Posted in Travel Planning

Portugal or Bust

Planning the Next International Adventure

In November, I reached out to you Readers and asked for ideas on  Planning Our Next BIG Trip .  Thank you to everyone who took the time to leave a suggestion!  After sifting through the answers on several social media platforms, I put together a list.  I did some research on each of the sites with the most votes before deciding on Portugal.  Portugal came up, I became intrigued and then it became clear to me that it was “The One”.

There are still a lot of questions to be answered as to the when and the final itinerary, but the outline is starting to form.

  • Porto                               2 days
  • Lisbon                             2 days
  • Algarve                           2 days
  • Ponta Delgada Azores 2 days (maybe)
  • Funchal Madeira          2 days (maybe)

The current itinerary is for 10 days plus 2 days for travel.  The only downfall is that this would use all but 2 of Mark’s vacation days for the year.  Ugh!

Some History

On our two previous trips to Europe, we traveled with a Tour Company.  For the first trip it was because we had never been to Europe and it felt safe and like there were more things we didn’t know than we did regarding international travel.  They planned out our 10 days in Italy and we just sat back and enjoyed the trip.  We did discover that we are not super crazy about being tethered to an itinerary that is not 100% our own.  On that trip, I was able to work in a few things not included on the list by simply petitioning the Tour Director and having a sound idea of time schedules and what I wanted to do.  Although it was a little pricey (who cares about the money, it was our 25th wedding anniversary) I have no regrets over the decision to use a Tour company for this trip.

For our second trip we were biting off a big chunk of Europe and traveling to 7 countries.  Since there was a lot of ground to cover (over 4000 miles) and there were a lot of logistics to that, we decided to do a Tour again.  I was prepared to save money on this trip though and took advantage of additional savings by booking during their Annual Sale, getting an Early Booking and Payment Discount and also utilizing a Past Guest Discount.  We waited 2 months after booking the main trip for their big Airfare Sale and basically got BOGO airfare (almost $700 less than our first trip).  Having done a Tour before, I knew what to expect for Optional Experiences and set a budget for those.  We spent approximately $1500 less for this trip than the first one just by being smarter the second time around.

What I liked about Tours:

  • Early Access/Easy Entry into Attractions
  • Included Tours
  • Having a Travel Director to “handle the little things”
  • Ease of  Inner Transportation
  • Low Stress

What I didn’t like about Tours:

  • Not much Flexibility to fit in specific things we wanted to do
  • Only visiting locations chosen by the Tour Company
  • Being in a large group ALL THE TIME
  • Short stops where you couldn’t really do or see much in the time allotted
  • Lots of added Costs

New Strategy

For the trip I am planning to Portugal, I am going to make all the arrangements myself. As seasoned international travelers,  I feel confident that we can navigate the logistics on our own this time. I have plenty of ideas for filling an itinerary and just need to pare them down to make it realistic.  The key is that there has to be a balance of relaxing days and exploration days.  I am also planning to work within a much smaller budget for this trip.

In order to challenge myself, I looked up the Best of Portugal 10 day Tour offered by Trafalgar.  The base price for the time frame we are looking at is $2725 per person without discounts, airfare, optional experiences or non included meals.  Once you budget those costs into the equation you are easily at $3500 per person.  I think I can beat that cost and am setting my HARD budget at $3500 for both of us for the entire trip!   That’s at least a 50% savings.  You might be thinking that I am crazy and that I could never do 10 days in Europe with airfare for 2 people at $3500, but I have a plan!

My SOFT budget goal is actually $3000 but I added a $500 contingency just in case.

Just because I plan to work within a smaller budget, doesn’t mean that I plan to skimp. I am just going to be smarter and use Points, Rewards and Miles to stretch my budget and allow me to enjoy some luxury.


Part 1 of my plan was signing up for the IHG Rewards Card in 2018 to help offset Hotel Costs on the trip.  I was already a Rewards Member, but adding the card gave us a huge jump in points.  When I got my card, it came with a sign up bonus of 100,000 points if you met a $3000 Spend Requirement in the first 90 days.  That was no problem.  I just switched a few bills over to pay from this card and bam, bonus earned.  During that time, there was also a Points Sale that allowed me to buy points with a 100% bonus match from IHG.  I did this buying 30,000 points for $300 and getting an additional 30,000 points match from IHG.  Since I used my IHG card, I got 10x points on the $300 purchase and it helped me meet my initial Spend Requirement.  Winning.  Since then we have also booked 2 stays with Holiday Inn using the card for 10x points and getting some slick bonuses too.


My Research has shown that there is a good selection of IHG Hotels in the 3 main cities that we will stay in.  I found a really cool beach front Holiday Inn in the Algarve that is only 25,000 points per night x 2 nights that is 50,000 points.  I also found a Crowne Plaza in Porto for 25,000 points per night x 2 nights that is 50,000 points.  In Lisbon, there are 2 Intercontinental Hotels and I am all about splurging for a little LUXURY.  The first one is 40,000 points per night and is located more centrally, while the second one is an  oceanfront gem costing 50,000 points.  Let’s say for budgeting that I go with the 50,000 x 2 nights for 100,000 points (the views look spectacular). That would make the total points for very nice hotels on those 6 nights in Portugal 200,000 points.  Since I already have 190,000 points that is very attainable.

