In 2017, I planned our first family vacation to Italy for the last two weeks in August. Our son turned nine that August and our daughter was four and a half. Based on several factors, the time was ripe to follow through on our long-held desire to spend time in Europe as a family.
This travel guide is a step by step look at the process of putting together a complete family vacation.
- Is it too soon for the kids?
- Where do we start?
- Make it Happen – Seven Steps to Planning a Custom Vacation
- Hotels
- Flights
- Research
- Itinerary
- Checklist
- Packing
- Go On Vacation
Is it too soon for the kids?
We had already flown with our children several times to the Caribbean for our winter vacations over the Christmas and New Year’s breaks and these kids had become familiar with flying. These flights were about four hours long and we found that they were pretty easy to take on planes. My son was content with the in-flight entertainment while my daughter usually fell asleep for the duration of the flight. They were and continue to be generally well-behaved kids and based on this, we were ready to take longer flights. As it turned out they were fine with the longer stretch of time on the plane (usually an overnight flight), the airport transfers and the jetlag.
Another significant development was that we were done with naps, diapers and strollers. As quintessential NYC kids they were restaurant-trained and accustomed to walking city streets for lengths of time that would accommodate sightseeing in other cities. They were also used to spending time in the many museums across New York City. I have always made it a point not to drag out our museum experiences and simply let the kids enjoy themselves as we walk through the galleries. The main objective is for them to feel comfortable in these creative spaces and to engage with the art on their own terms. They are often on the lookout for the interactive and educational components that are geared towards children as well as the museum shop on the way out. With the kids, I try to limit our visits to two hours or less to ensure that our time in the museum is fun and stimulating.
We concluded that these kids were ready for Europe. They are easy-going children and have proven to be far more resilient and adaptable than we had anticipated. These two characteristics remain key to the ease with which we have been able to travel as a family.
Where do we start?
Once Europe became a viable option we needed to pinpoint our destination. A wise and well-traveled friend advised us to start with Italy since our children were still young and she guaranteed that they would be welcomed with open arms everywhere. She also gave me the idea of spending time on the coast to give us a break from the rigors of sightseeing in a city. Up until then, my few trips to Europe were primarily spent sightseeing in a major city and I had never vacationed on a coast, something I had always wanted to do. My prior travel experiences were clearly delineated between relaxation on the beach, which I had designated for our Caribbean vacations, and researched sightseeing, which I had associated with major cities. The idea of experiencing both in Italy sounded heavenly.
I had briefly looked at some tour groups that catered to families and these companies offered trips that would cover Rome, Florence and Venice in the span of about ten days. A tour group such as this would have, at least in my opinion, had us moving around a lot and would have only given us but a glimpse into each city. The cost per person also seemed high for an experience that appeared to be rushed and pre-packaged. I understand that traveling with a tour group can be efficient, practical and fun for some but this did not seem appealing to me. I had prior experience making my own itineraries when I traveled around Japan in 2000/2001 while I was living there and teaching English. Back then all I needed was a good guidebook and a map. It may have taken me longer to get to the desired location but the process of finding my way while “lost” was often just as memorable. In 2007, my husband and I spent our honeymoon in Paris wandering around museums, enjoying picnics in the park and just soaking up the Parisian way of life following a loose itinerary that I had prepared beforehand.
That trip to Paris was the only time that I was able to visit Europe while in graduate school but I yearned to see more and catch up. However, my grad school days ended when I became a new mom and my focus had shifted. My husband and I had put Europe on the back burner but by 2017, we were both anxious to go back and this time with the kids. As I began to plan this trip, my intention was to create a customized vacation that would appeal to every member of my family with the only limitations being our time frame, our needs and our interests. It was determined that we would go for two weeks minimum, do some sightseeing but in a leisurely way and find our way to a beach for a stretch of time. This would be the first time that I would plan out this type of vacation and it has become the basic framework upon which I continue to organize our annual trips to Europe.
