date? With a vast dessert menu, this is sure to be a sweet excursion.

Tofte’s Table

If you’re interested in upscale dining in an intimate, relaxed environment by the river, Tofte’s Table in Waukesha has got your name written all over it. This restaurant is a place for making memories, laughter, and conversation, so their menu is full of plates that are meant for sharing. Unless you’re on a date with Joey Tribbiani (Joey doesn’t share food!), this place has the makings for an intimate and memorable date night.


Did someone say French food again? Pastiche has got the goods! Originally located inside Hotel Metro downtown, Pastiche has moved to Brown Deer and I will follow them wherever they may go. They cook from scratch, and they cook with love - so why not bring yours on a date there?


Whether you’re looking for a first stop on the date night, or exclusively looking for cocktails, a bar or lounge is a great place to start. Below are a couple options where you’ll get the perfect craft cocktail and maybe a small plate or two, and naturally a perfect date while you’re at it!


A back alley speak easy? Sign me up! Black Cat Alley is a staple of the city, but did you know that amongst the murals, the entrance to Shanghai Speakeasy is located back there, as well? It is, my friends. It is indeed, and inside you’ll find a menu of delicious craft cocktails but my personal favorite has to be the Dealer’s Choice - I promise, they won’t do you wrong.

The Ruby Tap

The Ruby Tap, a wine bar so nice, they made it twice! Take your pick between their Wauwatosa and Mequon locations, but regardless, you’ll be pleased to find dispense-your-own-wine options, bottle subscriptions, and truffle popcorn. Yeah, you heard me - I’m on my way now, too. Get your fill on wine and take some home while you’re at it, whatever your next step is in your date night it’s sure to be a little sweeter after the Ruby Tap!

Indulgence Chocolatiers

In the Walker's Point neighborhood of Milwaukee, you'll find Indulgence Chocolatiers where you can find hand crafted confections and pair them with fine wines, craft beers, cheeses, and whiskey, all while you watch the chocolatiers whip up more masterpieces in the kitchen. They call this place Indulgence for a reason, and isn't that what date night is all about?

Glassnote Candle Bar

Yes, a candle bar. In Walker's Point, you'll find a combination of a DIY candle shop and craft bar. What better way to spend time with your love than to create together while enjoying sumptuous libations? You can even make a signature scent to commemorate the date!


On a quiet little corner on Main St in Waukesha on the Fox River, you’ll find Crush Wine Bar & Shop and the perfect place for a quiet little date night. They’re serving wine and serving vibes with their modern interiors and sensational selection. Dare I say it, you should probably bring your crush to Crush?

Listen, I’ve given you plenty of options for your next SEVERAL date nights - so what are you waiting for? There’s no time like now to get those reservations in, get out with the ones you love, and give some of our local establishments the love that I’m sure they’ve all needed over these past few years. Happy dating!

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