Planning a Dream Birthday Trip on Points & Miles
The last international trip that we took prior to the pandemic was a surprise birthday trip for my dad’s 70th birthday in October, 2019. I had decided a few years ago that I would start saving points and miles to be able to take my parents on a trip of their dreams for their 70th birthdays. My mom did not want to travel internationally for hers, but my dad had a bucket list of European destinations he was dying to see, so we saved up to make it an epic adventure of a lifetime, thanks to travel hacking.
Travel hacking 101:
Travel hacking refers to strategies employed to earn airline miles, ideally without actually flying, along with other transferable points that can be used to cover the cost of travel expenses such as hotels and rental cars. If this is new to you, you can learn more about travel hacking here and here; the New York Times also ran this article recently which reviews the history of the hobby. Travel hacking has its extremes, from those who keep it simple and maximize rewards from everyday spending to get an occasional free trip, to those who employ sometimes ridiculous strategies to jetset abroad multiple times a year in luxury. I consider us somewhere in the middle within this crazy hobby (or rather than we, I should say, I am the obsessive points/miles person who is somewhere in the middle, and my poor husband is what the hobby deems “Player B” – along for the ride).
The first step was to make sure that we had enough points and miles to make this trip happen. I prefer loyalty programs that offer transferable rewards, so that I have a lot more options and flexibility while planning; if flying on a specific airline it may also make sense to max out opportunities with airline co-branded cards. At the time of this trip, I was acquiring most of my points through the Chase “trifecta”, and for this trip I also accumulated United and American Airlines miles through their co-branded credit cards. This requires a lot of attention to detail and organization, to maximize rewards and also minimize any fees that might not be worth it. I keep a spreadsheet to keep track of everything. We personally earned our miles through the following:
- Actual travel through work-related trips and continuing education (paid for by our employer).
- Credit card sign on bonuses
- Daily spend (1.5 points/$1 on Chase Freedom Unlimited is our best return)
- Maximizing bonus spending categories, such as restaurants (3 miles/$1 on Chase Sapphire Preferred), gas (2 points/$1 on Chase Ink) and quarterly bonus categories with Chase Freedom (5 points/$1).
- Our Chase Ink business card offers 5 points/$1 at office supply stores, where we buy gift cards (think Amazon, AirBnB, and other retailers that don’t offer a category bonus) and used those to buy every day necessities.
- Online shopping portals, sometimes coupled with office supply gift cards (a strategy that sometimes works, sometimes doesn’t). For example, to purchase my usual cosmetics and hair products on Sephora, I wait for a sale, use a shopping portal (MileagePlus for example, will alert you when the miles bonus for your favorite stores is high, and they offer holiday bonuses for even more extra miles), and pay a portion – but not all – of that purchase with an office supply store gift acquired for 5 points/$1. AirBnB has a double-dipping strategy with Delta – use a gift card acquired at an office supply store for 5 miles/$1, then book through the Delta-AirBnB portal for 1 mile/$1 earnings on Skymiles.
- Paying our taxes on a card – usually to generate enough spend to meet the requirement needed for a new credit card’s sign on bonus reward, but with Chase Freedom Unlimited, the value can sometimes outweigh the fees (especially when racking up enough miles for an expensive first class flight). The fees cannot outweigh the value of the points acquired.
Picking the destinations:
After my dad provided me a list of bucket list destinations (Paris, Barcelona, Jerusalem, Egypt….whew!), and an agreement that we should visit some new places that none of the four of us had ever been to, I began contemplating itineraries that made logistical sense, considering expense, comfort levels, and safety concerns. One of my dad’s absolute top spots that he wanted to visit was Barcelona, so I started there, looking at what else we could connect with a trip to Barcelona. To make things complicated, my parents were also eager to do some train travel, but not revisit places they had previously been such as Madrid and northern Spain. I utilized Rome2Rio and Rick Steve’s travel maps/connection times to get a sense of how to connect the dots. I realized we were limited on options that would easily connect by train to Barcelona. and if we wanted to visit another country we would have to fly….but nowadays, it is fairly cheap to purchase flights within Europe, and if an itinerary is going to include a flight, more options open up. I use Sky Scanner as a search engine to scout out options. It is also important to consider how much time your group wants to spend “on the road” in transit. Our “rule” is to try and spend at least three nights in each destination, which minimize the amount of packing/re-packing and transit time. I didn’t want this to feel like a backpacking trip. We scoped out all sorts of itineraries. Ultimately, we decided on Spain and Israel, as my dad really wanted to see Jerusalem. It sounds like a very odd combination, but when you consider that once you are in Europe, it’s not that much further to fly from Barcelona to anywhere else in Europe or the Middle East….and an afternoon spent flying is an afternoon spent flying. Our final decision was to divide our time between 3 places: Barcelona (dad’s pick), Seville (new to all), and Israel (new to all, dad’s pick).