Make it Happen – Seven Steps to Planning a Custom Vacation
We decided to go away the last two weeks of August and return a few days before the kids were to go back to school. Returning right before the new school year begins has proven to be beneficial in terms of getting the kids back into their school night routines after a summer of relaxed bedtimes. While on vacation, later bedtimes are helpful for heading out to dinner around 7:30 or 8:30 pm. Upon returning to New York from Europe, the jetlag has all of us naturally falling asleep around 8:00 pm, which is key for getting back into a school and work routine. The end of August is prime tourist season, however, with careful planning, it is possible to not let the influx of tourists in the cities or of Europeans also on vacation around the coastal regions to have a negative impact on our family vacation.
1. Hotels
After deciding how long and when, I then outline our destinations, which in 2017 would begin in Florence for four nights, then to the Cinque Terre for seven nights and back to Florence for three more nights.
I began working out the broad strokes of our first trip to Italy at the end of January that year. My main concern was to ensure that we booked our hotels sooner than later fearing that we would have fewer options if we waited too long. My philosophy is that it is never too soon to start looking and booking. Most recently, I booked the hotels for our August 2020 trip to Spain at the beginning of December 2019. In general, whether I book directly with the hotel or through Hotels.com, there is often the option to change my reservation(s) if a better deal is found along the way and if I had chosen a refundable option. For our first trip to Italy, I used Hotels.com to book one of the hotels and booked directly with the other two hotels. For later trips, I had become familiar with the Hotels.com rewards program, which offers a free night worth the average of the amount spent per night of ten nights booked and completed through their site. I like the idea of booking through Hotels.com because they have access to most hotels and there is plenty of flexibility if you select a refundable rate. I have taken advantage of the free nights and I must admit that they provide incentives for booking more vacations. For our upcoming trip to Spain, I redeemed close to $900 towards our stay at an upscale hotel in Madrid.
For many years, we had a credit card that offered rewards for a particular hotel chain but at a certain point, we decided that we did not want to be tied to one brand, and now the freedom to choose from an array of hotel types is refreshing when selecting hotels in Europe. The hotels where we have stayed catered to our desire for vacations that are safe, comfortable and convenient, with a hint of luxury. Traveling with the kids meant that I did not want to cut corners as I had when I was younger but actually spend a little extra on comforts like a convenient location and an outdoor pool which is always a treat for the kids after a day of sight-seeing. I rely on Google, Tripadvisor.com and numerous travel blogs to help me choose hotels and have yet to be led down the wrong path. I have not had one bad hotel experience.
It has not escaped my attention that my commitment to hotels may be anachronistic in light of the current milieu where Airbnb is on the rise and rapidly transforming the tourist industry worldwide. Despite Airbnb’s growing presence, for now I am content with a good, old-fashioned hotel stay.
2. Flights
After making hotel reservations, I start researching flights, which I also prefer to book sooner than later. Once I book the flights, I know there is no turning back and we are locked in. This is probably the most exhilarating part of the process because I know this trip is happening once the flights are booked.
By 2017, we had flown to the Caribbean several times and after flying with different airlines we realized that Delta was our favorite. Before this epiphany, I had opened a credit card that was linked to miles with another airline but I quickly realized that this credit card and airline did not suit our needs. After closing that credit card account and deciding that Delta was our preferred airline, we opened a Chase Sapphire card because we could use the rewards to travel with any airline. Through the Delta website, I also set-up our frequent flyer accounts so we could accrue and use miles from our trips. After several years of shopping around, I had finally found the right combination of the Chase Sapphire credit card and the Delta Skymiles program. I have settled into a system of booking through the Chase Travel website using whatever points we have to offset the price. I usually book economy seats and once the reservations show up in our Delta Skymiles accounts, I use our miles to upgrade to Delta comfort, which is the section right behind first class. I would love to fly first class but for a family of four, the cost is exorbitant while the pricing for Delta comfort is reasonable. We travel with neck pillows and that is our way of upgrading for free. Delta’s customer service is very accommodating and was extremely generous when compensating us for a ticketing error that could have potentially caused problems for our 2018 round trip to Rome. Instead of flying Delta comfort, which we had paid for, we had to fly economy. To make up for this error, we received a full credit for the flight and enough Delta cash to cover our 2019 trip to France when we flew into Paris and out of Nice. This experience sealed the deal for us and we have continued to enjoy our experiences flying with Delta.
