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6 Amazing Date Ideas for a Sydney Valentine's Day

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Section: Gentlemanly Pursuits - Blog

It’s that time of year again; the day when all the stops must be pulled out, and a serious effort must be made to prove your romantic capabilities to your partner. But forget the flowers and chocolate, we think that a memorable date is much more likely to impress. So here’s our list of 6 simple yet effective date ideas in our hometown of Sydney.

1 - Dessert Date

Going out for dinner is old news these days so why not get your ice cream fix and impress your date in one fell swoop. Gelato Messina is the place to go for those with a taste for the sweet and icy. Their dessert bar in Darlinghurst offers a wide variety of what they call ‘suggestive sundaes’ and you can even create your own; definitely a chance to work a little romance into the date there.

2 - Get your Dancing Shoes on

Now we love a bit of style here at Montagio and what better occasion to show off your new custom made suit than a night out Tango dancing. But you’ve got two left feet; fear not, just take your date out to some afternoon tango classes. It’s the perfect excuse to get up close and personal, and it’s seriously good fun. Just try not to step on anyone’s toes.

3 - Go to the Drive in

Relive your youth with a trip out to Blacktown Drive In. Some clever scheduling sees horror flick ‘Friday the 13th’ showing on Friday the 13th while ’50 Shades of Grey’ is your Valentine’s night treat. Either way it’s a great idea for an original date and is guaranteed to impress your date. Just be sure to check out the retro diner that’s described as ‘Happy Days’ in style for some post-movie grub.

4 - A Night Tour at the Observatory

You may remember taking a field trip to the observatory as a kid but trust us, it’s an entirely different experience when you’re on a date. The observatory’s location gives you great sunset views of the harbor, but it’s the night sky as you’ve never seen it before that will make it a night to remember. Valentine’s Day is always a special occasion at the observatory and this year you can enjoy stargazing, drinks, canapés and jazz music.

5 - Go for some Cocktails

Everyone loves cocktails – even teetotalers like the alcohol-free ones – and the cocktails at Li’l Darlin are quite possibly some of the best you’ll ever taste. They’re certainly the best we’ve ever seen as this group of cocktail bars pride themselves on offering the ultimate in cocktail eye candy. Not only that but they also have a new menu with some pretty tasty looking pizza and tapas options.

6 - Moonlight Cinema at Centennial Parklands

While you don’t really need another excuse to visit one of Sydney’s most beautifully established and lush parklands, don’t forget there’s Moonlight Cinema! It’s one of Australia’s favourite open air cinema experiences screening advance previews, contemporary, cult and classic movies on the lawns of the Belvedere Amphitheatre in Centennial Park. Why not check out their program over Valentine’s day? Depending on your date (and your motivations), you can choose from The Rocky Horror Picture Show or Breakfast at Tiffany's.

Whatever plan you make, turning up on your date in some new custom tailored threads will undoubtedly impress. Whether it’s casual shirts for the desert date and the drive in or, it’s a full custom tailored suit for tango dancing; at Montagio we’ve got it covered.

Image courtesy of Timeout


We tailor make mens suits, jackets and shirts for all occasions. Each garment is custom designed, precisely made-to-measure and is guaranteed to fit you perfectly. Unlike others, we offer you end-to-end service and a personalised styling session where we take the time to understand your needs to ensure you get the colour, style and fit you want.

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Named in GQ Magazine's "Best Tailors" list, and the highest reviewed tailor on Google, Montagio has paved the way for discerning men to get suited up with style. We offer a truly personalised experience, specialising in custom designed, perfectly fitted suits, shirts, coats, and shoes for for business, weddings, formal and casual events. Our showrooms are visually packed with designs that inspire plus thousands of fabric options, making it easy for you to get the look you want. Our expert stylists will advise and professionally fit you and frankly won’t let you walk out until we’ve tailored your perfect garment. Since 2010, we have custom tailored looks for thousands of happy customers. To experience the same red-carpet service, book your personal appointment today.

Steve Fambo

Hats off to the team at Montagio Custom Tailoring Sydney. I was immediately impressed once I stepped into their boutique showroom... more »

Scott Lasak

The suit and shirts I received were terrific and much better quality than ones I've found in stores off the rack. I would absolutely recommend them... more »

Yun Zhi Lin

I would highly recommend Montagio for anyone else planning a wedding or looking for a trendy tailor made suit... more »

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