A recent comment on Insta’ from the lovely Heidi, reminded us just how much our guests enjoy our dining tours! Her family of six adults booked our Surry Hills Tour last October via one of our trusted Travel Partners.

On the night we met in the foyor of the eternally elegant Shangri-la Sydney. before whisking them off to Toei  our new Korean/ Japanese find located on the border of Surry Hills and Darlinghurst.  Talented Chef/Owner Kevin Jeon has created a special snack menu just for us, including Corn Tart, Smoked Tuna Toast, and Fried Mantou, paired with matched cocktails. All the dishes are super yummy and well received by our guests - one of whom is a chef, so we were relieved when he approved of our menu choices.

We then move onto Mille Vini on lively Crown Street, via leafy Bourke Street admiring the many beautiful terrace houses as we stroll past. We point out a few key properties, including Sydney's first modern Rum distillery Brix Distillers and local pub The Beresford with an infamous history and curved bar. A perfect utility during the notorious 6 O'clock swill - due to an early-closing law that lasted almost 40 years in New South Wales - when patrons would line-up to fill their beer glass as quickly as possible before being thrown out onto the sidewalk. Those were dark times in Sydney town.

Mille Vini is housed in a former Stonemasons sandstone cottage in amongst the fashion and design shops, and specialising in rich Mediterranean-style food and an impressive wine collection. With the split-level dining room dressed in seasonal blooms and candles our guests enjoy the happy buzz that embraces them as they walk through the front door. We enjoy our entrees of Zucchini Flowers, Arancini and Wagyu Bresaola Brioche matched with fabulous wine whilst seated on the mezzanine level, floating above the busy main dining room.

After 45 minutes we head for Bar Conte on Riley Street.  Once a notorious crime-filled street Riley Street is now lined with handsome terrace houses, lush green courtyards, well-established trees and a sprinkling of old, restored pubs and contemporary restaurants. Upon entry you could be in 1920’s Tuscany but instead the former too-brightly-lit convenience store has been transformed into a warm, seductive room lined with vintage film posters, retro-furniture gracing the floor and a green marble-topped bar.

Known for its Negroni list, the restaurant also has a menu of fresh handmade pasta, rich risotto, and Northern Italian salads. Lines of fluent Italian float above our heads as the floor staff focus on perfecto service. Some of our guests can't finish their dish of Lamb Ragu, which is probably just as well as they will need room for our grand finale: a very Sydney dessert at Messina. We depart BC after some good conversation, digestion and appreciation of the jazz musician playing a live-set in the corner.

On our arrival at Messina there is a line of excitable young people awaiting their chance to order from the colour-filled countertop. This gives us time to fill our guests in on the story behind Messina (including owning a herd of Jersey cows in Victoria ) and what’s on offer on the chalked-up Specials Board. The novelty names - such as Little Bloke, Gingerbread Boy Band or Brownie-nator - and pumping dance music make for a vibrant environment, inspiring our guests to try something a little different when ordering their scoops in a cup or cone.

We happily score gelato frequent flyer points using our Messina payment app - handy for our next visit to the cinema. Once everyone has finished licking their way through various gelato flavours, the big black Merc’ van swoops in to take the family safely back to their hotel.

And another wonderful evening of dining with The Sydney Connection comes to an end.