3. Research
Since I tend to book hotels and flights far in advance, I have plenty of time to research. I seek out non-fiction and fiction books that will help me get into the frame of mind. I have this need to thoroughly research and learn about the history of where we are going. Call me crazy, but I feel that hiring a tour guide is cheating which is probably due to my background in Art History. All those years of graduate school left their imprint on me and I organize my research for each trip as if I am designing a course syllabus. Putting together reading lists and going through this material is probably just as fun for me as going on the vacation. In addition to texts, I seek out films, shows and art that will get me in the frame of mind.
When I started this process in 2017, I was finally ready for the type of mental challenge that I had put to the side when my focus had shifted towards family and opening a business with my husband. I was excited to read about art and history again with a fervor that I had not felt in years. There was so much transition between 2008 and 2017 and all of my brain activity was directed towards raising children, helping my husband run his physical therapy practice, learning how to navigate the very complicated education system of New York City and overcoming some personal health setbacks. I reveled in the excitement of using my brain to research a trip to Italy. The reading and viewing list for my ongoing “independent study” has become the foundation for my daily existence.
4. Itinerary
The next step is to create an itinerary and a checklist. The itinerary centralizes all of the trip information into a master document that I rely on while we are away. All bookings including flights, hotels, trains, admission tickets, dinner reservations and more are detailed within the daily breakdown of activities. The itinerary helps me visualize which days of the week we arrive at the destinations, will be sightseeing, be in transit, relaxing by the beach and more. This helps me ensure that the places we hope to visit on the designated days and times will be open to the public. Consulting the official websites of all desired places of interest is a must in order to ensure accurate information. I also take note of the places where it is recommended to purchase tickets ahead of time allowing us to skip the line on the day of our visit. Waiting on line is something I avoid at all costs.
Sightseeing & Relaxing
To assist with narrowing down places to see and things to do, I survey numerous travel blogs and tourist websites. When we are in a city, I prefer to spend the afternoons sightseeing and if we are staying at a hotel with a pool, I make sure to leave time before dinner to return to the hotel and let the kids swim. I am not overly ambitious when planning out which places to visit because while the main objective may be to see what these cities have to offer it is also important to do so at a pace that is enjoyable for all four of us. My goal is to create itineraries that will expose us to some of the major sites but also give us time to fall into the rhythm of that city, relax during our meals and treat the kids to time in the pool or just running around and playing in a park as we would do at home in New York City. The trick is to strike a balance that will accommodate the four of us.
I usually like to spend about four nights in a city before moving onto another region either by the coast or in the country. During our stays at these locations, the rhythm is a little slower because I do want this time to feel like a vacation laying on the beach, appreciating nature or just taking a beat to soak in our surroundings. I tend to mix in a variety of excursions to expose us to the rich culture of the area we are visiting but make sure that the kids needs are met with beach time, pool time and more.
Reservations – Restaurants, Beach Clubs
If we are going to the coast and private beaches are an option, I have made reservations in advance for beach chairs in the first row either directly with the beach club or through the hotel concierge. When it is prime vacation season at the end of August, it is best to secure these beach chairs sooner than later. The benefit of these private beach clubs is that you do not have to show up with any beach gear because they provide chairs, umbrellas, towels as well as food and drink service. As for meals, I am on the fence about making dinner reservations ahead of time. So far, we have had great experiences, arriving at a location and asking the hotel concierge to recommend and make dinner reservations. On one trip, I made most of the dinner reservations ahead of time based on recommendations from people we knew and through recommendations solicited from the hotels via email. In retrospect, I would have preferred leaving the meals more open-ended and had waited until our arrival to sort out dinners. We ended up changing many of the dinner reservations once we got our bearings straight and as our vacation took shape in ways that I could not have anticipated ahead of time. Plus, we tend to fall in love with certain restaurants and opt to eat there multiple times. This is a fun way to feel in step with the locals during these brief stays because we get to know the staff who are always happy to see repeat customers. In general, I prefer to have a rough idea of restaurants worth looking into but will wait to make reservations, if necessary, when we arrive.
Trains & Cars
In addition to flights and hotels, there are numerous other things that I book beforehand to avoid wasting time on our vacation making these arrangements. When moving from one city to another, I rely on the fast train service in Europe and can usually book these tickets about one to two months ahead of time. I always choose the seat class that allows for seat selection at the time of booking. It is in the forefront of my mind that we will be traveling with four carry-on suitcases and four or more additional bags, so it is paramount that we have reserved seats and do not have to worry about finding seats and space for our luggage.
