The Top 5 Recommendations For Booking Your Flights

For travelers who haven’t made travel planning their favorite past time activity, a part time job, or even their full time job (and believe me…it’s a full time job) – booking your own travel, and especially flights, can sometimes seem daunting. But read on, travel friends. Because we are not going to leave you high & dry! Here are some invaluable recommendations that will help you take flight when booking your own airfare.

Having a 3rd party involved with your flight reservations can often slow things down when you need immediate action during flight delays, cancellations, or missed connections. You need solutions fast and you’ll get the quickest & best resolution scenario straight from the airline if you book direct. This is truer than ever amidst our current travel climate. Getting notified of flight status updates, obtaining refunds or vouchers from the airline when flights change or cancel, or even speaking with them directly about special requests or needs makes booking directly with the airline much preferred to booking through a 3rd party that can impede that process. In fact, many airlines often discriminate when it comes to customer service issues regarding changes & cancellations – they may not even speak to the traveler directly if a 3rd party is involved. By booking & dealing directly with the airline, representatives have the authority to get things done and centers dedicated to dealing with these customer care issues.


Prime Booking Window
Booking your flights TOO early may cost you. Buying more than 6 months prior to your trip won’t allow room for deals or special offerings from the airline yet. Resist the urge to book your flights too far in advance. Sign up for alerts from your airlines of choice so you can be notified when prices start to drop – usually about 5 months before departure. On the other hand, booking flights too last minute will cost you and you may not find the schedules you need. Prices rapidly spike in the final 2 weeks before take-off. The prime window to book is between 112 to 21 days before departure (closer to the 112 needle for international flights).

Days of the Week
Many people book their airfare on weekends when they tend to have more time & energy to devote to travel planning. Airlines cash in on this. Book during the week. Tuesdays are particularly opportune days to book with many deals popping up on these days or other weekdays.

Routes, Fares, & Schedules

Early Mornings
It may be difficult for some of us night owls to rise before dawn for that early flight, BUT departing between 5am & 8am usually offers better pricing, saves a lot of stress without the crowds, and can avoid potential flight delays with the early morning airspace being relatively clear.

Sundays tend to be the most expensive day of the week to fly. If you can be flexible, you can save hundreds of dollars. Typically Tuesdays, Wednesdays & either Monday or Thursday can offer the best savings.

If you can’t find a good flight schedule from your home gateway city – or you prefer to connect domestically through a U.S. city as opposed to one in Europe – consider these gateway cities that offer direct flights to Barcelona & Lisbon respectively…

  • Philadelphia (PHL), Boston (BOS), New York (JFK & EWR), Miami (MIA), Chicago (ORD) & San Francisco (SFO)
  • Philadelphia (PHL), New York (JFK & EWR), Miami (MIA) & Washington Dulles (IAD)

Because your cruise departs from one city and arrives into another, you will either need to book 2 one-way fares or, better yet, a “multi-city” fare. When booking through your preferred airline, select “Multi-City” option and enter your details. The Airport booking codes are BCN for Barcelona & LIS for Lisbon. You will usually find much better pricing & more route options by booking this way.

Resist the temptation to book anything with too tight a connection. Account for flight delays, customs & additional security lines especially when traveling internationally. General rule? Allow at least 1 hour for domestic connections and at least 2 hours for international – maybe more. In my recent trip to Spain & Portugal to scout out our hotels, I had a 1.5 hour connection in both Paris (CDG) en route to Barcelona & Amsterdam (AMS) on my return home. It was nowhere near enough time for those massive airports and customs & security. With the arrival flight delayed, deplaning, having to go through a very long customs line, an even longer security re-screening line, and the arrival & connecting gates being at the furthest points possible from one another – in 25 minutes, I ran almost 2 miles among throngs of other travelers with no stop for a bathroom or beverage after a very long overnight international flight. I barely made it, but was dripping travel stress sweat head to toe. Do not set yourself up for this type of stressful frustration & risk of missing your flight. My return through AMS within the same time constraints was no better. Of course, if you can opt for the slightly pricier non-stop flight, it may save you in the long run…or…from at least a very long run.

Connecting Cities
Not all connecting cities are created equal. As I mentioned, CDG & AMS are two of the most frequented for Barcelona & Lisbon travel. They are amazing airports, but they are huge. Plan your connections accordingly. Alternately, opt for a connecting city like stunning Madrid and spend an overnight or two.

Arrivals & Departures
It is always recommended to arrive into the city from where your cruise departs AT LEAST a day prior to the cruise to account for flight delays, cancellations or missed connections. Do not plan to arrive into Barcelona or Lisbon the morning of your cruise departure and expect all things to go according to plan…and get you to your cruise check-in for an on-time departure. Arrive early to avoid any disappointment or unneeded stress in joining the ship. For those insistent on arriving the morning of your cruise (and ALL the good energy being sent your way!), ensure you arrive with enough time for customs, baggage retrieval, transportation to the pier, and checking in for your cruise no later than 3pm.
For Departures, again, why not stay a day or two after your cruise and enjoy the city or surrounding region? If you must fly home the day of disembarkation, ensure your flight departs no earlier than 1pm that day to account for ship disembarkation procedures, luggage retrieval, customs & immigration, transportation to the airport, and 3-4 hours at the airport for international departures. Please do not book return flights earlier than this to avoid frustration, stress or missed flights.

