Multi-generational family walking on the beach while on vacation in Wales
28,000+ Verified Traveler Reviews

Multi-Generational Travel Vacations & Tours

Traveling across generations can give your family a completely different experience and perspective as you bring the dream of new destinations to life. Grow closer with personalized excursions, create trips of a lifetime for every generation, and find new ways to surprise family members young and old. Whether eager to trek tropical trails, interested in visiting ancient ruins, or fascinated by the flavors of a private cooking class, working with a travel specialist can help customize each day to the preferences of every family member. Find more inspiration for your trip with our sample multi-generational travel itineraries below.

Explore Our Trip Ideas

Let these itineraries inspire your personalized travel experience

The ruins of Pompeii in Italy.

12 Day Trip IdeaFrom $5,400

Family Trip to Italy: Nature, Ancient Temples, and Cuisine

Rome, Agrigento, Taormina, Amalfi
Tuscany, Italy.

9 Day Trip IdeaFrom $4,100

Family Exploration of Italy's Historic Cities & Enchanting Countryside

Venice, Tuscany, Florence, Chianti, Siena +3 more
Navagio beach with shipwreck and flowers on Zakynthos island in Greece.

17 Day Trip IdeaFrom $7,800

17-Day Family Vacation in Athens and Western Greece

Athens, Zakynthos, Olympia, Costa Navarino, Nafplio +1 more
Sea front view to Hell's Island from Hvar, Croatia

9 Day Trip IdeaFrom $7,400

9-Day Family Vacation to Croatia

Split, Veli Drvenik, Hvar, Krka National Park, Cetina River +2 more
Elephants in Amboseli National Park, Kenya

7 Day Trip IdeaFrom $5,200

Kenya With Kids: 7 Day Family Safari

Amboseli National Park, Samburu National Reserve, Maasai Mara National Reserve
Hacienda Bambusa in Quindío Colombia.  Photo courtesy of Hacienda Bambusa

8 Day Trip IdeaFrom $4,900

The Real Encanto Tour in Colombia

Medellin, Santa Elena, Armenia, Salento

How Zicasso Works

Here's how we create life-enriching, luxury travel experiences

  1. 1.Share Your Travel Dreams

    Zicasso specializes in custom tours, vacations, and safaris tailored to your interests and preferences. From private African safaris to culinary experiences in Europe, submit a trip request to share your ideas and travel style.

  2. 2.Meet Your Travel Specialists

    To ensure a personalized experience, we'll carefully handpick and introduce you to two of our top travel specialists, each with unsurpassed destination knowledge and local insight aligned to your luxury travel dreams.

  3. 3.Design Your Perfect Journey

    Compare the expertise of two specialists with itineraries crafted exclusively for you. You can refine these further and choose your preferred proposal. Our unique process ensures a more creative, personalized, and expertly crafted trip.

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Kilkenny Castle in Ireland

8 Day Trip IdeaFrom $5,200

Family Trip to Ireland: Culture, Castles and Folklores

Kilkenny, Cork, Kerry, Dromoland
London city view from the London Eye pod in England

11 Day Trip IdeaFrom $5,900

Family Vacation Tour to England & Scotland

London, Edinburgh, Perthshire, Fort William, Loch Ness +3 more
The headland at Cape Cornwall in England

10 Day Trip IdeaFrom $5,900

Simply Splendid Southern England Tour

Portsmouth, Bath, Isle of Wight, Cornwall
Mother and daughter walk in Paris Tuileries Garden, France

8 Day Trip IdeaFrom $3,600

A Perfect Family Getaway to France Tour: History, Culture & Cooking Class

Paris, Giverny, Versailles, Mont St-Michel, Normandy
View of São Jorge Castle in Lisbon, Portugal

10 Day Trip IdeaFrom $6,800

10-Day Family-Friendly Vacation to Spain & Portugal

Lisbon, Albufeira, Barcelona, Madrid
Beautiful view of the resort on le morne peninusala mauritius with clear ocean, white sand, palms and blue sky on the

15 Day Trip IdeaFrom $19,100

Family Friendly South Africa Safari & Mauritius Vacation

Cape Town, Johannesburg, Sabi Sands Game Reserve, Mauritius

4.9

Reviews of Zicasso's Multi-Generational Travel Vacations & Tours

Based on 7133 verified traveler reviews.

Croatia Tour Review: Dubrovnik, Hvar, Split, Wine Tasting, Boat Ride, Krka National Park, 10 Nights

Overall, our trip was well planned and brought different views to Croatia with each destination we visited. The 3 destinations (Dubrovnik, Hvar, Split) provided us with a different view that allowed us to truly experience the country's culture and highlights.

Zicasso's travel agency had wonderful activities that allowed for a more personable experience. We particularly enjoyed the Karaka boat tour, Hvar wine tasting and island tour and Krka park tour. The tour guides were experienced, interactive, and knowledgeable.

