A $50,000+ family trip to Europe, booked with miles and points

I recently took a big family trip to Europe with my immediate family (my wife and two kids) and four other adult family members. We’ll visited Italy (Lake Como and Rome), then cruised to Malta, Sicily, and a number of Adriatic Sea destinations before wrapping things up in Athens. It’s was a pretty ambitious trip to plan for eight people (6 adults and 2 kids). When you add up the cost of flights and hotels, this trip would have cost well over $50,000 to book with cash. We covered the vast majority of it with our stash of miles and points, making a bucket-list-type trip both comfortable and comfortably within reach. This post outlines how I booked and stacked to save.

Flights

The adult family members joining us have all been abroad before, but at least one hasn’t been abroad in a long time and none of them are points and miles collectors. Part of the sell on a trip to Europe was that my wife and I would make sure the trip is comfortable.

That comfort begins and ends with business class flights to and from Europe. We booked:

• Air France Business Class from New York to Paris to Milan via Virgin Atlantic for 48,500 miles + ~$300 per passenger for the way to Europe (388,000 miles and about $2,400 in total).
• Air France Business Class from Athens to Paris to New York via Air France / KLM Flying Blue for 50,000 miles + ~$300 per passenger (375,000 miles and about $2,400 in total. Note that children ages 2-11 get 25% off the miles required, so their tickets were 37,500 miles and about $300 each).

To put this in perspective, a multi-city business class ticket from New York to Milan and then Athens to New York would have cost around $3,600 per passenger if paid in cash. Eight seats would have cost about $28,800 if we were paying cash rates. Instead, we spent a total of 763,000 miles and about $4,800 (combined between the flights).

The flights were solidly good. I find service on Air France to generally be very good and our flights were no exception. Service was particularly attentive on the way home, with a flight attendant offering to cut my son’s food for him, kneeling down to read something to him when she heard him call across the aisle to me to ask what something said, etc. Seats are comfortable, food is good. The seats themselves were showing a LOT of wear for our return flight to the US, but they were nonetheless comfortable. I’d gladly fly Air France business class again despite the surcharges (it cost more than $200 each way in taxes and fees).

Hotels

Grand Hotel Victoria Concept & Spa (Lake Como, Italy)

We originally had booked our first night of this trip at The View Lugano, across the border into Switzerland, but approximately the same distance from Milan Malpensa Airport as the Grand Hotel Victoria, which is an Small Luxury Hotels of the World (SLH) property that we booked via Hilton Honors. I had been really excited to check out The View — I believe the property only has about a dozen rooms and in pictures it looks like a Bond villain’s lair. I was excited to have scored three rooms, but it wasn’t meant to be.

We booked a return to the Grand Hotel Victoria for a couple of nights using a combination of Hilton points and free night certificates. As we had 6 adults and 2 children, we booked 3 total rooms:

• Two Deluxe Courtyard View Rooms
• One Prestige Park View Room

Both room types had been available as standard room rewards for 120,000 points per night, though prices have since risen to 140,000 Hilton Honors points per night. The Prestige Park View room regularly sells for a couple hundred Euro per night more than the Courtyard Deluxe Room, but it is worth noting that it is significantly smaller than the Courtyard rooms. If you have more than two people in your party, you absolutely want a Courtyard room. The Prestige Park View room was perfectly fine for two people, but we couldn’t have squeezed a rollaway in it.

While our kids had been free in the past, we had to pay a fee for our older son this time. Children age 6 and older cost an additional 130 Euro per night. While that’s more than I’d generally like to pay for a kid who doesn’t eat a ton at breakfast, I’d pay the fee again for us to enjoy the incredible spa at this place!

Room rates at the time we booked started at about $1,850 per room per night (and I checked regularly and never saw them dip lower). Three rooms for three nights would have come to $16,650 at cash rates. At 120K per bedroom per night, we essentially paid 1,080,000 Hilton Honors points (although a couple of nights were covered with Hilton Free Night Certificates).

We once again very much enjoyed the Grand Hotel Victoria. This was the third stay for my immediate family, though it was a first for everyone else. My kids were very excited to return to the spa and we enjoyed drinks on the lawn, strolling along the lake, getting gelato in Menaggio, and dinner in the restaurant. I’ll continue to dream of the cream puffs and cream-filled croissants from breakfast until we get there again someday.

Comfort Hotel Bolivar (Rome, Italy)

After checking out of the Grand Hotel Victoria, we drove our rental cars back to Milan and took the Italo train from Milan Centrale to Rome. Unfortunately, something broke on the tracks about 30 minutes into what was supposed to be a 3-hour train ride. We ended up sitting on the train with no electricity (and therefore no air conditioning) for hours (the interior temperatures hit more than 105 degrees Fahrenheit at one point). Eventually, Italo sent another train to pull us back to Milan and then we departed again, eventually arriving in Rome almost 7 hours behind schedule (turning the 3-hour train trip into about a 10-hour trip).

