Hopping Around Europe for Close to Free: Boston to Paris, Monaco, Venice and Santorini

Hopping Around Europe for Close to Free: Boston to Paris, Monaco, Venice and Santorini


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Image courtesy: Trish Hartmann

Trip Information

Reader Mark and his girlfriend are both graduating from college soon and are trying to plan a trip for next Summer around Europe. He’s looking at it as a last chance to get in some quality adventure time before he heads into the automotive industry and his girlfriend enters med school. Mark has been to Paris previously, but otherwise neither he nor his girlfriend have much experience traveling abroad. He wants to make the most of this opportunity, visiting not just Paris but also hopping to other European hotspots including Monaco, Venice and Santorini.

Current Program Status

Mark is still relatively new to the points scene, but has already done a nice job building his miles balance. He currently has about 58,000 United miles, a smattering of miles in various domestic programs and 30,000 SPG points. He also has an American Express Blue Sky card with enough rewards points saved up for a $300 travel credit.

Our Take

As you’ll see, that Blue Sky travel credit will come in just as handy as the miles! This was a deceptively difficult trip for us to figure out, and we’re still not certain we’ve found the very best way to do this trip. However, we have found a way to do this trip, and think the itinerary looks pretty promising. We’ll share some of the challenges in building this booking and show you how Mark stands to save thousands on a memorable graduation celebration

Working United’s Booking Engine

Our challenges with this trip have to do with geography and flight routings.

First, to review United’s award flight rules, they allow two open jaws and one stopover on roundtrip redemptions. No stopovers are allowed on one-way redemptions, but thankfully we’re looking for a roundtrip option here, which makes this itinerary eligible for a stay at a location along the way for greater than 24 hours. Keep in mind that a stopover has to be taken at a valid, sensible connection point in a chain of flights. For example, routing through Paris on the way elsewhere would allow for a stopover in Paris, which is exactly what we’ll be doing here.

Second, we didn’t realize until beginning our investigations of this trip that Monaco has no airport. The closest airport can actually be found in Nice, France! Finally, we need a way to get to Venice and Santorini also as part of this itinerary. There’s no practical way for an award ticket to accomplish this without the number of required miles rising or without another method of transport.

Now that we’ve laid out our challenges, let’s get to work tackling them!

Flying the Stopover

In assembling this puzzle, it became clear that beginning the journey with a flight into Paris was a good option. As a popular destination with many flights servicing the route, either from Boston directly or via a number of nearby connections, there are plenty of available Saver Economy routings throughout next Summer right now.

In further good news, whether Mark is able to make his reservation prior to United’s forthcoming chart devaluation doesn’t matter, as Economy flights on United and Star Alliance partners will still be the same 60,000 miles each roundtrip.

Looking ahead, it’s clear that this trip will deplete Mark’s miles account pretty thoroughly. Knowing that intra-European fares can be quite cheap, it looks likely that simply paying for some of the flights needed for this itinerary will be a better option than booking additional award trips. However, we can use Paris as a stopover on the way to either Monaco, Venice or Santorini. The question becomes, which combination of cash flights is most affordable? That way, we can choose our “final destination” for the outbound flight in order to capitalize on the cheapest fares when hopping to other cities!

For the dates we searched, we found the best option was to fly from Boston to Paris to Venice. However, the plan isn’t to go right from Paris to Venice! Rather, it makes more sense to book a roundtrip cash flight from Paris to Nice, the closest airport to Monaco, then continue the award booking on to Venice thereafter. Essentially, we’re putting one flight inside of another flight, following this pattern. United award flights are in bold:

  • Boston to Paris
  • Paris to Nice
  • Nice to Paris
  • Paris to Venice

In this case, flying Air Canada from Boston to Toronto then on to Paris seems like a solid bet. We chose May 31st as a starting date for our itinerary, but again, many options are available for this flight as well as the other award segments.

For Paris to Nice, we found an EasyJet routing for just $130 per person roundtrip:

As for getting from Nice to Monaco? That’s easily accomplished with a bus fare that comes in at just 1.50€ per person each way, with service running regularly between the cities throughout the day!

On to Venice and Santorini

The above includes a flight back to Paris from Nice because the flight back to Paris is cheaper than the flight from Nice to Venice would be, and Mark can then fly for just a few dollars of taxes and fees on his United award ticket. This flight connects through Vienna, flying on Tyrolean Air:

Santorini presents an interesting challenge. Either most flights to the Greek island are seasonal in nature and actually stop running in May or Economy award bookings simply haven’t opened up yet. The former seems more likely given the massive dropoff in availability, but the latter is possible and merits checking before booking, as the smartest thing to do if an award routing out of Santorini is available is to simply fly home from there.

