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A journey through Italy's sun-drenched heel — where life is slow, the food is incredible, and every view is postcard-perfect. We stay in two beautiful bases so you unpack once, eat where the locals eat, and spend afternoons swimming instead of driving.
Trip at a Glance
- DestinationItaly
- DatesMay 18 – 26, 2027
- Duration8 Nights / 9 Days
- Group SizeMax 12 Travelers
- Travel StyleCulture, Food & Wine, Scenic, Relaxed
- Activity LevelEasy to Moderate
- AccommodationTwo hotels, five and four nights
Highlights
- Sunset walk through the white lanes of Ostuni with an aperitivo waiting at the end
- Trulli of Alberobello early, before the day-trippers arrive
- Burrata tasting at a working dairy — you will never buy supermarket mozzarella again
- A private boat afternoon along the Polignano a Mare cliffs and sea caves
- Baroque Lecce with an architecture historian who grew up there
- Long lunch at a masseria, under the olive trees, with the family who farms it
Day by Day
9 days, 8 nights. Every day has an anchor and an escape hatch — nothing here is compulsory.
Private transfer from Bari airport to our seaside base. Nothing scheduled until an easy welcome dinner where you meet the group over local wine and far too much bread.
Morning in the old town on the cliffs, then a private boat along the coast with swim stops. Afternoon free for a nap or a very long espresso.
We arrive early, before the buses. A local guide explains why anyone builds a house you can dismantle, then lunch at a family trattoria in the Valle d'Itria.
Free morning. Late afternoon walking tour through the whitewashed lanes as the light turns gold, ending with aperitivo on a terrace over the olive plain.
A working farm morning — burrata pulled in front of you, olive oil tasting that ruins you for life — then a four-hour lunch under the trees. No plans after.
Scenic drive to Lecce with a stop in Grottaglie for ceramics. Evening at leisure in the Baroque old town.
Morning tour with an architecture historian, afternoon free for the pasticciotto crawl we will absolutely recommend.
The easternmost town in Italy — mosaic cathedral, castle walls, a swim if the sea agrees. Farewell dinner with the wines we met along the way.
Transfers to Brindisi or Bari airports. Extensions to Matera or Rome easily arranged.
What's Included
- 8 nights in hand-picked boutique hotels and one masseria
- All breakfasts, 5 dinners and 4 long lunches
- Private transfers throughout — airport to airport
- Private boat afternoon in Polignano a Mare
- All guiding, entries and tastings listed in the itinerary
- A travel designer on call before, during and after the trip
What's Not Included
- International flights (we are happy to advise)
- Travel insurance — required, and we will help you choose
- Meals not listed, and personal spending
- Optional spa treatments and private extensions
- Gratuities for local guides and drivers
We would rather show you this list than surprise you with it later.
Important Info
- PaceTwo bases, no daily packing. Most days have one anchor activity and a free afternoon.
- WalkingOld towns mean cobblestones and gentle hills — expect 3–5 km on foot on touring days, at a conversational pace.
- WeatherLate May averages 24°C / 75°F. The sea is swimmable for the brave and lovely for everyone by afternoon.
- GroupMaximum 12 travelers. Solo travelers are genuinely welcome; the single supplement is $690.
- AccessibilityLimited mobility can be accommodated with notice on most days — talk to us before booking and we will be honest about what works.
Questions about this trip? Ask a human.
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