Fun Things to Do in Italy for Billionaires: The Haute Retreats Edition
When you travel at the highest level, the fun things to do in Italy look very different. Italy is full of beauty, history, and delicious food. You’re closing the doors, renting the yacht, and allowing your villa concierge to plan every aspect of your stay rather than merely going on a group tour or standing in line at museums.
In a nutshell, fun things to do in Italy when you travel like a billionaire include sailing the Amalfi Coast on a private yacht, renting a fully staffed villa in Tuscany, scheduling after-hours tours of the Vatican or Uffizi, taking a helicopter ride between Capri, Rome, and Lake Como, and taking part in rare wine tastings and chef’s table dinners with no menu.
What are the most fun things to do in Italy? is the central question addressed by this guide.From a luxury, villa-first standpoint. It is intended for visitors who prioritize access, time, and privacy. Here at Haute Retreats, we curate Italy using custom villas as your foundation and a network of reliable partners who can discreetly open the doors that really matter.
The Most Fun Things to Do in Italy If You Travel Like a Billionaire
The most fun things to do in Italy when you travel like a billionaire and stay in a private villa are listed below in short order.
- Hire a superyacht with a private chef and onboard masseuse to cruise the Amalfi Coast and Capri.
- Make reservations for a fully staffed Tuscan estate that includes truffle hunting during the season, a private chef, and a sommelier.
- A renowned art historian will lead you on an after-hours tour of the Uffizi or the Vatican Museums.
- Instead of wasting hours stuck in traffic, take a helicopter ride between Rome, Tuscany, and the Amalfi Coast.
- Enjoy lunch at a famous hotel by the lake while cruising Lake Como on an antique wooden Riva boat.
- With Michelin-trained chefs and carefully chosen wine pairings, host chef’s table dinners in your villa.
- Take advantage of private access for test drives and track experiences at Lamborghini and Ferrari.
- Organize a private palazzo party for your loved ones or close friends in Venice or Florence.
- Get away to the Dolomites or Alps for mountain solitude, heli-skiing, and spa treatments at your chalet.
- In Milan, Rome, or Florence, combine serious dining, gallery visits, and covert shopping.
So that you can plan a trip that is stress-free but unforgettable, we break down these fun things to do in Italy by region in the sections below.
Fun Things to Do in Italy on the Water – Yachts, Lakes & Islands
Sail the Amalfi Coast & Capri by Private Yacht
The most fun things to do in Italy that many visitors remember taking place on the water. That entails a private yacht with an adaptable captain, a chef who understands your tastes, and no set schedule on the Amalfi Coast.
After spending one day anchored off Positano and another discovering secret coves close to Nerano, you could cruise to Capri for a late swim at dusk and lunch at a beach club. To ensure you never touch a phone, your villa concierge can set up smooth transfers from your Amalfi villa to the marina, stock the yacht with your preferred Champagne, and make restaurant reservations.
Explore Lake Como by Vintage Wooden Boat
Fun things to do in Italy get more cinematic on Lake Como. Imagine leaving your lakefront villa on a traditional wooden Riva and cruising past lush gardens and old palazzi while your captain tells you tales about the families who own them.
You can have a private visit at Villa del Balbianello, travel by boat to a luxurious hotel for lunch, then return to your villa for a terrace aperitivo and dinner prepared by a chef. Your Haute Retreats concierge can add live music, a photographer, or an intimate rather than staged proposal setup if you’d like.
Island-Hop Sardinia and Sicily by Superyacht
Fun things to do in Italy include swimming in crystal-clear turquoise bays, lunch on a remote beach, and long afternoons spent alone with your guests and crew in Sicily’s Aeolian Islands and Sardinia’s Costa Smeralda.
A typical day might include sunset cocktails back at the villa while your private chef finishes dinner, morning departures from your villa to the harbor, and a full-day cruise with jet skis and water toys for the kids.
Fun Things to Do in Italy for Food & Wine Lovers
Private Villa Chef Tables in Tuscany & Umbria
The best fun things to do in Italy for foodies frequently take place on the premises. Your kitchen becomes the focal point of a Tuscan or Umbrian villa: a sommelier selects wines from Brunello to Super Tuscans, a private chef creates a menu based on your preferences, and the terrace serves as your dining area.
You could begin the week with a long, leisurely lunch beneath the pergola, move on to a dinner that focuses on truffles, and end it with a formal tasting menu by candlelight. Even though you don’t do anything, every evening feels unique because everything can be customized, from the playlist to the table arrangement.
Truffle Hunting & Barolo / Brunello Vintage Tastings
Truffle hunting and private cellar visits are two of the most genuine and fun things to do in Italy. Join local truffle hunters in the forests around Alba or San Miniato in the fall, and then come back to the villa for a cooking demonstration based solely on what you’ve discovered.
We regularly set up private tastings at leading producers in Piedmont and Tuscany, such as vertical Brunello tastings, library vintages of Barolo, or comparative flights led by the winemaker. You can take care of shipping back home, vehicles, and translation.
