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Sydney Stories

Vibrant city, local streets & Manly Beach vibes

Inclusions

    • 5 nights boutique hotel accommodation

    • Hotel-to-hotel luggage transfers (max 20 kgs per person)

    • Easy-to-follow maps and route guides with step-by-step instructions

    • Insider tips on where to eat, drink and visit along the route

    • Neighbourhood guides to each area you stay in

    • Concierge service for optional activity and restaurant bookings

    • Opal card for Sydney Ferry and light rail connections

    • Emergency phone support

    • Flights

    • Airport transfers

    • Meals and drinks

    • Optional activity costs

    • Guide (this is a self-guided walking holiday)

    • Taxi or public transport if you need to skip a stage

    • Travel insurance (mandatory)

Need to knows

  • To secure your holiday, a 20% deposit is required. Your deposit is fully refundable within 48 hours of submitting your booking request.

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    Once we receive your booking request and deposit, our travel specialists will confirm hotel availability and finalise your booking. If we’re unable to accommodate your preferred dates or offer a suitable alternative, your deposit will be refunded in full.

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    The remaining balance is due 60 days before your walk begins. If you’re booking within 60 days of departure, full payment is required at the time of booking.

  • We understand that plans change. Our cancellation policy aims to be fair to you, while also recognising the time and effort we put into organising your perfect WALKDAYS holiday:

    • More than 60 days before your holiday: You can either forfeit your deposit or reschedule once for free (within 12 months)

    • 60 to 31 days before your holiday: Receive a 50% refund of your total trip cost including deposit, or reschedule once for free (within 12 months)

    • 30 days or less before your holiday: Unfortunately, we can’t offer a refund at this stage, as everything is already locked in

    • No refunds are available for no-shows or unused days of your holiday

  • We require all international guests to have suitable travel insurance that covers trip cancellation, medical expenses, personal liability, and any unforeseen disruptions. This is for your peace of mind as well as ours. If you're a local traveller, we still recommend domestic travel insurance to cover things like potential luggage loss and cancellations due to illness or unforeseen events.

     

    Before your trip, we’ll ask you to share your policy details. If you’re unsure what level of cover you need, we’re happy to point you in the right direction.

  • All WALKDAYS holidays can be done solo, with detailed route guides and concierge support to help you feel confident and connected along the way. Please note that a single room supplement applies, as accommodation is priced per room. This ensures you still get the same great hotel experience, with a room all to yourself. Just choose “Solo walker” when booking, and we’ll take care of the rest.

  • The Sydney Stories walk begins in the Sydney CBD (central business district) and finishes at Manly Beach. Transport to the starting point and from the finish is not included in your WALKDAYS package - if you would like assistance with organising pre-booked airport transfers, please contact us. 

  • Once you’ve dropped your bags at your Day 1 hotel, we’ll take care of the rest. You’ll receive WALKDAYS luggage tags to help identify your bags - just add your names, attach the tags, and we’ll transfer your luggage to each hotel along your route. You can bring up to two bags per person, with a combined weight limit of 20kg. 

  • This is a risk warning for the purposes of section 5M of the Civil Liability Act 2002 (NSW). It applies to every WALKDAYS trip.

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    Our trips are self guided. There is no guide or leader with you. You decide when to set out, how fast to walk, whether to keep going, and whether conditions are safe for you on the day.

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    You must be able to walk the daily distance shown on this page, at the grade shown, carrying a day pack, unassisted, in conditions typical for the season. That applies to everyone on the booking.

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    Walking our routes involves risks we cannot remove. They include falls, slips and trips on uneven, loose, wet, sandy or rocky ground and on stairs; cliff top and coastal paths with steep drops and unfenced or partly fenced edges; heat, sun exposure and dehydration; sudden changes in weather; track closures, storm damage, erosion, bushfire and smoke; surf, rips, submerged objects and marine life if you choose to swim; traffic where routes cross or follow roads; limited or no mobile phone coverage; delayed emergency response in remote sections; snakes, ticks, insects and other wildlife; the actions or inaction of other track users; and becoming lost or separated from your group. These risks can result in serious injury, permanent disability or death.

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    Our routes cross land managed by national parks, councils and other authorities. You must follow their signs, closures and warnings. Where those differ from our notes, the signs win.

