All The Romantic Italian Destinations On Matt James & Rachael Kirkconnell’s Trip

Season 25 The Bachelor Matt James and girlfriend, Rachael Kirkconnell recently traveled to Italy and visited multiple destinations that you will also want to add onto your itinerary.

rachael kirkconnell matt james italy
Instagram @rachaelkirkconnell

The famous duo from the dating show franchise, Matt James and Rachael Kirkconnell, embarked on a romantic adventure exploring Italy back in February. They stopped in Milan, Lake Como, Venice, Florence, and Rome to discover local culture, food, and popular sites. When in Italy, don’t miss these places that have been Matt-and-Rachael approved.


The first destination the couple visited was Milan, where the airport is located. Here, James and Kirkconnell strolled around admiring the city architecture and shops, while pausing for food.

Panini De Santis

Corso Magenta, 9, 20123 Milano MI, Italy

Panini De Santis is a sandwich shop in Milan that was established in 1964 by a married couple. Matt and Rachael visited this shop more than once on their trip in Milan. The menu is extensive, so you will certainly find a dish to satisfy your taste buds. On their first visit, Matt got the “Ronny” sandwich, and Rachael opted for the “Sheila.”

De Santis

Volemose Bene

Via della Moscova, 25, 20121 Milano MI, Italy

This is where the pair decided to stop for dinner. At Volemose Bene, you will find delicious Roman cuisine featuring dishes including: Tagliata coi Carciofi Saltati, Spaghetti A’Carbonara, and Bucatini A’Matriciana.

matt james
Image by @mattjames919 on Instagram


After Milan, the duo ventured to Lake Como and admired the beauty of the town by going on a boat ride, stopping by Bar Caffé Rossi in Bellagio for snacks and drinks. Afterward, they headed back to Milan.

Bar Caffé Rossi (Bellagio) Giuseppe Mazzini, 22, 22021 Bellagio CO, Italy

Rachael Kirkconnell
Image by @rachaelkirkconnell on Instagram

At Bar Caffé Rossi, you will find different wines and numerous beer options. It also serves a mean breakfast. Located on Lake Como, the interior space is regal while the views are breathtaking. Sitting outside is the way to go especially if the weather is nice!


After Milan, Matt and Rachael traveled to Venice. They walked around town and rode on the iconic gondolas in order to reach their home away from home for the night.

Captain Candy

Merceria II Aprile, 5037, 30124 Venezia VE, Italy

One place they stopped at was Captain Candy, a popular candy shop just two minutes away from the Rialto Bridge. Rachael got the bestseller: a “raspberry stick,” to which she said “reminded her of SweeTart ropes.”

Captain Candy Venice. INSTAGRAM @kellyplph
Captain Candy Venice. INSTAGRAM @kellyplph

Caffé Florian San Marco, 57, 30124 Venezia VE, Italy

Caffé Florian is one of the places where the reality stars took a break with delectable Italian coffee. This legendary café opened in 1720, making it the oldest café in the world. It is a must-stop when coming to Venice if you are looking to immerse yourself in the rich history of the city.

Caffe Florian, Venice
Image by @rachaelkirkconnell on Instagram

Ristorante La Piazza Venezia

S. Marco, 615, 30124 Venezia VE, Italy

For a true Venetian dinner, the pair chose to indulge at Ristorante La Piazza Venezia where Italian and Traditional Venetian Cuisine are served. First and second courses comprise of fresh seafood and meats, pizza, salad, and more. A romantic hotspot in the heart of the city.


The next destination Matt and Rachael visited was the amazing city of Florence where they stopped for pastries, ventured around town, and took advantage of photo ops.

Trattoria Anita Firenze

Via del Parlagio, 2R, 50122 Firenze FI, Italy

This was a favorite amongst the couple, since Rachael wrote via Instagram story “might be our best meal yet.” Trattoria Anita serves authentic Italian food, with dishes such as Linguine Alla Pescatora, Bocconcini Di Pollo Al Curry, Roast Beef, and much more.

Giardino delle Rose

Viale Giuseppe Poggi, 2, 50125 Firenze FI, Italy

Located in the Oltrarno District, this beautiful garden is a must-see when in Florence. It was developed by Giuseppe Poggi in 1865 and has only grown in beauty ever since. There are numerous roses, magnolias, waterlilies, lemon trees, and even a Japanese Garden. The best time to visit is when the roses are in bloom!

