Make Your Next Trip Extraordinary

Extraordinary School-Break Trip Ideas for Your Family

by Wendy Perrin | March 2, 2020

One of the key lessons I’ve learned from my travels (and from yours) is that the right trip designer can transform a family vacation, taking what could have been a week of stress and disagreement and turning it into a miracle. Below is a sampling of family trip reviews from your fellow readers who are WOW List travelers. In each case, the trip designer delivered transcendent family memories, thanks to relationships with the right local fixers. Read more traveler reviews to get more unusual family trip ideas and, for additional inspiration, don’t miss these unexpected spring-break destinations, this collection of family vacations that adults will love too, my tips for how to make sophisticated destinations fun for the whole family, and this video I shot on one of my own family trips about the strategies I use to keep everyone happy.  Happy school-break travel brainstorming!

Spring Break

Hot springs in Costa Rica

Hot springs in Costa Rica. Photo: Shutterstock

Costa Rica: “We swam in thermal hot springs, zip-lined through the rainforest, walked the hanging bridges of the rainforest canopy…”

“Traveling as a family of six is not easy! We have four children between the ages of 8 and 15, each more adventurous than the next. We needed a spring break that would keep them entertained but also allow us the leisure time we really needed. Priscilla put together a perfectly balanced vacation for us in Costa Rica. Everyone was happy! She suggested we spend our week in two areas—Arenal (volcano and rainforest) and Manuel Antonio (beach). In Arenal, we swam in thermal hot springs, zip-lined through the rainforest, walked the hanging bridges of the rainforest canopy, and went white-water rafting. In Manuel Antonio, we spent quality time at the beach, surfing, boogie boarding, and relaxing. Priscilla and her team arranged all of our travel details (flights, hotels, activities, transfers to and from), and they really went out of their way to make sure our vacation was memorable. All we had to do was sit back and enjoy!” —Kara Lawler



PRAGUE, CZECH REPUBLIC - mathematical hall of the Strahov convent library

The mathematical hall of the Strahov Convent Library, Prague, Czech Republic. Photo: Shutterstock

Vienna and Prague: “I told Gwen that our 17-year-old son is passionate about playing piano, particularly the music of Classical- and Romantic-era composers…”

“I told Gwen that our 17-year-old son is passionate about playing piano, particularly the music of Classical- and Romantic-era composers. She asked questions to understand how we like to travel, especially when it came to what would interest our son, and then planned and executed an absolutely amazing trip to Vienna and Prague for us. Our itinerary included visits to Mozart’s and Beethoven’s apartments in Vienna; the cemetery where Beethoven, Schubert, Strauss, and Schönberg are buried; and an exhibit that included one of Mozart’s original manuscripts. In Prague she arranged visits to a collection that included the original score to Beethoven’s third symphony, as well as access to the Strahov Library, which travelers typically only get to view from a distance but where we got to wander among the stacks! We also got to spray paint our ‘tags’ on the famous Lennon Wall! Gwen paired us with fabulous guides who, by the time we left, felt more like friends than mere guides. Our Vienna guide was from a musical family, so she had unique insights into Viennese musical history.” —Adam Amsterdam



Lisbon, Portugal skyline with Sao Jorge Castle

Lisbon, Portugal. Photo: Shutterstock

Portugal: “We were traveling to Portugal with my one-year-old grandson…”

“We were traveling to Portugal with my one-year-old grandson, and this meant a lot of consideration had to be given to where we stayed, how we traveled, and what we did. Goncalo—who is the 13th of Wendy’s travel specialists I’ve used—scored on all aspects. First, he found us a two-bedroom apartment in Lisbon with a full kitchen, a washer/dryer, and a kids’ playroom. What a perfect choice this was. Second, when we did a full-day trip to Sintra, he suggested that instead of Pena Palace (which I’d been to on a previous trip), we go to Quinta da Regaleira and Convento dos Capuchos, which were much easier to navigate with a small child. On our first day in Lisbon, he personally conducted our walking food tour, educating us about Portuguese foods (and drink) and taking us to great places I’d missed entirely on my earlier trip to Portugal. When we departed Lisbon for the Douro Valley, our car was delivered to the hotel and turned out to be a major upgrade from what we’d rented (and lots more comfortable). Our Douro Valley hotel was wonderfully located, our rooms were very spacious, the private boat for our morning cruise on the Douro River was spectacular, and the wine tour he chose for us was the best I’ve ever done, including the best port wines I’ve ever tasted.” —Jan Heininger



aerial view of Famous palace Versailles with beautiful gardens and fountains in France

