The Well-Heeled Are Headed to Puglia, the End of Italy’s Boot

The heel of Italy’s boot is its hospitable heartland, at least to a growing contingent of savvy travellers who find themselves turning to Puglia time and again, perhaps at first for its rusticity, but now for its lavish resorts. It’s been a long time coming for the historically overlooked region and its 500 miles of coastline, most of which is devoid of the crowds overstuffing other parts of the country.

“Puglia is authentic but contemporary, relaxing but full of vibrant energy,” says Aldo Melpignano, owner of Borgo Egnazia, a luxury resort that has helped put the region on the map for international travellers. “It’s becoming more and more an international travel destination, but you can still discover hidden gems and unspoiled places.”

Charming towns line the Adriatic coastline like whitewashed pearls on a string, from Lecce to Brindisi, onward to Ostuni and Monopoli, continuing north to Bari and Trani. The countryside in between showcases the remnants of conical trulli, traditional stone-hut residences, found amid endless olive groves. Its every facet has a distinct Puglian feel, an inimitable aura of charm and hospitality that cannot be replicated.

The Growth of Puglia’s Luxury Scene

“Sometimes when you are in a luxury resort in the Côte d’Azur or Sardinia or Mexico, you feel like you could be anywhere, you don’t have a sense of place” says Vito Palumbo, CEO of Tormaresca winery. “When you are in Borgo Egnazia or Torre Coccaro, though, you know you are in Puglia, you know that you’re in a masseria that has been revamped into a beautiful resort with a very strong Puglian identity.”

At Tenuta Bocco di Lupo, the long, sandy white road that serves as its entrance beckons travelers to its grand estate and cellar.
Jake Emen

It’s been a quarter century since Tormaresca was acquired by wine conglomerate Antinori, whose financial backing and know-how helped modernize its efforts, transforming its distinctive terroir and native grapes—such as Primitivo, Negroamaro, Aglianco, and Fiano—into sought-after varieties. In more recent years, Palumbo has grown into a role as the face of Tormaresca, but also as the de facto ambassador for Puglia on the whole, dedicated to touting the appeal of his home region.

Puglia’s beloved masserias, or farm estates constructed in village-like fashion, replete with small walkways and central gathering plazas, offer a different spin on Italian luxury and hospitality, versus the villas of Tuscany, the cliff top properties along the Amalfi coast, or the grand dames of Venice and Florence.

One of the initial masserias to make a splash was Masseria Il Melograno, whose grounds are studded with gnarled and wizened 600-year-old olive trees and purple bougainvillea flowers. But when Borgo Egnazia opened in 2010, following a six-year, reported €150 million project, it set the region on a luxurious new path, gaining recognition as one of the top properties in Italy and across continental Europe.

With that kind of success, it was perhaps inevitable that large, international brands would follow course. Rocco Forte added Masseria Torre Maizza to its portfolio in 2018, and in early 2021, Four Seasons announced an Ostuni project, signalling it would be a new construction with direct beach access and 150 villa-style guest rooms. Around the same time, Belmond purchased Masseria Le Taverne, a 17th-century farm estate, and is amid extensive renovations while aiming to maintain the property’s heritage and character.

The best of both worlds can be found at a restaurant such as Osteria del Tempo Perso in Ostuni,
Jake Emen

“Puglia’s popularity has grown significantly for those looking to explore a different part of Italy and to discover the region’s spectacular coastlines and beautiful beaches, rich history, and exceptional culinary offerings,” says Bart Carnahan, Four Seasons president of global business development and portfolio management.

The Roots Are in the Vineyards and the Olive Groves

At the heart of Puglia’s culinary movement is an appreciation for its local ingredients, from burrata to olive oil and a wealth of fresh seafood.

