Frequently asked questions

You may find the following frequently asked questions about the Wineglass Bay Sail Walk 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 on-line 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 five rooms aboard the Lady Eugenie. Two rooms have one double bed, and three 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. Lady Eugenie has two rooms with double beds and three rooms with two single beds. If the group is full, we guarantee sharing with another guest 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 50-litre pack and a day pack on the morning of your departure. You will pack all the gear you need for the duration of your trip into the 50-litre pack. 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?
    You will need lightweight, lace-up boots (preferred) or walking shoes (acceptable).  Boots/shoes must be worn in to minimise the risk of blisters.  Sandshoes, elastic-sided boots and similar are not acceptable.

    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 hand rails, 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 five comfortable cabins on board, all with air conditioning, bathrooms and showers.  During the evening you can relax in the delightful and spacious saloon with 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.
  • What time does the trip commence and conclude?
    For all itineraries, after breakfasting at your accommodation in Hobart, we ask you to be ready in the foyer of the Salamanca Inn (10 Gladstone Street, Battery Point) by 7.30am. You will meet your guides and other group members, as well as receive a briefing and gear check.

    4-day south-north itinerary: We board our bus for a 1.5-hour drive to Triabunna on the first day, concluding at the Salamanca Inn at 6pm on the fourth day, with an airport drop off at 5.30pm.

    6-day south-north itinerary: We board our bus for a 1.5-hour drive to Pirates Bay on the first day, concluding at the Salamanca Inn at 6.00pm on the sixth day, with an airport drop off at 5.30pm.

    Your trip will return to Hobart via the airport stopping at a Coal River Valley 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?
    The Salamanca Inn (10 Gladstone Street) is our preferred hotel. Our walkers receive a discounted room rate. When booking the Salamanca Inn, please ensure you mention you are walking with us at the time of booking.  Bookings can be made directly with the hotel by emailing or by phoning +61 3 6223 3300 (please state Wineglass Bay Sail Walk and your walk departure date).

    If you chose to stay at another of Hobart’s hotels prior to your departure, we ask that you are ready in the reception area the Salamanca Inn by 7.30am sharp on your morning of departure.
  • 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.

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