Booking Flights:
I prefer to fly open jaw (in one city and out of another) to avoid backtracking. I always recommend ending your trip with a few days in a big city with lots of international connections – if another earlier portion of your trip experiences a delay (think: train strike, cancelled ferry) you’ll have a cushion…and if your particular flight is delayed or cancelled the day of your departure, you will have plenty of alternate options. You never want to be stranded in a remote area with limited transportation connections, trust me! Also consider any time changes when you plan your flights (it takes longer to fly West to East) and cost differences in flying one direction vs the other. Don’t get so hung up on a specific itinerary that you don’t think out of the box.
In our case, my hope was to fly my parents first class (with us kids back in economy), and first class seats can be extremely hard to book on points and miles, so the order of our itinerary was partially dependent on award seat availability. We looked at different airlines/partner airlines to determine which would be our best flight options (I prefer as few connections as possible, just to keep things simple for my parents) by using Sky Scanner and Kayak to explore potential flight routes. Expert Flyer can help determine how many points are needed through the various arlines. The airline that made the most sense for us to get to Spain was American Airlines/Iberia. Had we all been traveling first class, we would have been set, at 30k miles apiece with American’s MileSAAver® awards. To fly my parents first class on a MileSAAver flight, I did not have enough American Airlines miles to fly all 4 of us, nor did I yet have quite have enough American Express miles to be able to transfer to American or any of its partners in enough time to be able to book the MileSAAver awards (and I needed to act quick, as SAAver flights don’t last and the non-saver redemption rates can be astronomical). Right around the time the tickets were released for our travel dates, however, American Airlines had a Black Friday sale offering big bonuses for purchasing miles, bringing the cost down to 1.89 cents per mile. I don’t typically ever recommend purchasing miles as it never seems to work out in the purchasers favor and I find it to be a bit of a gimmick; however, if your goal is to fly first class or your base ticket is really expensive, and you are able to find one of the sales, it might be worthwhile. I spent about what I would have spent for two economy tickets to Spain in order to purchase enough miles to get my parents their first class seats. Not an ideal travel hack if your goal is flying free, but an example of the troubleshooting one must sometimes do to meet a specific goal. One leg down! (Fees/taxes: award tickets come with a $5.60 fee, costing $22.40 for all four of us. I did also pay for the miles, though in theory with more time I would not have had to do this. Cost savings: $13,340 for the 2 economy tickets – yes, you read that right, that was the going cost to fly out of our small, very expensive small-town airport; the 2 first class tickets at the time priced out at a whopping $23,600 for both. Hence, I felt like I still came out ahead, even with having to purchase some miles.)
I had stocked up a lot of Chase Ultimate Rewards points in hopes of using them for flights for hotels. Since I was not able to use those points for our flights to Spain, I had enough left over that we could all splurge to fly first class on a direct flight from Tel Aviv to San Francisco then onward to home airports on the return trip for 75,000 miles each on United. This was in the new Polaris seats, which are a pretty incredible ride for we who never fly first class. The flight TLV–>SFO was over 14 hours long, so it was well worth the use of miles to be able to really enjoy the experience and arrive refreshed and ready to work the next day. I topped off our United miles account with points transferred from Chase, and we were all set with our major tickets! (Cost savings: $9400 for all four seats; we paid $398 in fees/taxes).
Connecting the two destinations: Barcelona has direct flights to Tel Aviv on El Al airlines, easy enough, but with no way to redeem miles for free flights since El Al at the time did not partner with any of the major airline programs or transfer programs. That flight I would have to purchase out of pocket, but it was not an expensive flight for the four of us to fly economy on that leg. Had we had a different European destination, I would have looked into flying for free using Iberia or British Airways Avios (they are interchangeable, with a low number of points needed for most short haul flights), or booked the flight in the Chase Ultimate Rewards portal using Ultimate Rewards points.
Lodging:
Big box hotel? Small family run inn? B&B? Apartment? Things to consider besides cost include (1) location, (2) safety (depending on the country), (3) ambiance, (4) how much assistance I might need for things like making reservations and transportation. My preference when traveling to Europe nowadays is to rent a local apartment. There is no front desk to help, but with most things bookable on the internet or by e-mail with Google translator, it hasn’t been a problem for us in Europe. I enjoy being able to live like a local….and we’ve met some wonderful hosts in the process. For a group, I also like apartment rentals because we are all in the same place (no wasted time spent trying to call other rooms or find out when the others have gone down for breakfast), and it can be a big cost savings compared to booking 2+ hotel rooms. I decided on this trip I would mix apartment rentals with hotels, one so that I could use points and miles to cut down the cost of our lodging expenses, the other was based on the convenience of location. For the Spain portion of the trip, Seville and Barcelona, I wanted to stay in the most walkable areas of the town so that major sites and good local restaurants were easily within reach. Seville had a plethora of great apartment rentals on the Chase Ultimate Rewards platform (redeemable with points) and on Airbnb. I opted to skip a points redemption and went instead for a lovely small two bedroom AirBnB apartment with a huge balcony overlooking the Seville Cathedral, and I could not think of a more atmospheric way to experience Seville. I booked using AirBnB gift cards purchased online at Staples (via a shopping portal, of course, for a bonus 1 mile/$1) using our Chase Ink business card for 5 miles/$, and booked via deltaairbnb.com to earn additional Delta SkyMiles with the booking.