The light at the end of the tunnel was the Comfort Hotel Bolivar in Rome. This is a Choice Privileges property in the middle of Rome, less than a 10-minute walk from the Roman Forum and within less than 15 minutes on foot to the Colosseum, Trevi Fountain, Spanish Steps, and all of the other major sites in central Rome. We’ve stayed here at least 2 or 3 times before and would again for the location and price.

Speaking of price, we paid 20,000 Choice Privileges points per night. I actually purchased the points when they were on sale for 0.7c per point, spending $140 per room per night, which compared very favorably to cash rates. Since we needed space for 6 adults and 2 children, I booked two rooms that accommodated 3 people each and one room that accommodated 2 people. The cash rate for the two-person room was $519 per night and for the three-person rooms it was $634 per night at the time we booked, which means that if we had paid cash, this two-night reservation for three rooms would have cost us $4,842. Instead, by purchasing the points for three rooms for two nights, we spent $840.

Let me be clear: there is no planet on which this place ought to cost $500 per night. The lobby is really cute and service is generally quite good, but rooms are feeling pretty tired. I’m not sure they have replaced mattresses or comforters since our first stay about a decade ago, and at the cash rates they are charging these days, they ought to have the margin to do both. Still, the place is relatively clean, it is fantastically located, and the breakfast room on the top floor still provides great views of Rome and a simple but filling breakfast. This hotel is not exciting, but you aren’t going to find a hotel this well-located for a better deal on points (particularly if you’re transferring from Citi or Wells Fargo at 1:2 or you’re buying points on sale like we did).

After the Comfort Hotel Bolivar, we took a Holland America cruise that began in “Rome” and ended in Athens.

Grand Hyatt Athens

At the end of the trip, we spent three nights at the Grand Hyatt Athens. I reviewed this hotel here. In short, we were satisfied enough with the hotel for its good club lounge, solid breakfast, and good use of a suite upgrade award, but service wasn’t great, they don’t honor the Globalist parking benefit, and the neighborhood mostly consists of adult entertainment venues. As the title of the post says, it was a mixed bag.

We spent 42,000 points per room (one night was 12K points and the other two nights were 15K) for three rooms plus a suite upgrade award. The lowest refundable rates for the two-person rooms were $240 per night. A “family” room for three people would have cost about $350 per night. Two of those 3-person family rooms plus one room for two people would have come to $2,820 for three nights. We paid 126,000 points plus a single suite upgrade award (and I should note that the suite would have cost $550 per night during our dates). We did have to pay a 15 Euro “Resilience fee” per room, which is a climate-related tax that everyone must pay in Greece, so that came to around $50 USD for the three rooms.

Rental Cars

We booked almost all of our rental cars on this trip through Priceline.com (originally, we had booked through RentalCars.com, but we ended up changing some reservations) thanks to big rewards offers from Capital One Shopping. That made them feel like a great deal at the time, though unfortunately I have lost almost all of the decent redemption options. Many readers keep reporting in the comments of their post that “good” options have returned for them, but I still have very few gift card redemption options, most of which are for stores where I just don’t shop. I still have the Expedia Global Hotel Card option, but twice this week I have looked for places to stay through that site and one time the major chain hotel I needed wasn’t available and the other time nothing was available in a smaller town with plenty of independent hotels and vacation rentals that show up via other hotel booking platforms. All that is to say that while the rewards looked great at the time we booked, I’m not sitting with a lot of Capital One Shopping rewards and waiting for better redemption options to come around.

Milan: Avis via Priceline

We had an offer from Capital One Shopping for 19% back on rental cars at Priceline.com. We reserved 3 mid-size vehicles (we had 8 people and too much luggage for two vehicles) for three days. Each vehicle came to about $190 with taxes and fees (This was a one-way rental picking up from MXP airport and returning at Milan Centrale train station), though the rate before taxes was $119. We got $32.74 back in Capital One Shopping rewards.

If you valued the Capital One Shopping Rewards at face value, that’s a net cost of $157.26 per vehicle ($471.78 for three vehicles for 3 days).

Messina, Sicily: Sicily by Car

For our cruise stop in Sicily, we wanted to rent a vehicle and drive to Taormina to visit the old Greek Theater there (highly recommended you visit Taormina! It’s lovely!). This was one of a two instances on the trip where I found it made more sense to rent directly with a local company than it did to reserve through a portal. We only wanted to rent one vehicle, so we rented a big passenger van and paid $242 for the privilege. It would have been cheaper to rent 2 smaller vehicles, but we wanted the simplicity of driving (and parking!) one.

Corfu, Greece: Corfu Sunrise

The other instance where we rented a car from a local outfit without booking through any sort of portal was Corfu Sunrise in Greece. Rather than pay for multiple taxis, we wanted a car to get around Corfu. This rental company had an office about 200m from the entrance to the cruise port (although note you have to walk quite a bit out of the way to get from the terminal building to the street before doubling back to the office). We once again wanted a single car that would accommodate the whole family, so this rental cost us $146.38 for the day. Smaller vehicles would have again been a more economical option.