Budget vs Standard
Don’t always grab the cheapest flights. “Budget Airfare” often seems to be too good to be true and often, it is. There are usually fees for everything from checked and even carry-on bags to anything else they can think to charge for…like dry peanuts & pretzels…sometimes costing as much, if not more, than a standard ticket. So if you’re not booking “budget” how CAN you save on airfare?

Savvy travelers and amateurs alike will offer all kinds of advice on how to book your flights. Here are OUR suggestions based on a whole LOT of experience.

Website Tracking
It’s true. Booking websites can track your flight research and increase their prices by assuming you’re likely to make a purchase on a flight you’ve been searching. Remain under wraps by browsing or buying your tickets in a private browser or “incognito mode.”

Google Flights
Start your search with Google Flights. Their search engine is super easy, fast, & informative. Zero in on the best airfare then check and book directly with the airline.

Book Direct
By booking direct with the airline, you’ll guarantee mileage accrual and credits toward your status, loyalty benefits while traveling, the 24-hour booking grace period (more about that in a moment) and direct customer service. You’ll often get the same fares you would by booking through an OTA (Online Travel Agency like Kayak or Expedia) especially if you sign up for those deal alerts through your airline of choice. AND you cut out that middleman – being able to work directly with the airline reps that have authority to actually resolve issues that might crop up during your trip. Another bonus? If you have that co-branded airline CC (like Delta Skymiles AMEX), you’ll earn even more miles when you book direct. If you aren’t comfortable booking online, you have the option to call the airline’s reservations department and they will be more than happy to assist you with your flight booking. Sometimes they may add a small fee to a reservation made by phone, but that nominal cost may be worth the peace of mind. Another travel booking service will most likely charge you the same, if not more, in service fees. So you may as well give that to the airline and get what you pay for.

A Note About OTAs (Online Travel Agencies)
It’s important to weigh the options when considering booking with an OTA like Expedia or Kayak versus directly with an airline. Sometimes you’ll be able to find a cheaper fare on an OTA compared to directly through the airline. At other times the price will actually be cheaper with the airline. And are those savings with the OTA worth the potential hassles? OTAs appear to offer cheaper deals – and you can often score with these discounted fares. BUT you may end up paying more in hidden fees (like cancellation & change fees, luggage add-ons, etc.) and you will certainly see the true cost when they can’t help you with that missed connection, flight delay or cancellation because they are one-step removed from the airlines themselves – and also often unreachable. OTAs are not known for their stellar customer service. You’ll also be the first “bumped” since OTAs are notorious for overbooking flights & hotels and sometimes you won’t even be notified your reservation is no longer confirmed until you show up to find out the OTA overbooked you. Pre-COVID, booking with an OTA was more enticing for the possible savings. But now, being able to work directly with the airline if problems arise could easily outweigh any savings you might have gotten from the OTA. It’s important to consider what you may be giving up:

  • How much would I be saving?
  • What is dependable customer service worth to me?
  • What’s the possibility I’ll need to change or cancel my flight?
  • Am I maximizing my opportunities to earn miles?
  • How much is that 24-hour free cancellation worth to me?

You can generally earn miles through OTAs but not always depending on the fare class they contracted with the airline. With OTAs, you’re paying for a travel agent you aren’t even getting.

OTAs in a nutshell…Cancellation & change fees are more punitive, getting a refund is like pulling teeth, you may not earn mileage or elite credit, customer service is essentially non-existent, the deals aren’t always that good (or worth it), & heaven forbid a storm or other travel disaster comes along during your travels. Good luck.

If you have AAA or are an AMEX Platinum or Centurion member, these companies offer great travel services for booking international air – if you do not want to book direct or are not comfortable booking on your own.


Not confirming ALL of the important details before hitting that “Book Now” button like your life depended on it can and will cost you. Make sure you have selected the right airport (i.e. in New York, Washington D.C., or even Portland, OR as opposed to Portland, ME), departure & arrival dates (Jul can look like Jun), times (am/pm, time difference with time zones, & red-eye flights into Europe having you arrive the next day), and make sure your personal information is EXACTLY how it appears on your passport.

That 24-hour Grace Period
Airlines (if you book direct) must allow you a 24-hour grace period to cancel the flight you just booked without penalty (it’s a federal law if the flight touches U.S. soil). At the very least, it gives you time to recheck all of those important details and make sure you didn’t make a mistake when you were booking that flight at midnight while your eyes were glazing over. This grace period doesn’t necessarily apply to bookings made through OTAs.

Check your emails for your confirmation(s), print or save your documents as a PDF on your phone, and download the airline’s App to have your flight details & status updates on you at all times – especially if the airline has made any last-minutes changes.  

And speaking of updates…
We’ll offer more tips for preparing for your flights, tips during air travel, and how to mitigate the effects of jet lag as your trip gets closer so stay tuned for our updates.

For now, we hope these recommendations help you find fantastic flight options for your cruise at fares that will allow you to spend more of your travel budget on the ground in Europe!

Rebekah is Redwood Travel Partners’ Director of Travel Services and Senior Travel Advisor. She has worked in the travel industry for over two decades as a Travel Advisor and Cruise Planners franchise owner, Cruise Director, and performer at sea and has traveled to over 95 countries on all 7 continents.
Redwood Travel Partners is an independently owned and operated Cruise Planners franchise formed as the official travel partner for charter cruises while offering a full range of travel services.

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