Overall, it was easy to communicate our needs and questions. Would be easier to just use email instead of the portal.

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Italy Tour Review: Sicily, Taormina, Agrigento, Palermo, Cefalu, Mount Etna, Erice, Castelbuono, Savoca, Valley of the Greek Temples, Wine Tour, Godfather Experience, Farm Cooking Class, Cheese and Pastry Tastings, 7 Nights

Zicasso’s travel professional crafted an unforgettable Sicily trip for our group of seven. After discussing our preferences, she designed a flawless itinerary, incorporating unique experiences that became trip highlights. Her communication was exceptional, with prompt responses to our questions before the trip and daily updates for the next day's activities, including driver and guide details, which were incredibly helpful.

We stayed at superb hotels in Taormina, Agrigento, Palermo, and Cefalù, each with stunning views and private tours. Sicily’s warm, hospitable people stood out compared to other European destinations. At our hotel on Via Leonardo da Vinci in Taormina, the staff greeted us warmly, setting a perfect tone. Other stops included Mount Etna, Erice, Castelbuono, and Savoca. All of these locations were great, but don't miss Castelbuono!

Two standout experiences were private meals with families. Near Erice, a chef and his family welcomed us into their sea-view home, preparing amazing Sicilian meals that felt like dining with family. In Palermo, another home chef and her husband created a similarly memorable evening, with lots of great conversation and stories.

Every driver was professional, friendly, and informative, while our guides — often archaeologists or historians — were engaging and knowledgeable.

Highlights included a welcome dinner in Taormina, a farm cooking class, two wine tours with lunch, a Mount Etna hike, a Valley of the Greek Temples tour, town and village tours, cheese and pastry tastings near Cefalù, and a farewell dinner. The Godfather tour in Savoca was special, with our guide introducing us to a local who played Apollonia’s mother, waving from her balcony.

Our travel professional's meticulous planning and personal touches made this trip extraordinary. Thanks to Zicasso for matching us with the tour company and we highly recommend them for a perfect Sicilian/Italian adventure!

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Croatia Tour Review: Split, Hvar, Ston, Oyster Experience, Cooking Class, Snorkeling, Boat Ride, Hiking, Biking, Wine Tasting, Local Cuisine, 7 Nights

Zicasso's tour company is fantastic. They designed a perfect custom itinerary for us that included boating, hiking, biking, wine tasting, and much more. Our days were filled with interesting activities and meeting some of the most lovely people as our guides.

Though there were too many highlights to list them all, a few unexpected ones were a cooking class near Split that included shopping for fresh ingredients, snorkeling, lunching off a luxury boat near Hvar, and lunch at an oyster farm.

We had the most lovely guide in Dubrovnik who works for the tourist board and gave us the insider's guide to places in the old town. We even had an authentic meal, one that takes days to prepare, outside of Hvar. There is so much to love about Croatia. This tour company will help you find it.

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Switzerland, Italy Solo Vacation Review: Zurich, Lucerne, Interlaken, Zermatt, Lake Como, Venice, Florence, Sorrento, Amalfi, Rome, Skydiving, Gondola Ride, Amalfi Coast Cruise, Scenery, Nature, Local Cuisine, 3 Weeks

My first solo trip was something I had dreamed about for years. I wanted it to be more than sightseeing. I wanted adventure, comfort, safety, and freedom without the stress of planning it all alone. Through Zicasso, I was connected to two specialists and Zicasso's travel consultant stood out immediately. She delivered an itinerary that gave me everything I asked for and more: maximum cities, maximum fun, and maximum value, all without compromise.

Before deciding, I researched and compared tours, packages, and individual prices online. The travel consultant’s proposal came out on top for value and content. While the other agent offered fewer cities and activities at a higher price, her plan was ambitious without being overwhelming. She booked my trains, arranged private transfers where needed, and selected boutique-style hotels that exceeded expectations. I was honestly surprised at how good they were. I stayed at hotels in Interlaken, Florence, and Sorrento. Each was clean, comfortable, and perfectly located for exploring. I had prepared myself for budget trade-offs, but instead, I found thoughtfully chosen hotels that balanced affordability with real quality.

Every document, train ticket, and activity confirmation was uploaded into the app. It became my lifeline throughout the trip, with every detail at my fingertips. The structure gave me confidence, while still leaving me free to explore.

Switzerland came first: Zurich, Lucerne, Interlaken, and Zermatt. Each city felt like stepping into a postcard. Interlaken gave me the adrenaline rush of skydiving, while Zermatt charmed me with its close-knit magic and alpine beauty. Italy unfolded with equal ease: Lake Como, Venice, Florence, Sorrento, Amalfi, and Rome. Every destination felt curated, yet natural, from gondola rides in Venice to boat tours on the Amalfi Coast.

