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The Family Travel Plan...Means a Lot of Planning

You can still have a once-in-a-lifetime vacation with your clan, but it’s a lot of work. Here’s how to do it right.

family travel

This world we share is really quite small. And I really want to see all of it. Of the many lessons that I have learned in the past year, those two have stood out the most.

First, it is impossible to underestimate how interconnected our world is. Exhibit A is the microscopic terrorist known as COVID-19 that spread across the planet so quickly and brought life as we knew it to a halt.

Second, there’s nothing like being prohibited from traveling to make you realize how much travel means. I’ve come to appreciate how seeing and experiencing the world is so central to who I am. (OK, I founded one of the fastest-growing luxury travel agencies in the world, so I am biased.)

As the globe reopens and we enter into this post-pandemic world, there is a lot to rethink about how you plan your family’s travel. Skylark works very closely with our best clients to plan out their travels, often years in advance (and sometimes just hours).

In an effort to help our clients plan their travel lives, we have come up with a list of life-changing trips that your family should take before your kids graduate high school…or college.

Before going into some of the specific vacation ideas, here are some thoughts we are sharing with clients right now about travel planning for the next couple of years.

Find a Reliable Single Point of Contact

You want someone who can coordinate your travel itinerary and arrange the many different components of the trip while making it all feel seamless (even if it isn’t). Trip planning today is complicated by everything from international “sterile” transfers and connecting airports, to finding the right time slot for museums that have imposed new entry requirements and having the right paperwork or QR code at the ready. All of this is easier if you work with a travel advisor who has expertise in all of the different elements of your vacation planning.

In particular, flights are going to be a very, very complicated part of the equation going forward, with ever-changing schedules, rules, entry requirements and required documentation at check-in. Not all travel advisors are air travel experts—in fact, many of them leave flight booking to someone else. Be careful here because although we all want to avoid situations that require it, 24/7 support is a must.

Related The Next Best Destinations 2021

But with flight schedules shifting more frequently (see below), you want a single advisor to work with your airlines, hotels and other operators to modify your trip schedule as needed. If you have divided these responsibilities across multiple contacts, none of them will want to take responsibility. It’s important that your travel advisor can not only get you a great deal on airfare, but also knows which flights are less crowded, which airlines are sticking to their schedules, who’s better at social distancing and how to get you home quickly in case of an outbreak or emergency.

Plan Far, Far Ahead

If you are a parent of school-age children with strict vacation schedules, you will really need to plan in advance for the next couple of years. Because last year caused so many vacations to be postponed (and associated deposits held by hotels and private tour operators), there is just much less availability in 2021 and, believe it or not, 2022. You should be planning now for the end-of-year holidays and even next spring break and summer vacation to ensure your family gets to see the world.

Those of you without kids in school should still be thinking ahead, too. Travelers are booking right now for late summer, fall and holiday trips. And it’s not too early to start thinking about 2022.

Pack a Plan B

In the past when you planned in advance, you could rest assured that the worldwide flight schedule was pretty stable for the next year. Not anymore. The good news is that the airlines are ready: They have their flagship long-haul aircraft being prepped and ready, and you may actually fly lay-flat in business class from Miami to JFK as these planes are put back into service.

The bad news is that the airlines are going to be dropping flights into the schedule (and taking them out) with much less warning than in the past. That means there may be lots of schedule changes, possibly right up until your departure date. This does have a benefit to the traveler, if you do not approve of that change (there is fine print here), you are able to get a full refund for the tickets. That might actually be in your favor, since better flight options may have come onto the market since you first booked.

We have also become accustomed to having daily nonstops to most international destinations. That’s not the case today. You may have wanted to leave on Friday, but you may just have to wait until Saturday to get a nonstop flight or that perfect connection home. For this and other reasons, many are now taking advantage of private jets (see story on page 36). Last, how about a real Plan B? For every major vacation, Skylark is suggesting that its clients have a full backup plan—that is, a safer, closer-to-home alternative. Even as the world reopens, parts of it may also reclose for short periods of time, and often last-minute. So having another plan will reduce this stress. You might even want to book that backup vacation—as long as it’s fully refundable.

Don’t Be Afraid to Ask

Virtually every traditional rule is in the process of being rewritten. Don’t be afraid to ask for what you want. Work with your advisor to ask for enhanced, more flexible cancellation policies. We are actively working with our partners around the globe to customize vacations. While doing that, we are negotiating specific COVID-related language around deposit payment schedules, cancellation flexibility and policies on returning deposits and honoring credits. For clients who are chartering yachts this summer (think: expensive upfront payments), we are insisting on COVID addendums for all of our bookings. A simple request that ensures peace of mind.

Know Your Kids’ Interests—And Share Them

Our hotel partners and private tour operators around the world are getting more creative with tailoring each client’s vacation. We have seen real improvements over the past decade with wellness, food and wine, cocktail classes and so forth. But we are really starting to see it for the next generation. By understanding your children’s interests, our partners have the ability to really take their (and your) vacation to the next level. This is not your normal kids’ club—I am talking about Malliouhana’s ice cream school, Family Twist’s canal-side painting classes and countless Paris scavenger hunts.

Related Ask an Advisor: Travel Advice in the Post-Pandemic Era

Share your kids’ loves and passions with a travel advisor, so they can create an unforgettable learning experience for your family disguised as a vacation.

