Sydney & Beyond: The Ultimate 5 Day Itinerary

More than a rushed weekend, planning a five-day itinerary in Sydney means there’s plenty of time for it all. You can revel in Sydney’s nightlife, go to town on the street eats and feast your eyes on incredibly pretty scenery. And then you’ll still have time for exploring what lies beyond the city itself. In particular: the insanely spectacular NSW South Coast. Enter: the ultimate ‘have your cake and eat it too’ holiday.

Lucky for you, we’ve detailed a 5-day City To Surf Experience that’ll take you from the centre of the action in Sydney to the laid back beach lifestyle of Gerroa in the South Coast.

Keen to tick off some bucket-list items? Did Covid cancel your euro-trip? Want to swap out a 21st party for an epic adventure instead? Ready to focus on the fun instead of the trip logistics? If you’re nodding yes, then this itinerary is for you!

And to make the most of the five days, we’ve curated the best places to go, our favourite spots to eat at and must-do experiences throughout the journey.

What to do with 5 days in Sydney & beyond: the ultimate itinerary

Friday

Touch down to Sydney early Friday evening, put your bags away at Wake Up! Sydney Central, and set out for your first night of the trip! As you’ll be based in the heart of the CBD, you’re spoilt with countless options of where to head tonight. But, nay fear! We’re here to alleviate the decision-making. Take your pick from our below favourite bars and restaurants:

For dining with views:

The Glenmore: Based in the rocks, The Glenmore Hotel is an Aussie icon with rooftop views to boot. We’re talking 180º views of the Sydney Harbour while you tuck into that chicken parmi.
The Opera Bar: It doesn’t get much more iconic than here. Taking up prime real estate adjacent to the Opera House, expect to have your evening bevvies with a side of unrivalled Harbour Bridge views. Welcome to Sydney!

For a fun atmosphere:

Flying Fajita Sisters: This colourful Mexican cantina, serves up authentic Mexican cuisine with a festive flair. Opt for the sizzling fajitas, delicious tacos, or simply set your eyes on their lovingly long tequila menu.
Side Bar: Lucky for you, Sydney’s favourite late night destination is right below your doorstep. If you’re a fan of cocktail buckets, good tunes, and an even better vibe, consider Side Bar your go-to late night venue.
Bar Reggio: What do you get when you combine $3 BYO, non-nonsense Italian food, and wildly enthusiastic vibes? Bar Reggio. This is a particularly good option for groups.

Saturday

AM

Your first full day in Sydney! To kick things off, fuel up with your free daily breakfast and coffee* at Roy’s Cafe while soaking up the morning rays in their outdoor courtyard.

Take to the streets, and head towards Surry Hills, one of Sydney’s coolest cultural hubs. Surry Hills is bursting with all the shops you could ever want – from the wacky to the wonderful – so you’ll want to spend time shopping here. Add to your hit-list:

Storeroom Vintage and UTurn Recycled Vintage for all your op shop needs
Pigeonhole, Elms and pretty much all of Crown Street, which’ll have you set for clothing and homewares.
Little Tokyo, Authentink and Hibernia Tattoo Studios. If you’re keen for new ink – these are three of Sydney’s (perhaps even Australia’s) best studios.
Oscar & Friends Booksellers for those wanting to pick up new fiction for the trip in a quintessential, charming bookstore setting.

PM

Duck into the outrageously fun Cuckoo Callay in Surry Hills for lunch, or grab some picnic goods and set up for instagrammable views at Mrs Macquarie’s Chair. This is one of our favourite spots to chill out in Sydney.

Keen to keep adventuring? Of course you are! Walk through the Royal Botanic Gardens, get up close and personal with the grand Opera House, and soar to new heights with a walk over the Sydney Harbour Bridge. Since you’ve made it to the north side of the bridge, it’d be rude not to take a dip in the North Sydney Olympic Pool while ogling at the enormous view above you. At just $8.50 a ticket, this is a perfect summer activity if you’re on a budget.

Tonight, say hello to $5 drinks and $10 food specials over Happy Hour at Side Bar, before doing the inevitable: kicking back there for an awesome rest of your night.

Sunday

AM

Rise and shine! There’s another complimentary breakfast at Roy’s Cafe waiting for you, before you make the most of Sydney’s outdoor playground. Today, you’re headed for Bondi Beach and its neighbouring suburbs.

Start off the beach-bound adventure, by catching the train to Bronte. (PS. Public transport is capped at $8.05 on Saturdays/Sundays – major win!) It wouldn’t be a proper trip to the East without a dip in one of the many beaches or oceanside swimming pools here. Our pick is the Bronte Baths. Not as crowded as its cousin over at Bondi Icebergs, but just as delightfully scenic! Dry off, and then set off on the Bronte to Bondi Coastal Walk. It’s iconic for a reason and even as locals, we could never tire of it.

Once you’ve made it to Bondi and snaparazzi’d out your entire camera roll, stroll over to the weekly open-air Bondi Markets. Here you’ll undoubtedly discover one-of-a-kind pieces, wicked street food (we know you’ve already eaten, but hey! Surf Camp is tomorrow, so you’ll need the energy), and sweet summertime tunes.

PM

When that arvo sun strikes, you’re ready for a drink, right? Perfect, we know just the place! Salty’s Bondi located right on the Bondi beachfront is a must. Head here for lunch, or once happy hour strikes at 4pm. Either way, be set for only the very best Bondi vibes. Grab a margarita (we hear ‘The Big Kahuna’ is a crowd favourite), and settle in.

It’s been a big day and tonight, we suggest taking it easy, so you’re well rested for tomorrow’s Surf Camp journey. Head to Spice Alley (walking distance from Wake Up! Central), and enjoy delicious Asian street food, set in a hawker-style food market.

Monday – Wednesday

After a few nights taking advantage of Sydney’s nightlife, street eats and incredible views, it’s time to enter the next phase of the trip… Surf Camp!

Hop on the 9:27am train from Central Station (the station is directly opposite Wake Up!, so you can still enjoy a semi-sleep in!), and strap yourself in for a two-hour journey along the French Riviera. Or, at least the Aussie version of it! Honestly though, the sweeping views you’ll witness as your carriage winds through the Royal National Park and passes through coastal towns, will absolutely set the scene for your next few days to come.

Upon arriving at Kiama, the Surf Camp crew will be there to pick you up and take you to basecamp, in beautiful Gerroa. From hereon, consider your itinerary absolutely stress-free. Everything is included here at Surf Camp, including your breakfast, lunch, dinner and of course… the surf gear! Simply pack your togs, any drinks, and your best shakas. The rest is taken care of.

What does a typical Surf Camp experience look like?

A lot of surf, a lot of meeting new people and a lot of bonding over face plants or new drinking games… or a mixture of the two. Our Marketing Team recently experienced Surf Camp for themselves, and have dished out a full rundown of their trip.