Versailles palace gardens, France. Photo: Shutterstock

France: “Our kids were able to see important places in a way that made them fun…”

“We spent four days in each of Normandy, Brittany, and Paris. We are a family of five (three kids, aged 9, 15, and 17), so we needed a variety of activities to engage the youngest to the oldest. Jennifer planned several day trips that were specifically designed for our kids, where they were able to see important places in a way that made them fun, from a treasure hunt in the Louvre to a bike ride around Paris to a crossing of the Bay of Mont St. Michel. Our favorite guide was Isabelle, in Paris, who took us to Versailles and to our WOW Moment—a private boat ride down a canal in Paris, complete with a skipper, picnic, and wine. It was amazing!! Isabelle was an absolute delight: warm, funny, engaging, and extremely organized. She was able to maneuver us to avoid several long lines at Versailles on an incredibly hot, crowded day. I studied in Paris in college, and I know more than the average traveler about France and its history, but I learned so much from Isabelle.” —Christa Sullivan




Newfoundland scenery

Newfoundland scenery. Photo: Newfoundland and Labrador Tourism

Atlantic Canada: “Jill arranged excursions which we never could have arranged by ourselves and about which my three grandchildren never stop talking…”

“For our three-generation family trip to Atlantic Canada—Nova Scotia, New Brunswick, Prince Edward Island, and Newfoundland—Jill arranged excursions which we never could have arranged by ourselves and about which my three grandchildren never stop talking. These included a boat trip where we dug for clams, pulled up lobster traps, gathered fresh mussels and oysters, and had a wonderful lobster boil on a secluded beach. Another boat excursion was to islands dark with puffins, murres, razor bills, cormorants and other birds, and a boat tour of coastal resettled communities during which we saw whales. We also had a songfest in a private home with guitar and accordion. And we (and some say this was the best) hiked along the shore with Lori, a chef, who pointed out plants which were edible and then used them to make a sumptuous lunch. The vistas of inland lakes, pine forests, and ocean fronts were magnificent. This was a visit of a lifetime.” —Richard Goldin




Green rice fields on Bali island Indonesia

Green rice fields on Bali island. Photo: Shutterstock

Bali: “We were welcomed into homes in villages that we would never have had access to.”

Diane planned a 30-day itinerary throughout Indonesia for our family—five-year-old twins and my wife and me. Although we travel often, we never could have planned such a seamless vacation. We were welcomed into homes in villages that we would never have had access to. Diane’s three decades of traveling in Indonesia and discovering gorgeous idyllic islands and new hotels was evident, as was her obvious expertise in routing our journey. She has relationships with villa owners/managers in areas of Indonesia that would have been nearly impossible to find on our own. These accommodations are not in guidebooks. We could not have been happier with our trip that Diane planned for us.” —Garrett Bandy



aerial view of Sonora Resort in the Discovery Islands, British Columbia

Sonora Resort in the Discovery Islands, British Columbia. Photo: Tim Baker

Western Canada:  “A photographer gave us a personal tour of several waterfalls, giving us photography tips along the way and taking family photos…”

“My husband and I and our two teenage daughters wanted to go to British Columbia, but to avoid any really crowded areas. Marc suggested we spend a few days in Whistler, then a few days on Sonora Island, and end in Vancouver. He set us up for fun activities in Whistler—RZR cars, white-water rafting, zip lining—and we were treated to a WOW Moment: A photographer gave us a personal tour of several waterfalls, giving us photography tips along the way and taking family photos; although I am the photography buff in the family, he was able to engage the whole family and everyone really enjoyed the experience (thank you, Wendy!). We then took a seaplane to Sonora Resort, which the entire family agreed was heavenly. So remote, with beautiful scenery and gourmet food. On our eco-adventure tour we were lucky enough to be in the middle of a pod of about 100 dolphins. The food at Sonora Resort was so delicious that on the first night at dinner our daughter said, ‘Thank you for bringing me here.’ Finally, in Vancouver, Marc suggested the Fairmont Pacific Rim for us, which also was in a fabulous location. Since we are foodies, he planned a food tour at Granville Island, where there are so many booths that it was helpful to have an expert direct us; the tour allowed us to sample more items in small quantities than we could have done on our own. Although I was very involved with the details of our trip, I didn’t have to figure out where to go or how to get there or worry about logistics during my vacation. That made it a true vacation for me.” —Nancy Wolf



the hilltop village of Gordes, Provence, France

Gordes, Provence. Photo: Pixabay

France: “He absolutely knows where you should go and the time you should do it…”

