Planning your Trip

By:  Jennifer Milano, written April 2015, updated October 2016

Health & Safety

Before booking a trip, there are two important items to check out.  First, health and safety.  For health, you can visit www.cdc.gov and look at your destination to identify the health risks, and determine whether you need vaccinations and/or medications.  When traveling with children, for instance, you may not be willing to travel to a malaria-infested location or region experiencing a current Dengue fever outbreak.  After identifying health concerns, of course consult with your physician or a travel medical clinic to help make your healthcare decisions.  When traveling to developing countries, I always ask my doctor to prescribe a course of Cipro, an antibiotic that can help with bacteria-based gastrointestinal ailments.

For safety, you can start with www.dos.gov to check travel warnings issued by the United States government.  You can also read the travel warnings imposed by other countries’ governments, which often differ from U.S. warnings.  You can find travel information by the U.K. government here:  https://www.gov.uk/foreign-travel-advice, and by the Australian government here:  http://www.smartraveller.gov.au/zw-cgi/view/Advice/.

Weather/Seasons

After satisfying health and safety concerns regarding your chosen destination, next you should look at the weather.  The rainy season usually offers better deals, but you may or may not want to travel then.  Read up on how rainy it is - just a passing shower here and there or full-on daily downpours?  You may be restricted to certain travel times due to school or work vacation schedules, but to the extent you can avoid peak tourist season in your destination, you will find reduced costs and crowds.  Also, it is helpful to check calendars for local holidays and festivals.  Your trip may be driven or enhanced by a local holiday celebration, or it may be hampered by bigger crowds or closings of restaurants or sites.  

Personally, I avoid the major holidays when possible, finding plenty of cultural opportunities in smaller festivals or daily experiences (but part of that is that my husband hates crowds, and I am disappointed when a restaurant or site I’ve been wanting to experience is closed).  In summer, many European restaurants close for 2-4 weeks for vacation, and despite the best planning you will organize your day around lunch at a recommended cafe in a village someplace only to find a “chiuso/cerrado/ferme” sign on the door.

Passports, Visas & Security

I keep our passports updated at all times, making sure none of our passports expires within six months of travel (some countries will restrict admittance for travelers with passports expiring within three-six months of travel).  If you do not have a valid passport, you will want to get one as soon as you are contemplating international travel.  If you are a U.S. citizen, click here for details.  You should also check entry and exit requirements for the countries to which you are traveling to determine if you need a visa or other documentation.  You can use the U.S. Department of State website, but I advise searching for a source from the countries you are visiting, to ensure you are receiving accurate and up-to-date information.

My husband and I obtained Known Traveler Numbers through the TSA Pre-Check program, so we can access the quicker security line at most U.S. airports, as long as we are taking one of the airlines with which TSA Pre-Check participates (the list of participating airlines is shorter than you think).  Children 12 and under can go with their parents through the Pre-Check line.  Once a child turns 13, you need to apply and get TSA Pre-Check status for him or her.  Be certain that you input your Known Traveler Number in your airline profile when you make your reservation, or before checking in online.  If you skip this step, your boarding pass will not show that you have Pre-Check status, and you cannot use the Pre-Check security line.  We think that despite its limitations, TSA Pre-Check has been well worth the hassle (waiting in line at an approval center) and expense (currently, $85 per person, good for five years) of getting approved.  Click here for more information on TSA Pre-Check.

Another option is Global Entry, which provides travelers with the same benefits as TSA Pre-Check, plus expedited entry through U.S. immigration and customs.  The downsides to Global Entry?  Cost ($100 per person, good for five years) and a more involved application process (you must travel to one of the international airports that has a Global Entry Enrollment Center).  My husband, kids and I all have Global Entry and since we almost never check bags, we are out of the airport within 15 minutes of exiting the plane. If you tend to check bags, Global Entry may not be worth it for you, as after you sail through immigration, you will likely be stuck at baggage claim.  Click here for more information on Global Entry.

We also have CLEAR, which theoretically allows you to skip the identification check at the airport. Instead, you visit a CLEAR kiosk with CLEAR staff escorting you to the front of the identification check line. Sometimes this works well. Other times, the CLEAR line is longer than the regular line, and it is common to be randomly selected to show your i.d., anyway. The upshot: I will pay a significant amount of money for a shorter line, or at least for the option to get in the shortest line. Click here for more information on CLEAR.

Where should I go?

