How I Bought Discounted Business Class Tickets to Portugal

For any flights over five hours Allan prefers to fly business class due to his stature and proclivity for blood clots.   Therefore I spend days scowling the internet looking for deeply discounted business class tickets.  Since we have an upcoming seven week voyage to Europe and northern Africa, including a cruise down the Nile, I recently scored a killer deal from Boston to Portugal on Azores Airlines for only $1,675 USD round trip per person in executive class.   As an added bonus, the itinerary includes a five day layover in the Azores at no additional cost.

How I Bought Discounted Business Class Tickets to Portugal

How I Bought Discounted Business Class Tickets to Portugal. View of Winthrop, just outside Boston's Logan Airport. A good friend, Heidy, grew up here.
How I Bought Discounted Business Class Tickets to Portugal. View of Winthrop, MA, just outside Boston’s Logan Airport. A good friend, Heidy, grew up here.

When I first started searching for business class tickets to Europe out of my home airport of Cancun, Mexico, prices fluctuated between $5,000 – $8,000 USD round trip per person.  That’s more than twice what we paid last year to fly from Boston to Beijing.  Therefore I figured there had to be a less expensive executive class option.

Hence I initiated inquires using the east coast of the USA as my starting point.  I thought flights might be cheaper than leaving from Cancun.  That’s when I found the business class fares on Sata (Azores) Airlines from Boston, MA to Lisbon, Portugal.  This includes a 3 day layover on Terceira Island in the Azores on the way over.  Then on the way back to Boston from Lisbon we enjoy 2 full days on the island Ponta Delgada, Azores.

In other words, we’re paying roughly half-price compared with other business class alternatives.  And we get to explore the Azores, which weren’t even on my radar, at no additional cost.  Here’s what I did.

How I Bought Discounted Business Class Tickets to Portugal. View of Boston on our landing into Logan Airport. I used to live on the Charles River near the bridge to the bottom of this photo.
How I Bought Discounted Business Class Tickets to Portugal. View of Boston on our landing into Logan Airport. I used to live on the Charles River near the bridge to the bottom of this photo.

Be Flexible on Dates

Our schedule is flexible for our seven week trip to Europe and Africa other than a cruise down the Nile which is already set in stone.  Therefore I used flexible dates on both ends of my flight query.  Plus I kept changing my dates till I found an option that worked price wise.  Flexibility with a few days on either end of a voyage can make a difference in the bottom line.

How I Bought Discounted Business Class Tickets to Portugal. Charlotte Airport taken during a connecting flight to Boston. Charlotte is a hub for American Airlines.
How I Bought Discounted Business Class Tickets to Portugal. Charlotte Airport taken during a connecting flight to Boston. Charlotte is a hub for American Airlines.

Be Flexible with Your Departure City

When I originally searched for departures from Cancun to various European and north African cities, costs compared with the purchase of small economy vehicle.  Then I began searching other departure destinations.  I knew I could fly to Miami, Boston or New York at little to no cost from my home in Mexico either with miles or with discounted fares.

Since these cities are hubs, I suspected they would offer some lower priced fares.  And by sticking to the East coast I helped ensure a shorter flight as compared to say California and most likely a less expensive ticket.

How I Bought Discounted Business Class Tickets to Portugal. View of the harbor as we land in Miami. If I ever moved back to the US, it would most likely be in the Miami area.
How I Bought Discounted Business Class Tickets to Portugal. View of the harbor as we land in Miami. If I ever moved back to the US, it would most likely be in the Miami area.

Be Flexible with Your Destination

Our original plan was to start in Portugal and then head to Morocco, Egypt, Turkey, Jordan, Israel and France.  However, we didn’t necessarily need to visit countries in a certain order.  We could always vary our trip depending on price and schedule.

Therefore I started looking for flights into a number of cities, including European hubs like Frankfurt and Brussels.  These places often have discounted fares, plus they provide short budget flights around the continent.  So once I’m in Europe, getting around is easy and economical.

How I Bought Discounted Business Class Tickets to Portugal. Miami International Airport. This is the 40th busiest airport globally.
How I Bought Discounted Business Class Tickets to Portugal. Miami International Airport. This is the 40th busiest airport globally.

Use Multiple Websites

I started my search on Kayak, since I often find the best deals.  However, I also used Google Flights since they have a friendlier and more easily customizable interface.  But in the end I wound up booking on Priceline since they offered the lowest rate and ideal itinerary this time.

How I Bought Discounted Business Class Tickets to Portugal. View of Boston Logan Airport after take off. I spent the first 18 years of my life living in the Boston area.
How I Bought Discounted Business Class Tickets to Portugal. View of Boston Logan Airport after take off. I spent the first 18 years of my life living in the Boston area.

Try Multi-City Itineraries

I didn’t originally search for a multi-city itinerary.  That’s where you fly into once place, then go somewhere else other than the city of origin.  Actually I had initially looked for round trip tickets.  But when the $1,675 round trip fare from Boston to Lisbon appeared, it included a short layover in the Azores.

This prompted me to wonder: if extended my stay in the Azores, would this negatively impact my bottom line?  Consequently I decided to search using a multi-city itinerary.  First I chose Boston to Terceira, Azores for the first leg.  Then I selected a flight out of Terceira to Lisbon 4 days later.  For my return flights I elected Lisbon to Ponta Delgado, Azores 6 weeks later.  And finally we fly from Ponta Delgado to Lisbon 3 days after.

Amazingly even with the added days the trip price remained the same.  Later I learned Azores Airlines offers free stopovers on these islands for up to 7 days for flights leaving from the US.  I would have never known this if I hadn’t chosen a multi-city itinerary.

How I Bought Discounted Business Class Tickets to Portugal. Landing in Logan Airport. Logan is a hub for Azores Airlines, Delta and JetBlue.
How I Bought Discounted Business Class Tickets to Portugal. Landing in Logan Airport. Logan is a hub for Azores Airlines, Delta and JetBlue.

To Summarize

Essentially remain flexible with your dates and cities of departure and origin.  Also traveling during low or shoulder season often lowers your total cost.  Lastly, be persistent.  Don’t get frustrated.  Deals do exist.

Do you have any questions or comments?

Please let me know in the comment!

Happy travels,

Matt Weatherbee

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Matt Weatherbee

Hi, I’m Matt.  In 2008 I quit my job, sold everything and drove from Boston to Mexico to start a business.  Now I live and work in the Carribean, and spend my free time traveling the globe.  Learn more.

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