“This was a very difficult trip to plan. We gave Philip only a couple of weeks to plan it, we had nine people coming and going at different stages, we were traveling with a 6-year-old, it was the busiest season in France, we had changes to the itinerary and/or restaurants on a daily basis … and Philip and his team truly outperformed all my expectations. He saved our trip. He got us to the best places, he absolutely knows where you should go and the time you should do it. From the balloon flight to the wine tasting, he and his team made this trip unforgettable.” —Steven Morton



sumo wrestlers training in Tokyo Japan

Earthen dohyo training ring for wrestlers at a sumo stable in the Ryogoku district of Tokyo, Japan. Photo: Ben Simmons

Japan: “One of our favorite experiences was attending a sumo wrestler practice…”

Scott arranged the most memorable private moments for our family in Japan. One of our favorite experiences was attending a sumo wrestler practice, sitting within arm’s reach of the athletes. The photos are amazing! We also loved creating a new family memory with our kids (18, 21, 25) during a taiko drumming lesson. Since our family loves music, it was a great way to experience local culture and laugh together! Other private experiences that we would never have been able to appreciate without Scott’s expertise included a five-hour cooking class and dinner in the home of a local Japanese chef. We loved learning about Buddhism and meditating with a monk. All of these were possible thanks to our unbelievable guide, Kiko-san, who also interpreted for us. She was kind, patient, knowledgeable, and respectful of our family dynamic.” —Dale Sindell



The old town of Tbilisi, Georgia, with the fairy tale Clock Tower of puppet theater Rezo Gabriadze

The old town of Tbilisi, Georgia. Photo: Shutterstock

Georgia (the country): “Never did I dream that my kids would be singing karaoke with Georgian children after lunch in their Soviet-era apartment.”

“Through every step of planning my family’s trip to the Republic of Georgia, Zulya made sure that she was meeting our travel needs and goals. Georgia is not flooded with obvious tourist attractions, so we received a well-rounded itinerary that allowed us to experience its natural wonders and connect with the culture. Never did I dream that my kids would be singing karaoke with Georgian children after lunch in their Soviet-era apartment. Some other favorite activities included cooking with local families in their homes, hiking in the Caucasus mountains, and visiting Gergeti church via horse. I think the main reason it was so pleasant to work with Zulya is that she truly cares that you have a wonderful experience on your trip. She is an ambassador of the countries she represents, and we look forward to working with her to travel to other Silk Road destinations.” —Melissa Pollack





British Museum, London

British Museum, London. Photo: Pawel LiberaLondon and Partners – Visit London

London: “…a spy adventure at the British Museum, and a half-day of movie making throughout London…”

We went to England over Thanksgiving and used Philip to plan our trip. His team arranged spectacular tours for us, including early entry into the Tower of London (we got to see the Tower and the crown jewels before they were open to the public), a spy adventure at the British Museum, and a half-day of movie making throughout London. (The latter involved the children being filmed with wands and capes at various locations around London where Harry Potter was filmed. They will put this together into a movie.) The highlight for me was the tour of the Churchill War Rooms with the director emeritus of the War Rooms, who took us behind the scenes and allowed us to sit in the actual chair that Winston Churchill sat in. Our guide and our driver and the ‘spies’ and ‘movie directors’ were incredibly friendly and knowledgeable and did an excellent job getting the children involved and engaged.” —Frank Richards



Christmas and New Year’s

Florence, Italy. Photo: Shutterstock

Florence, Italy. Photo: Shutterstock

Italy: “In Florence we visited a noble family estate and cooked a five-course meal…”