Hands-On Cooking With a Private Nonna
Cooking alongside an Italian chef or nonna in your own villa kitchen is one of the most emotional and straightforward fun things to do in Italy, which surprises many tourists.
You could spend the morning preparing fresh pasta, tiramisù, and traditional sauces for your family instead of attending a group class. Then, you could have a long lunch on the terrace. You get recipes that feel unique rather than generic, kids can participate, and menus can accommodate allergies and preferences.
Fun Things to Do in Italy for Culture & Private Access
After-Hours Vatican, Uffizi & Hidden Palazzi
Travelers who are interested in culture will find that seeing works of art without the crowds is one of the most fun things to do in Italy. This frequently entails private or after-hours access, guided by a knowledgeable guide, to locations such as the Uffizi in Florence or the Vatican Museums and Sistine Chapel in Rome.
You can ask questions, stay where you want, and stand in front of the pieces that really matter to you rather than being swept along in a group. After that, leave for a waiting vehicle, head back to your villa for an aperitivo, and take in the quiet that follows the day’s intense visuals.
Venice Like a Billionaire – Palazzo Evenings & Private Boats
When you have your own private space in Venice, fun things to do in Italy become more surreal. This could entail closing a historic hall for a private dinner or family gathering, staying in a palazzo by the canal, and taking private water taxis rather than public transportation.
To help you see Venice as a peaceful, contemplative city rather than a bustling cruise destination, your concierge can arrange for masked musicians, a private visit to an artisan workshop, or an after-hours candlelit stroll through St. Mark’s.
Fun Things to Do in Italy for Wellness & Slow Luxury
Spa Retreats on Lake Como & in the Alps
Lake Como and the Italian Alps are obvious choices if you’re looking for fun things to do in Italy that include serious wellness. World-class spas with hydrotherapy circuits, saunas, hammams, and views of lakes or mountains can be found in numerous villas and neighboring hotels.
With in-villa massage therapists, yoga instructors, cold plunge setups, and sound baths available on your terrace or by the pool, Haute Retreats can bring the spa right to your home. Additionally, your chef can modify menus to fit a performance or detox focus without compromising enjoyment.
Mountain Chalets & Heli-Skiing Escapes
Some of the most thrilling and fun things to do in Italy during the winter involve snow. In the Dolomites or Alps, private chalets provide ski-in/ski-out access, committed ski instructors, and heli-skiing with knowledgeable mountain guides for those who want.
You can spend your afternoons by the fireplace, in your own spa with a sauna and hot tub, or at the dinner table while the chef prepares local mountain fare like polenta, wild game, and aged cheeses.
Fun Things to Do in Italy for Billionaire Families
Villa-Based Experiences Kids and Teens Actually Love
Fun things to do in Italy should be suitable for both adults and kids when traveling with a family. That could include game rooms, tennis courts, heated pools with lifeguards, movie rooms for movie nights, and lawns for casual play in a well-selected villa.
Additionally, we can set up kids’ yoga, pizza-making classes, treasure hunts throughout the estate, or supervised time so parents can sneak away to wine tastings or spa treatments without feeling pressed for time. The objective is a rhythm that feels natural, where adults feel truly rested and children are involved.
High-End Day Trips that Still Feel Effortless
Outside of the villa, family-friendly activities in Italy include private trips to Pompeii with kid-friendly guides, Vespa sidecar tours of Rome, or interactive workshops in Florence (mask-making, leather, and paper marbling). Experiences with Lamborghini and Ferrari can be tailored for parents and older teens who love cars.
The day feels more like an adventure than a logistical one because every transfer, ticket, and timing are taken care of for you.
Sample 7-Day “Travel Like a Billionaire” Italy Itinerary
Days 1–2: Rome – Antiquity & After-Hours Vatican
Start in a luxurious villa or penthouse in the heart of Rome. Take a leisurely stroll through the historic district, stop for gelato, and have a simple dinner on your terrace on the day you arrive.
A privately guided tour of ancient Rome, including the Colosseum, Forum, and Palatine Hill, followed by relaxation at the villa and an evening visit to the Vatican, is one of the most effective and fun things to do in Italy on Day 2. You’ll be able to see the Sistine Chapel without the crowds during the day and get home in time for your chef’s late supper.
Days 3–4: Tuscany – Estate Life, Wine & Truffles
Take a car or helicopter to Tuscany, then settle into your rural estate. Vineyard lunches, truffle walks, cooking classes, and long afternoons by the pool are the focus of these two days of slower, more fun things to do in Italy.
A chef’s table experience at the villa might take place on Day 3, and a private wine tour with cellar access and home delivery could take place on Day 4. Stargazing over the hills and a glass of Brunello by the fire mark the end of the evening.
Days 5–7: Amalfi Coast or Lake Como – Yachts & Water Time
Enjoy some fun things to do in Italy that are related to water to round off your week. Yacht days between Positano, Amalfi, and Capri are part of the Amalfi Coast; Riva boats, lakeside lunches, and spa treatments are part of Lake Como.