Giardino delle Rose
Image by @rachaelkirkconnell on Instagram

All’antico Vinaio

Via dei Neri, 76 r, 50122 Firenze FI, Italy

All’antico Vinaio is where the couple tried paninis. Although Rachael said it was good via her Instagram story, the De Santis ones was preferable. Situated in the heart of Florence, the menu consists of sandwiches made with local bread: schiacciata, options come in La Schiacciata Del Boss, L’Inferno, and The New Yorker.

Trattoria 13 Gobbi

Via del Porcellana, 9R, 50123 Firenze FI, Italy

Matt and Rachael devoured tasty Italian dishes at Trattoria 13 Gobbi in an intimate Italian setting with genuine local cuisine. Some options on the menu include Porchetta Arrosto, Chitaronni, and Tagliata di Bistecca. Don’t miss the tiramisu here!

Trattoria 13 Gobbi
Image by @mattjames919 on Instagram


The final city the duo visited before heading back to Milan to fly home was Rome. Here, they dove into sightseeing famous landmarks such as the Colosseum, the Trevi Fountain, and Vatican City.

The Colosseum

Piazza del Colosseo, 1, 00184 Roma RM, Italy

While in Rome, Matt and Rachael decided to tour the Colosseum, also known as Flavian Amphitheater which opened in 80 A.D. as the largest amphitheater in the Roman Empire. The Colosseum was used for gladiator fights, chariot racing, animal fights, and other public shows.

Rachael Kirkconnell matt james italy
Image by @rachaelkirkconnell on Instagram

Gelateria Come il Latte

Via Silvio Spaventa, 24/26, 00187 Roma RM, Italy

This is another spot where they tasted true Italian gelato. The menu here is massive with unique flavors including: Stracciatella, Ricotta Fichi Caramellati E Nocciole, Passion Fruit, Zabaione, Banana E Cioccolato, and many more.

Fontana di Trevi

Piazza di Trevi, 00187 Roma RM, Italy

Also known as the Trevi Fountain, Matt and Rachael visited this famous landmark created by Nicola Salvi, who passed before its completion. In 1762, it was finished by Giuseppe Pannini. It is said that if you throw a coin into the fountain, you will return to Rome one day.

Trevi Fountain
Image by @rachaelkirkconnell on Instagram


Via della Paglia, 1/2/3, 00153 Roma RM, Italy

On Instagram story, Rachael wrote that Tonnarello is “a must if you go to Rome.” The casual eatery known for meatballs also carries a lovely selection of pizzas and pastas. There’s live guitar accompanying your local meal, we highly recommend patio seating if you want to take in the bustling city vibe.

Image by @mattjames919 on Instagram

Soho House Rome

Via Cesare de Lollis, 12, 00185 Roma RM, Italy

While in Rome, Matt and Rachael stayed at the Soho House. The selective private member club is situated in the San Lorenzo neighborhood. The 10-story building sports amenities such as a beautiful rooftop, a gym, a drawing room, and more.

Stadio Olimpico

Viale dei Gladiatori, 00135 Roma RM, Italy

They also attended a fútbol game at Stadio Olimpico to watch AS Roma play. It opened in 1953 and is the largest sports facility in Rome with the ability to seat 70,000 spectators. The premise does not offer stadium tours, so the only way to visit Stadio Olimpico is to attend a game.

matt james italy
Image by @mattjames919 on Instagram

Mimí e Cocó

Via del Governo Vecchio, 72 00186 Rome, Lazio, Italy

Mimi e Cocó is another place the couple stopped for food and drinks. This cozy bistro serves numerous signature dishes, including; pasta, salads, pinsa, and more. They also have a popular wine bar with a great assortment of different vinos. Let’s not forget, its Compari bar is pretty spectacular.

Mimi e Coco
FACEBOOK Mimi e Coco


The Colosseum

Piazza del Colosseo, 1, 00184 Roma RM, Italy

The pair could not come to Rome without visiting the famous Vatican City. They explored and admired St. Peter’s Basilica. Vatican City is an independent city-state ruled by the Pope. When in Rome, stop at St. Peter’s Square and the aforementioned Basilica, as well as the Sistine Chapel and Vatican Museums.

Rachael Kirkconnell matt james italy
Image by @rachaelkirkconnell on Instagram
Kennedy Kollar

Content Associate

Kennedy is an entertainment junkie hailing from Pennsylvania. When she is traveling, you can find her searching for the best gluten-free foods as well as matcha and chai teas. She loves immersing herself in new cultures and wishes to visit the less-traveled hidden gems.

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