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Cleveland Date Night Guide: Little Italy

Welcome to the Cleveland Date Night series! This series will highlight some fun date night ideas in and around Cleveland. Find more date night ideas here.

Little Italy, also known as Murray Hill, is located on the east side of Cleveland, nestled between University Circle and Case Western Reserve to the west, and Lakeview Cemetery on the east. This place was one of 5 Italian settlements in the area, and in 1911, about 96% of people living here were from Italy and 2% had Italian parents! 

These days, it is an enclave well-known for its art, food, and boutiques. The Italian connection is still unmistakable in the area, as most of the restaurants and shops have Italian flair!

With so many delectable Italian eateries and lovely shops, Little Italy always makes for an unforgettable Cleveland date night.

To set up this Cleveland date night, start with a fun activity, then grab some drinks, have dinner, and perhaps enjoy a tasty dessert after! 

How to Plan a Date Night in Little Italy

Step 1: A Fun Activity 

Whether you love sightseeing or shopping, here are some fun activities to enjoy on a Little Italy date night.

Lake View Cemetery12316 Euclid Ave – Maybe this sounds a bit odd for a date night activity, but on a nice evening when the sun is still up, wandering around this historic cemetery is quite lovely. 

Haserot Angel at Lake View Cemetery
Haserot Angel at Lake View Cemetery

If you’re here in the spring, you can perhaps walk along Daffodil Hill and take photos. You’ll also be delighted by the magnolias and cherry blossoms in bloom if you come at the right time. And then in autumn, the Japanese maples turn a vibrant red color. 

Aside from the flora of Lake View Cemetery, there are famous sites to see here, too, like John D. Rockefeller’s grave, the James A. Garfield Memorial, Wade Memorial Chapel, and plenty of sculptures. 

The Sculpture Center1834 E 123rd St – If you are able to start your date night before 4 pm during the week or 5 pm on a Saturday, definitely visit The Sculpture Center. Be delighted with rotating exhibits and plenty of sculpture art to enjoy. 

Walk around Little Italy – Various Places – Little Italy has many treasures to find just by walking around! Enjoy the gazebo in Tony Brush Park. Pop into shops like La Bella Vita for Italian-inspired goods, Moonstruck for vintage goods, Mayfield Smoky Shop for cigars, and Murray Hill Market for food items. 

There are also galleries to enjoy like Tricia Kaman Studio, Verne Collection, and Keller Art Glass. Don’t forget to enjoy the mural wall while you’re here too! It is on the main street through Little Italy on Mayfield Rd. 

Little Italy mural
Part of the mural on Mayfield Road

Little Italy Wines12414 Mayfield Rd – This adorable wine shop in Little Italy is full of great Italian wine. If you’re searching for more specific wines like Lambrusco or Nebbiolo, then this is the place to be. They also offer wine tastings on most Saturday evenings from 3-8 pm. 

For $10, you can try a few wines and learn more about the grapes and vineyards they come from. 

Little Italy wine shop
Inside Little Italy Wines

Step 2: Grab Some Drinks

If you’re already doing a wine tasting, maybe this will be a little redundant. But if you want to grab some drinks before dinner, here are a couple places to go! 

Tavern of Little Italy12117 Mayfield Rd – This little tavern has quite the outdoor space! So if you’re here in the summer, definitely check out their very Instagrammable back patio. 

With a bar both inside and on the patio, you’ll be able to grab some snacks and drinks before your hearty Italian dinner. The aperol spritz here is fantastic, as is their wine selection. There is even a mule menu as well as a water menu! 

Tavern of Little Italy patio
Tavern of Little Italy patio
Aperol Spritz at Tavern of Little Italy
Aperol Spritz

Lounge Leo2161 Murray Hill Rd – For a casual drink spot, this lounge is perfect. Grab a pint of beer or mixed drink and enjoy either the high top tables or go downstairs for more comfortable seating to sit and relax before dinner. 

Step 3: Have Dinner

You’re coming to Little Italy to eat Italian food. I mean, that is the whole point of coming here, right? With phenomenal Italian and Italian-American cuisine, you’ll definitely get your fill of pizza, pasta, and antipasto anywhere you go.

Here are some great Italian eateries for your Little Italy date night:

Guarino’s12309 Mayfield Rd – Known as Cleveland’s oldest restaurant, this place can trace its roots back to 1918 when Vincenzo Guarino operated a pool room and tavern while his wife, Mary, started preparing meals there for family and friends. 