Barcelona has a lot more restrictions in place on apartment rentals, and in the more walkable areas where we wanted to stay, rentals are banned – hotels were the only option. This was a great time to utilize Chase Ultimate Rewards Points to stay in a bit more upscale hotel with all the conveniences and be able to easily walk through the old city. It was a good mix of different experiences, and I was able to redeem Chase ultimate rewards to cover 2 rooms for 3 nights each at the highly recommended Ohla hotel entirely for the four of us – and we scored another dreamy rooftop deck with great city views (Fees: none. Cost savings: $1,954).
For our stay in Israel, we wanted to stay in Tel Aviv – more specifically, in the ancient port of Jaffa rather than Tel Aviv itself. Looking at redemption options, we had enough Marriott rewards points to cover free nights for one of 2 rooms at the W Jaffa, a newly renovated property that incorporates a lot of historical features and looked like an amazing property. After a few more months of contemplation, the W Jaffa had some limitations – it was a little too far to be walkable to the main market and shopping area in Jaffa, and there was no view of the ocean (which I knew my parents would really love). Plus, we had to pay full price for one of our two rooms, which at $400 per night was not a savings. Instead, we opted to stay at the more reasonably priced Casa Nova Boutique Hotel. This property was not bookable through Chase Ultimate Rewards so we booked through hotels.com to utilize 2 free night certificates I had accumulated from booking a bunch of rooms for a relay race (our race mates paid us back, and I got the bonus of the free night awards!) and cut the cost further by using Hotels.com gift cards earned through our health insurance’s program, Vitality (the steps from all those 5K races added up!). Sometimes it’s a trade off between getting a completely free room and getting the location or amenities that you want….and a free room is also not worth it when your additional nights end up being far more expensive, or you will wind up spending more money and hassle on taxis and transportation.
Refining transit and transportation
I made a huge list of things we wanted to see and do in both countries, including many day trips. It was clear that we needed another two weeks of travel to do everything we wanted, so cuts had to be made. We decided in Spain, we would alternate between a day trip and local activities, to minimize the amount of time needed for transportation. When it comes to day trips on the train, I also see if there are any day trips that might be incorporated into a transit between two lodgings. For example, we knew we wanted to see Córdoba (Cordova), which is a day trip by train from Seville. However, Cordoba is also on the train route to Barcelona, which was our next destination. Many European train stations have luggage lockers or luggage storage areas, and sure enough, Córdoba did! This worked out fantastic that we could break up the five hour train ride between Seville and Barcelona with a few hours in Córdoba, minimizing the amount of redundancy of travel and breaking up a long train ride into two smaller chunks.
I utilized the Rick Steves guide books and Rome2Rio to determine transportation options and to estimate how much time we would spend on day trips. I also tracked this in a spreadsheet. For traveling in Europe, it is important to pay attention to how many times you plan on utilizing the train, as it may be more economical to purchase a euro pass or train pass.In our case, it was going to be cheaper for us to just purchase point-to-point tickets. I purchased these in advance as prices can go up closer to the travel date, particularly for longer and more popular routes like the ride to Barcelona.
For a road trip, or a day trip where you might be incorporating multiple sites, you can use a route mapping app (RouteXL, Mapquest, or similar) to help you determine the most efficient path.
Planning activities:
Last step was to pin down the exact activities and tours that we wanted to do in each town. Be cautious about using 3rd party booking agencies like Viator – we have thankfully had good luck with them, but I always look up the actual company providing the service, and I compare rates and cancellation policies booking direct versus through the 3rd party site. I also check the Chase Ultimate Rewards portal. What I love about Chase Ultimate Rewards is that you can also use points to cover tours and experiences, not just flights and hotel rooms. This can be an additional way to potentially shave more cost off your dream trip. If I cannot book through Chase and choose to book through Viator, I use an online shopping portal like United’s MileagePlus shopping portal or Chase’s Ultimate Rewards shopping portal to accumulate additional miles for each dollar spent booking the tour, and I try to book when the portals are offering a higher mileage bonus for each dollar spend. For this trip I was able to secure some tours with a 5 mile/ 1$ bonus through the United MileagePlus shopping portal, which at my current valuation of 1.6 cents per dollar, works out to about a 7.5% discount. We also utilized Airbnb experiences for the first time to book a cooking class. Their portal doesn’t offer as many different ways to sort and sift through the different offerings as easily, and it’s hard to get any additional discounts or bonus miles for your spend on Airbnb (besides booking with gift cards as I described above)…but there are some options here too, and we were very happy with our cooking class.
