When a friend decides to celebrate his 50th by renting a lakefront villa in northern Italy, you go and you go BIG. A large group of us flew in from different cities and met on the edge of Lake Maggiore for a week that managed to be both relaxed and a complete and total party filled with all of Jason’s favorite things: great people, great wine, and great food. His wife and our dear friend Mandy did an incredible job planning an itinerary for 25 people that had just enough free time and group activities that it was both relaxed and choose-your-own adventure, but still felt like we had enough time with each other. It was a well-paced trip built around good food, easy mornings (or no mornings for those that felt like it), and one absolutely incredible villa that was such a joy to call home for a week.
If you’re interested in planning a luxury group trip to Lake Maggiore, or simply visiting the lakes region on your own, here’s what I’d recommend you do, see, eat, and explore.
Why the Villa Matters for a Luxury Group Trip to Lake Maggiore
We stayed at a private villa right on the edge of Lake Maggiore just outside of a small quiet charming town of Ranco. We ended up at Lake Maggiore over Lake Como because it honestly, felt more authentic and true to what we were looking for. The homes and villas in Lake Como were significantly more expensive with less value. Our luxury villa was lake front, had a pool, plenty of common space, and enough privacy for everyone to find their own rhythm and while we had a few planned group activities, outside of that there was plenty of time for all of us to wake up at their own pace, ease into the days, and gathering or grouping up for excursions when it made sense. Everyone contributed something to the house and the week (I cooked breakfasts quite a few days, of course).
Our first afternoon was a welcome pool party and our friend Meredith hired a wonderful bartender to serve us up custom cocktails and spritzes for us to enjoy over music and a long afternoon of people getting reacquainted after long flights. A couple of nights over the course of the week we brought in caterers for dinner at the villa which I always recommend when you’re staying in a space this magnificent: make sure that you find times and ways to really enjoy it and get your fill of the accommodations. There’s nothing more wonderful than long, slow meals right where we you are staying. It’s the best way to really settle into and celebrate the end of your trip.
If you’re planning a luxury group trip to Lake Maggiore or something similar in another location, make sure your villa, castle, or riad, depending on where you’re planning your group trip, has enough shared space, good kitchen access, and enough separation that no one feels crammed in. For large group trips with a lot of togetherness, the number one suggestion I have is that you find a property that works for everyone during the absolutely necessary and needed quiet moments, not just the big ones.
Why Large Luxury Group Trips Actually Make Sense
I am a big proponent of large luxury group trips like this. One of the best parts of traveling this way is that with the right group size, you suddenly have access to properties that would otherwise be completely out of reach.
This trip to Lake Maggiore wasn’t the first time I’ve done this. Last year, I organized a similar trip to Malta. Thirteen of us went because I found an absolutely stunning castle built in the 18th century. This past November, I organized a second large group trip to a riad built in the 18th century in Marrakech (more to come from that trip!). In both places, we stayed in homes that were completely unique to the location and the destination came after I found the property. In the case of Malta, the palace we stayed in was endless gardens and patios that made it feel like we were living outside the entire week. In the case of Malta, I had found a sprawling riad with layered courtyards and rooftop dinners. Neither of those experiences would’ve been possible if we were traveling solo or as couples and thanks to my amazing group of friends, these properties weren’t just feasible, but elevated.
When you’re with a group of ten, fifteen, or twenty-five people, you’re splitting the cost of something exceptional. That can mean a chef-prepped dinner in your own kitchen instead of fighting for reservations, or a sunset view you don’t have to share with strangers. It also gives the trip a nice loose structure if you don’t overplan. When you’ve all committed to being in the same place, for the same amount of time, it sets a wonderful foundation for intimate interactions with new people. You get the spontaneous late-night hangs and the quiet coffee mornings without needing a schedule or go somewhere to find your friends. In short, the trip itself feels generous in a way most travel doesn’t simply because of the wonder of your accommodations.
You also get to settle in, which is underrated. You’re not moving every couple of nights or dealing with check-in and travel fatigue. You’re just living somewhere else for a week. When the space supports that, and the people are up for it, group travel becomes something entirely different from a vacation. It has quickly become one of my favorite ways to see the world.
Exploring Lake Maggiore by Ferry and Finding Time in Stresa
One of the easiest and best ways to experience Lake Maggiore is by ferry. You can hop between towns and islands without having to rent a car or deal with parking, which is a win when you’re traveling with a group or if you just want to go explore solo for the day. We spent our group excursion day exploring two of the Borromean Islands: Isola Bella and Isola Madre, and both were well worth the time.
