Santorini is the postcard everyone knows, and this trip shows you the version they do not: quiet lanes before the crowds arrive, family wineries and a private boat day with no schedule except the sun.
What is included
- Six nights in a boutique cave hotel with breakfast and caldera views.
- Private catamaran day with lunch and drinks on board.
- All transfers and a local guide on the days that need one.
- Winery visits with tastings and a long Greek lunch.
Day by day
Arrive in Santorini
Private transfer to your cliffside hotel in Oia. Evening welcome dinner overlooking the caldera with your guide.
Oia and the caldera
Morning walk through Oia's lanes, then free time for photos and shopping. Optional sunset viewing from the old castle.
Sailing day
Full day on a private catamaran with swimming stops at the hot springs and red beach. Lunch cooked on board.
Wine and villages
Visit three family wineries in Pyrgos and Megalochori with tastings and a long lunch among the vines.
Free day
A day of your own. Our guide can suggest beach clubs, ancient Akrotiri or a spa afternoon.
Fira and Imerovigli walk
Follow the caldera path from Fira to Imerovigli with a local guide, finishing with sunset drinks.
Departure
Breakfast and private transfer to the airport or ferry. Onward travel can be arranged.
Prices and dates
| Departure | Room | Price per person |
|---|---|---|
| 14 May 2027 | Double | $1,890 |
| 11 Jun 2027 | Double | $2,090 |
| 10 Sep 2027 | Double | $1,990 |
| Any date | Single supplement | +$480 |
The sailing day alone was worth the trip. We have already told three friends to book.Hannah Collins, honeymoon traveller