i love an itinerary. i just don’t want one that requires a clipboard and a small jog between bookings.

i want good coffee, beautiful food, wines worth talking about and enough time to actually enjoy where i am. preferably with somewhere lovely to come home to.

after a very full orange wine week, i’ve been thinking about the weekend i’d put together for someone coming here. the places i’d send a friend, in the order i’d actually do them.

so here it is. arrive friday, stay three nights and leave monday with a few bottles, something you didn’t need for the house and a strong opinion about coming back.

you can do it with friends, with someone you love or on your own. you don’t need a special occasion. wanting a lovely weekend is enough.

if you're planning a little more time in the region, i've got more ideas for visiting orange too.

first, come and stay at mine

make stay awhile, orange your base for the weekend.

it’s my four bedroom, two bathroom home, with room for up to eight guests. bring some friends and make a long weekend of it, or book it for a quieter escape.

and yes, there’s a hammock. we’ll get to that.

if you're still deciding on accommodation, i've also put together a guide on where to stay in orange.

check dates and book my airbnb here

friday evening: straight into holiday mode

arrive, settle in and take yourself to the oriana.

the garden bar is delightful. this is where i’d start the weekend, with a drink, something to eat and absolutely no intention of discussing work.

they sometimes run $1 oyster specials, so check what’s on for your dates. if you time it well, excellent. if you don’t, you’re still in a lovely garden bar in orange. hardly a disaster.

order dinner, settle in and let the weekend begin. a dirty martini would not be out of place. neither would a second look at the menu.

then home for a good sleep. saturday has plans.

saturday morning: a big walk and a very good breakfast

wake up and head out for a big walk, finishing at byng street local store.

my order is coffee and the ricotta with poached eggs on sourdough. i went twice over wine week, which should tell you how i feel about it.

walk back to the house, shower and get ready for your winery day. leave yourself enough time to do this without applying mascara in a moving vehicle.

saturday afternoon: see saw, then macquariedale

these would be my two picks for the day. they’re near each other, so you can spend your afternoon enjoying them rather than driving all over the region.

first stop: see saw

book the seasonal food and wine tasting at see saw. it’s such a lovely way to experience the wines with food chosen to go with them.

richard learmonth is a bloody legend, as is mon the winemaker. i loved my experience here. ask questions, try something different and give yourself time to enjoy it.

second stop: macquariedale organic wines

then head to macquariedale and finish the afternoon with a tasting and a cheese platter.

book their tasting with a grazing platter so the food is part of the plan. wine, cheese and nowhere you need to rush off to for a while. this is the afternoon you came for.

book macquariedale’s tasting and grazing platter

arrange your driver before the weekend, including your dinner stop and the trip home. then the only difficult decision is which bottles are coming with you.

saturday evening: dinner at fiorini’s

from macquariedale, head back towards town for dinner at fiorini’s osteria italiana.

sim and eleni spoiled us when we visited. oysters, octopus, a special nettle pasta and pistachio tiramisu. honestly, incredible.

the menu is seasonal, so see what’s on when you visit. if that pistachio tiramisu makes an appearance, you know my position.

book your table at fiorini’s

then back to the house, into your pjs and off to bed. a full day out with a lovely home to come back to is one of my favourite combinations.

sunday morning: coffee, then a little culture

head back to byng street if you’re already attached to your breakfast order. i understand.

or try provence boulangerie for a change. another lovely option for coffee and breakfast.

then spend some time at orange regional gallery.

the colourful installation in my photos is nike savvas’ purple haze, on until 15 november 2026. it’s incredible to stand amongst all that colour. if you’re coming after that, check the gallery’s current exhibitions through the same link.

sunday midday: byrne farm

next, head out to byrne farm for a tasting.

jeff and caitlin’s beautiful chardonnay is reason enough to go. the setting makes it very easy to settle in and enjoy being there.

i also met the baby geese on my visit. considerably harder to leave than anticipated.

book your tasting and organise your return transport. eat before or after your visit, rather than assuming a winery tasting includes lunch.

book a tasting at byrne farm

sunday afternoon: the hammock has your name on it

back to the house. find your book. get in the hammock.

that’s the activity.

no extra cellar door. no quick errand. no filling the afternoon because you feel you should be doing more.

read, have a little sleep or stare at absolutely nothing. this is your weekend too.

keep dinner easy at home. after saturday, nobody needs you to produce a nettle pasta.

monday morning: a little shopping before you go

pack your bags, have breakfast and check out at the agreed time. then fit in a little browse before heading home.

my picks are jumbled and the white place.

allow room in the car. “just looking” has failed me before.

then a final coffee and home you go.

before you come

book the house, saturday dinner, your tasting experiences and transport first. check current menus, opening hours and specials for your dates, particularly over public holidays.

bring a warm layer, your book and something you feel lovely in.

that’s my orange weekend. good food, beautiful wines, local people doing wonderful things and an afternoon where nobody needs anything from you.

come and stay awhile.

i’ll leave the hammock to you.

know someone who keeps saying they need a weekend away? send them this. the planning’s done.

subscribe for more places worth going, practical solo travel advice and a little encouragement to actually book it.

jen x