We have reserved car services from train stations when our hotel was a good distance away and wanted the transition to be easy considering we were arriving with luggage. In other cases, when the distance was short, a taxi or Uber was sufficient. Rental cars and car services are also booked ahead of time for any excursions we plan to do on our own and not with a tour guide or group. I recommend booking a rental car sooner than later because the inventory of vehicles with automatic transmissions can be limited. These reservations are always refundable and easy to change as I did multiple times for our trip in France last year. I reserved our rental through the Auto Europe website and found the customer service very helpful as was the process of picking up and dropping off the car in different cities. I did pay for the navigation system that was sent to my home ahead of time because I was not sure if Google maps or the Maps apps on our iPhones would navigate us in English. As it turns out, both of these apps were able to direct us in English and we ended up not using the navigation system. I go into further detail about our first car rental experience in my post about Provence.
Rental car, Hotel Le Pigonnet, Aix-en-Provence, France 
Trenitalia train from Rome to Salerno, Italy
Making these practical arrangements ahead of time leaves me with less to think about while we are away and limits the potential for unwanted surprises or disappointments. A detailed itinerary ensures that all of the practical aspects of the vacation are predictable. This means fewer unexpected setbacks or time wasted and more of the magical and unpredictable moments that we seek when in new places.
5. Checklist
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Passports
At the very top, of every checklist should be passports. Make sure everyone has a passport that will be valid at the time of travel. You do not want your passport to expire while you are out of the country. With minors, you have to do everything in person and with both parents present so it is important to get this process going as soon as possible so you do not have to pay extra to speed up what is already a pricey process. Make photocopies of the passports and/or take photos of them on your phone. Download the Mobile Passport app on your phone and you will save time when you return to the U.S. by breezing through customs. It is free and only one adult per family needs the app. Before the trip set up the app with the passport information and pictures of each person traveling. As soon as your plane lands in the U.S., open the app and go through the quick and easy re-entry application. Once you leave the plane, follow the signs for Mobile Passport and as we have found, there will be no more two or three people ahead of you. This fast and easy process makes for a very happy homecoming.
Credit cards & money
Make a note to alert your credit card company and the bank you use to get cash from ATMs about a week before you are due to leave to let them know that you will be overseas. Once the credit card company and banks know what countries you will be in and the length of time, you will be able to charge and get cash from ATMs without fear of your credit card company or bank placing a freeze on your accounts believing these transactions to be unauthorized because they are taking place outside of your home country. I also get about 100 Euros from my local bank so we arrive with local currency in our wallet as soon as we land. After that, we use our credit card whenever we can and get cash out of ATMs along the way.
Cell phones
Check with your cell phone carrier to find out their rates and deals for when you are abroad. I generally turn off my cellular data and roaming and just use the Wifi while in the hotel. With Wifi, I can call, text and go online without extra charge. The international plans have changed dramatically over the years and have become pretty reasonable. If we do need to turn on one of our phones, our carrier AT&T, charges a flat rate of $10 per day and that phone has unlimited voice, text and date for a 24 hour period.
Print reservation confirmations and ticket vouchers for everything
Right before you leave, print out a copy of your final itinerary, confirmations for every paid reservation and all ticket vouchers so you have hard copies that you can use during the trip. This avoids wasting time and money turning on the cellular data on your phone while away from a wifi spot in order to find these confirmations and tickets. It may be old-fashioned, but it is honestly the easiest way to go through your daily schedule without hassle. I have a folder with a printout of my itinerary and every reservation and voucher arranged in chronological order so I have what I need as we go day by day.
6. Packing
Start shopping sooner than later so you have time to make sure you have the right products. For our first trip to Italy, we decided to only use carry-on luggage to avoid the possibility of losing any checked luggage. We each get one carry-on suitcase and one backpack or other type of soft bag, which is more than enough space for the four of us. Carry-on continues to be our preferred method because summer clothes are generally not bulky, especially the kids’ clothes which do not take up their entire carry-on suitcases leaving more space for the adults. We usually do a load of laundry mid-trip to cut down on over packing. In some cases, we have used the hotel laundry service which can get expensive for a small load but on our last vacation we found a laundromat in the town of Aix-en-Provence where we were able to drop off and pick up the following day and this was a much cheaper option. We will probably continue to go this route on all future trips.
