Cost: £2,100 PP
Deposit: £200 PP
Full Balance Due: 6th March 2026
Wines, Olives, Oceans & The Trulli
Adventure to the Sun-Drenched Shores of Southern Italy
Friday 5 June 2026 to Friday 12 June 2026 (7 Nights)
Twin Share – £1,400pp
Single – £2,100pp
WingsItaly sets off for a truly special escape to Puglia, a captivating region where the charm of the Adriatic coast meets the warmth of Italian tradition, near Otranto, ancient stone streets, crystal-clear waters, and stunning coastal beauty come together to create the perfect backdrop for an unforgettable week.
Your home will be Cale d’Otranto, a beautiful resort unlike any other — famously brought to life by the celebrated architect Gae Aulenti, designed with minimal windows and doors to blend into its natural surroundings. This architectural marvel is more than just a resort, it’s a living, breathing expression of art, nature, and Mediterranean soul.
During this adventure, you will explore some of Puglia’s most iconic sights — including the Trulli of Alberobello, fairytale stone houses with conical roofs that seem plucked from another time.
Sun, Sea, Wine, and a Little Mischief. The pace is slow, the views are endless, and the wine flows freely with an extensive all-inclusive drinks package at the resort* — it’s all waiting in Puglia
Bring your appetite and make some memories worth flirting with.
Your adventure begins the moment you arrive—greeted with a warm welcome at the airport and a private transfer to your hidden seaside sanctuary.
Welcome to Cale d’Otranto, an exclusive paradise nestled within a secluded cove, accessible only by boat. Where life moves to the rhythm of the waves and the clink of glasses raised in celebration. Whether you’re soaking in the golden glow of an Adriatic sunset, or dancing barefoot under the stars — every moment is effortlessly indulgent.
And when it comes to indulgence, the resort’s very generous all-inclusive drinks package* ensures your glass is never empty. From expertly crafted cocktails and chilled Prosecco to bold Apulian Reds and refreshing local Whites, every sip tells a story of southern Italy’s rich traditions.
As part of your adventure, you’ll spend a day exploring the enchanting town of Otranto, just a scenic 10-minute drive away. This sun-drenched coastal treasure, rich in history and charm, invites you to wander its ancient streets.
You’ll explore Puglia’s rich tapestry — wandering the iconic Trulli houses of Alberobello, tasting wines beneath the vines of family-run estates, and sailing along a rugged coastline carved with hidden caves and secret coves.
You’ll sip and swirl your way through a local vineyard, learning about Puglia’s centuries-old winemaking traditions while sampling some of its boldest reds and most refreshing whites.
Highlights of your Puglia Escape
🏨 Stay at a One-of-a-Kind Coastal Resort.
Relax at Cale d’Otranto, a striking, artist-designed resort with no doors and windows at the reception. Enjoy turquoise sea views, lush gardens, and cliffside sunsets.
🍷 Vineyard Visit & Wine Tasting.
You’ll taste your way through Puglia’s celebrated wines and learn about its deep-rooted winemaking traditions, all in a sun-drenched countryside setting.
🏛️ Orientation Tour of Otranto.
Explore the charming old town, admire the stunning Cathedral Mosaics, and soak up the atmosphere of this historic seaside fortress town.
🏡 Discover the Trulli of Alberobello.
Wander through the magical, conical-roofed houses of Alberobello, a UNESCO World Heritage Site and one of Italy’s most photogenic villages — straight out of a fairytale.
⛵ Boat Trip Along the Adriatic Coast.
Sail past hidden coves, dramatic cliffs, and sea caves on a relaxing cruise. Enjoy a leisurely onboard wine, sunbathe on deck, or take a dip in the clear waters.
🍋 Comfort & Indulgence at Every Turn.
Stay in Comfort Rooms each featuring a stylish en-suite bathroom and thoughtful touches designed to make your stay feel effortless. A restful retreat awaits after every day of adventure.
Your home for this adventure is Cale d’Otranto
Cale d’Otranto is a charming superior beachfront resort nestled in Mediterranean greenery along a crystalline bay in Torre Santo Stefano, just a few kilometers from the historic city of Otranto.
Surrounded by crystal-clear waters, coves, and a lush pine forest, the resort offers exclusive access to one of Puglia’s most enchanting coastal stretches.
Stay in beautifully renovated rooms blending traditional Apulian architecture with modern comforts. Every detail is curated to ensure relaxation and tranquility.