Isola Bella is known for its palace, originally built as a summer home by the Borromeo family in the 17th century. The interiors are dramatic, with stone grottos, grand halls, painted ceilings, and big lake views from almost every room. The gardens are formal and built to impress, with layered terraces, fountains, and white peacocks walking around like they own the place. It’s touristy, sure, but the scale and detail of the place make it worth seeing. You can take the full palace tour and still have time to wander the grounds before catching the next ferry.
Isola Madre is quieter and more spread out. It feels more like a botanical garden than a destination built for show. The main villa is smaller, and the gardens take center stage. You walk through shaded paths lined with old trees, flowering plants, and a mix of exotic birds that move through the space like they belong there. Make sure you stop on the patio at the cafe for a spritz in the sunshine. The vibe doesn’t disappoint.
After the islands, you should head to Stresa, but honestly, it can also be it’s own excursion it’s so charming. If you are there solo or in a small group, I would recommend lunch or dinner at Il Vicoletto. Tucked down a small alley, the service was impeccable, the patio was quaint, and the food was delightful. Afterward, meander down the lakefront bike path and have drinks at the iconic Hemingway Bar. If you have enough time, wander around Parco Pallavicino, which, honestly, is kind of a trip. Part zoo, part gardens, part park, you can wander amongst some goats and llamas and think, with extreme curiosity, why this place with 50 different animal species even exists.
Wine Tasting in Valtellina as a Full-Day Excursion
It would have felt completely out of character for me to NOT go wine tasting in the area, so one of the days I organized a group excursion for a few of us to go wine tasting in Valtellina. It’s a few hours northeast of Lake Como and absolutely worth it. The shift in scenery was immediate and to get there we had to drive around the eastern edge of Lake Como, which offered us an opportunity to stop there for dinner on the way home. Valtellina itself is absolutely STUNNING with incredibly steep hillsides terraced with vines, incredible alpine light, and a narrow valley string of towns that’s been dedicated to making nebbiolo for the world for centuries.
We visited two wineries. Radis is younger and minimalist, with an intentional approach to low-intervention wines run by the son of an apple farmer and his brother-in-law. We had an unique and intimate experience with him and got to tour both his winery and the cooperative where he makes, stores and sells his wine. If you go to Valtellina you absolutely must visit Ar.Pe.Pe, a fifth-generation winery that takes its time with everything. They were unfortunately closed the day we visited but we were able to find their wine at dinner that evening and it was a standout.
Valtellina is not a walk-in tasting kind of place and it’s quite a drive from where we were, but absolutely worth the effort. You’ll want to book ahead and give it the full day. Arrive early enough to pop into Ristorante San Carlo for lunch and on your way back home, walk down the cobblestone steps and narrow streets of Varenna to have a beautiful meal in the intimate Osteria Quatro Pass.
What I’d Do the Same Way and What I Missed
This trip worked because it had space in it. There were moments for everyone to come together, and just as many where people could drift off and do their own thing. The villa supported that and so did the rhythm we set from the beginning. Some people stayed up late every night partying and talking into the wee hours of the morning, and some of us went to bed early. No one felt like they were missing out when they stayed in and our group dynamic, despite being such a large number (25 of us!) stayed flexible and low-pressure, which is exactly how it should be.
Mandy did an exceptional job planning a luxury group trip to Lake Maggiore for us and she mirrored my belief that there should always be one group activity day, a few group dinners and everything else should be flexible and open to interpretation. I can say with certainty that on my next group trip, I’ll absolutely keep the same mix of casual group hangs and low-lift structured experiences.
Not to be missed: For Jason’s actual birthday dinner celebration, we were hosted for a private group tasting menu dinner at Il Sole di Ranco, a family-run Michelin-starred restaurant just down the street from our villa. It was elegant without being formal, with one long family style dining table in a private room. We dressed up (we all wore stripes!), took our time (by the cheese course I think half of us were ready to fall asleep from the amazing food), and let the evening stretch out. It was a solid counterbalance to the more relaxed dinners we had at the villa.
What I missed? After having dinner in Varenna on Lake Como, I absolutely wish I could have wandered that idyllic little town quite a bit more. I would have liked to take the ferry across Lake Maggiore to Switzerland. I would have loved to explore more of the small towns around these massive lakes. There are endless opportunities for exploration here and I can’t recommend it enough.
If you’re planning a luxury group trip to Lake Maggiore, or anywhere really, start with the property and build out from there. Don’t overschedule. Give people a reason to gather and room to be alone. When you get the mix right, it sticks with you. This one certainly will for me.
What a dream way to end my first trip to Italy, which also included Rome and Florence.
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