Packing List:
- Passports and photocopies of passports
- Folder with printed itinerary and all printouts of reservation and ticket confirmations
- Electronic devices, USB cords, universal chargers. Most hotels have USB ports for charging phones and all other electrical devices but not all hotels and sometimes you may want more ports than are available in the hotel room. It is good to bring a USB cord for each device and at least one or two universal chargers in case you need to charge directly from an outlet.
- Clothes. My motto is functional but fashionable. I pack plenty of shorts, t-shirts, tank tops, underwear and socks for the kids. I also include a couple pairs of lightweight long pants for my son to wear to dinner as well as a few extra skirts and dresses for my daughter. My husband packs plenty of t-shirts, tank tops and shorts and just one or two long pair of pants and button down shirts for dinners. I bring an array of light dresses, lightweight pants, tank tops and t-shirts that can be worn to sightsee or for dinner as well as a bunch of bathing suit cover-ups that can easily transition to walking around town and eating in a restaurant. On the plane, we usually wear light long pants or leggings and bring a light jacket or sweater because it tends to get a little chilly on the plane.
- Shoes. I try to limit the shoes because they are bulky. We each have a comfortable pair of walking shoes; sneakers for my husband and kids and walking sandals for me are like walking on clouds. We each bring a pair of flip-flops and water shoes for the rocky beaches. The kids bring another pair of shoes like Toms for my son or cute sandals for my daughter while my husband has another pair of lightweight sneakers and/or shoes and I bring a couple pairs of fun sandals for the evenings or days of light walking. Plan for everyone to wear their bulkiest shoes on the plane.
- Bathing suits. We average about four or five per person because we swim almost daily.
- Prescription medications. Make sure that you will have enough of any prescription medications to cover the duration of your trip. Check the TSA website and with your doctor to see if a doctor’s note for any of the medication or equipment is required.
- Over the counter medications and supplements. Take the obvious such as Tylenol, Advil for pain, Benadryl for those who have severe allergies, and any other remedies needed on a daily basis as well as some Band-Aids and anti-bacterial ointment. Do not have to go overboard but just enough just in case. If you need more, there are always plenty of pharmacies around.
- Sunblock. Pack enough travel size sunblock to get through the trip. You can buy from a local pharmacy but we have preferred brands and try to avoid unnecessary trips to pharmacies to get toiletries if possible.
- Goggles (if you prefer) and swim vest(s) for children who still need a little help in the pool or ocean.
- Toothbrushes and travel toothpaste but if you forget many hotels supply both these days.
- Feminine products for those who will need them while away. I prefer to bring the brands I like if I know for certain that I will need them on vacation.
- Jumbo or extra large plastic zip lock bags for wet clothes, water shoes and child’s swim vest if necessary. Also use zip lock bags of varying sizes for toiletries to avoid any spills in luggage.
7. Go On Vacation
After endless hours of planning and researching it is time to go on the vacation of our dreams. Thanks to the careful planning, we have had blissful vacations with just a few minor hiccups. I go into the vacation with the mindset that we are there to enjoy our time together as a family and hopefully see and do as much as we can but will not be devastated if some things fall by the wayside. We do adhere to the schedule with respect to tickets purchased for various sites and train tickets for when it is time to change locations but there is flexibility and room to make changes along the way.
Above and beyond everything else, these vacations are designed for us to bond as a family. They give us a break from our daily routines, the minor headaches of running a business and the opportunity to reconnect with each other and ourselves. Since my children are 4 and half years apart, I have noticed that on vacations their friendship is revived and the bickering amongst them becomes less frequent. This subtle shift in their relationship contributes to the pleasant and mellow vibe that sustains us for two plus weeks while we are away. Walking through history or just being surrounded by beauty has expanded our outlooks that naturally enhance our personal development and I am so grateful my children have been exposed to all of these experiences during their formative years. While we are away, our daily routines are temporarily forgotten until we return home feeling refreshed and renewed every time.
My joie de vivre is planning vacations spent with my family and looking at art. Voila!
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