Where to Travel in 2020 with Kids | Ciao Bambino!

Where We’re Going in 2020: Greece, Botswana, the Dolomites and More!

Dead tree in Sossusvlei, in the Namib Desert, Namibia. Photo by Tiago Fernandez/iStock
Dead tree in Sossusvlei, in the Namib Desert, Namibia. Photo by Tiago Fernandez/iStock

Hello, 2020! We’re on a mission to help traveling families fulfill their vacation dreams this year … including our own. From off-the-beaten-track Africa to Greek beaches and the jungles of Central America, here are the places around the globe that our CB! Family Travel Advisors can’t wait to explore this year. Inspired to start planning? Reach out — we’re ready when you are!

Where to Travel in 2020 with Kids
Gaudi’s La Sagrada Familia in Barcelona. Photo by Lisa Frederick

Where to Travel in 2020: Ideas from the CB! Team

Susan Robinson


I’m planning to join a friend and fellow CB! Family Travel Advisor for a visit to beautiful Puglia and the Amalfi Coast in Italy. Puglia is the perfect “second visit to Italy” destination, and I look forward to becoming more familiar with family-friendly accommodations and experiences in the area. The Amalfi Coast continues to be a must-see for a trip to Italy, so selecting the best home bases for my clients’ visits will be the focus of my time spent there. I’d also love to head north to the Dolomites, as it has been on my bucket list for years — it’s the perfect add-on for families who want to spend some unconstructed time together at the end of an Italian adventure.

Costa Rica

Costa Rica offers so many opportunities for fun and relaxation in one destination. Dolphin encounters, beach barbecues, hiking through rain forests, and, of course, ziplining are just a few of the experiences on my CR list. It’s the perfect family destination, as there is truly something for everyone no matter what the age. (To be honest, I’m most looking forward to the outdoor spa treatments and white-faced monkeys.)


My daughter plans to study abroad in Barcelona in 2020. Since she’s the youngest of our three girls, it will be a fabulous opportunity to plan a family getaway to visit her, just as we did for her older sisters during their study-abroad semesters in Milan and London. As an art major, I’m looking forward to seeing the Gaudi sites and visiting the Picasso museum. We will want to experience the food markets with a culinary guide and make our way to both Montserrat and the Costa Brava for day trips. We are also considering a few days of add-on adventure to nearby Portugal.

Where to Travel in 2020 with Kids
The Church of the Holy Sepulchre in Jerusalem, part of the Holy Land. Photo by Bernhard Richter/iStock

Helen Buckner


We have been to Greece before and spent time in Athens, Delphi, Kefalonia, Santorini and the Peloponnese peninsula. This time I am looking forward to seeing islands and areas that we haven’t visited yet: Crete, Naxos, Paros and some others, plus going up to the Halkidiki area to see an amazing resort not too far from Thessaloniki. I love Greece!

Holy Land

My family and I are going on a trip to the Holy Land following the footsteps of Jesus. My father was born just outside Bethlehem, so we will be trying to locate his former property. I have been there before, but my husband and children have not — this will be an amazing experience for the whole family! My husband and I have read through the Bible this past year, so we are all really looking forward to it.

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Mandy Cecchetto


To escape the Canadian winter, our family has decided to trade snow angels in for sand castles and head to Florida in the New Year! We plan on visiting Fort Lauderdale, Miami and Disney World.

Where to Travel in 2020 with Kids
Elephants in Botswana. Photo by Janaina Matarazzo/iStock

Barbara Weindling

Southern Africa

I had traveled to Zimbabwe and Botswana’s Okavango Delta a number of years ago, and this year, to celebrate a birthday milestone, I decided to return with the whole family. For my teenage son and his friend, the history of this region is fascinating, and they chose a visit to Robben Island off Cape Town, where Mandala was imprisoned. For my husband, we are traveling to Zambia to explore the area around Livingstone and spectacular Victoria Falls, as well as visit the wineries near Cape Town. And I selected the family-friendly luxury lodges in Sabi Sands Private Reserve by Kruger National Park and Chobe National Park in Bostwana for a chance to view the wildlife and witness a different part of Botswana.


This is a winter escape from cold and snowy New England so the family can come together and relax in the Caribbean, a quick direct flight from our home in the Northeast. We chose an all-inclusive option so that our teen son could roam freely and enjoy activities unencumbered, with plenty of options to feed a picky eater in constant need of snacks.