New Twists to Classic Trips

Despite the uncertainties around fight schedules, the world is easier to get around. With the introduction of the super-efficient long-haul Boeing 787 and Airbus A350, connectivity from virtually every major city in the U.S. to any major city around the globe is going to be one connection (or a nonstop) away.

Also, the airlines’ traditional hub-and-spoke map has been redrawn, so you may find yourself transferring through the Middle East or Turkey, instead of London or Paris. This will give you a new set of exotic options to add onto your next vacation.

New Luxury Offerings

There are also lots of new offerings in every corner of the globe. For example, consider taking part of your vacation on a small ship—a very luxurious small ship, such as Aqua Expeditions in Peru or Lindblad’s cruises in the Galapagos. Even bicycling becomes easier with our top partners like Backroads, which offers electric assist bicycles for guests—ensuring that no one is left behind.

For the Foodies

As I think about my travel plans, I can’t wait to visit some of my favorite restaurants and bars. Sadly, many of these establishments won’t be open on my next trip, and perhaps never again. However, we have already begun to work with our concierge partners around the world for new recommendations and are being updated as top chefs reappear and restaurants are resurrected in the top dining destinations. And, yes, Lo Scoglio will be open just like it always is in Amalfi this summer.

Top 10 Destinations for Families

1. France

Paris, the pinnacle of cuisine and art, is only being elevated with the new Cheval Blanc Paris opening this summer. But go further and amplify your experience: Visit Monet’s gardens at Giverny, then head to Normandy for the greatest American history lesson of your life. Oenophiles should see the vineyards in Champagne or the Loire. And art pilgrims are heading to Arles, where Frank Gehry’s Luma Tower opens in June. Of course, you can’t go wrong with the grandeur of Grand-Hotel du Cap-Ferrat or the newest wellness destination of Lily of the Valley.

2. Peru

Machu Picchu and the Sacred Valley are life-list experiences for many—so seek out expert advice on getting acclimated, choosing a lodge and organizing hikes to maximize your time. In addition to Belmond’s exquisite collection of hotels and tours, spend a night on the Belmond Andean Explorer for a unique view of the country. From there, Aqua Expeditions will take you deep into the Amazon in unparalleled comfort, and Lima’s restaurant scene is unmissable (don’t miss La Mar or Central).

3. Patagonia

Journey from the Argentine pampas to the glaciers and peaks of southern Chile—and all the hiking, fly-fishing and wildlife-watching in-between. The luxury lodges—we love Tierra across the whole country—are object lessons in sustainable design.

4. Morocco

The desert kingdom seduces with its cuisine, artistry and ineffable romance. Get lost in the souks of Fez (and reemerge with armloads of just-purchased lamps, jewelry and rugs), but be sure to spend some time at the spa at Royal Mansour. Dine on fragrant couscous in Marrakech. And spend a night in the Sahara, sheltered by a star-filled sky and enjoy your own personal kasbah at Dar Ahlam.

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5. East Africa

We usually send clients to South Africa for their first safari; it’s user-friendly and combines well with stops in Cape Town and the wine region. Repeat visitors should look at Rwanda, Kenya and Tanzania, which have a vastly different terrain, wildlife and culture from the south. Plus: Kilimanjaro is a mountain that most people can climb. Singita, an amazing partner with lodges across Africa, elevates safari to a level befitting of its own profile.

6. Amalfi Coast

Positano, Ravello, Capri: One of Europe’s most captivating coastlines has superb cuisine and impossibly romantic hotels like Le Sirenuse. How to do it right? See the coastline by pedalo (paddleboat); skip the Blue Grotto and take the lift to Monte Solaro for the best Capri views; and order the sea urchin at Lo Scoglio.

7. Galapagos

Darwin’s islands are an essential stop for students of evolutionary science, or anyone who’s ever been captivated by the strange wonders of nature. Or just funny looking birds. There are land-based resorts, but you’ll see the most on a boat. The options range from private yachts (Quasar’s Grace) and luxury catamarans (Celebrity’s Xploration) to larger ships like the 96-passenger National Geographic Endeavour II.

8. Japan

Culture shock guaranteed, but in the safest and friendliest way possible. Food, etiquette, shopping—everything in Japan is different, and everything is extraordinary. Our first-timer’s itinerary takes in the art, shopping and kinetic energy of Tokyo; an R&R stop in the spa town of Hakone; the historic temples, shrines and gardens as well as the newest Aman in Kyoto—and plenty of sushi, noodles and dumplings in between. Art lovers can not miss Naoshima on any visit.

9. Iceland

Like Yellowstone on steroids, the island nation is heaven for anyone interested in geology and the strange beauty of nature. Our usual plan: A stay at the Retreat at the Blue Lagoon (where you can bathe away from the crowds), then a few nights at Deplar Farm, a one-of-a-kind luxury basecamp with access to volcanoes, waterfalls, glacier walks, heli-skiing and, of course, the Northern Lights.

10. Costa Rica & Nicaragua

A case study in biodiversity and sustainability, Costa Rica is also the source of non-stop family fun, with everything from ziplining to whitewater rafting to surfing. Split your time between a coastal resort like the Four Seasons and the wildlife-filled region around the Arenal Volcano at Hacienda Altagracia and Nayara Tented Camp. Nicaragua is similar but less developed and more “hidden.”

Paul Tumpowsky is the founder and CEO of Skylark. Want help planning your family’s next dream vacation? Drop him a line at p@skylark.com.

For more stories from our recent travel issue, check out the digital magazine here

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