Frequently asked questions

You may find the following frequently asked questions about our Wineglass Bay walks useful as you plan your trip.

  • How often do trips depart?
    Our trips depart regularly from late October through until early May each year (please check on our online calendar or contact our office for departure dates).
  • The itinerary
    Please note that on occasion our itinerary may need to change due to weather conditions. We do try to keep changes to a minimum and your guide and skipper will keep you up to date with any planned changes whilst on your trip.
  • What about accommodation?
    We have four guest rooms aboard the Lady Eugenie. Two rooms have one double bed, and two have two single beds. We will do our best to accommodate your room request; however, due to space limitations, we cannot guarantee a specific room type will be available.
  • How many guests will be on my trip?
    Each trip requires a minimum of four and a maximum of eight guests. If booking as a single walker or in an odd-numbered group and the trip fills to capacity, you will share a room with another walker of the same gender. 
  • How fit do I need to be?
    As long as you exercise regularly and have moderate fitness, you should enjoy this walking holiday. You need to be capable of walking between 9 and 14 km each day, including walking along beaches, some hill climbs and some uneven terrain. There is plenty of time to explore, as well as sit and rest each day. There are also alternative options, should you wish to stay on the boat or choose a more relaxed walking alternative.
  • How much weight do we carry?
    We provide a duffel bag and a 25L day pack on the morning of your departure. You will pack all the gear you need for the duration of your trip into the duffel bag. Your gear will be stowed on board Lady Eugenie, so you will only require a day pack for all walks (provided by us). If you follow the gear list, your day pack should weigh approximately 5kg.
  • What style of boots/walking shoes do I need? And what about boating shoes?
    Please refer to the guide below for recommended footwear for this walk.


    If you have any questions about footwear, please contact our team on (03) 6392 2211 or

    Whilst on the boat, we ask that you wear clear soled shoes to limit damage to the deck.   There are many styles of boat shoe available, but if you are looking for a good option that isn’t too expensive, Dunlop Volleys or similar are perfectly fine.
  • Do we need travel insurance?
    We strongly recommend travel insurance. Consideration needs to be given to our cancellation policy, injury, evacuation, delayed flights, illness, etc. Please see our Booking Terms & Conditions for details and contact us if you have any questions.
  • How many guides are there?
    Every trip has an experienced guide, skipper and crew. 
  • What is Lady Eugenie like? Do I need to help sail the yacht?
    Lady Eugenie is a luxurious, 23-metre (75-ft) ketch-rigged yacht. She is five metres wide which makes her stable, safe and comfortable for both novices and sailing enthusiasts.

    Her clipper bow, complete with a bowsprit you can walk on, is perfect for watching dolphins and other marine life. With beautifully maintained teak decks and classically varnished handrails, Lady Eugenie’s spacious decks are the perfect setting for relaxing and taking in the scenery. The central cockpit provides plenty of comfortable seating, with a picturesque alfresco dining setting: a magical place to take in the sunset.

    There are four comfortable cabins on board, all with air conditioning, bathrooms and showers.  During the evening you can relax in the delightful and spacious saloon with a dining table and comfortable lounge.

    Lady Eugenie is your home whilst you are on board. You don’t need to assist with sailing, but if you are keen to learn more about sailing please speak with our skipper.
  • How about food?
    All meals are provided, including scrumptious three-course dinners using fresh produce. Meals are prepared by our gourmet cooks/guides. We are happy to cater for special dietary requirements, we just need to know in advance. Evening meals are served with a carefully selected range of Tasmanian wines. *Please note in the best interests of our guests and staff we promote the responsible service of alcohol.
  • What time does the trip commence and conclude?
    For all itineraries, please have your breakfast before joining us at our walkers' base (164 Murray Street, Hobart) where you will meet your guides.  We collect from MACq01 between 7.00am - 7.10am, followed by the Old Woolstore Apartment Hotel between 7.05am - 7.15am. The shuttle bus will not collect from these locations unless we’re advised that you need collection. If you would prefer you can make your own way to our walkers' base for 7.30am sharp. Here you will meet your guides and other group members, as well as receive a briefing and gear check.

    Signature Walk (four day): We board our bus for a 1-hour drive to Orford on the first day.

    Signature Walk: We board our bus for a 1.5-hour drive to Fortescue Bay on the first day.

    Your trip will return to Hobart (approximately 5.15pm) via the airport (approximately 5pm) stopping at a vineyard with time for you to repack your bags and enjoy some canapés and Tasmanian sparkling wine before we say farewell.
  • What pre- and post-trip accommodation options do we have in Hobart?
    Discover discounts for walkers here:

    The Old Woolstore Apartment Hotel, 1 Macquarie Street, Hobart (our shuttle will pick you up from in front of reception between 7.05am - 7.15am)

    This multi-award-winning hotel has a reputation for being one of Australia’s most welcoming and relaxing inner-city hotels. The rooms are spacious and the hospitality is friendly. To book visit

    • Enter your check-in and check-out dates, number of rooms and guests
    • Hit 'Book Now'
    • Once the booking page loads, select the 'Add Code' tab and change the discount code to 'Rate Access/Corporate Code'
    • Type in the code TWC and click 'Add' to receive your exclusive offer
    The Henry Jones Art Hotel, 25 Hunter Street, Hobart (please make your way across the road to MACq01 for shuttle if required which will depart between 7.00am - 7.10am)

    A hotel where art and history collide. Hobart’s oldest waterfront warehouse has been transformed into Australia’s first dedicated art hotel with views capturing the bustling wharf. Close to galleries, restaurants, bars and cafés.

    The Henry Jones offers luxury boutique accommodation with warm friendly service. To book please email and quote 'Tas Walking Co' to receive your 10% discount.

    MACq01, 18 Hunter Street, Hobart (our shuttle will collect you in front of reception between 7.00am - 7.10am)

    MACq 01 lives on Hunter Street on the old Hunter Island, one of the earliest sites of European settlement in Tasmania. Surrounded by yachts, docks, convict-built sandstone warehouses and a huge expanse of open water, the hotel boasts gorgeous views alongside supreme convenience.

    MACq 01 is the perfect place to start telling your own Tasmanian story. Accommodation is available in a variety of luxurious suites and rooms. Each of the hotel’s 114 rooms are linked to a real character central to the story of Tasmania - heroes, villains, explorers, inventors, convicts, bushrangers, first people, industrial giants, political mavericks and much more.

    To book please email and quote 'Tas Walking Co' to receive your 10% discount.

    If you are staying anywhere else in Hobart please make your way to our walkers base (164 Murray Street, Hobart) by 7.30am.

  • Are there age restrictions?
    The minimum age for guests walking with us is 12 years old.  There are no upper age restrictions, however, for guests walking with us who are 69 or above, we do require a GP to sign off on a letter we provide.

Need help deciding? Talk to an expert

We're here to help 9am – 5pm Monday to Saturday, otherwise, email us anytime and we'll be in touch.