Everyone has their own ingredients for a dream trip. It might be an irresistible opportunity to see someone, or something. A chance to accompany a friend on a work or personal commitment that you realize is practically a puddle jump from fantasy island. Or a longstanding bucket-list item that won’t be delayed or denied any longer.
Whatever the motivation, a dream trip involves a unique combination of alchemy and carpe diem—clear-eyed planning with a bit of tossing pragmatism to the wind. Every traveler we spoke to for this article said, in some fashion, I’ve been wanting to do this for a long time.
These ten dream trips were all planned the WOW way. What have you been wanting to do for a long time? And what are you waiting for? Tell us about your dreams via the black button below and we can help you make them come true.
The Philippines and Indonesia: Letting school curriculum be the compass
The island of Cebu in the Philippines is one stop on this family’s dream itinerary. Photo: Shutterstock
Andrea Mathis’ family travels are often inspired by her children’s global studies programs. With the Philippines on the curriculum in 2025, she set her sights on visiting over spring break, part of an itinerary that also includes Indonesia, Singapore, and Hong Kong.
“When we found out our first-grade daughter would be studying the Philippines this year, our nine-year-old son immediately noted the relative proximity to Sumatra, where you can see wild orangutans. We have become enamored with wildlife after spectacular safaris. And we have never truly camped before, so why not start in a jungle among wild orangutans?
No parent ever said traveling with children is easy! But it’s the most rewarding thing we’ve ever done as a family. Like anything else in life, the more you do it, the easier it becomes. We realize it’s all worthwhile when they ask intelligent questions and demonstrate a genuine appreciation for how others live. And our three-year-old daughter is convinced the Chocolate Hills in the Philippines are actually made of chocolate, so she’s pretty excited about that.” —Andrea Mathis
This trip was arranged by WOW List Philippines expert Andrea Oschetti. To get your own WOW trip, start with our trip questionnaire, reached via the black button below.
Italy: Tuscan villas as the home base for a family celebration
Some rental villas in Tuscany come with their own pools, chefs, and cars. Photo: Shutterstock
As their 50th wedding anniversary approached, Richard and Marci Abt toyed with the idea of a big party with their large, close-knit family. Instead, they decided to create a moveable feast in Tuscany with their four children and spouses and 10 grandchildren, ages 3 to 18—in all, a traveling entourage of 20.
“Plans snowballed into an extravagant, wonderful trip to Italy with two Tuscan villas, each with its own swimming pool and car, and a private chef. We are thinking of the villas as a home base to relax and explore the wine country. Some can go into Rome and Venice. I really want to see La Scala in Milan, the motherland of opera houses, and visit Pompeii again. The kids will enjoy golf cart tours in Rome and the swimming pool with their cousins. I like everything, and I like being with everyone.” —Richard Abt
This trip was arranged by WOW List Italy expert Jennifer Virgilio. To get your own WOW trip, start with our trip questionnaire, reached via the black button below.
Colombia: Three couples let their tastebuds lead the way
Colombia has become a magnet for foodies thanks to restaurants like Medellin’s Carmen. Photo: Amakuna
Each year, Stacey Rozen and her husband travel with two other couples, their destination determined by curiosity and mutual enjoyment of eating, drinking, laughing, and experiencing new things.
“This year we were looking for something on the exotic side, with different climates and cultures, but not crazy far away. South America is always appealing and typically a little less expensive, and we hadn’t been to Colombia. So we’ll be splitting 10 days between a few hotels—first in Bogota, then in the coffee region of Pereira at a coffee hacienda, then to Cartagena, then relaxing at the beach in Barú. We are big coffee drinkers and foodies and we love to do it all, from roadside stands to fine dining. We pretty much have traveling together down pat, respecting each other’s likes and dislikes. Once we get on the same page with a trip, it all works.” —Stacey Rozen
This trip was arranged by WOW List Colombia expert Boris Seckovic. To get your own WOW trip, start with our trip questionnaire, reached via the black button below.
Kenya and Zanzibar: Introducing children to Africa’s wildlife and ecosystems
Giraffe Manor in Nairobi, Kenya, is one of the hotels on this family’s dream itinerary. Photo: Shutterstock
Wanderlust is baked into Kim Segal’s DNA, and that hasn’t changed since having children. When she and her husband learned they’d be attending an August 2025 wedding in London, they knew it was a perfect departure point to share one of their favorite experiences with their 6- and 8-year-old boys: going on safari.
