Italy has always been a dream destination, a place I’ve imagined walking through ancient streets and indulging in incredible food. This year, it felt like the right time to finally make it happen, and planning the trip with points and miles seemed like the smartest way to stretch our travel budget. For our family, finding ways to make the journey comfortable, especially with the little ones, is key. We discovered so many great options for flying and staying, opening up possibilities for an unforgettable Italian adventure in 2026.
Planning Your Italian Escape
Italy offers such a diverse range of experiences, from the historical grandeur of Rome to the romantic canals of Venice and the artistic heart of Florence. Milan adds a touch of high fashion and modern energy. What’s exciting is that several major U.S. airlines now fly directly to Italy, with some even expanding to smaller cities, making access easier than ever. Thinking about our travel style, we wanted a mix of iconic sights and charming local towns.
Major Airport Hubs
When considering flights, Rome Fiumicino Leonardo da Vinci International Airport (FCO) and Milan Malpensa Airport (MXP) are common entry points. Other key airports include Naples International Airport (NAP) and Venice Marco Polo Airport (VCE). For those looking to explore beyond the main hubs, airlines are now offering routes to places like Palermo (PMO) and Catania (CTA) in Sicily.
Choosing Your Airline Partner
American Airlines provides good coverage to Italy from various U.S. hubs like Charlotte, Dallas/Fort Worth, Chicago O’Hare, New York JFK, Miami, and Philadelphia. While their business class might not be the most opulent, it offers predictability and lie-flat seats, which are essential for long-haul comfort with children. We found that looking at off-peak dates can yield significant savings in miles.
Delta Air Lines also has an extensive network, flying from hubs like Atlanta, New York JFK, Minneapolis/St. Paul, Boston, Seattle, and Detroit. Their Delta One business cabin is a strong contender for comfort, and the service is generally excellent. For us, knowing we can arrive feeling somewhat rested makes a huge difference.
For a truly luxurious experience, especially if you can snag a first-class seat or a well-appointed business class, Emirates offers a unique fifth-freedom route from New York JFK to Milan Malpensa aboard their A380. This flight is renowned for its exceptional onboard service and amenities. It’s a special treat if you’re focused on a premium travel experience.
United Airlines also has a robust presence, flying from hubs such as Chicago O’Hare, Newark, Denver, San Francisco, and Dulles. Their Polaris business class is a definite highlight, featuring comfortable lie-flat seats with direct aisle access and upgraded amenities like Saks Fifth Avenue bedding — perfect for getting some sleep on the overnight flight.
Leveraging Loyalty Programs
Booking with American Airlines miles through their AAdvantage program often involves dynamic pricing. This means award costs can vary greatly, but diligent searching can uncover reasonable deals, particularly on less popular travel days. We found that for a one-way economy ticket from Philadelphia to Rome, around 19,000 miles plus minimal taxes made it quite accessible. Premium economy and business class were also options, though at higher mile costs.
Alaska Airlines Mileage Plan is another excellent option for booking American Airlines flights if saver award space is available. Their distance-based award chart can be advantageous, and we noted that an economy flight from Philadelphia to Rome might cost around 27,500 miles. Earning Alaska miles can be a bit trickier, but transferring Bilt Rewards points is a great strategy.
For Delta flights, their SkyMiles program also uses dynamic pricing, which can sometimes lead to very high redemption rates for premium cabins. However, holding a Delta co-branded American Express card can offer a discount, making it more appealing. We also explored booking Delta flights through Air France-KLM’s Flying Blue program. While Delta One space is rare through Flying Blue, economy tickets can often be found for under 30,000 points one-way, which is a fantastic value.
Emirates Skywards is your go-to for that specific JFK-MXP route. While first-class awards are largely restricted to elite members, business and economy awards are bookable, though at a higher mileage cost. An interesting alternative for Emirates flights is booking through Qantas Frequent Flyer. This partnership can offer good redemption rates, and importantly, it doesn’t require elite status for first-class bookings.
ITA Airways, Italy’s flag carrier, is set to join the Star Alliance. While finding business-class award space on ITA can be challenging, economy award availability is often plentiful. Virgin Atlantic Flying Club is a prime partner for booking ITA flights, offering reasonable mileage costs for economy, especially from the East Coast. Air France-KLM Flying Blue also partners with ITA, though usually at a slightly higher price point.
Booking United flights through United MileagePlus often involves dynamic pricing, with economy awards starting from around 20,500 miles and business class from 80,000 miles. The advantage here is the minimal taxes and fees. Air Canada Aeroplan is another excellent program for booking United flights, offering competitive rates for both economy and business class, and Aeroplan points are relatively easy to earn through various transfer partners.
Experiencing Italy with Family
As a family, we always look for ways to blend iconic sightseeing with experiences that capture the essence of a place. Italy, with its rich history, art, and food, is perfect for this. Seeing the Colosseum with Lily and Ethan sparked their imaginations, and Michael loved learning about the engineering of it all. Even the little ones were fascinated by the sheer scale and the stories of ancient Rome.
Navigating Accommodations
Finding points hotels in Italy is incredibly rewarding. Major cities like Rome, Venice, and Milan are well-covered by various hotel loyalty programs. For Rome, we looked at options like The Tribune Hotel, which falls within the World of Hyatt program’s sweet spot, often requiring between 17,000 and 23,000 points per night. For a more luxurious stay in Rome, the is an option under the Hilton Honors program, starting from 85,000 points.