If you are starting from scratch and have no idea where to go, think about your goals for the trip.  What do you like to do?  What do your travel companions enjoy doing?  Are you seeking adventure, relaxation, and/or connection with local people and culture?  Do you want quick, easy connections or be somewhere more remote and less-touristed?  What is your budget?  You can narrow down your choices by the safety, health and weather concerns discussed above, and by financial concerns such as airfares, currency exchange rates and land costs.  Google’s flight tool allows you to search by region or budget, which can help focus your search, as well.

In addition to checking online sources (including this website!), I sometimes find it helpful to read a travel guidebook for the places in which you are interested.  You can often find guidebooks in your local library, so you can have a free, quick read to get a sense of your chosen country or region.  For Europe, I tend to favor Rick Steves's travel guides.  For other areas, I usually read Amazon book reviews to decide which guidebook to read or purchase.  I often use the little tape-style post-it notes to tab the book, writing on each tab so I can easily find information once we are on the road. Or, I create a Google doc with an itinerary and links that I can easily access while traveling, and which contains all of my accommodations, restaurant and ticket reservations.

Budget

The two things that limit my travel are time and money, and I’m guessing it is the same for most people. If your budget is limitless, you likely will be more comfortable.  Many of the world’s best hotels have become out-of-reach for all but the super-wealthy. But with a limited budget, you can still have an amazing travel experience.  In fact, if you want to meet other travelers and natives, and immerse yourself in the local culture, you are better off staying in small guesthouses. If you want space and the convenience of a kitchen, you can save quite a bit of money by staying in a house or apartment rental. Watch out for scams. If your apartment rental comes with a free airport pick-up, steer clear. This is code for “we aren’t going to give you an address.”

Accommodations

Resources for rentals:  

Hotels:

  • I rely heavily on tripadvisor.com.  I apply filters on items that are must-haves for that particular trip, e.g., a swimming pool, and spend hours reading reviews, narrowing down my choices, checking the hotels’ websites looking for rates and deals and emailing hotels asking for early booking discounts.  I wish there were more filters on tripadvisor, like "has rooms that accommodate four people", although tripadvisor recently added an "air-conditioning" filter, which is great.  I also use the “Specialty Lodging” tab, and have found some of our favorite accommodations that way.  In Italy, for example, we like to do farm stays with the kids.  I don’t do Priceline or deals where I can’t choose my hotel - I’m too picky about what I want and unless it’s just for a night in New York or Boston, I want to select my hotel based on my preferences.

  • whatahotel.com is a great place to book a high-end hotel and receive perks.  You normally pay the same rate as on the hotel’s official website, but you will get perks such as complimentary breakfast, food and beverage credits and free wifi.

  • jetsetter.com often has good deals, marking down hotels substantially.  However, they are usually for the upcoming couple of months, making it harder to find a deal months ahead of time.  I use this most often for local travel that I don’t plan very far in advance.                 

  • One challenge for families is finding hotel rooms that will accommodate all of you.  Rules vary.  Where in the U.S. normally children under 18 can share a parent's room at no additional cost and hotels routinely offer rooms that accommodate four people, in Europe you will often find hotels charging for children over age 2 or 3, or sometimes 12 - it just depends.  And it is hard to find hotels that accommodate four or five people.  You can do it, it just takes research.  Or, read my destination pages for recommended hotels that can fit your whole family!      

  • A tip:  Email the hotel concierge directly when you make your reservation listing your requests or concerns.  You can usually find the manager's email in his/her replies to TripAdvisor reviews, or on the hotel's website.  Sometimes an email to the hotel manager accomplishes nothing, but in some cases, it will secure you a complimentary upgrade, early check-in or a room away from the elevator.  I always refer to TripAdvisor somewhere in the email, so the manager knows I use the site and will likely review my experience.

Airfare

I longingly remember the days I could fly from New York to Europe for $600 nonstop in peak season.  While there are lots of deals out there, particularly if you don't mind changing planes in the middle of the night, they are scarce.  Resources: 

  • Recently, I flew Aer Lingus from New York to Amsterdam via Dublin, for just under $800 roundtrip in summertime (versus $1500 to fly nonstop).  Was it a little more stressful having connections to make?  Yes.  Was it worth the savings?  Yes.  The connections for our trip were fairly smooth, the Aer Lingus flight attendants were friendly, and on the way back to the U.S., travelers clear immigration and customs in Dublin!  This means that you arrive back to JFK just as you would from a domestic trip, and avoid long lines just when you are at your most exhausted point.  Caveats: (1) At the time of my travel, Aer Lingus did not participate with TSA Pre-Check. Check before you book if this is important to you; and (2) I learned when I returned home that my request for partner frequent flyer miles on United was rejected. Read the fine print on your fare class if mileage credit is important to you.