“We will fly from London to Nairobi, then head out to Lewa Conservancy in Central Kenya. There are villages nearby where we can visit schools (something I definitely want my kids to experience—seeing how kids study in other parts of the world, and interacting with kids even if they can’t speak the same language, as the language of play is universal). They have an anti-poaching unit that you can visit to learn more about the reasons people poach, and the steps they’re taking to protect the wildlife.
From Lewa, we fly to Zanzibar, where we will spend several nights at a beautiful hotel on the beach. We then route back through Nairobi to finish up at Sheldrick Elephant Orphanage and Giraffe Manor—the boys are going to get such a kick out of having breakfast with the giraffes! (We had to build the entire trip around when a family room was available there, 18+ months in advance.) I’m excited for my children to see and experience a culture that may be distinctly different from what they know, but to realize we’re all so much more similar than different; and for them to start thinking about how we help others, how we protect our planet, how we make the world a better place.” —Kim Segal
This trip was arranged by WOW List East Africa expert Dan Saperstein. To get your own WOW trip, start with our trip questionnaire, reached via the black button below.
Thailand, Laos, and Cambodia: Revisiting favorite places through a partner’s eyes
An arts and culture immersion in Bangkok is the first stop for making memories together. Photo: Timothy Baker
The last time Mary Santiago visited Thailand, her husband was unable to come along. Now he gets to join her in some of the experiences she’s raved about, while creating memories in new places together.
“I LOVED my time in Thailand so much that I’m even looking into a second home there. In Thailand, we’ll be focused on food, culture, and the arts in Bangkok, Chiang Mai, and Chiang Rai. Plus elephants. The elephant experience in Chiang Rai is one of my fondest memories ever for any vacation, and years later I can’t stop talking about it, so I needed to show Scott.
I know very little about Laos, but I hear the culture and nature is just beautiful, so we added a quick stop. In Cambodia we’ll explore Angkor Wat/Siem Riep, and Shinta Mani Wild. How cool is it to zipline into your hotel to check in, and then just relax for three days near waterfalls and be pampered after our epic trip? We booked a waterfall room (which is tented), and the pictures are unreal!” —Mary Santiago
This trip was arranged by WOW List Southeast Asia expert Daniel Fraser. To get your own WOW trip, start with our trip questionnaire, reached via the black button below.
Egypt: Seeing iconic sights in the most personalized and authentic ways
A traditional dahabiya sailing along the Nile in Egypt. Photo: Billie Cohen
Twice before, Craig and Stephanie Smith have booked trips to Egypt, but life got in the way (thank goodness for travel insurance, they hasten to add). Stephanie has been fascinated by Egypt since seeing the Ramses II exhibit in Boston as a child. She and Craig particularly value small boutique hotels and stellar guides who can share local culture as well as history, as if experiencing a place through a knowledgeable friend.
“We are looking forward to seeing all of the iconic pyramids, temples, and tombs in person. We are eager to get a glimpse of the brand new Grand Egyptian Museum. We love having private access to experienced guides. Having a guide who takes care of all of the logistics ensures that we don’t have to worry about anything other than soaking up the history and culture, and makes the trip so much more enjoyable.
We decided that now that we were finally going to make our Egypt dream come true, we wanted to do a private trip rather than a group tour. It allows more flexibility, because Craig has multiple sclerosis, and if he is not feeling great, we can adjust the day’s activities without impacting other travelers. Many of the sites are in common with our previous itineraries, but this time around we chose a dahabiya rather than a standard Nile cruise. We like the idea of a smaller cruise with a more personalized touch, so classic and romantic!” —Stephanie & Craig Smith
This trip was arranged by WOW List Egypt expert Jim Berkeley. To get your own WOW trip, start with our trip questionnaire, reached via the black button below.
Australia: Two sisters blend luxury and adventure across the entire continent
Tasmania is one of the far-flung spots on this sister trip. Photo: Shutterstock
Lynne Harrison and her sister Maureen are fulfilling a long-held dream to travel throughout Australia. Lynne prefers adventurous travel and road trips; Maureen is accustomed to more upscale arrangements with her husband, who passed away five years ago. Together they’ve planned an elaborate, seven-week itinerary weaving between luxury and simplicity, and finishing with a 29-day cruise back to the U.S.
“We got a big map of Australia and chunked out routes around the places we wanted to go. We were a little shocked to see how far apart things were, and realized it was going to take seven weeks. We’re doing a transcontinental train from Sydney to Perth, then driving back along the south coast, through Margaret River and the Great Australian Bight, staying in roadhouses. We’re also going to Tasmania and Uluru, and there’ll be plenty of opportunity for adventure as well as luxury.
