How Miles & Points Turned a Honeymoon Trip Into a 6-Country Round-the-World Adventure!

Signing up for credit cards through partner links earns us a commission. Terms apply to the offers listed on this page. Here’s our full advertising policy: How we make money.

Update:   One or more card offers in this post are no longer available.  Check our Hot Deals for the latest offers.  Welcome to the next installment of our Reader Success Series where Million Mile Secrets Readers share how they booked a trip with miles & points to get Big Travel with Small Money! Jessica and Devin are our newest reader success story to show folks it’s possible to travel without spending a lot of money.

A big thank you to both for sharing their story!

Please introduce yourself to everyone and tell us how long you’ve been involved in the miles & points hobby.

Our names are Jessica Rogers and Devin Miles.  Jessica got started with the hobby in late 2014.  When she and Devin started dating, she immediately got him hooked, too!

What was the goal of your trip?

A whirlwind around-the-world honeymoon, although it started out much smaller than that.

The original plan was a romantic vacation for 2 to the Maldives.  But as we were planning, we scored some super cheap flights from New York to London, and ended up making that the jumping off point for a 6-country adventure!

How long did you collect miles and points for your trip? 

We thought it would take us about a year and a half to collect enough points – particularly Hilton points – to stay at the Conrad Maldives Rangali Island for a week.

But we ended up vastly overshooting the number of Hilton points we needed, which worked out because we built-in some other stops.  We didn’t pay for a single hotel night on our trip!

We also wanted to experience the top-notch luxury of flying First Class on Singapore Air.  That was more challenging.  And the lesson we learned is you need to book those premier airline rewards super early, otherwise you won’t find a seat.

Which points did you save to take your trip?

We stayed exclusively in Hilton hotels, so we burned a ton of Hilton points on this trip.  We also racked up Citi ThankYou points to get the best options using points for flights.

What cards would you recommend to someone starting out with miles & points?

Well, thanks to the Chase 5/24 rule, we probably should have gone about our credit card strategy differently.

But our “all-purpose” flexible points card is the Citi ThankYou® Premier Card.  We had Citi Prestige® Card for a year, but they scaled back the value before our second year.  Because we don’t golf, a lot of the perks were lost on us.  The basic Citi ThankYou Premier is a solid card, though.  And you’ll get a TON of value out of the partnership with Singapore Airlines.

We’d recommend the Citi® Hilton HHonors™ Reserve Card – those 2 free nights once you meet the sign-up goal are great – and the Hilton Gold elite status is key to making the most out of a stay at the Conrad in the Maldives.  Every day you’ll get free breakfast, free tea time (with cakes and sandwiches!), and free happy hour with canapes.  You’ll want those things free, because the food and alcohol in the Maldives is craaaazy expensive!

How did you search for and find the award flights?

We took a lot of flights on this trip, and paid for many of the cheaper ones out-of-pocket.  But we booked them at different times, so it really spread the surprisingly small cost of those flights across many months.  But I’ll start with the piece de resistance: the First Class flight on Singapore.

We live in Washington, DC, and had been planning to fly Singapore Air to New York – JFK, and then catch a JetBlue flight back home to DC.

We waitlisted ourselves on 5 Singapore to JFK flight options.  We were a bit frustrated, because the Singapore to Frankfurt portion of the JFK flight was available in First Class, but not the Frankfurt to JFK portion – and the Singapore Air online system doesn’t allow you to mix cabins when you’re booking with points.  Eventually we asked a friend who does a lot of flying with points, and he tipped us off about a new Singapore Air route from Singapore to Houston.

The tip-off worked like a charm!  We easily found seats on the Singapore to Houston flight, which allowed us to spend 23 hours in the luxury of First Class, with all the champagne you can drink.  We even got to take home TWO pairs of Singapore airlines designer pajamas each!  The lesson here: sometimes you have to get creative with routing to maximize the value of your points. 🙂

Definitely worth mentioning here that flying back from Houston to Washington, DC, was practically free for us.  We have the Southwest Companion Pass.  We cannot possibly say enough good things about what an amazing deal the Companion Pass is. 

It has allowed us an incredible amount of travel freedom over the time that we have had it.  If you are a couple, or have a best travel buddy, or a family member you travel with: get the Companion Pass.  Do it.  It is, hands down, the best deal in travel in the United States!

So, about the other flights, since the Singapore flight was the final piece of the travel puzzle:

We took a short JetBlue hop from Washington, DC, to New York to spend a day with friends and to do some sightseeing in New York.  Got that flight on sale, and paid out-of-pocket because we’re trying to rack up enough JetBlue points to fly Mint.  For 2 people, one-way, it was only $96 total.  And because we have one of the JetBlue credit cards, we racked up 6X JetBlue points per $1 on the purchase, plus airline miles.

After our day in New York, we flew TAP Portugal from JFK to Lisbon, then Lisbon to London.  This was a super sweet deal!

We follow Secret Flying on Facebook, and it popped up randomly one day – an error fare with round-trip flights from JFK to Europe for $270 per person!  That’s such a ridiculous steal that we couldn’t pass it up.

This particular deal was actually what caused the trip to morph from just heading to the Maldives to a round-the-world adventure.  The tickets were so cheap, we ended up not even taking the return flight.  And we thought TAP Portugal was actually a nice flight.  Good in-flight entertainment systems, decent food, and fairly comfortable seats for basic economy (and $270!).  We’re flying them again to Paris for New Year’s Eve – again for a stunning $280 round-trip.