Some things to order here include the lasagna made from a 50-year-old recipe, the cheese or meat ravioli, and the chicken piccata. Their fried calamari is also a must-try! Plus, they have one of the best patios in Cleveland!

Guarinos Patio
Guarino’s patio
Calimari at Guarinos
The fried calamari is really good!

Mia Bella12200 Mayfield Rd – Another great Italian place, this restaurant serves up Italian dishes with a Mediterranean twist. Think shrimp saganaki as an appetizer and a creamy lobster ravioli. Honestly, the menu here is so good that anything you order will be amazing! 

La Dolce Vita12112 Mayfield Rd – This Italian restaurant has some great classics like caccio e pepe, mushroom risotto, and caprese, as well as modern Italian-American fare like chicken parmesan, making it a lovely spot for both authentic Italian and Italian-American eats.

Valerio’s12405 Mayfield Rd – Whether you are craving fresh appetizers like prosciutto-wrapped melon or mushroom ravioli, this place keeps it real with its Italian cuisine. That is because the owner came over from Italy in 1995. The head chef and owner, Valerio, even trained at a Florentine cooking school. If you’re searching for a place that’ll take you to Italy through your tastebuds, this is it! 

Etna Ristorante & Wine Bar11919 Mayfield Rd – Founded in 2009, this place actually has ties to Valerio’s because the head chef and owner here, who also immigrated in 1995, is Valerio’s brother-in-law. So this place definitely has traditional Italian recipes as well. Tuck into fresh Italian food, great seafood, and a nice wine list here! 

Trattoria on the Hill12207 Mayfield Rd – This family-owned and operated restaurant has some tasty eats like stuffed hot banana peppers for an appetizer, and great main dishes like their veggie lasagna, gnocchi in a tomato basil sauce, and fettuccine alfredo. 

Angelos Nido Italia Restaurant12020 Mayfield Rd – This restaurant has an Italian feel the moment you walk inside. While you’re here, you’ll definitely enjoy delicious options like their calamari, veal scaloppini, and linguine in clam sauce. 

Maxi’s12113 Mayfield Rd – If you’re craving a sit-down place for pizza, this is the spot. With 15 pies on the menu ranging from mushroom and roasted red pepper to smoked salmon pizza, you can’t go wrong. Other favorite food items include the little neck clams, frog legs, and calamari. 

Mamma Santa’s12301 Mayfield Rd – If you’re searching for a casual date night restaurant, this pizza place is perfect! Yes, they do have pasta and sandwiches, too, but the pizza here is what you want. This popular place serves up amazing pizza with a deliciously crispy crust. Order up an everything pizza or the customer favorite: pepperoni, mushroom, and sausage, and you won’t be disappointed. 

If you haven’t noticed, ALL of these restaurants are on the same street. Yup, Mayfield Road through Little Italy is where you find most of the shops and restaurants for your date night! 

Step 4: Get Dessert

While you’re in Little Italy, you must save room for dessert. I know that is a tough challenge when the food here is so good and hearty. But trust me, you don’t want to miss dessert here! 

Presti’s Bakery12101 Mayfield Rd – Located conveniently on the same street as all the other restaurants in Little Italy, a stop at Presti’s Bakery is necessary to wrap up your date night! This place serves up so many kinds of cakes, cookies, gelato, pastries, and other Italian classics. From cannolis and cassata cake to tiramisu, you can’t go wrong with whatever you order here! 

Presti's Bakery in Little Italy
Display case (one of them) at Presti’s

Where to Park in Little Italy

Luckily, there are a lot of places for street parking all over Little Italy and the surrounding area. On weekend evenings, however, spots can be limited as this is a popular place to be for a date night, so you may want to get here early.

There is also a parking lot on 119th street that is permit only from 6 a.m.-5 p.m. Monday-Friday. However, after 5 p.m. during the week and on weekends it is available for the public. Rates are between $3-5 depending on how long you park there and can be paid on the Parkmobile app. 

You’ll also find a parking lot on the corner of Circle Dr and Cornell Rd with rates from $4-10. 

Lastly, if you prefer not to drive, there is an RTA metro stop right in Little Italy. So if you’re coming from downtown or another part of the city with RTA, you can take the metro in to save on parking! 


Which of these spots would you enjoy for a Little Italy date night?

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