Day 5 is travel and arrival, Day 6 is a full day on the water, and Day 7 is set aside for your favorite activities, such as a final shopping trip, another yacht day, or just lounging around the villa before taking off by private jet or helicopter.
How Much Does It Cost to Travel Like a Billionaire in Italy?
Staffed Villas & Estates
The ideal villa serves as the foundation for the best fun things to do in Italy. Depending on the season and location, rates can easily reach several thousand to tens of thousands of euros per night for serious estates with numerous suites, large grounds, and full staff (chef, butler, housekeeping, and occasionally a driver or concierge on-site).
In order to avoid having to choose between the villa and what you want to do around it, Haute Retreats usually advises pairing the property itself with a thoughtful experience budget.
Yachts, Helicopters & Private Guides
After the villa, the most important line items are frequently yacht charters, helicopter rides, and first-rate guides. Because they buy back your time and safeguard your privacy, these are essential components of the most fun things to do in Italy for many visitors.
A private guide can turn a crowded landmark into a very intimate experience, a single helicopter transfer can save half a day of driving, and a yacht day can replace several land-based excursions.
Dining, Experiences & Extras
Depending on group size and preferences, daily spending on dining and experiences varies greatly. While some guests want every night to feel like an event, others prefer casual villa dinners and sporadic Michelin evenings. Planning a large experience budget, as a general rule, enables you to say “yes” to impromptu fun things to do in Italy, such as a last-minute boat trip, a special bottle from a cellar, or an additional spa day, without second-guessing yourself.
It’s also crucial to note that you don’t have to be a billionaire to use their playbook. Many of the same fun things to do in Italy can be found at more affordable prices with careful planning (shoulder seasons), strategic locations, and the right villa.
Why Billionaire-Level Travelers Choose Villas Over Hotels in Italy
The most alluring and fun things to do in Italy are more accessible from a private villa than even the finest hotel suite for travelers with extremely high net worth. The first reason is privacy: your family or group is the only ones with access to the grounds, pool, and entire property. There’s no need to dress for the lobby, no shared lounges, and no strangers at breakfast.
Focus is the second reason. The employees at a villa work exclusively for your group. Spa therapists show up on your schedule, meals are served when you’re ready, and kids are free to follow their own schedules. Pizza nights, pool parties, gala dinners, and private concerts are just a few examples of the fun things to do in Italy that take place in villas.
From the initial villa recommendation to the final farewell at the airport, Haute Retreats specializes in this degree of curation in Italy.
FAQs – Fun Things to Do in Italy (Billionaire Edition)
What are the most fun things to do in Italy if I travel like a billionaire?
The most luxurious fun things to do in Italy include chartering yachts on the Amalfi Coast or Lake Como, staying in fully staffed villas in Tuscany, booking after-hours museum visits in Rome and Florence, flying by helicopter between regions, hosting chef’s table dinners in your villa, and arranging bespoke experiences like truffle hunting, Ferrari drives and private concerts.
Where do billionaires usually go in Italy?
Billionaire-level travelers are often drawn to Lake Como, the Amalfi Coast and Capri, Tuscany’s wine country, Venice, Sardinia’s Costa Smeralda and the Dolomites. These locations make many of the most exclusive fun things to do in Italy possible: yacht days, palazzo events, large estates for family gatherings and high-end ski or spa retreats.
Do I need to be a billionaire to enjoy these kinds of experiences?
No. While some itineraries genuinely are built for billionaires, many of the same fun things to do in Italy can be tailored to a broader range of high-end budgets. Choosing shoulder seasons, focusing on one or two regions instead of many, and selecting the right villa can give you access to yachts, chefs and private guides without exceeding your comfort zone.
How many days do I need in Italy for a billionaire-style trip?
For a “taster” of the best fun things to do in Italy, five to seven days is enough to combine one major city with one region (for example, Rome and the Amalfi Coast, or Florence and Tuscany). For a fuller experience that includes multiple regions and more villa time, ten to fourteen days allows the trip to breathe and avoids constant packing and unpacking.
What is the most luxurious area of Italy?
There is no single answer, but Lake Como, Capri and the Amalfi Coast, Tuscany’s most prestigious wine estates, Sardinia’s Costa Smeralda and certain corners of the Dolomites are consistent favourites. Each area offers its own version of the most desirable fun things to do in Italy – from Riva boat rides and vineyard dinners to heli-skiing and hidden beaches.
Is Italy good for luxury family vacations with kids?
Absolutely. Some of the most rewarding fun things to do in Italy are designed around families: villa pools and gardens, pizza-making classes, treasure hunts, kid-friendly guides at historic sites and flexible dining at home. A well-chosen villa can accommodate everyone’s needs, from toddlers to grandparents, without sacrificing elegance or comfort.
Ready to plan?
Haute Retreats can assist you in creating a trip that feels less like a vacation and more like a masterfully crafted chapter in your family’s history if you’re picturing these fun things to do in Italy from the seclusion of a villa, with chefs, concierges, and reliable local experts in place.