Indulge in fresh, local cuisine served with a view. Restaurants celebrate the rich culinary heritage of the region, offering everything from seafood specialties to traditional pasticciotti.
It’s your Mediterranean dream come true.
Cale d’Otranto Facilities
- Bars & Lounges: Two lounges, a poolside bar, and a snack bar/deli.
- Two outdoor pools, one poolside bar, sun terraces with loungers
- Water sports: canoeing, kayaking, snorkeling, scuba diving (extra charge)
- Private beach with loungers included.
Cale d’Otranto is set in a beautiful, secluded seaside cove with hilly terrain, stone pathways, and stairs throughout — there are no lifts. A moderate level of mobility is recommended; however, a buggy system is available for those who require assistance.
Includes:
- Private Airport Transfers from Brindisi Airport and Transfers Throughout the Itinerary
- 7 Nights Bed & Breakfast at Cale d’Otranto www.lecaledotranto.com
- Half Board with a mix of 7 Lunches or Dinners– Meals include unlimited local wines – Red, White & Rosé
- All bedrooms en-suite and complimentary Wi-Fi
- Sun loungers at the resort
- Drinks Package: Includes microfiltered water, wine, and soft drinks (orange soda and cola) during meals; snacks and aperitifs in the evening
- 7:30 am – 11:00 pm:
- Cafeteria service (espresso, decaf coffee, milk, cappuccino, barley coffee, ginseng, tea, and herbal tea)
- Soft drinks from draft (water, fruit juice, pineapple, granite and ace taste)
- 12:00 pm – 11:00 pm:
- Non-alcoholic fruity cocktails, national digestives (Eg, Amaro), and liqueurs (beer, spritz, prosecco, sambuca, limoncello)
- 8:30 pm – 11:00 pm
- A national selection of spirits: Gin, Rum, Vodka, Cocktail of the Day
- 7:30 am – 11:00 pm:
NB: Drinks in cans or bottles, premium brands, fine spirits, ice creams, and everything not listed above are not included
- Orientation Tour of Otranto
- Full-Day Excursion to the Trulli of Alberobello
- Evening entertainment: live music, theme parties, disco, DJ night, outdoor shows
- Vineyard Visit with Wine Tasting
- Boat Trip with Lunch & Drinks
- Luggage will be delivered to your room upon arrival for your convenience
- Personally Hosted by WingsItaly. Our expert hosts ensure an elevated, worry-free experience with exceptional attention to detail and care
Not included:
- Flights
- Personal expenses throughout the trip
- Drinks and beverages outside of the itinerary
- Any excursions and transport not part of the planned itinerary
- Sun parasol at the resort
- Travel Insurance
- Personal tips & gratuities throughout
Important Information
Passport validity
For UK passport holders your passport must be:
- Issued less than 10 years before the date you enter the country (check the ‘date of issue’).
- valid for at least 3 months after the day you plan to leave (check the ‘expiry date’).
ETIAS (European Travel Information and Authorization System)
The rules of travel to most European countries have changed. Starting in the first half of 2025 UK citizens are required to have a travel authorization to enter 30 European countries for a short stay.
ETIAS travel authorization is an entry requirement for visa-exempt nationals travelling to a number of European countries. It is linked to a traveler’s passport. It is valid for up to three years or until the passport expires, whichever comes first. If you get a new passport, you need to get a new ETIAS travel authorization.
With a valid ETIAS travel authorization, you can enter the territory of these European countries as often as you want for short-term stays – normally for up to 90 days in any 180-day period. However, it does not guarantee entry. When you arrive, a border guard will ask to see your passport (and other documents if required) and verify that you meet the entry conditions.
NB – There is no official date for the ETIAS currently confirmed but when it is introduced it will be your responsibility to ensure that you have arranged this. We will update everyone when the ETIAS is required with information on how to apply for this online.
Travel Insurance
Please ensure that you have adequate personal travel insurance to suit your requirements in place before you travel.
The latest FCO travel guidance –
Your Journey to Otranto Awaits
Puglia, Italy | 5 June – 12 June 2026 (7 Nights)
Secure your place on this exclusive adventure.
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Puglia, Italy Single Room
Puglia, Italy Single Room
Cost: £2,100 PP
Deposit: £200 PP
Full Balance Due: 6th March 2026
Puglia, Italy Twin or Double Share Room
Cost: £1,400 PP
Deposit: £200 PP
Full Balance Due: 6th March 2026.
Puglia, Italy Twin or Double Share Room
Cost: £1,400 PP
Deposit: £200 PP
Full Balance Due: 6th March 2026.