  • Use your miles.  This is becoming more and more difficult to do, particularly if you have a family, want non-stops, are traveling in peak season, or have a pulse.  Personally, I find Delta miles easier to redeem than American or United, which often require two airplane changes unless I want to leave at 1:00 am.  To earn miles, I have a Starwood American Express card, which allows me to redeem on multiple airlines, and often at a ratio of better than 1:1.  I have also applied for new cards that offer the first year without a fee and lots of miles, deposited the miles, and canceled the cards before the annual fee kicks in.  While this may affect your credit rating, my understanding is that any effect is short-term. My Delta American Express card allows me to board the plane earlier and earn miles for flights.

  • For long-haul, multi-stop airline travel, try airtreks.com.  I used this company in 1997 for a 5-month backpacking trip, and again in 2002 for a 7-month backpacking trip.  I’ve priced them out recently for shorter, multi-leg trips, but with only a few stops it was less expensive to book airfare myself.  I also used them in 2017 for a multi-stop itinerary in Africa when I wanted to use one airline to South Africa and another airline from Zanzibar back to the U.S., which I could not have booked on my own without paying exorbitant one-way fares.

  • I use google.com/flights to find fares, and normally book directly on the airline website so that if I need to make changes later on, I am dealing directly with the airline rather than a third-party travel company.  There are all sorts of opinions about finding low fares based on the day or time you search, but I think starting as early as possible is your best bet.  I find that airfares rarely go down, and usually go up, the longer I wait to book, but of course, that isn’t always the case. It also seems that the more I check a route on google flights, the more the fare rises, so I try not to check too often before booking.

  • Keep your eye out for a deal.  For a span of 2 days in January 2015, and again on two occasions in 2016, you could buy TWO roundtrip tickets from New York to Milan, Italy on Air Emirates for $700 roundtrip for travel before mid-May - that’s $350 per person, roundtrip, nonstop.  How did I hear about it?  I hang out with other people who are travel-obsessed like I am, and one of them was on an email list from Air Emirates and forwarded it around.  Could I take advantage of it?  No - I had booked our spring break tickets already.  Usually planning ahead is a good thing, but not always - in this case, my hyper-organized sensibilities meant I missed out on a deal.  Again, if I had unlimited time to travel, I could have tacked on another vacation in May.  But I don’t.  I work, my husband works, my kids are in school, and the deal required a minimum seven-night stay.

  • Book legs on different airlines, e.g., fly Virgin Atlantic to London, then book your flight to Pisa on EasyJet.  Or fly Delta to San Diego and then fly Alaska Airlines to Maui.  This can often save you money but beware that if your first flight is delayed and you miss your next flight, the airline has no obligation to re-book you because you haven’t booked the full itinerary through that airline.  For this reason, I try to leave plenty of time between flights, and/or make sure my travel insurance will cover a missed connection that the airline won’t (caveat: read the fine print in your travel insurance policy, as most policies won't cover missed connections unless your first flight was several hours late).  I’ve read advice to plan 24 hours between such connections, as you would for a cruise ship departure, but often that isn’t practical and can waste valuable travel time.  Weigh the risks and benefits, insure what you can, try to take early morning flights to minimize the risk of delays, and cross your fingers (the latter advice not consistent with my Type A planning, conceded).

  • Check out Scott Keyes's site, scottscheapflights.com.  He looks out for airline mistake fares and deals and alerts followers by email.  This works best if you have a flexible travel schedule.  Also, while you can sign up for emails for free, if you want "premium" service, meaning all of the deals Scott finds, it costs $15 per month.

  • Before reserving your seats, enter your flight number into www.seatguru.com, which will tell you pertinent information about your plane (such as whether it has a power source or in-flight entertainment), as well as about each seat (like whether a particular seat is a poor choice because passengers often bump into it on their way to the bathroom).

  • Don't want to deal with it?  Consider paying an expert to book your flights for you.  Cranky Concierge will book your flights, track them and deal with any changes that need to be made.  For $60 roundtrip domestically, or $90 roundtrip internationally, Cranky Concierge will book flights for up to four people.  Or, if you booked your trip yourself but your flight is canceled, you can contact Cranky Concierge and for $150 they will rebook you and you can avoid standing in a long line or waiting on hold with the airline to fix it.  For experts on using points, miles, including stopovers and any other tricky itineraries, click here for an article by Condé Nast Traveler including several other recommended airfare companies.