“Puglia is Italy’s most important region for extra-virgin olive oil production,” Palumbo says, citing overall output and a breadth of styles, with at least 60 types of olives found on millions of trees. Yet, as with the region’s wine, the quality of its olive oil was long overlooked, with the majority being sold in bulk. “Puglian olive oil is going places, and it’s the same story as the wine. There are more strong Puglian olive oil brands than Tuscan ones now.”

Travellers can spend a day on a farm or dairy learning how to make cheese or pressing their own olive oil, perhaps in between visits to its emergent wineries. At Tenuta Bocco di Lupo, the long, sandy white road that serves as its entrance beckons travelers to its grand estate and cellar. There, they can taste wines under its eponymous label, such as an Aglianico from Castel del Monte; Pietrabianca, made with Chardonnay and Fiano from Castel del Monte; and Fiano di Bocca Di Lupo.

Then there’s Tormaresca’s Calafuria, the best-selling rose wine in, and from, Italy. But it’s through the aforementioned offerings, along with bottles such as Torcicoda, a Primitivo from Salento, as well as the Masseria Maime Negroamaro, that Palumbo plans to establish the bonafides of his two estates in the region. What he and his winemakers have found is that Puglian wines made with intention, and reflective of their home place, are more than capable of great ageing potential, with rich character that consumers can expect to develop and unfold in the decade or two to come, while still being able to be poured today and enjoyed. “We want the Puglian influence,” Palumbo says.

Puglia’s restaurant scene has soared as well, with 10 Michelin-starred outposts in the region and scores of other fine-dining establishments. A prestige institution such as Quintessenza, in Trani, is helmed by the four Di Gennaro brothers, each of whom has a different role in the operation of a space devoted in full to showcasing and elevating Puglia’s bounty.

The best eating though may be in casual, local spots with seaside views or beachfront settings, from the Coccaro beach club and restaurant, to the Trabucco Tormaresca in Trani, a sceney waterfront bar stylised as an old fisherman shack. The best of both worlds can be found at a restaurant such as Osteria del Tempo Perso in Ostuni, where classic Puglian dishes are showcased with the best ingredients, but without unneeded adornment or reinvention, with the service and setting that elevates food with humble origins into a destination dining experience.

Travellers to Puglia can indulge in it all: the excellent food and wine that will satiate the most discerning of palates and the luxurious accommodations that need not play second fiddle to anywhere else in the country, offered with the trademark embrace of the region’s hospitality.

“The ancient traditions of this region represent a unique heritage,” Melpignano says. “What really makes the difference in Puglia is the people: Always heart-warming, they have the sense of welcome in their blood.”

Happy is the family whose members—parents, grandparents and grown children—trust each other enough to cooperate on shared goals, especially financial ones. When that is truly the case, Uncle Sam’s tax rules can help as well.

This matters especially now that mortgage rates are above 7%, and many families are looking for ways to help younger members. If the elders have resources and are confident younger ones can cooperate, a family loan could make homeownership possible while providing the elders with a useful income stream.

Other strategies can actually lower taxes, such as when funding 529 plans or Roth IRAs, or when someone inherits a traditional IRA with required withdrawals larger than they will need.

Here are three strategies useful for functional families.

Intrafamily loans

It is perfectly legal for families to lend money to a relative for a down payment or even a private mortgage.

But it is important not to cut corners, says Ryan McKeown, a CPA with Modern Wealth Enhancement in Minnesota. If the loan is for a down payment, be honest with the mortgage provider and have a formal agreement. The lender owes tax on the interest payments received.

If the loan is for a private mortgage, both sides should have legal representation with a formal written agreement, including payment terms. The lender owes tax on the interest, and the borrower often can deduct it if he or she itemizes.

To avoid IRS trouble, the interest rate shouldn’t be lower than the agency’s Applicable Federal Rate at the time of the loan. Currently that is about 5% for loans longer than nine years; about 4.5% for loans three to nine years; and about 4% for loans three years or less. Currently, traditional mortgage rates are generally above 7%.