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    Everyone travelling is asked to read this warning. The person who makes the booking signs it for the group on our booking form, and agrees to pass it on to everyone travelling with them.

Trip FAQs

  • The Sydney Stories walk can be done year-round. Sydney summers (Dec - Feb) are typically hot and sunny - daytime temperatures average between 25°C and 30°C (77°F and 86°F), but can soar well above 30°C. Spring (Sep - Nov) and Autumn (Mar - May) bring milder temperatures, and the days are often still warm enough to be able to enjoy swimming and water activities. Winter (Jun - Aug) brings colder weather and water temperatures. Sydney’s spectacular Vivid Light Festival that runs from late May to mid June is a popular drawcard for winter visitors.

  • The Sydney Stories Walk is designed for travelers who enjoy exploring on foot at a relaxed, steady pace. You don’t need to be an athlete - this route is suitable for anyone with average fitness.

    • Daily walks range from 6 to 11 km

    • Routes are graded easy to moderate

    • Expect urban footpaths and well-maintained coastal paths, with some stairs and gentle inclines

  • That depends on your pace and how often you pause to explore along the way! Your day is designed to be unhurried and filled with much more than walking - you’ll have plenty of time to enjoy stop-offs and activities along the route for a truly authentic Sydney experience.

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    By mid-afternoon, you’ll typically arrive at your boutique accommodation. The rest of the day is yours to relax and explore your new neighbourhood - whether it’s aperitivos at a neighbourhood wine bar in Surry Hills or catching the sunset over Manly Cove.

  • For most people, comfortable trainers will be absolutely fine as the routes are well-maintained and mostly paved. If you prefer extra support, a pair of lightweight walking shoes or low-rise trail shoes can be a good option.


    We also recommend bringing:

    • A day pack for water, sunscreen, and layers

    • A hat and sunglasses for sun protection

    • A light rain jacket or umbrella, just in case

    • Swimwear and a quick-dry towel for ocean dips

    • A refillable water bottle (filtered tap water is available throughout)

  • We’re here to help! Routes can be customised as part of our bespoke service, from adding or removing days to tailoring the itinerary for your interests and needs. Drop us an email to get started.

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    Have less time in Sydney? Check out our Sydney Stories Edit 4 day itinerary.

  • Yes - if your kids are good walkers! We generally recommend our walks for kids aged 8 and up, as most routes include 6-11 kms of walking each day. For something designed especially with families in mind, check out our Harbour Play itinerary — a family-friendly walking holiday that blends sightseeing strolls with fun activities the whole family will enjoy.

General FAQs

  • Absolutely - you can make small changes (like names or dates) up to and including 31 days before your walk, subject to availability. Your first date change is free if it's within 12 months of the original trip date, after that, a small fee may apply.

  • Unpredictable weather is part of the travel adventure! While we can’t offer rainy day refunds, we’re here to help. If severe weather hits, our WALKDAYS concierge team will suggest great indoor alternatives. For more typical weather shifts, it’s all about being prepared and flexible. Pack a light rain poncho or umbrella, sun protection, plenty of water, and adjust your schedule to the conditions. A rain shower might be an opportunity to meet some locals at a nearby cafe or visit a cultural gem.

  • While our routes are designed to be easily followed as self-guided walks, we can arrange guided walking tours on request as part of our bespoke service. Contact us to discuss your needs.

  • About three weeks before your holiday, our concierge team will get in touch to see if you’d like help booking any of our optional activities, such as harbour boat rides, surf lessons or museum visits. We can also assist with restaurant reservations, rooftop bars, or other local spots along your route - so you can spend less time planning and more time enjoying your holiday. Prices for optional activities will be provided in writing before booking and charged to your credit card once approved. No surprises, just extra ease.

     

    We’re also here to help when you’re on the route - from emergency phone support to adverse weather planning.

  • We don’t have a dedicated app, but don’t worry - you’ll still have everything you need at your fingertips. Each guest receives a comprehensive info pack about six weeks before departure, including your detailed itinerary, route guides, and local area tips. We also provide easy-to-use digital maps to guide you along the way, whether you're on a coastal trail or exploring a city laneway.

