Bradleys Head to Gubbah-Gubbah

Wander through Angophora forests and military history as we trace the harbour’s edge from the iconic Bradleys Head to the storied heights of Middle Head. This is a morning designed to help you breathe with the tide, transitioning from the gentle rhythm of the coast to the grounded stillness of the bush.

📍 Meeting Point: Bradleys Head (exact location texted upon booking)

📅 Date: August 8, 2026

🕘 Time: 8:00am – 12:00pm

📏 Distance: Approx. 10km (one-way, with shuttle return to the start in the Seek Sista Van) 🥾 Activity Level: Moderate

👣 Group Size: 3–6 Sistas (plus your guide, Kirsty)

🫶 Why You’ll Love This Hike

Iconic Harbour Views: Uninterrupted vistas of the Opera House and Bridge as we wind around the headland.

Scented Gum Forests: Moving through the fragrant Angophoras and native bush of the National Park.

The Transition: A steady wander from the harbour’s edge at Chowder Bay up to the sweeping lookouts of Middle Head.

Gubbah Gubbah Heights: Reaching the historic sandstone lookout for a true sense of perspective.

Connection: A steady-paced morning with a small group of like-minded women with a shared cuppa along the way.

📖 Description

Our morning begins at Bradley's Head, where the fresh salt air instantly clears the mind. We’ll follow the shoreline on a well-maintained track that feels worlds away from the city, despite the skyline being in constant view. After passing the historic naval sites and the soft sands of Chowder Bay, we’ll gently climb toward Middle Head (Gubbah Gubbah). Here, the landscape shifts to dramatic cliffs and military history. We’ll find a quiet spot to pause for our signature tea and coffee break, soaking in the vastness of the ocean before we conclude our journey.

🙋‍♀️ Who can join?

This experience is available to Seek Sista members.

• Roam-Free: ($0)

• Plus-Perks: ($30 / quarter)

• Not a member yet? 👉 You can Join or Upgrade Here

  
  

Track Grade Breakdown

• Grade: 3 (Moderate)

• Details: The trail is mostly well-formed with some uneven sections, stone stairs and gentle inclines. A basic level of fitness is required as we will be walking for roughly 3.5 hours at a steady, social pace. It is perfect for those who enjoy a bit of a heart-rate boost without a gruelling climb.

  
  

🚗 Getting There

For a comfortable return trip in the Seek Sista Shuttle Van, there are 3 pickup points to choose from. Exact locations will be texted upon booking:

• Pick-up Point 1 – St Ives

• Pick-up Point 2 – Gordon Station

• Pick-up Point 3 – Mosman

• Driving Yourself: There are paid parking fees within the National Park. The exact meeting location coordinates will be texted upon booking.

  
  

✅ Inclusions

• Guided 4-hour hike with Kirsty, your friendly, experienced, and first-aid trained guide who personally hikes every route in advance.

• Licensed and insured to operate within NSW National Parks

• Tea or coffee served during the hike

• Return shuttle in the Seek Sista Van from the end of the trail back to the starting point and designated pickup locations

• Morning tea/coffee at a scenic midpoint

• A supportive, small-group environment

  
  

🚫 Exclusions

• Personal snacks and additional beverages.

• Travel insurance (recommended but not included).

  
  

🎒 What to Bring

• 1.5–2L of water

• Hiking shoes with good grip

• Lightweight clothing layers

• Hiking poles (recommended)

• Hat and sunscreen

• A small daypack for your essentials

• Morning Tea style snacks (eg fruit, muesli bars, small sandwich)

  
  

📑 Minimum Group Size & Cancellation Policy

Minimum group: The experience will proceed with a minimum of 3 participants. If the minimum is not met, we will contact you at least 48 hours before the event to offer a full refund or transfer to another date.

Cancellations: You’ll receive a full refund if you cancel at least 72 hours before the experience. Cancellations within 72 hours are non-refundable, but you’re welcome to transfer your spot to a friend. All cancellations must be communicated via email to kirsty@seeksista.com.au

Event postponement: If the hike is cancelled by Seek Sista due to weather, track conditions, or safety concerns, participants will receive a full refund or the option to transfer to a new date.

✍️ Waiver & Pre-Trip Details

Once booked, you will receive a follow-up email containing a link to our digital waiver form. Please ensure this is completed prior to the morning of our hike. You’ll also receive an invitation to our event WhatsApp group for final coordination, real-time updates, and the chance to connect with your hiking buddies before we hit the trail!