We took a cheap short hop on one of the discount carriers from London to Germany.  One word of advice when booking all of these flights on different carriers – make sure you are aware of the baggage allowances and carry-on policies!  On the flight to Germany, we bought the mid-tier ticket that had a greater baggage allowance, so we wouldn’t have to pay extra at the airport.

We flew on Condor Air from Frankfurt to the Maldives.  It was a red-eye, and so we opted for Economy Plus seats, which cost about $600 each for one-way flights.  If we’d had Lufthansa miles, we could have used them on Condor.  But the Economy Plus seats were actually incredibly nice!  The food was tasty, and the little amenity kits were pretty sweet.  We had no complaints about that flight.  And it was totally worth the cost to upgrade, since we were able to get some decent sleep.

The final flight we booked was to get from the Maldives to Singapore.

There aren’t very many options to get out of the Maldives.  We ended up on Tiger Air, which is like the Spirit Air of Asia (except they were on time).  The flight was super cheap, but boy was it uncomfortable.

The plane was very old, and they couldn’t have fit more people on that plane even if they wanted to, because the seats were so close together.  We could have used Singapore miles (you actually use the miles to get a voucher to purchase Tiger Air flights), but it wasn’t worth it.  The total cost for two of us was only $300.

How did you find your hotel accommodations?

We started with the recommendation of Million Mile Secrets on the Conrad Maldives Rengali Island, and worked from there.

Million Mile Secrets also recommended the London Park Hilton, which is a beautiful hotel, although I think it would have been a much better choice in the spring or summer than the winter, because it overlooks Hyde Park.

But it’s a short walk to Buckingham Palace and the Queen’s Gardens, which even in November was pleasant.  Depending on how much you enjoy strolling, or how much time you have for your visit, we might recommend something a bit closer to Big Ben or the Tower of London.  But the hotel itself was beautiful, with a great breakfast spread.

In Cologne, we opted for a hotel that was right next to the train station, because we knew we would have to walk our bags to the train.  The Hilton Cologne was perfect – literally a short block to the train and the Dom (we had a view of the Dom from our bedroom window), which also had an adorable Christmas market.  It turned out to be the perfect location for our brief stay in Cologne.

And, as I mentioned previously, we ended up having enough Hilton points to stay for free at all of these locations. 🙂

What was the most challenging part about planning your trip? How did you solve it?

Getting the First Class seats was definitely the hardest part.  We solved it by opting for a different, and definitely longer, route.  But if you’re going to spend a few extra hours traveling, we highly recommend you do it flying First Class on Singapore Air!

Give us a few recommendations or tips for what to do at your destination.  Parks, restaurants, hidden gems, etc.

In London:   Make brunch reservations for Duck and Waffle.  Great view of the city, with ridiculously delicious food!  A friend also turned us on to this amazing little bar in the suburbs – Every Cloud, 11A Morning Lane, Hackney, E9 6ND.  If you like specialty cocktails, that’s definitely your place. In Cologne:   Get your hiking shoes out and take the many many (manymanymany) stepped stairway to the top of the cathedral!  You’ll get amazing views of the city and countryside.

In the Maldives:   The Conrad in the Maldives is absolutely top-notch.  The underwater restaurant is worth the experience, although it’s extremely expensive.  Do plan on doing some snorkeling in the house reef, which was full of exciting fish.  And definitely upgrade to the overwater bungalow for at least one night of your stay.  They don’t do automatic upgrades, but the cash upgrade was reasonably priced and absolutely worth it. In Singapore:   The Cloud Forest, in the Garden by the Bay is totally amazing, and worth a visit.  It was a great way to beat the heat and cool off, while seeing some really beautiful plants and sculptures.  Plan a long layover in Singapore – you can see a huge amount of the city with great ease.

What did you learn about yourself on the trip?

We learned you should check the price of things in the Maldives before you drink them – that rose champagne you just ordered a few glasses of may turn out to be $40 per glass!  And that international First Class is amaaaaaazingly luxurious! 🙂

But on a serious note, we learned we love a mix of the big touristy destinations and off-the-beaten-path places (like the bar we recommended in London).  And thanks to the many options and opportunities we’ve been given through miles, points, and airfare watching, we learned we no longer feel the need to cram every moment of our trip with constant activity, which gets exhausting!

It was nice to travel at a reasonable pace, and to mix historic and touristy items with local gems and causal strolls.

What would you say to folks looking to plan a similar trip? Or to those who haven’t taken a miles & points trip yet!

You’re seriously missing out. 

We honestly cannot believe how many places we’ve gone, friends we’ve visited, and amazing adventures we’ve had for the small amount of money we’ve paid thanks to this hobby.  For a big trip like this, our best advice is to sketch out an idea of what you want to do, so you can start collecting points, but then be flexible.  If you’re flexible, and a great deal pops up or avails itself to you, grab it and go for it.

Also, if you’re taking a complicated trip like this, we strongly recommend making an itinerary to take with you, as well as a spreadsheet with all of the critical information – addresses for hotels, flight numbers, confirmation numbers. 

We brought along a little folder, and discarded copies of reservations and ticket confirmations after we’d checked in along the way.  And do build-in plenty of time in transit for things to get a little wonky.  Everything on this trip went smoothly, but we’ve had other trips where a delayed flight caused a great deal of stress to try to fix things.

Want to Share Your Story?

If you’d like to be considered for our reader success story series, please send me a note!  Emily and I would love to hear about how you travel with miles and points!