Need to know more? Drop us an email

6 days | from $2,150 AUD

Year-round availability

Cancel in the first 48hr for free

Book now to enjoy 10% discount

Plan your adventure

Got a question? Drop us an email

Accommodation

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Nights 1 & 2  - Sydney

Paradox Sydney | 5 star

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Set within a restored 1856 sandstone building, Paradox Sydney offers a timeless blend of heritage and modern design. The hotel is ideally located near Circular Quay and the Royal Botanic Garden, and its beautifully appointed guest rooms feature king beds, marble accented bathrooms and espresso machines.

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Nights 3 & 4 - Surry Hills

Ace Hotel | 5 star

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Housed in a former brick factory, the Ace contrasts industrial heritage with a stylish modernist aesthetic. Guest rooms give laid-back local vibes, with bespoke furniture, turntables and curated vinyl collections. The rooftop bar & restaurant is a popular local haunt, and the hotel’s events program showcases the local music scene.

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Night 5 - Manly Beach

Elysium Manly | 5 star

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Overlooking Sydney’s iconic Manly Beach, Elysium Manly delivers relaxed coastal luxury just steps from the sand. The rooftop pool and sundeck offers the perfect spot to unwind after a day on foot, while the spacious, light-filled rooms feature king beds, balconies and walk-in showers.

Itinerary

  • Drop your bags at Paradox Sydney and ease into the trip with a ramble through the lush Royal Botanic Garden for your first breathtaking harbour views. Get up close to the famed white sails of the Sydney Opera House and soak up the bustling waterfront atmosphere at Circular Quay. After an (optional) rest back at your hotel, follow our curated route through the city’s laneways and landmarks, discovering hidden treasures along the way. As the day winds down, toast your first night in Sydney with sunset drinks and dinner at one of our hand-picked spots.

     

    Distance: 7km + Royal Botanic Gardens ramble

     

    Optional activities:

    • Picnic in the Royal Botanic Garden

    • See the inside of the Sydney Opera House on a guided tour

    • Experience a thrilling jet boat ride on Sydney Harbour

    • Toast your arrival in the Harbour City with a sunset spritz

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  • Today begins with a scenic ferry ride to McMahons Point for one of Sydney’s most beautiful harbourside walks. Stroll past sparkling Lavender Bay, uncover a lush secret garden and walk under (and over!) the iconic Harbour Bridge. Enjoy jaw-dropping views from the Pylon Lookout and refuel with a classic pub lunch in Sydney’s oldest quarter, The Rocks. Explore the cobbled lanes of The Rocks and stop off for a drink at one of its historic pubs before enjoying your last night in the city.

     

    Distance: 8km

     

    Optional activities:

    • Take a ride on the iconic Luna Park Ferris Wheel

    • Get jaw-dropping views from the Harbour Bridge Pylon Lookout

    • Explore the colourful Rocks Markets (weekends only)

    • Enjoy a pub lunch with a view on The Glenmore Hotel rooftop terrace

    • Step back in time at the Susannah Place house museum (Thurs - Sun)

    • Visit Sydney’s Museum of Contemporary Art

    • Join a distillery tour and gin tasting at Hickson House (Thurs - Sun)

    • Relax with a drink at one of the The Rocks’ historic pubs

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  • After breakfast, visit the landmark Queen Victoria Building to admire its ornate architecture and elegant boutiques before the crowds arrive. Next, it's across the colourful Pyrmont Bridge to the dazzling new Sydney Fish Market. Take the time to explore the bustling market before enjoying a fresh seafood lunch by the water. Save room for dessert in the foodie precinct of Darling Quarter before continuing to urban Chippendale - home to the acclaimed White Rabbit Gallery. From here it’s a short journey to Surry Hills, your lively neighbourhood base for the next two nights.

     

    Distance: 9km

     

    Optional activities:

    • Visit SEA LIFE Sydney Aquarium in Darling Harbour

    • Enjoy a luxe seafood lunch at the new Sydney Fish Market

    • Relax in the tranquil Chinese Garden of Friendship

    • Sample indulgent treats from Darling Quarter’s inventive food vendors

    • Join a free guided tour at the White Rabbit Gallery, home to a world-renowned collection of contemporary Chinese art

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  • Today’s curated neighbourhood trail winds through the lively, café-lined streets of Surry Hills and fashionable Paddington - famed for its markets, upscale boutiques and Victorian terrace houses. Along the way you’ll uncover hidden laneways, hip coffee spots, irresistible bakeries, modern art galleries, designer fashion and vintage treasures. End your day like a Surry Hills local, with our insider's guide to the area’s most-loved aperitivo spots, neighbourhood restaurants, pubs and late night bars.