In addition, the lender could use the $19,000 annual gift-tax exemption (described below) to forgive some or all of the interest or principal annually. If both lenders and borrowers are married, that is up to $76,000 a year. There is no tax for the borrower on such forgiveness, because it is from a gift.

If you’re going this route, McKeown advises against having a fixed plan to forgive the debt. Instead, do it in one-off letters specifying the amount—and keep careful records. Otherwise the IRS might try to treat the loan as a taxable gift.

Asset gifts

Powerful tax-saving moves for families often use gift-tax provisions. Under current law, anyone can give anyone else up to $19,000 of assets annually, free of gift tax. That means a married couple with three grandchildren could give them a total of $114,000 in 2026.

The gifts can be cash or other assets, like stock. For noncash gifts, the cost basis—which is the starting point for measuring taxable gain after a sale—“carries over” to the recipient. So if someone buys $1,000 of stock and gives it away when it is worth $5,000, the recipient’s cost basis is $1,000. If the recipient later sells the shares for $8,000, the taxable gain is $7,000.

Here’s an example showing how gifts could save a family taxes. Grandma is a widow of modest means, while her child and spouse have prospered. The couple has two children, and they want to contribute $5,000 to a 529 college-savings plan for each—but they need to sell stock to do it. Their tax rate on the sale would be 18.8%, and they would need to sell about $11,000 of stock.

However, Grandma’s federal tax rate on the stock sale is 0%. If the couple gives $10,000 of shares to Grandma, she could sell them, pay no tax, and fund the grandchildren’s 529 plans. This saves about $1,000 of tax.

These moves are legal, and they could be used in other ways, such as to help a young person fund a Roth IRA.

But trust among family members is essential: Under the law, givers can’t put conditions on a gift. Grandma could use her stock proceeds to take a cruise, but she makes 529 contributions instead.

Mark Sellner, a retired tax attorney and CPA living in Sarasota, Fla., uses this strategy. His children sell stock he gives them and fund 529 plans for his grandchildren.

The family’s tax savings aren’t huge, but he likes other benefits. The sales by his children don’t boost his adjusted gross income, which in turn could raise his Medicare Irmaa premiums or his 3.8% surtax on net investment income.

Sellner doesn’t worry about his children using the funds for another purpose.

“There can’t be any strings attached to gifts. Of course, it is up to us to decide whether to make them in the future,” he says.

Two caveats: The “kiddie tax” applies to most children under age 24, and it is levied at the parents’ rate on investment income above $2,700 in 2026. Consider this before making gifts to a young person.

Investors who give away stock also forgo the step-up, an important provision that exempts assets held at death from capital-gains tax.

Sellner knows he’s losing a step-up, but says, “The children could use a little more now. Why should they wait 20 years to get it?”

Disclaimers

A disclaimer is a highly useful strategy in which one heir renounces an inheritance in favor of another heir. Assuming family members cooperate, this can save taxes.

Here’s one example. Dad died and had a large traditional IRA that he left to Mom. She has enough assets and income to cover her expenses, and she lives in a state with a stiff estate tax. The inherited IRA would put her estate over the threshold.

Also surviving are three young-adult children. If Mom disclaims all or part of Dad’s IRA within nine months of his death, that amount could go directly to the children. They will have 10 years to empty the account, and the family as a whole will likely save estate and income taxes.

Disclaimers have many key details, especially regarding beneficiary documents. Although heirs have great freedom in choosing what assets to disclaim, the rules about who gets disclaimed property are rigid. It is best if the original owner names tiers of heirs so that if one disclaims, the next recipient is clear.

The Well-Heeled Are Headed to Puglia, the End of Italy’s Boot

Strong family financial planning can help reduce taxes and support younger generations. From intrafamily loans and asset gifts to inheritance disclaimers, strategic cooperation can create meaningful financial benefits—when families have the trust and structure to make it work.

Intrafamily loans

Asset gifts

Disclaimers