And then Maureen found this cruise deal that was the equivalent of a business-class ticket back to the States. So we thought, Well, why not? After two months of driving like mad right across Australia, we’ll just park ourselves on a cruise for 29 days. Because this is a major bucket-list trip, we’re willing to spend more than we would ever normally spend on a vacation. You hit retirement, and you’re suddenly aware of the things you want to do, and if you don’t hurry up and go, your friends and family are not going to be able to do it with you. I think that underscores the ‘let’s get on with it.’” —Lynne Harrison
This trip was arranged by WOW List Australia expert Stuart Rigg. To get your own WOW trip, start with our trip questionnaire, reached via the black button below.
Chile: Smart pacing for exploring the country from top to bottom
Unrushed downtime is important for soaking up Patagonia’s Torres del Paine National Park. Photo: Johnno49/Pixabay
Now retired, Matthew Wilson and his wife Lyle York can prioritize the time and planning it takes for the style of travel that they’ve found suits them best.
“We want to see places with natural beauty and wildlife, and we want hikes/excursions. We also want to visit the occasional big city. Chile and the Andes have been on our radar for years. Most of the places we’re staying are small, all-inclusive lodges in lovely places: Patagonia, Valparaiso, Atacama.
We’ve learned that pacing is important. Trying to do too much in too little time becomes unenjoyable. Our three-night-minimum rule gives us at least two full days in a specific place. Pacing also applies to guides. Guides can be extremely helpful and add to an experience. But being guided every minute gets to be exhausting. No matter how good the guide, you need downtime. Our rule of thumb is that guides are great when they get you access to something special or help you avoid crowds or save you time by solving logistical problems. But if you want to wander around a city, or check out a museum, you don’t really need a guide. Out in nature, guides become essential. They know where to go—hiking, kayaking—and where to find scenery and wildlife.” —Matt Wilson
This trip was arranged by WOW List Chile expert Jordan Harvey. To get your own WOW trip, start with our trip questionnaire, reached via the black button below.
Norway and Denmark: The Aurora Borealis lights the way, via dogsled and snowshoe
Alta, Norway is one of the best places for spotting the northern lights. Photo: Shutterstock
Marianne Hane and her husband enjoy building trips around opportunities to glimpse the aurora borealis. Lightseeing in Alta, Norway shimmers with the possibility of ice-bars and reindeer herds, plus a stop in Copenhagen to sample Danish museums and restaurants.
“We wanted to try to catch the aurora borealis again while the sun is most active in its 11-year cycle. We decided to go to Alta, Norway, because it seems that it is a good location to see it, along with creature comforts that look attractive. We’ll be taking three private nightly tours to see the northern lights, a dog-sled tour of the forests around Alta, a snowshoeing trip to ice fish in a lake, and visiting the Sami tribe to see their way of life tending their reindeer herd. We’ll also be touring the Sorrisniva ice hotel and having a drink in the bar. We have never been to Copenhagen before, and are looking forward to seeing the Louisiana Museum of Modern Art and Glyptoteket.” —Marianne Hane
This trip was arranged by WOW List Norway expert Jan Sortland. To get your own WOW trip, start with our trip questionnaire, reached via the black button below.
Dubai and the Maldives: Family dune-bashing and island-basking
This family will end their trip on a tropical island in the Maldives. Photo: Shutterstock
Mary Ko and her husband are all too aware that the clock is ticking on their window to travel with their three kids (the oldest is 12) before school and college-prep commitments take over the calendar. Their latest trip includes an excursion to the observation deck of the world’s tallest building, a dune-bashing jeep adventure and desert BBQ, and a five-night stay at a secluded tropical island resort in a UNESCO Biosphere Reserve.
“We were in India and realized it was our best vacation, so we’ve decided to go big and far and jump on the short window before our kids have college applications and jobs. Vakkaru Maldives looks ridiculous and amazing—might be our fanciest stay ever. The girls will want to see sea life, and my husband wants to relax. With young kids we like a little adventure, and a little chill time—kids need it, and we do too. Go while the kids are young! Do a morning outing and a mellow afternoon. Teach them to take polite bites of new food. My kids still remember the spider as big as my daughter’s head landing on her in Costa Rica, and being completely carsick on a serpentine road in Montenegro. Laugh about the chaos! Let it go.” —Mary Ko
This trip was arranged by WOW List U.A.E. and Maldives expert Justin Parkinson. To get your own WOW trip, start with our trip questionnaire, reached via the black button below.
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