I will note that I picked this place in part because of excellent reviews. I was therefore a little surprised when the person checking the vehicle back in tried to suggest that we put a scratch on the rear bumper. We had essentially driven to a single beach and parked in a place where nobody would have been near our bumper. Thankfully, I had taken a walkaround video at pick up and the person checking in the car barely even glanced at it once she saw that I had video before waving it off. I’m glad that I have the habit to always do a pick up video and a drop off video.

Athens, Greece: Hertz via Priceline

Our final stop on the cruise was Athens. We booked a van one-way for pick up from the cruise port and return at the airport. This was not a cost-effective decision at all. Rather, our flight out was scheduled for 6:30am, which meant leaving the hotel around 3:15am. My wife gets nervous about sleepy taxi drivers in the middle of the night, so we rented a car mostly in order to be able to drive to the airport at the end. We otherwise would have needed three taxis from the port to the hotel and for the 30-40 minute ride from the hotel to the airport, but instead we rented one large van.

This was very pricey at about $600 for three days, but we got $128.83 back via Capital One Shopping (which was based on the rate of $468.27 before taxes and fees). Like our other Priceline experience above, the actual cash back was higher than advertised as our offer was for 19% back but we actually got about 27.5% back as compared to the rate before taxes & fees (I wouldn’t expect to earn on the taxes and fees).

Cruise

We took our 12th cruise of the last ~2.5 years aboard the Holland America Oosterdam. Our port stops included:

• Valletta, Malta
• Messina, Sicily
• Dubrovnik, Croatia
• Kotor, Montenegro
• Corfu, Greece
• Cephalonia, Greece
• Crete, Greece (Chania)
• Napflion, Greece
• Athens, Greece (the cruise ended in Athens)

We had a great time on the port stops! We have visited most of these stops on previous cruises / trips to Europe, but we were happy to go back to those places on a bigger family trip.

This was a “free” cruise from the match to Wynn Platinum last year (as a reminder, Wynn briefly offered a match to Platinum. We first matched our Caesars Diamond, which at the time came courtesy of the partnership with Wyndham, to Fontainebleu Gold and then we matched Fontainbleu Gold to Wynn Platinum). In order to get a “free” Holland America cruise, we needed to spend two non-consecutive nights at Wynn. We booked rooms at Encore via Amex Fine Hotels & Resorts to meet the terms.

When I initially booked the cruise, I had no problem booking our 10-night “Malta, Sicily, and Aegean Jewels” cruise with the Wynn offer (in fact, there was an issue with their payment system on the day when we booked and we had to call back a few days later and have them re-book the reservation so we could pay). However, a couple of weeks later, Holland America reached out to say that the Wynn offer wasn’t valid for a European sailing. We pushed back explaining that they accepted the booking and that we had made reservations for flights and hotels for 8 people already based on having booked the cruise. They asked for proof, so I pulled together email confirmations for flights and hotels. To Holland America’s credit, they honored the cruise booking for us and another family member who had done the match and booked the same cruise.

As has been the case with our other European cruises, we loved the port stops. I can not highly enough recommend a European cruise for family travelers. You get to see a different European place every day without having to pack up and fly / take the train / etc. With kids, I really appreciate unpacking one time and seeing 8 or 9 cities. And on each cruise, we’ve found a place where we’d be excited to return but may not have discovered were it not for a cruise stop.

All that said, I wouldn’t sail on the Oosterdam again.

The short story is that while the staff were wonderful, the ship itself stunk. I’ll try to write a full review, but the short story is that there wasn’t much to do and the free game room was very restrictive and had a bunch of broken games. That said, we were primarily on this cruise for food and lodging, and in that regard we got what we paid for.

Speaking of what we paid for it, this was the most expensive of our “free” cruises. The “free” offer was for an ocean view cabin, but we paid an upgrade fee to move to a balcony cabin and we paid additional fees for our kids (the free offer is based on double occupancy and excludes the $120 per person in port taxes), so the cruise came to a total of about $3,000 with all of those additional costs. If we only had two passengers and stuck with the ocean view cabin, it would have cost us about $500, so most of that cost was from upgrading to a balcony cabin and bringing the kids. One couple who joined us on the trip paid $3,234.48 for a double-occupancy interior cabin on the same cruise, so we got a good discount when you consider that we booked for four passengers in a balcony cabin (and had $200 in on board credit).

Random picture highlights

Bottom line

We had a great trip, visiting numerous fantastic cruise ports, staying in some good hotels (and the fantastic Grand Hotel Victoria), and we got to and from Europe comfortably in Air France business class. Adding up the cash rates for our flights and hotels alone, the cost would have been $53,112. Add in the full cruise fare and rental cars and we would have easily been at close to a $70,000 trip. It blows my mind that we are able to use miles & points, elite status, status matching, shopping portals, and other various techniques to make a trip like this an affordable family trip. None of us would have remotely considered this trip if we were paying full price, but this trip illustrates how this hobby puts very cost-restrictive trips like this into reach.

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