Make Your Next Trip Extraordinary

Christmas and New Year’s Trips Tested By Your Fellow Travelers

by | February 29, 2020

Christmas and New Year’s vacations are not easy to plan.  They must fit the number of days you can take off from work or the kids get off from school, they must work no matter the weather, they should take you to places where everyone else isn’t, and they need to provide worthwhile value—and, ideally, wonderful memories—since it’s an expensive time of year to travel. Luckily, our readers have done the hard work for you, finding creative and rewarding holiday-time trips that tick all the boxes…with a little help from our WOW List of top travel specialists. Read on for inspiration for your next holiday trip. And don’t miss Wendy’s list of unexpected holiday travel ideas and spring break trips, as well as more reader suggestions of school-break trip ideas for your family.

Christmas in London

Christmas in London. Photo:

London: “There was even a small Christmas tree in our room…”

“It has become our practice to consult Wendy Perrin’s WOW List whenever we plan a trip. This time our goal was to spend Christmas in London. Although we had been to London several times, we know that the holidays can be a challenge due to closures on the holiday. We spoke with Jonathan about our previous visits to London and our desire to see and do something new.  We had a hotel in mind that we had stayed in before, but Jonathan strongly advised us to select another hotel, The Stafford, and we are so happy we took his advice. It is a much smaller hotel than the one we were thinking of, and that proved to be a big factor in feeling like we were ‘going home’ at the end of each day of touring London. The hotel staff treated us royally, and the hotel was decorated beautifully for the holidays; there was even a small Christmas tree in our room. As we had already seen most of the highlights of London on previous visits, Jonathan suggested other tours we would not have thought of. One was a Charles Dickens walking tour; our guide was extremely knowledgeable and entertaining, and we now understand how London during Dickens’ time influenced his writing.  Another highlight was a private “Behind the Glass” after-hours tour of the Churchill War Rooms. We had seen the War Rooms before, but nothing can compare with going there in the evening when it’s closed and actually going into the rooms that are not accessible to the public. These are experiences we would not have discovered on our own. Jonathan also executed a surprise ‘Wendy WOW Moment’ for us during our stay. It was a private tour and tasting in The Stafford’s amazing wine cellar, which was built in the 17th century and used as an air raid shelter during WWII!  The master sommelier, Gino, gave us the tour and made the experience very special!  Jonathan certainly added value to our holiday, and, given the short time frame of the trip, planned the perfect amount of activity while also allowing us plenty of time to explore London on our own and walk about enjoying the beauty of the lights and the amazing window displays and decorations everywhere.” —Susan Ketchum Philbrick

Read reviews of Jonathan. Then contact him to maximize your experience of Britain.

Northern Lights, Norway

Northern Lights, Grøtfjord, Kvaløya, Norway. Photo: Gaute Bruvik –

Norway: “We saw the Northern Lights three of the four nights, and the experience was illuminating!”

“We contacted Jan almost too late to put a trip together that would include the Northern Lights over the Christmas New Year’s holiday, but he put it all together seamlessly! Everything was like clockwork. All flowed together to visit three locations — Oslo, Alta in the Arctic Circle, and Stockholm. All hotels, restaurants, guides and drivers in the cities were spot on. Our experience in Alta was way beyond what we expected. Jan told us that in 30 years if his clients stayed in the Arctic Circle four nights, 100% of them saw the Lights. We saw the Lights 3 f the 4 nights, and the experience was illuminating! But we also had wonderful experiences during the day. Dog mushing was a highlight, as was snowshoeing and ice fishing and snowmobiling. Every person we dealt with was kind, warm, and made us feel relaxed and refreshed as we experienced these new to us activities. They all knew Jan and praised him highly. Jan is terrific.” —Lois Chess

Read reviews of Jan. Read his Insider’s Guide to Norway. Then contact him to maximize your experience of Norway.