In Milan, offers a high-end experience within the World of Hyatt portfolio, usually costing between 35,000 and 45,000 points. For a more budget-friendly option within the Marriott Bonvoy program, the is a solid choice, with rates starting around 23,000 points. provides another option in the city.
Venice presents its own unique charm. For a splurge, is a stunning Marriott Bonvoy property that can cost upwards of 103,000 points per night. A great alternative is the Hilton Molino Stucky, Venice, which typically goes for around 62,000 Hilton Honors points.
Practical Travel Tips
When traveling to Italy in 2026, remember that the currency is the Euro. It’s essential to have credit cards that do not charge foreign transaction fees. This not only saves money but also allows you to continue earning points on your spending. Cards like the Bilt Mastercard are excellent for no foreign transaction fees, and they offer benefits that can be quite useful across different types of purchases.
Packing for Italy with children involves a bit of planning. Comfortable walking shoes are non-negotiable for everyone, as you’ll be doing a lot of exploring on foot. Layers are also key, as the weather can change. For cameras, we always make sure to pack extra memory cards and portable chargers to capture all the beautiful moments. Journaling is also something I love to do, and having a small notebook and pen handy is always a good idea.
How can we make flights more comfortable for kids
Bringing along comfort items like neck pillows, blankets, and their favorite small toys can make a world of difference on long flights. Engaging them with travel-themed games or coloring books also helps pass the time. We find that packing snacks they love, even if the airline provides meals, can also be a lifesaver.
For entertainment, pre-downloading movies and shows on tablets is a must. Many airlines now offer Wi-Fi, but it’s not always reliable or free, especially on international routes. Having a backup plan for entertainment is always wise.
What are some kid-friendly activities in Italy
Beyond the major historical sites which can be captivating with a bit of storytelling, visiting gelaterias is always a hit. Many cities have parks and piazzas where children can safely run around. For instance, in Rome, a visit to the Borghese Gardens offers a chance for kids to play and for us to enjoy some beautiful scenery. In Florence, taking a pizza-making class can be an incredibly fun and delicious experience for the whole family.
Exploring smaller towns can also be more manageable with younger children. The pace is often slower, and there are fewer crowds. We found that simply wandering through charming streets, stopping for gelato, and letting the kids discover little discoveries was just as rewarding as visiting the grand museums.
Maximizing Your Points and Miles Strategy
The world of travel rewards can seem complex, but with a bit of research, it’s possible to unlock incredible value for your trips to Italy. The key is to understand how different loyalty programs work and which credit cards align with your travel goals.
Transferable Points Powerhouses
Transferable points from programs like American Express Membership Rewards, Chase Ultimate Rewards, Capital One miles, and Citi ThankYou points are incredibly versatile. These points can be transferred to various airline partners, often at a 1:1 ratio, allowing you to book flights across different alliances and airlines. This flexibility is crucial when searching for award availability on popular routes to Italy.
For instance, American Express Membership Rewards can be transferred to Emirates Skywards, Virgin Atlantic Flying Club, and previously mentioned partners like Flying Blue and Aeroplan. Chase Ultimate Rewards offer similar flexibility, with transfers to United MileagePlus, Air Canada Aeroplan, and Virgin Atlantic Flying Club being particularly useful for Italian travel.
Strategic Credit Card Choices
Choosing the right co-branded airline credit cards can also amplify your earnings. Cards like the Delta SkyMiles American Express cards offer benefits like the TakeOff 15 discount on award redemptions. Similarly, United co-branded cards can provide mileage discounts for MileagePlus members.
For flexible travel rewards, cards like the Capital One Venture X Rewards Credit Card or The Platinum Card® from American Express offer substantial welcome bonuses and ongoing earning potential that can be converted into valuable flight redemptions. It’s always wise to check current offers, as they can significantly boost your points balance early in your travel planning.
When is the best time to book award flights
Generally, booking award flights as far in advance as possible, ideally six to twelve months out, offers the best chance of securing premium cabin seats or desirable routes. For instance, Delta and United often release some of their award inventory early.
However, last-minute award availability can sometimes pop up, especially if you are flexible with your dates and times. Airlines sometimes release additional seats closer to departure, or award bookings may get canceled. Monitoring award calendars and setting up alerts can be beneficial for last-minute opportunities.
Flexibility with your travel dates is paramount. Traveling during the shoulder seasons, such as April to May or September to October, often provides a good balance of pleasant weather and potentially better award availability compared to the peak summer months. Off-peak dates, like February, can reveal some of the best mileage deals.
Understanding Award Charts and Dynamic Pricing
Some programs, like Alaska Airlines Mileage Plan, still utilize award charts, which can provide predictable redemption rates based on distance and cabin class. This can be very helpful for budgeting your points. Other programs, however, have moved to dynamic pricing models, meaning award costs fluctuate based on demand, similar to cash ticket prices.
While dynamic pricing can sometimes lead to higher costs, it also means that during off-peak travel periods or on less popular routes, you might find surprisingly good deals. It requires more diligence in searching for awards but can be very rewarding when successful. Always compare the cash price of a ticket against the mileage cost to determine the best redemption value.
When considering Italy as a destination, the wealth of flight options and the availability of points hotels make it an attractive choice for travelers aiming to maximize their rewards. Planning ahead and being strategic with your points and miles can lead to a truly exceptional and more affordable Italian experience in 2026 and beyond.