I like to use a spreadsheet again to block out chunks of the day where activities take place, budgeting the time it takes to get to the location, and also jotting notes to myself on anything we need to do in advance, such as purchasing museum tickets in advance (which nowadays is a must – be sure to visit the websites of any museums or major attractions in Europe and book ahead of time; popular attractions like La Sagrada Familia do sell out). A spreadsheet provides a nice visual of how packed your day’s itinerary might be and whether you have time to add an additional activities…or need to back off and allow some downtime to recoup. Since this was a surprise trip for my parents and they did not know what to expect, we handed them a version of the itinerary with the chunks blocked out but without any details, so they would at least have an idea of the plan of the day and which hours they would be busy with activities and which hours were dedicated for rest and relaxation.
For a more detailed itinerary with booking numbers, contact info, and the like, I use the TripIt app to track all of our plans – which can be accessed offline.
Managing the “White Space”
In healthcare we often think about utilizing what is called white space, that time in the hospital in between various tests and consultations. These are the down times where nothing is really happening but if not well managed, can lead to stress and anxiety. On a trip, I also look at the white space, which I consider the space in between the activities and highlights of your trip, the time spent either waiting or in transit. This is often the make or break of our experience traveling. This might be the downtime in an airport during a layover, or the chunk of time between arrival and getting to your lodging. I’d like to have an idea of how to make that span of time as smooth, relaxing, and enjoyable as possible. In the airports, we like to utilize lounge access as a great way of relaxing and refreshing in between flights, and quite frankly, we love enjoying the amenities – particularly of the European lounges. I researched in advance how to maximize our layovers. In Dallas, we had access to the Centurion Lounge through our American Express platinum card which allows you to bring two guests into the lounge for free. This is a benefit we find well worth keeping our American Express platinum card for since I also utilize these lounges a lot on work travel. In Madrid, we would have a layover before our flight to Seville, so I checked to see what lounges might be accessible to us based on the terminal we would be in. Thankfully, there was a lounge which we had access to through our Priority Pass card, which comes with both the Chase Sapphire preferred/reserve credit card as well as American Express platinum. The Priority Pass card allows you and one guest to access the lounge for free. The Madrid lounge is fantastic, with great food options and the largest collection of Spanish wines I had ever seen in a lounge before (we counted over 20 bottles).
For transportation from the Seville airport and then later to the Barcelona airport, I researched in advance the best option for us; we went the taxi route. Sometimes a private car or cab can be quicker, safer, and more direct; but in other countries sometimes the light rail or subway might actually bypass heavy traffic and be a quicker, easier option.
At the Barcelona airport itself, I looked to see what terminal we would be departing from for Tel Aviv, and sure enough, we also had access to another Priority Pass lounge which we could utilize before our flight to Tel Aviv. This was great as it gave us a place to eat a light dinner, as we weren’t sure quite how long it would take us to clear customs on either end.
In Tel Aviv, it is possible to pay a fee to bypass the long immigration lines both entering and leaving the country through their VIP service. We opted to do this and it was well worth the fee. You can also pay extra to include lounge access, but we felt this was a bit unnecessary. Given that we were only traveling to Israel for a few days, we wanted to maximize every minute of time there, and immigration lines can be notoriously long (i.e. 3 hours). This ended up being incredibly helpful since at that point in the trip, my mom’s knee was starting to bother her from all of the walking, and we were able to have help with luggage and someone who could direct us the quickest route through and out the airport to our prearranged taxi. On the flight out from Israel to the United States, we all had first class seats and we were all anticipating a super fun in-flight experience, so lounge access wasn’t as pertinent. We did check out the Tel Aviv Priority Pass lounge just to see what it was like, but it was small, cramped, and not much to write home about. Can’t win it all! Lastly, we enjoyed the Centurion SFO lounge on arrival back to the States, which was a comfy place to kill a several hour layover.
Bottom Line:
It takes some work and dedication, but it is possible to take a luxurious dream trip beyond your usual travel budget, using points and miles to save on costs. We were able to fly mostly first class flights for $420.40 in taxes and fees, plus the cost of our El Al economy flight. I was able to save close to $2500 on lodging using Chase Ultimate Rewards points and Hotels.com free night certificates – and could have potentially booked all lodging for free though Ultimate Rewards, but my love for local apartment rentals prevailed. The lounge access provided by our American Express Platinum and Chase Sapphire cards easily saved the four of us $400-$500 in food and beverage costs (and both cards are worth the annual fees due to the other rebates and perks we are able to take advantage of).