Monteverde Costa Rica

Monteverde, Costa Rica. Photo: Shutterstock

Costa Rica: “An amazing beach where we could watch the sunset daily and take day trips scuba diving, surfing, and fishing…”

“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

Read reviews of Priscilla. Read her Insider’s Guide to Costa Rica. Then contact her to maximize your experience of Costa Rica.


patagonia mountains in front of lake and boat

Patagonia. Photo: Knowmad Adventures

Patagonia: “We received the best rooms in our room categories everywhere we went…”

“I’m a detail person and planner by nature and have always planned my own vacations, so it was a big step for me to use a travel specialist. I did so mainly because I’ve read Wendy’s work for years and really wanted to give it a try. The big question was: ‘Is it worth it to use a travel specialist and potentially pay more money?’ The answer is: ‘Yes!’ We wanted a trip to Argentina and Chile over Christmas/New Year’s and, thanks to Jordan, we managed to fit in Buenos Aires, Patagonia, Easter Island, and a cruise aboard the Stella Australis to see glaciers, penguins, and Cape Horn. It seemed like, because of Jordan’s relationships, we received the best rooms in our room categories everywhere we went. At Patagonia Camp, Jordan had really stressed getting a yurt with a Jacuzzi, and he was so right: It was awesome, and other people were sad they had not booked one. At Los Cauquenes Resort in Ushuaia, our room, 101, was also awesome; the large picture window with the full-on ocean view was unbelievable, and we had an amazing sunrise from our bed. When there was ‘unrest’ in Santiago, Jordan’s team pre-empted any possible situation by moving us to the Ritz-Carlton Santiago’s club floor; we shared the club room with other travelers whose travel agencies had not taken care of them in the manner ours had. Overall, we felt special and taken care of, and isn’t that how everyone wants to feel on vacation!” — Judy Calvert

Read reviews of Jordan. Read his Insider’s Guide to Chile. Then contact him to maximize your experience of Chile and Argentina.


Grace Bay, Turks and CaicosGrace Bay, Turks and Caicos. Photo courtesy Turks and Caicos Tourism Board.

The Caribbean: “There were 16 family members ranging in age from 3 to 74…”

“We traveled to Turks and Caicos in late December to celebrate my mom’s 70th birthday. There were 16 family members ranging in age from 3 to 74. Lindsey and her team did a wonderful job of finding a property that suited all of our needs—not an easy task for a multi-generational trip such as this one. The Somerset is small and intimate, and we all appreciated having privacy when required (each of our units came with two bedrooms, full kitchen, and so on—with more space than we could have imagined). There was an infinity pool and a white-sand beach, and our kids appreciated the nightly outdoor movie screenings, replete with pizza and popcorn. Lindsey was amazing at answering my many questions over email, always in a speedy manner and with lots of detail. She had lots of recommendations for dinners and excursions, all of which were spot on.” —Shawna Cohen

Read reviews of Lindsey. Read her Insider’s Guides to Finding Your Perfect Caribbean Resort and the Best and Worst of the Caribbean. Then contact her to maximize your experience of the Caribbean.


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

Read reviews of Marc and Boris. Read their Insider’s Guide to Bogotá. Then contact them to maximize your experience of Colombia.


Gentoo penguins in Antarctica

Gentoo penguins in Antarctica. Photo: Jennifer Santoyo

Antarctica: “It was the best trip we ever had…”

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

Read reviews of Ashton. Read his Insider’s Guide to Antarctica CruisesThen contact him to maximize your experience of Antarctica.


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 Brady suggested an itinerary to Mexico City and two truly magical colonial cities—Puebla and San Miguel de Allende—and the result was fantastic! He 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. Brady 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

Read reviews of Brady and Zach. Read their Insider’s Guides to Mexico City, Puerto Vallarta, and Riviera Maya. Then contact them to maximize your experience of Mexico.


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

Read reviews of Zach and Brady. Read their Insider’s Guides to Mexico City, Puerto Vallarta, and Riviera Maya. Then contact them to maximize your experience of Mexico.


Iguazu Falls Argentina

Iguazu Falls Argentina. Photo: Shutterstock

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

Read reviews of Maita. Read her Insider’s Guides to Buenos Aires and Mendoza, Argentina’s Wine CountryThen contact her to maximize your experience of Argentina.


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

Read reviews of Maria and Brian. Read their Insider’s Guides to Tuscany, Umbria, Florence, and Venice. Then contact them to maximize your experience of Italy.

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