Travelling is something that many of us really enjoy doing and something that we dream about for a long time with careful planning before we make happen. As I sit here by a pool in the countryside of Tuscany, Italy, I reflect on all the planning and saving we had to do to get here. Thankfully, we are big on points and miles using reward credit cards and we saved up enough to where most of our accommodations were free, or paid for with points/miles. We won’t be able to do a trip like this for quite some time again, but it definitely was an amazing trip – 2 weeks, 6 cities. I learned a few tips and tricks that benefitted us greatly and wanted to share a few strategies to help you plan your own dream vacation – it is possible!

For a brief overview of our trip:

• Business class on Emirates – A380 – the double decker plane! Free with points (145,000 each) aside from the $200 taxes. 
• 1 night in Genoa – cost $120 but we got $50 credit from Chase Sapphire card
• 2 nights on the Italian coastline – Rapallo. Free on Amex points
• 3 nights in Florence, free on Chase points
• 3 nights in Tuscany in a villa – free using Bank of America cash back
• 3 nights at the St Regis in Venice – free using Marriott points and got an upgrade to a junior suite using suite nights 
• 1 night in Milan – free using annual night certificate via my Chase Marriott card
• 1 night in NYC – $200 off using my Amex Platinum

Start planning early and often

The planning for our big Italy trip technically started 7 years ago when we were last it Italy (queue the eye roll, yes I know that’s silly) and Mrs Money halfway joking but turned out to be something we took seriously said – ‘Let’s come back here for our 10 year anniversary’. We decided to see if we could make it happen and although we didn’t start hoarding points right away, we started dreaming!

I would say we started planning this trip about a year in advance, and had probably been saving up points the year prior to that. We started with the big purchase – the plane ticket. Europe flights can range anywhere from $600-$2,000 depending on the destination (less popular spots vs something like Rome/Paris/London), the time of year (Americans love Europe in the summer), the number of stops you make, and of course the class of travel. If you’re dreaming of something fancier, first class can be $5,000+.

Start doing research by checking out itineraries on different airlines. Try something like Google flights or Kayak to start getting a sense of the dollar cost for your flight. Although I’m no expert, you’ll often see prices in dollars start high, then dip a few months prior then go back up closer to the flight. Alternatively if you’re looking to pay with points/miles, it’s typically better to lock in early. We booked our July 2023 flights in November of 2022. I had a buddy who I’m grateful for who told me to stop agonizing over it and to just book it! 

Some airlines will only show you the miles required if you have an account with them but I generally find travel bloggers – The Points Guy and OneMileataTime being my favorites – giving good directional sense of prices, meaning you don’t have to have a bunch of different accounts with different airlines just to check prices. 

Prices might change and typically it’s better to book early – but also remember that many will allow for free cancellations and you potentially don’t have to pay anything up front, meaning it doesn’t hurt to lock something in as you can change later if needed!

The Tuscan pool that I wrote this article from!

Flexible points currencies are valuable (as are flexible plans)

For a good while I was very focused on accumulating Delta Skymiles. I live in a Delta hub and it just makes sense that I’m more often flying Delta. However, I’ve found that Delta charges around 300,000 Skymiles for me to go from my home city to Europe in first class. That’s a LOT of Skymiles. On the flip side, I’ve found United offering round trips for 120,000-180,000 for first class. The downside is that I’ll need to make a connection in a city. 

For us, we wanted to see if we could make first class happen. I’d read about a Emirates flight that you could do from NYC to Milan (Italy) or Athens (Greece) for 155,000 miles in first class. Wow. It’s always our dream to fly first class to Europe but flying on Emirates, one of the nicest airlines in the world; that would be the ultimate dream. We (and by we I mean I, lol this was not Mrs Money’s favorite activity) started checking out fares last fall. I probably watched for 2 months before finally making it happen and booking it. We ended up booking with 145,000 miles. 

Neither Mrs Money nor myself have ever flown Emirates (until this trip!) and therefore we had 0 Emirates miles. Well that’s not entirely true…Emirates ran a promotion a year ago whereby new Emirates miles members could get 2020 miles in honor of Dubai hosting the World’s fair, which I think happened in 2021. So, we both were 142,090 miles shy of the miles we needed. What we did have were American Express and Chase points, and enough to make the flight happen. We moved miles from those partners and booked the flight!

Outside of the flight, we would also need hotels, and as much as I love a good Marriott hotel, I didn’t have enough Marriott points to make it happen, and even with the ability to move our Chase and Amex points, we still didn’t have enough to stay at the hotels in Italy, at least not in all Marriotts. Instead, we found that both Chase and Amex had a great travel portal where we were able to turn our points into stays. We stayed at some amazing hotels during our time here, all with points! 