The other nights on the trip, we will be in some crazy locations that mostly offer Boutique Hotels. These add on islands are where we get the SLOW TRAVEL and RELAXATION that brings balance to the trip.  As of yet we are still deciding which or both of these added locations we will be able to fit in.  Mark needs more vacation days!  My theory is that once you have spent the money on the flights to visit Europe, you might as well see and do as much as you can while there to get the most bang for your airfare buck.

Optional Stop  1 – Ponta Delgada & Furnas in the Azores

Ponta Delgada in the Azores (not sure we will get there yet) does have two Marriott hotels.  I don’t have many Marriott points right now, so if I want to stay there, I will have to start working on that.  Points range from 25,000 to 50,000 points per night.  At worst, we budget for those and the rate is around $200 per night x 2 nights so $400.  There are also less expensive places we can stay.

Optional Stop 2 – Funchal in Madeira

The other location we are looking at is Funchal on the Portuguese Island of Madeira.  It is located alongside of Africa and has a subtropical climate that is the reason it is referred to as Europe’s Maui.  There are some swanky places to stay on this island and I have narrowed it to 2 places (if we can fit this into our itinerary).  One is an All-Inclusive Oceanfront Resort with lots of Amenities for around $250 per night.  This place looks incredible and with Airport Transfers, food, drinks and spa treatments included it’s not a bad value.  The other place has 3 oceanfront infinity pools and offers a package that includes 5 on site restaurants for your dining.  The cost there with the meal package is about $220 per night.  Either way our budget would be $500 for 2 nights.

Funchal – Madeira

Using IHG Rewards for 6 nights, and $400 or $500 for the bonus island stays (if we decide to do both islands, we will stay in cheaper digs in Ponta Delgada or try to use points), I am setting the Hotel Budget at $600


Once our dates are firm, I plan to enlist the help of Scott’s Cheap Fights and/or Airfare Watchdog to monitor international fares to Portugal. I am also building a stockpile of points that may help to offset some of this cost.  Fingers crossed!


I am setting our Roundtrip airfare budget for 2 at $1300.

Inner Travel

There are some logistics to making this trip happen that would require us to have additional transportation.

  • Flights from Porto or Lisbon to Ponta Delgada are about $60 per person.
  • Flights from Ponta Delgada to Funchal are about $100 per person.
  • Flight from Funchal to Faro is also about $100 per person
  • Car Rental between the Algarve and Lisbon apx 4 days at $130



Until we are sure of our itinerary it is hard to set an accurate budget for this but for now we will go with $650


Meals, Tours, Shopping and Whatever

We will want to try a lot of the local fare.  Portugal has a sweet tooth so coffee and pastries are the normal for breakfast.  They eat a big meal at lunch consisting of heavy soups and stews.  Food Budget $600.

I am not a heavy lunch person because it makes me feel sluggish afterward.  We will have to figure this out or plan on a lot of nap times for me.

I always tell Mark we can sleep when we die. 


Food + Booze = Happy

There are some places that will require entrance fees or tour costs. Port Tastings!  Tours/Fees Budget is $150

When I am on a vacation like this, shopping is way way way down on my list of priorities.  I am sure that I will acquire a few bottles of Port to take home, corny t-shirts for each of us, maybe a book and something little for the kids and my girlies. I think that a $200 budget should cover these expenses.


  • Hotels                    $   600
  • Airfare                  $ 1300
  • Inner Travel        $   650
  • Meals/Tours/Etc  $   950

    Total Trip Budget    $ 3500


Final Thoughts

Our final decisions on the Optional Stops could only reduce the cost of the trip.  If we choose to just spend the 2 days in Madeira and forgo the 2 days in Ponta Delgada, our costs would be significantly less than I have budgeted.  It would eliminate 2 nights hotel, 2 one way fights and a Whale Watching Tour for a reduction of over $600 in costs.  We would be filling those days by using 1 extra Hotel Rewards night on mainland Portugal and adding a 1 night stay in Evora for about $120 or an extra night in Madeira for $250 (which would reduce meal costs as well).

I  want to get the most out of our time there without trying to do so much that we get overwhelmed.  With 2 more vacation days to use for Mark, we could do it All!  But for now, his time off is our biggest hurdle.  I am sure we will figure it all out soon so that we can start making our reservations.


If you have traveled to any of these destinations and have suggestions,  favorite sites or travel tips to share, I would love to hear them!  Just leave your comments at the end of the post.











Just an Art and History Nerd from MI Who Loves to Travel, Explore, Save Money, Share Tips, Enjoy the Best Foods & Adult Beverages🍷🥂🍸 Then Blog About It!