Set Departure | Tasmania

Wineglass Bay

by sail & walk

Climb challenging peaks & sail picturesque islands

This amazing walk, the only one of its kind in Tasmania, takes in the spectacular beaches, peninsulas and island trails found in national parks along the east coast. Share with us the wonders of Maria Island, Freycinet Peninsula, Schouten Island and the Tasman Peninsula. This walk is supported by the spectacular Lady Eugenie, a 23-metre (75-ft) luxury classic ketch. Superb 3-course dinners are served either aboard Lady Eugenie or in the relaxed surrounds of a barefoot beach dinner under the stars.

Lady Eugenie is a luxurious, 23-metre 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.  There’s nothing more exhilarating than turning off her engine, relaxing and harnessing the power of the wind in her sails.

Lady Eugenie has just five comfortable cabins on board, all with air conditioning, bathrooms and showers. The central cockpit provides plenty of comfortable seating, with a picturesque alfresco dining setting and a professionally equipped, separate galley for the crew guarantees delicious meals made from local produce. Guests are welcome to relax in the delightful and spacious saloon with dining table and comfortable lounge. With beautifully maintained teak decks and classical, varnished hand rails, Lady Eugenie’s spacious decks are the perfect setting for relaxing whilst taking in the stunning scenery of Tasmania’s east coast and are a magical place to watch the sunset.

You will love

  • Tassie devils, wombats & fur seals
  • Reach areas only accessible by boat
  • Changing landscapes
  • Walk & Sail itineraries of 4 & 6 days
  • A maximum of just 10 guests


Please note:

This itinerary is based on the 6D|5N guided walk on Tasmania’s East Coast staying on a luxury Ketch. Please contact us for further set departure details and alternative itineraries.


Meet in Hobart and travel to Fortescue Bay and begin todays walk. This 4-hour return walk begins with a gentle ascent on a well-crafted track, before climbing atop the towering dolerite sea cliffs this peninsula is famed for. Along the way, you’ll pass through heath and woodland vegetation before the view opens up to magnificent rock formations. Your guides will point out well-known sea stacks including the Candlestick and the Totem Pole.

Arriving back at Fortescue Bay, we transfer via tender to our 23-metre (75-ft) luxury ketch, Lady Eugenie. This will be your floating home for the next five nights.

Once aboard, enjoy a gourmet dinner of local Tasmanian delicacies whilst taking in stunning views of sheltered Fortescue Bay (8.5kms; 4 hours walking).


Disembark on the beach at Fortescue Bay and choose to relax and swim at the beach or a short walk to Canoe Bay and back through small pockets of rainforest and coastal vegetation.

Return to the Lady Eugenie for lunch and then set sail, slow-cruising toward North Bay to spend the evening anchored off the coast of the Forestier Peninsula, near the very spot that Abel Tasman first landed in 1642 (6kms; 3 hours walking).


Embark on a scenic morning’s sail past Marion Bay, Cape Bernier and the south end of Maria Island to arrive at the World Heritage-listed convict site of Darlington. Once populated with prisoners, it is now home to an array of architectural relics and abundant wildlife.

Disembark, and ascend 630m high Bishop and Clerk (4 to 5 hours return). Traverse the high cliff edge of Fossil Bay, enjoy sweeping views toward Schouten Island and Freycinet Peninsula.

Late afternoon, retire to the comfort of our luxury yacht for pre-dinner nibbles and a delicious meal to celebrate the challenges and triumphs of our day (12kms; 5 hours walking).


Following a leisurely breakfast on board Lady Eugenie, set sail for a 4-5 hour journey toward the spectacular Schouten Passage, sailing past large sedimentary deposits and towering dolerite columns to the pink granite boulders and mountains of the Freycinet Peninsula. En route, get an up-close view of an Australian Fur Seal colony of Isle du Phoques.

Disembark on the secluded Schouten Island for a scenic 3-hour walk, climbing to the top of Bear Hill or enjoy a more leisurely afternoon relaxing on-board or at the beach snorkelling and swimming (6kms; 3-4 hours walking).


Over breakfast we decide whether we ascend Mt Graham and take the high route to Wineglass Bay or opt for the less challenging but equally stunning coastal section of the Freycinet Peninsula circuit track.

Arrive at Wineglass Bay, take a refreshing swim and then meet Lady Eugenie for the final night’s gourmet meal under a setting sun (9kms; 5-7 hours walking).


Bid the skipper farewell, observe the busy shorebirds and towering forms of the Hazards mountain range above, ascend gently between pink granite boulders overlooking the white sands and turquoise waters of Wineglass Bay below. A steep descent on a well-constructed track leads to an awaiting bus for the return journey to Hobart.

Visit a Coal River Valley vineyard for canapés and celebratory drinks before returning to Hobart via the Hobart Airport (5kms; 3 hours walking).


5 nights / 6 days

5 nights / 6 days

AUD $3995 per person Twin Share

AUD $3995 per person Twin Share

START: Hobart, Tasmania     |     Finish: Hobart, Tasmania


AUD $ 3,995
per person
Twin Share


  • Full board accommodation on the luxury ketch Lady Eugenie; there are two cabins with one double bed each and two with single beds each (1 x bunk each)
  • Non-alcoholic beverages, plus a limited selection of Tasmanian wines
  • National Park passes
  • Use of daypack and rain jacket for duration of the walk
  • All bedding and linen
  • A qualified guide for the duration of the walk
  • Return transfers between Hobart at the start and finish of the walk


  • Flights
  • Travel Insurance
  • Any taxes and/or visas
  • Any extra or additional accommodation or arrangements
  • Gratuities and any personal purchases

Minimum – 4 guests (to confirm the departure)

Maximum – 8 guests per departure

4 and 6 day itineraries available
Minimum 4 | Maximum 8 guests
Grade: moderate
Private charters available
Experienced guide, skipper and crew
Operates late October through to early May
Terms and conditions apply – please request a copy of our booking form for all details.
Please contact us for pricing, dates and a full itinerary

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