Train tickets in Europe

Sometimes, using the official rail sites works for U.S.-users, and other times they do not.  If you want to give it a try, choose "U.K.," for your country on the rail site's home page.  This has worked for me in the past, but more often than not my purchase is rejected, perhaps because I am using a U.S.-based credit card.  If you choose "U.S.A." for your country of residence, you will be re-directed to raileurope.com.  Rail Europe works fairly well, but I have found that it does not display all of the train options all of the time.  My friend, Harriet, recently used www.capitainetrain.com to book her European train tickets, and highly recommends the site for its ease of use and comprehensive list of options. 

Before you purchase any type of rail pass from any site, compare the price of the pass to the individual tickets.  A pass is not always a good deal, especially given the restrictions (e.g., you may need to pay a fee for the reservation-only faster trains between cities that you will undoubtedly want to take).

Car rentals        

I use kayak.com to search and compare rates, usually booking directly with the car rental agency using whatever loyalty program makes sense to earn miles or points.  For Europe, we often use autoeurope.com to book our car rental with a local agency for us. We also carry our own child travel booster seats, which are always free to check with the airlines, and avoid paying the exorbitant fees the car rental agencies charge for child safety seats.

When we arrive at the airport, we often split up and my husband books it to the car rental counter to avoid the long line that will inevitably form, while the kids and I wait for the luggage or stop for the bathroom or a snack.  Also, if we are renting a car from the airport, I consider this aspect when booking a flight.  For example, flying into Pisa is so much easier than Rome, and I know that we will get our car and find our way out of the city much, much faster and with less stress than at Fiumicino.  

I also like to have a paper map, if the GPS instructions are taking us in circles or our phones aren't working.  The best local maps are purchased, well, locally.  Stop at a gas station or newsstand and invest in a detailed map.  Also, before you leave your wi-fi haven, take a screen shot with your phone of the address, directions, contact and/or or map page of your destination.  If you are relying on your phone and lose service, you can refer to your camera roll for information. Also take a photo of where you park - at an airport, on the street, or in a lot, just in case.

Cell phones

We always pay AT&T’s daily rate for service while traveling abroad. It is worth the cost to not worry about it, and have access to data when you need it.

Credit cards and Money

According to my husband who is the credit card expert in the family, the only card that has no foreign transaction fee for purchases made in foreign currency AND has no annual fee is the Capital One World Mastercard.  It offers cash-back, and is our main family credit card.  We also have a Starwood American Express card, which I think provides great travel benefits as you can redeem points for hotel stays and for travel on many airlines.  Converting 20,000 Starwood points yields you 25,000 miles on most airlines.  Finally, I have a Delta American Express card, which gives us early boarding as well as some other benefits.

We normally use an ATM card while abroad, pulling cash out in local currency as that tends to give you the best exchange rate with no or minimal fees.  My Charles Schwab ATM card reimburses ATM fees worldwide, although even the ATM fees are worth the convenience and savings of using an ATM card.  Caveats:  (1) Before you depart, you should research that your card will work at your destination; and (2) Sometimes airport ATMs are either malfunctioning or hard to locate.  These days, you can use Apple Pay or a credit card for almost every purchase anyway. If the exchange rate is good and we are someplace we travel to frequently, we pull out extra cash to bring home for our next trip. It makes me feel extra prepared to have a stash of Euros in my travel closet. (You read that right, I have a travel closet.)

Travel insurance

In my more carefree travel days, I never purchased travel insurance.  Now that I have children and make most of my arrangements well in advance, often requiring nonrefundable prepayments, I usually buy travel insurance.  Being an attorney, I actually read the fine print on these policies, and try to select the one that comes closest to meeting my needs.  For instance, when we traveled to Greece and were taking ferries, I wanted a policy that covered costs caused by a travel strike.  When booking flights on different airlines for same-day travel in Costa Rica, I wanted a policy that covered missed connections due to airline delays.  For the latter, I found that travel insurance companies typically cover you for connections due to delays in the range of 3-5 hours, which is often useless for travelers who want a closer connection time.  For trips that are lower risk, I forego the insurance.  For example, when we flew to San Diego and stayed with friends, paying for the car rental on the day of pick-up, the only financial risk I was taking was the change fee for the airline tickets should I need to cancel, or, the worst-case scenario, the cost of a one-way ticket home if an emergency required our immediate return.  In that case, to me the cost of insurance outweighed the benefit of purchasing it.

Hiring an expert

If all of this sounds too daunting to take on, you can pay a travel expert to book your trip for you!  If you go that route, you should at least research the options to find the right person.  Here is a list of agents vetted by Wendy Perrin, formerly of Conde Nast Traveler and now of tripadvisor.com.