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    Distance: 8km

     

    Optional activities:

    • Visit independent galleries like the renowned Brett Whiteley Studio

    • Browse the popular Paddington Markets (Saturdays only)

    • Unwind after your walk at the luxe Capybara bathhouse

    • Enjoy an indulgent head massage at Tokyo Headspa

    • See a classic movie at the art deco Golden Age Cinema

    • Bar-hop or pub-crawl around the lively streets of Surry Hills

    • Enjoy craft rum tastings at Brix Distillers

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  • This morning you have the option of visiting the famous Carriageworks Farmers Market (Saturdays only), before journeying to Manly. Alternatively, a stroll through Hyde Park and along historic Macquarie Street takes you to Circular Quay, where you’ll board the iconic Manly Ferry. Explore Manly at your leisure, or follow our relaxed trail past golden beaches, hidden coves and coastal lookouts, stopping for café breaks, a swim, or the classic beachside fish & chips along the way. As the afternoon melts into evening, unwind at your hotel’s rooftop pool before enjoying sunset drinks by the water and dinner at a local Manly favourite.

     

    Distance: 7 to 9km

     

    Optional Activities:

    • Find seasonal local produce and artisanal delights at Sydney’s beloved Carriageworks Farmers Market (Saturdays only)

    • Get a fascinating look into Sydney’s colonial past at Hyde Park Barracks

    • Visit Macquarie Street landmarks such as the Australian Museum, Sydney Mint and State Library

    • Take a dip at Fairy Bower Rockpool, swim at Shelly Beach or splash in the surf at Manly Beach

    • Rent a bike to explore Manly’s extensive coastal bike paths

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  • Start your final day like a local - rise early to watch the sunrise over the Pacific and join walkers on the promenade, before breakfast at a coastal chic café. For a last adventure, snorkel the marine-life-rich waters off Shelly Beach, take a surf lesson or join a kayak tour. Prefer a slower pace? Browse Manly’s local markets, surf shops and fashion boutiques before you leave. Our WALKDAYS concierge can assist with recommendations and bookings to ensure your final day in Sydney is unforgettable.

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    Distance: 3 to 6km

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    Optional Activities:

    • Catch a unique sunrise at the Manly Wormhole

    • Snorkel at Cabbage Tree Bay Aquatic Reserve

    • Take on the waves with a surf lesson at Manly Beach

    • Explore Manly Cove and North Harbour by kayak

    • Browse the Manly Markets (Saturdays and Sundays only)

    • Shop Manly’s local boutiques for fashion finds and coastal style

    • Hop on a free shuttle bus to the Quarantine Station

Sydney Stories 6 day walk map, the city’s hidden laneways, harbour and history on foot

Map

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Golden sunset over Manly Beach, a romantic end to a day’s coastal walk

Overview

Discover the diversity that makes Sydney such a vibrant city on this 5 night / 6 day walking holiday that blends harbour vistas and beachside vibes with a generous dose of café culture and urban cool. Travelling by foot and ferry, you’ll see the best of the city, soak up the sparkling magic of Sydney Harbour, stroll scenic coastal paths around Manly Beach and adventure through some of Sydney’s liveliest urban neighbourhoods. Armed with our insider tips and area guides, you’ll uncover hidden gems, have culinary adventures, mingle with the locals and soak up the character of each unique neighbourhood - all at a relaxed walking pace that lets you truly experience the city’s charm.

Highlights

  • Take in sparkling harbour vistas from Sydney’s finest foreshore paths

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  • Sightsee as you wander hidden lanes, historic streets and coastal tracks​

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  • Uncover local secrets on handpicked trails through lively neighbourhoods

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  • Enjoy iconic Sydney experiences - ride the Manly Ferry, walk across the Harbour Bridge and explore the dazzling new Fish Market

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  • Savour the best of Sydney’s café culture and multicultural dining scene

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  • Stay in boutique hotels in the heart of the city, lively Surry Hills and by the sand at Manly Beach

Get the Sydney Stories (6 day) brochure

Everything you need to know, in a handy PDF

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