“Italy can be overwhelming because there is so much to do, see, and eat, but Maria planned a spectacular trip to Florence, Bologna, and Rome for me, my teenagers, and my fiancé over the Christmas/New Year’s holiday.  In Florence we visited a noble family estate and cooked a five-course meal (and learned how to make tortelloni) with the family chef, had a tour of the wine cellar, and joined one of the family members for lunch. We learned of the family’s wing of art at the Uffizi, which we visited the next day. Meeting people who have a direct hand in the life and culture of Italy was special. In Rome, our food lovers’ adventure on Vespas with Toni was a complete standout. My 6′ 4″ son was mortified to ride on the Vespa—and got over that fear in one minute. We were a team of five Vespas! Don’t mess with us! As for Bologna, I am a dental surgeon and am really glad Maria recommended visiting the Teatro Medica at the University of Bologna with my kids. I am sure there is no way I could’ve arranged such a trip.” —Wendy Halpern



Argentina: “It wasn’t something you can plan on your own—which is what made it so special.”

“Our family of five had an amazing trip to Argentina organized by Maita. We hiked on a glacier, got soaked on a boat that we rode into one of the Iguassu waterfalls, went bird watching in Iguassu with an ornithologist and nature photographer, and had a wonderful private boat experience on a quiet arm of one of the lakes in Bariloche. Maita’s team suggested great hotels and was able to obtain rates at some that were lower than those available online. They also booked a fantastic New Year’s Eve Party in Buenos Aires that we will long remember. And we had a fantastic surprise WOW Moment. I prefer not to specify what we did for our WOW Moment, since I wouldn’t want to spoil a possible future WOW Moment for someone else, but suffice it to say it was our favorite meal in Argentina. It wasn’t something you can plan on your own—which is what made it so special.” —Rita Solomon



View of Journalist's Park with Monserrate and the Candelaria district of Bogota, Colombia

Bogota, Colombia. Photo: Shutterstock

Colombia: “Juliana, an artist in Bogotá, shared her perspective on museums and the graffiti district…”

“My family of two adults and three teens, ages 12 to 18, traveled to Colombia over New Year’s, spending seven days in Bogotá, Quindío (the coffee region), and Cartagena. Marc and Boris made great choices about which regions we should visit and for how long, what activities we should do, and where we should stay. They even got us into a wonderful boutique hacienda in the coffee region at a very busy time of year. All our tours and activities were fabulous. Juliana, an artist in Bogotá, shared her perspective on museums and the graffiti district. Camilo, a biologist and ornithologist, took us on a hike in the countryside and helped my husband with his birdwatching. Tavo is a musician who gave us a great perspective on Cartagena. A big highlight was our last day, when we took a private boat trip out to the Rosario Islands and spent time at a beach club. The kids got so much out of every day of the trip and continue to rave about it to everyone—a real accomplishment with teens. Thank you for suggesting Colombia as a destination in the first place and for setting us up with Marc and Boris. We all plan to return to Colombia and are evangelizing it as a destination for other Americans.” —Jarvis Weld



Palacio de Bellas Artes, Mexico City.

Palacio de Bellas Artes, Mexico City. Photo: Billie Cohen

Active Mexico: “We were always learning, exploring, and connecting with knowledgeable and fascinating local people.”

“There was no shortage of challenges to planning a last-minute Christmas trip to Mexico for me, my husband, and our 18-year-old daughter and 16-year-old twin boys. The beaches were expensive and jam-packed. So Zach’s team suggested an itinerary to Mexico City and two truly magical colonial cities—Puebla and San Miguel de Allende—and the result was fantastic! They handled all the logistical details, so we didn’t have to worry about a thing. We are a very active family and always want to be doing and learning. They understood this and designed a wonderful itinerary that opened our eyes to this complex, beautiful, sophisticated, culturally rich country. From our private cooking class with a renowned chef in Puebla to our historical and cultural bike tour down Mexico City’s Paseo de la Reforma and through the Bosque de Chapultepec to our private tour through the National Museum of Anthropology in Mexico City—they opened the Museum just for us!—we were always learning, exploring, and connecting with knowledgeable and fascinating local people. The result was a trip that left us with great respect and affection for our southern neighbor and helped us see the history of our continent from a completely different perspective. This is truly the best of travel. We will be WOW Listers for life!” —Kristen MacLeod



pool at Quinta Real Oaxaca

Quinta Real Oaxaca.