We ended up staying at 2 Marriotts; the St Regis in Venice and one in Milan. I have the Marriott credit card where in addition to a few perks and being able to earn points, I get a free night each year. Conveniently the Milan Marriott was in the range where I could get a free night! The St Regis Venice was a whopping 292,000 Marriott points, well worth it but definitely the most expensive hotel we’ve stayed at. I had to move some Chase points to make it happen in addition to clearing out my Marriott stash. 

Flexible point currencies like Chase and American Express are definitely helpful tools to have in your tool belt as you’re looking to book a vacation. The flexibility they give you in your ability to move to hotel or airline partners (like I did with Marriott and Emirates) and/or booking directly (like I did for hotels and the rental car) are great! 

The beautiful double decker A380!

Cash points are helpful too 

I ended up running out of Chase/Amex/Marriott points on this trip and was able to use our Bank of America reward credit card points as well. They are great and simply allow you to erase charges. This came in handy when we booked Tuscan villa as well as some AirBnb experiences we booked; a sailboat cruise and a walking tour. We also used some cash back points to erase the $190 in train tickets we had bought. Finally it was great to have a few points to erase a few dinners here and there, although we spent most of our points prior to eating many dinners! 

Points and miles are a game and if you do your research and play by the rules you an often win and get your choice of hotels, cars or flights. However there will always be times that you find yourself spending cash and putting it on a credit card, and it’s times like this that cash back points are valuable! 

Be strategic with your spending / earning 

Between Mrs Money and I, we have 9 credit cards. Yes it’s a bit much but we stay on top of them and each card provides us with specific benefits whether when it comes to earning or comes to redeeming or travel perks. To achieve our travel goals this summer, we had to be strategic about how we both earned points and then redeemed points. 

We started by identifying our big goals – flying business class on Emirates. We knew we each needed 145,000 points. We then confirmed how we could get those points and both Chase and Amex are Emirates transfer partners. Then we started keeping an eye on how many points both of us had and got strategic about our spending. Mrs. Money has a great card that gives 4x points on restaurants and groceries. Our Chase cards give us 2x points on a few of the same spending areas. So, we focused our spending on Mrs Money’s card, ensuring she had enough points in the bank. 

From there we loaded spending on my Marriott card, as I knew we wanted to ball out at the St Regis in Venice. Hindsight I wish we booked earlier as the points kept going up until we booked at 292,000 points. My Marriott card gives 3x on gas, groceries and restaurants and then 2x on other spending. 

After that, we put most of our spending on my Bank of America card as we knew we’d have a few purchases that we wouldn’t be using points for, and also because I had a decent stash of BOA points so it just made sense to use them for some portions of the trip. These points have definitely come in handy for several expenses like the sailboat and one hotel. 

With a little planning you focused efforts you can be sure you’re earning and spending the most points possible!

Points don’t earn interest 

Mrs. Money and I started this vacation with probably close to 1 million points spread across several different currencies and we ended with probably <50,000, ie. we spent most if not all the points we had in our stash! 

I’m a big believer in not hoarding points forever and instead being strategic in how I earn and how I spend my points. Points and miles do not earn interest, and in many cases they get devalued; I.e. they lose their value. I’ve seen this time and time again whereby hotels and airlines will raise the prices in points/miles. Even during the time we booked our trip we saw Emirates nearly double the number of miles required for the flight to Milan. I was so glad I booked when I did! 

Save points for bigger trips and vacations but don’t hold them forever! 

Learn how to have backup plans 

Travel is never perfect and with so many itineraries and plans, something is bound to go awry! It could be a delay due to a mechanical issue or weather, it could be that your hotel’s a/c breaks down prior to your arrival, or it could be a strike that might affect your trip in one way or another. All of these scenarios actually happened on our Italy trip! Thankfully we have learned over time how to make backup plans! A couple of tips that have helped us in our travels:

• If your flight is on the same itinerary, the airline should be able to make you alternative travel arrangements, I.e. if your first flight is delayed and you miss your connecting flight. If not it might be a bit difficult as the one airline doesn’t know or care as much that another airline delayed you. 
• Know that if you’re delayed that other flights/trains might be delayed too. This is especially true with weather delays. 
• Many reward credit cards have coverage for when travel goes awry including trip delay, lost or delayed baggage insurance. Take a few to learn about what coverages you might already have available to you! 
• Be creative about finding internet and not being afraid to book last minute! Twice during our trip we had to do just that: once with a flight and once with a hotel. In both cases we got refunds and were able to find last minute arrangements that didn’t break the bank! 

Just like how life will toss you some curveballs every now and again, so will travel! Know what coverage is provided to you, and learn how to make last minute arrangements when necessary! 

We’re thankful for have had the chance to take an incredible European vacation and are grateful for the chance to have had most of it paid for using points and miles from our reward credit cards! Best of luck planning your own vacations and I hope these tips help make them a little cheaper!