The Dolomites

We were there this past summer and were awestruck by the beauty of the mountains and scenery, hiking up to refugios for fabulous lunches.  Now I am going back to check it out in winter as a ski destination. I’ll be fulfilling a longtime dream to take part in a ski safari: skiing from one resort to another; staying in luxury ski lodges and more-than-comfortable “mountain huts” accessible from the lifts and slopes; and enjoying wonderful local food and drink.

Japan … or Morocco

Spring break is still up in the air, but the vote is between these two disparate countries and cultures.

Where to Travel in 2020 with Kids
Florence’s iconic Ponte Vecchio. Photo by Lisa Frederick

Amy Annis


I travel annually to Tuscany to lead a group of adults in the region for a week of yoga, wine and culture. Every year, my family builds travel time around that to explore new places and learn new cultures. My clients often inspire me and my Tuscany bucket list gets longer and longer each time. Before the retreat, I usually linger in Florence for a day or two … that city never gets old. I have explored many of the neighborhoods and museums on my own but always look for a unique food experience and, often, a short day trip from the city. One place I haven’t visited yet is Bologna (which is a foodie haven), so I think we will take the train and explore the unique food markets there for a day.


This year I am adding Barcelona to the mix. That area of Spain is one of the few I haven’t explored yet with family. My daughters are passionate about Spanish-speaking cultures (two majored in them in college and both have spent a semester studying in Spain). The northern areas are so different from those in the south, and my daughters tell me that Catalunya is a whole new world unto itself. I hope to give it adequate time and get my cultural fix with the Gaudi architecture and some downtime to explore the beaches and coastline villages.


Finally, Greece is on the docket. We are just in the planning stages but would like to stay away from the more touristy islands and investigate some lesser-known areas that are ideal for family travel. I haven’t organized this leg yet, but we will fly into Athens to see some of the great ruins there first. After that, possibly Rhodes, as my family is fascinated by learning more about the Ancient Wonders, or Corfu or Crete … ah, decisions!

Where to Travel in 2020 with Kids
The Namib Desert, Namibia. Photo by Tiago Fernandez/iStock

Nicky Schick

Belize and Guatemala

The first family trip planned for 2020 will take us to Belize and Guatemala. We were looking for a one-week trip for spring break that doesn’t require a long flight and meets all the members of my family’s requirements for an awesome vacation. I want to be close to beautiful beaches, my husband wants culture and my 8-year-old daughter has to see animals. Belize and Guatemala offer the perfect mix that will make us all happy. Mission accomplished!


I am especially excited to be joining an overland and fly-in Namibia safari without the family. The trip will give me the opportunity to fly along the coast to view shipwrecks, seal colonies, abandoned diamond camps and sand dunes. I’ll also be tracking black rhinos and desert-adapted elephants. There will also be an opportunity to climb some of the world’s highest freestanding sand dunes at Sossusvlei and to visit The Nest at Sossus, a new private villa located on the Namib Tsaris Conservancy.


My whole family fell in love with South Africa in 2018 and immediately started dreaming of coming back to this amazing continent. My daughter did some research and decided that she wants to see Africa’s highest mountain (Mt. Kilimanjaro), Africa’s deepest lake (Lake Tanganyika) and the source of Africa’s largest river, the Nile (Lake Victoria). And in addition, she wanted a few days at a fabulous beach. Can you guess where this trip will take us? If you guessed Tanzania, you are right! We will explore famous game parks such as Ngorongoro Crater, Serengeti National Park, Lake Manyara National Park and Tarangire National Park, and stay in a mobile camp to witness the Great Migration. We’ll finish the vacation on Pemba Island with some intense pampering for me.

Where to Travel in 2020 with Kids
Tulum, one of the stops on Princess Cruises’ Western Caribbean itinerary. Photo by Princess Cruises

Anna Sizer

Caribbean Cruise

Living in Wisconsin means our family knows how to survive and embrace cold, snowy winters. But part of embracing the cold also means taking some time each winter to escape it and find a place to warm our toes in the sand. In March, we plan to enjoy a 7-day Western Caribbean Princess Cruise. This Virtuoso cruise option features their Medallion technology, which makes boarding faster, allows you to order refreshments that find you and provides the best WIFI at sea. My teenagers are looking forward to the freedom to explore the boat and enjoy the teen-focused experiences.


As soon as school lets out, we are returning to one of our favorite places: Italy. This time, we plan to focus on experiencing more of its coastal beauty. We will start in Rome and head to Naples for the best pizza on the planet, to the Amalfi Coast for fishing and rugged shorelines, and to Puglia to visit its whitewashed hill towns and masserias (farmhouses) along the coastline.

Relevant Links:


Where to take the kids in 2020: Our readers weigh in!

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