Relaxing Mexico:  “Three nights in Oaxaca for its colonial and prehistoric attractions, then three nights at the beach in Huatulco…”

“Just before giving up my Mexico trip planning as impossible, I turned to Zachary to see if he could help with the logistics. Our family of four wanted to spend three nights in Oaxaca at Christmas for its colonial and prehistoric attractions, then three nights at the beach in Huatulco. Minimum-stay requirements of five or seven nights during the holidays presented obstacles. Plus, traveling from Oaxaca to Huatulco by mountain road would be long and treacherous. We could fly, but we would have to go through Mexico City, wasting a day. Zach drew on his relationships, avoided minimum stays, and secured well-located rooms for us in outstanding hotels: Quinta Real Oaxaca, an exquisite former convent, and Camino Real Huatulco, a beautifully designed seaside resort. To make it all work, he identified non-stop flights that were not readily accessible to us online. Best of all, he provided Gabriel, an outstanding guide in Oaxaca who is the alpha educator of choice for universities and Smithsonian visitors. We benefited from the depth of Gabriel’s knowledge of history, nature, art and architecture. Zach’s resources and persistence made it possible for our family to enjoy a wonderful holiday trip.” —Barbara Schoenfeld



Monteverde Costa Rica

Monteverde, Costa Rica. Photo: Shutterstock

Costa Rica: a 50th wedding anniversary and a group of ten with active teenagers and a mobility-impaired grandparent

“I can’t say enough about the trip Priscilla helped me plan for my parents’ 50th wedding anniversary. We were traveling with ten people over Christmas, including four active teenagers who are up for any adventure and my father who didn’t want his physical disability to stop the adventure or fun for his grandchildren. Priscilla found us the perfect home on an amazing beach where we could watch the sunset daily and take day trips scuba diving, surfing, and fishing. After five days, we moved to the Monteverde Cloud Forest for the sky walk, zip-lining, and endless hikes. What really made this trip special was the planning that Priscilla did in finding us the perfect naturalist guide, Eddie, as well as the perfect physical therapist, Alonso, to travel with us for the 10 days we were away. Alonso provided my father with the best care possible and had the knowledge and ability to work with him in the pool and help him do things he has not been able to do, like taking short walks on the beach. Having Alonso with us allowed my mom to get the vacation she so needed and took all the daily stress away. As for Eddie, the naturalist guide, from the moment we met him at the airport, he got the kids engaged and interested in learning about Costa Rica. When we were out hiking, he not only helped us find the monkeys, quetzals and sloth, but educated the kids on the Cloud Forest and the environment. It was an amazing trip!” —Kristen Ebner



Gentoo penguins in Antarctica

Gentoo penguins in Antarctica. Photo: Jennifer Santoyo

Antarctica: “Ashton was perfect in assessing what everyone wanted…”

Ashton planned the trip of a lifetime to Antarctica for us! It was my last continent, and I cried when I arrived and cried when it was over. I had thought I wanted to fly over the Drake Passage because I was terrified of getting seasick, but I’m really happy I listened to Ashton. He said that flying over the Drake can mean delays on either side because of weather, and unless you have flexibility in your schedule, it’s not advisable. He highly recommended a ship that has the best stabilizers to handle the Drake, has excellent naturalist guides, and would work for my 17-year-old. Also, my husband wasn’t as excited about Antarctica as I was and preferred more luxurious accommodations than the fly trips offer. So we kind of had to agree on the trade-off to make the trip happen: my bucket list vs. Marty’s desire to be more comfortable on a nicer boat. Ashton was perfect in assessing what everyone wanted. Marty now agrees it was the best trip we ever had, and we all want to come back on the longer trip, which would include South Georgia Island, where the king penguins are. I will also use Ashton again for the North Pole, hopefully soon.” —Tina Sarafa



Be a smarter traveler: Read real travelers’ reviews of Wendy’s WOW List and use it to plan your next trip. You can also follow her on Facebook, Twitter @wendyperrin, and Instagram @wendyperrin, and sign up for her weekly newsletter to stay in the know.


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  1. Farnoosh Tabesh

    Hi, we were Looking to book a family vacation. Over the. 4 of July weekend. I was wondering if I could get some help.
    Thank you

    1. Billie Cohen

      Thanks for the great question. To make sure Wendy sees it, please click over to the Ask Wendy page and submit it via the form there. That way it will go right to her inbox.

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