Take a look at the award flight calendar from Santorini Thira National Airport to Zurich to the right as an example.

The same is true for flights to other European cities with Star Alliance partners, such as Oslo. As such, we’re left with no apparent choice but to find a cash route from Venice to Santorini, and then to a city from which Mark and his girlfriend can return home on a United award flight.

As it turns out, simply returning to Venice makes the most sense for the dates we searched.

Flights each way on European carrier Volotea come in around 65€ a piece.

For both passengers, the total cost comes in at $356.67, converted from Euros to US Dollars.

Unfortunately, the only flight available to Venice that day arrives about 5 minutes after an eligible award flight home is set to depart, so this itinerary will require one last night in Venice.

The next morning, Mark and his girlfriend can begin to head home, this time on Swiss from Venice to Zurich to Boston:

Finding the Miles

As a reminder, we have an award flight with a stopover in Paris and an open-jaw between European arrival and departure cities on United covering the biggest pieces of this trip, but we also have two cash flights interwoven into the itinerary. Here’s the full chronological order:

  • Boston to Paris via Toronto (United Award – Air Canada)
  • Paris to Nice to Paris (EasyJet – $130 each)
  • Paris to Venice (United Award – Tyrolean)
  • Venice to Santorini to Venice (Volotea – $178.33 each)
  • Venice to Boston via Zurich (United Award – Swiss)

Got it? Whew!

Given the above, the total cost for two passengers on the cash flights will be roughly a combined $616.66.

To cover this, we’d recommend considering the Barclaycard Arrival, with its bonus of $400 towards travel expenses after spending just $1,000.

Because Mark would earn 2x points on all spending, including the spending he does meeting the minimum spend requirement, and because the card offers a 10% rebate on all redeemed miles, Mark would pay only $140.99 out of pocket for both passengers on both of these flights if he books the Volotea flights first.

For the two United award seats, a total of 120,000 miles and $306.40 in taxes and fees will be required.

The taxes can be almost entirely offset by Mark’s $300 travel credit on the American Express Blue Sky, but he’s still a bit more than half short of the miles needed for this itinerary.

We assume Mark can scrape together the remaining 2,000 miles he needs for his own flight, so the goal will be to find 60,000 miles for his girlfriend.

The best choice here is either an Chase Ink Plus/Bold or Chase Sapphire Preferred. If Mark’s girlfriend could be eligible for a business card, Ink would make the most sense, with its bonus of 50,000 Ultimate Rewards points after $5,000 of spending.

As we’re sure you know by now, United is a 1:1 transfer partner with Ultimate Rewards, so those points are as good as United miles!

Because Ink earns 5x points on purchases at Office Supply stores and on telecom expenses, spending $1,250 of the necessary $5,000 at an office store – whether on computers, supplies or even gift cards – would ensure that Mark’s girlfriend makes it to 60,000 points purely by meeting the minimum spend requirement.

The trip is feasible via Sapphire Preferred, as well, with its 40,000 point bonus after $3,000 in spending. In this case, it’s more important to take advantage of

Of course, making purchases through the Ultimate Rewards Mall can also help cover the gap while also working down the minimum spend requirement. With merchants like Kohl’s offering 10 bonus points per dollar, finding the last 20,000 points to go along with the 40,000 point sign-up bonus isn’t nearly as impossible as it sounds!

Wrapping Up

This trip rests on earning the United miles necessary to cover the second ticket. Ultimate Rewards is definitely the best way for Mark’s girlfriend to get there quickly, whether by way of Ink or Sapphire Preferred. Purchasing miles is always an option if Mark ends up just a few thousand away, but we’re confident that the miles can be earned in this case.

Combined with the travel credit on his American Express and the one that can be easily earned on the Arrival card, the cost of this trip is brought from thousands to, at most, hundreds.

Trip Component Cash Price Points + Cash Savings
United Award Flights: BOS->CDG->VCE->BOS $3,634.20 for two passengers 120,000 United miles + $306.40 Taxes/Fees – $300 AmEx Travel Credit $3,627.80
Volotea Cash Flight: VCE->JTR Roundtrip $356.66 for two passengers $356.66 in Arrival credit $356.66
EasyJet Cash Flight: CDG->NCE Roundtrip $260.00 for two passengers $119.01 in Arrival credit + $140.99 in cash $119.01
Total: $4,250.86 120,000 United Miles + $300 AmEx Travel Credit + $475.67 in Arrival Credits + $140.99 in Cash. $4,109.87 (97% Off)

Happy travels!

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About PointsAway
Casey Ayers is a consultant and entrepreneur with a passion for travel. After amassing enough miles and points to travel anywhere in the world for almost free in less than six months, he developed PointsAway as a way to help others make travel dreams big and small come true.
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