What I loved most was the balance between structure and freedom. Pre-booked activities and restaurant reservations gave me a strong framework, but I could just as easily decide to spend an afternoon wandering Florence, eating gelato, or sitting in a piazza. The rhythm of the trip was perfect, structured enough to tick off bucket-list highlights, yet relaxed enough to feel like a real vacation.

Food was freestyle, but memorable. Highlights included a Japanese-Peruvian restaurant in Zurich with its elegant Japanese-Peruvian flavors, a different Japanese restaurant, a restaurant in Como with its modern fusion menu, an Indian restaurant for comforting classics, and international favorites like those in one of the restaurants in Rome. Between those meals and plenty of gelato and crepes, every stop added its own flavor to the journey.

As a solo traveler, safety mattered. I felt comfortable walking around in the evenings and was usually back in my hotel by 1am to stay rested for the next day. What really gave me peace of mind was the travel consultant’s constant support. Communication was fast and responsive. I never had to wait long for answers, whether through the app or email. There was a moment when I made a mistake with the trains and missed an activity. She immediately stepped in and worked to reschedule it or secure a refund that same day.

Earlier in the planning process, I also had a card issue due to an address error. Even though policy would not normally allow it, she and her team patiently waited until I received the refund before finalizing the booking, just weeks before my trip. That flexibility and care spoke volumes.

The difference was clear. She used my budget to its fullest potential, giving me more destinations, more experiences, and better hotels than the alternative option. She managed to combine the efficiency of a fully organized tour with the freedom of independent travel. Everything was planned, yet everything was still mine to shape.

This trip was everything I wanted: good food, beautiful views, safety, and absolute reliability. It was an organized journey with freestyle flexibility, which is exactly what solo travelers dream of. The travel consultant’s planning let me chase adventure while always knowing I had a safety net. Switzerland and Italy gave me memories I will never forget, but it was the behind-the-scenes planning that made it possible. If you want a trip that is your way, your budget, your pace, but without the endless hassle of managing it yourself, the travel consultant at this agency is the person who can make it happen. My first solo trip became my dream trip and that is the highest praise I can give.

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Italy Trip Review: Milan, Florence, Lake Como, Venice, 11 Nights

When we started planning our trip to Italy, I knew I wanted to work with a travel agent—specifically, someone who specialized in Italy and was based there. After reaching out to several agencies and reviewing their responses, we chose Zicasso and, more specifically, our travel agent. She is based in Milan and from my very first interaction with her, I knew we had made the right choice.

Our trip could not have been more perfect. Our agent put a lot of thought into every location and planned activity. At the outset, we had a few discussions with her about what we wanted from the trip and, after that, we were happy to leave most of the details in her capable hands. Our goal was to explore mid-to-northern Italy and everything—from the hotels and tours to the free time and transportation—was beautifully organized.

Our 11-night trip started in Milan and ended in Florence, with overnight stays in Milan (one night), Lake Como (three nights), Venice (three nights), and Florence (four nights). Initially, I was hesitant about staying at Lake Como for three nights, but our agent encouraged me to do a little research. I’m so glad she did, as it turned out to be incredible. We had more self-guided time at Lake Como, which was perfect as we adjusted to the time change. In Venice, our itinerary became more structured, but we still had plenty of time for our own explorations. By the time we reached Florence, we had activities and tours planned for every day, which was just what we wanted.

A highlight for my family was a full-day trip into Tuscany, where we visited San Gimignano, an organic vineyard in Chianti, and finished with a tour of Siena. Our day trip to Rome allowed us to see the main attractions and we concluded the journey with a tour of Florence and the Accademia Gallery. Every tour our agent arranged was spot on.

Throughout our trip, she was wonderfully communicative—always available when we had questions, but never intrusive. She even helped us with a couple of last-minute requests: booking a hotel in Milan for one night and arranging train tickets to Verona for an impromptu visit to Juliet’s balcony. Whenever we needed something, she was there.

When we return to explore the mid-to-southern part of Italy, there’s no question that we’ll be asking her to plan our trip again. I highly recommend her to anyone looking for a seamless, thoughtfully curated Italian adventure.

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Italy, Greece 45th Anniversary Review: Rome, Athens, Santorini, Florence, Colosseum, Vatican, Parthenon, Walking Food Tour, Tuscan Wine Region, 10 Nights

We enjoyed all of the planned tours in Italy and Greece. Favorites included the Vatican, Colosseum, Roman walking food tour, and a day exploring the Tuscany wine region.

We loved all of our hotels (favorites being our hotel on Via Emilia in Rome and then our hotel on Nikodimou Street in Athens). All of our drivers at our various locales were always on time, even early, and were friendly and engaging.

We did have various questions come up and any time of day/night, Zicasso's travel professional and the tour company were responsive and so helpful.

Our long-awaited 45th anniversary trip came off seamlessly. I appreciate all of the time and planning that went into planning our venture. I will happily recommend you to our friends and family.

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