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Illustration standing in for Hobart and River Derwent: wooded banks closing in on either side over slate-green water in morning light
3 days · Skippered day sail

Three days from Hobart to Bruny Island

Three days down the Derwent and into the D Entrecasteaux Channel, with cold water, big margins and genuinely quiet anchorages.

Home · Itineraries · Three days from Hobart to Bruny Island
Length3days aboard
Legs3anchorage to anchorage
Charter typeSkippered day sailA professional skipper runs the boat for a few hours
Workable seasonDecember to Marchoutside it, expect to be weather-bound
Leg by leg

The route

Hobart and River Derwent
DayFromToDistanceNote
1Hobart waterfrontBarnes Bay18 to 25 nmDown the Derwent on the afternoon southerly. First leg kept simple.
2Barnes BayGreat Bay or Simpsons Bay10 to 16 nmChannel sailing. Short leg, long afternoon ashore.
3Simpsons BayHobart waterfront22 to 30 nmLongest leg, done early. The Derwent builds in the afternoon.

The D Entrecasteaux Channel between Bruny Island and the Tasmanian mainland is some of the best protected sailing in Australia, and almost nobody outside Tasmania uses it. Three days gets you out of Hobart, down the channel, and back without rushing. The water is cold and the weather changes fast, and those two facts shape everything else.

Who this suits and who it does not

It suits experienced sailors who want scenery, quiet and a real sense of latitude. It suits people who would rather have a bay to themselves at fifty five degrees of wind chill than share Whitehaven with forty boats. Food and wine along the channel is a genuine draw.

It does not suit warm water swimmers. You will not be swimming much, and if you go in you will get out quickly. It does not suit crews without cold weather gear, and it does not suit anyone who has only sailed in the tropics and assumes the same margins apply. They do not.

It is also not a good first bareboat. Most visitors here are better served by a skippered charter, which is how this itinerary is written. See charter types.

The shape of the days

Legs of ten to thirty nautical miles, rounded planning estimates. The channel is sheltered but the Derwent itself is open and can be windy.

Day one runs down the Derwent and across into Barnes Bay at the north end of Bruny. It is a straightforward reach in the usual afternoon southerly and it puts you into good shelter on the first night.

Day two is short by design. A ten to sixteen mile channel hop leaves most of the day for going ashore, which is much of the reason to come.

Day three is the longest and is done in the morning. The Derwent funnels and the afternoon breeze builds up the river, so beating back to Hobart at four in the afternoon in twenty five knots with a tired crew is a poor way to end a good trip.

Decision points

Frontal changes are the decision point in Tasmania and they are the reason southern itineraries need large margins. A front can swing the wind through ninety degrees or more in an hour and bring a sharp increase in strength. Every anchorage choice here should be made for the wind after the front, not before it. Barnes Bay, Great Bay and Simpsons Bay each favour different directions.

The second decision is whether to go further south at all. Beyond the southern end of the channel you are in open water with a Southern Ocean swell, and that is a different trip needing a different boat and a bigger window.

The third is simply the season. Tasmania works for longer expeditions from December to March, with a longer shoulder season for Hobart day sailing. Southern waters generally run roughly November to April. See weather and seasons.

What to book ahead

Book well ahead for anything over the New Year period. The Sydney to Hobart starts on 26 December and Hobart is full, on the water and ashore, for the following week. Prices ashore reflect it.

Book accommodation and hire cars before the boat if you are flying in. Hobart in January is tight.

Provision in Hobart, which is easy and good. Bring more warm and waterproof clothing than you think you need, including for the person who insists they will be fine. See provisioning and costs.

One honest warning

Cold water is the warning. The Derwent and the channel are cold enough year round that a person in the water loses function quickly, well before they look like they are in trouble. That changes the whole risk picture for a man overboard. Wear a lifejacket on deck, clip on at night and in a breeze, and have a practised recovery plan rather than an assumed one. Read safety and commercial vessel rules.

The second warning is the speed of the change. Tasmanian forecasts are good but the timing of a front is not precise, and a two hour error puts you in a different world. Build the margin in.

Regional detail is on the Hobart and the Derwent and D Entrecasteaux Channel and Bruny pages. Operators are in the operator directory.

Checked 11 September 2026

2 operators could run this

All skippered day operators here
Ask before you commit to this route
  • Is the quoted figure per person or for the whole vessel?
  • How much hands-on sailing is actually on offer?
  • What is the passenger limit for this route and forecast?
  • Is food and drink included, provided, or bring-your-own?
  • Does the vessel's certificate cover every leg of this route, or does one leg cross into a different operating area?
Full booking checklist
Where this itinerary came fromBuilt from the gateways, anchorages and indicative passages published on the Hobart and River Derwent page, plus the hazards that page records. Distances are rounded estimates, not measured tracks, and no operator was contacted for comment.Methodology
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This is an editorial suggestion compiled from public sources, not navigational, safety or weather advice, and it can be wrong. Passage planning is the skipper's responsibility. Checked 11 September 2026. See the disclaimer.