Solo travel is my bread and butter. I've been to over 100 countries completely alone with just a small backpack. It's my happy place, and if you ever get the chance to travel solo, I'd recommend it to anyone.
So when I drew the solo slot for this challenge, I was thrilled.
Then I saw the destination.
Here's the thing: Italy is my least favorite country in the world. I think it's overrated, overpriced, and overcrowded. You can come stone me in the village square later.
So before I show you the trip, let me get something off my chest.
Where I'd actually send you instead
If you like wine and the Italian landscape, go to Albania. It's right across the water, visa-free for everyone, gorgeous, and a tenth of the price. If someone dropped you there blindfolded, you wouldn't know you weren't in Italy. The only thing you lose is getting to tell people you went to Italy.
If you're into Roman history, go to Tunisia. It's easy to get to, culturally and historically way more interesting, the food is amazing, and it's extremely cheap.
There's a Roman colosseum, ruins everywhere, and parts of Tunis feel more like Greece than North Africa. It's touristy too... just less so than Italy.
And if you want to avoid crowds entirely, there's always Libya. 😉
If you like old European cities and nature, go to Slovenia. It's two hours from Venice, Ljubljana is a wonderful, chill, romantic city, and Lake Bled is one of the most picturesque places on the continent, surrounded by mountains ripe for hiking. Also significantly cheaper than Italy.
Okay. I feel better.
Anyway, there is one trip to Italy I'll never forget, and it's the one I'm recreating for you here with points.
The Dolomites
In 2022, I hiked the Alta Via through the Italian Dolomites with my best friend.
It was amazing. The landscapes were dramatic, there were no crowds, everyone spoke German despite us being in Italy, and by the end my legs felt like they were going to fall off.
Most people are probably not up for hiking 100 miles.
The good news is there are plenty of ways to experience the Dolomites without your entire body going numb for a week, and that's the trip I built.
Quick refresher on the challenge rules: solo traveler, departing the West Coast, Thanksgiving week, on a budget of 200,000 points and $2,000, with points from at most three credit cards.
I only needed two cards in this case: any American Express card that earns Membership Rewards points, and the Chase Sapphire Preferred® Card.
And here's the beautiful thing about booking solo: you only ever need to find one award seat. One seat means you can mix and match programs and grab scraps of availability that would never work for a family. This trip is basically a highlight reel of that.
Getting there: the Virgin Atlantic trick
The flight over is Delta, nonstop from Seattle to Amsterdam on November 21.
But it's not booked with Delta miles. It's booked through Virgin Atlantic Flying Club, which prices that exact seat at 30,000 points + $6.
Want to know what Delta itself was charging for the same flight? 86,100 SkyMiles for basic economy, or 96,000 for Main Classic.
And here's the kicker: booking through Virgin gets you Main Classic. The 96,000-mile fare class, for 30,000 Virgin points.
It gets better. I booked this mock trip in late July, while American Express was running a 30% transfer bonus to Virgin Atlantic, so every 1,000 Membership Rewards points became 1,300 Virgin points.
That brings the real cost down to about 23,000 Membership Rewards points for a nonstop to Europe during Thanksgiving week.
So yeah. Always, always search partner programs when you want to fly Delta.
The $116 hop to the mountains
From Amsterdam, a quick Transavia flight gets you to Innsbruck, Austria the next afternoon for $116. 👇
Why Innsbruck for a trip to Italy?
Because it's the best gateway to the Dolomites, and it's where I started my own hike. Starting in Innsbruck and ending in Venice lets you work your way south through the mountains instead of backtracking. You could do the whole thing round trip from Venice instead, but the one-way flow is the move.
The route: four stops, seven nights
Innsbruck deserves more than a pass-through, especially after a long travel day. So night one is at the Holiday Inn Innsbruck.
Notice that "NEW TO IHG" badge?
IHG discounts brand-new properties by 15%, which knocks the rate from 18,000 down to 15,300 points for the night.
Stack the 100% transfer bonus Chase is currently running to IHG One Rewards on top of that, and the whole night costs just 8,000 Ultimate Rewards points. Yay!
From our starting point in Innsbruck, you can easily book busses and trains to cover the exact route I’m laying out, all without too much time on the road.
From there it's two nights at 1477 Reichhalter, a Member of Design Hotels, in the little town of Lana.
It's a gorgeous old gasthaus, it's bookable with Marriott Bonvoy points, and the two-night stay runs 86,000 points, transferred 1:1 from Membership Rewards.
Then two nights in Cortina, the heart of the Dolomites.
Then two nights in Venice to finish.
Let's talk about those last two stops, because they're where the budget gets creative.
Cortina, and the best $405 of the trip
Cortina d'Ampezzo is the perfect base for day trips into the mountains, including a lot of the terrain I covered on my 2022 hike.
The stay: Franceschi Park Hotel, a 4-star, booked through the Chase Travel portal for $405 all-in for two nights.
Why the portal? Because when a nice independent hotel has no points program, paying cash through the Sapphire Preferred portal still keeps everything in one ecosystem, and $405 for two peak-season nights in Cortina is just a fine price.
While you're there, do this: take the cable car up Lagazuoi and hike down (or hike up and ride down, if your knees have opinions).
Here's a photo I took from the top during my hike. 👇
It’s worth the effort.
Venice, and the art of buying the last few points
The trip ends with two nights at Hotel Indigo Venice - Sant'Elena, in a genuinely great location in old Venice, at 46,000 points a night.
That's 92,000 IHG points needed, and the budget was running on fumes. Here's how it got covered.
The remaining 39,000 Ultimate Rewards points became 78,000 IHG points via that same 100% transfer bonus, leaving a 14,000-point gap.
And for that, IHG happens to be running a buy-points promotion of up to 100% bonus.
Buying 8,000 points triggers the 80% tier: 8,000 + 6,400 bonus = 14,400 points for $108. 👇
Add it up and we’ve got 92,400 IHG points against the 92,000 needed.
Getting home: United, of all programs
The flight home is Venice to Seattle on November 29 for 44,000 United MileagePlus miles + $57.23, booked with Ultimate Rewards transferred 1:1.
It lands in Seattle at 5:10 p.m. on Sunday. Home in time for dinner, laundry, and a full night of sleep before work.
Two things worth knowing about this booking:
First, there was a British Airways flight bookable through Cathay Pacific's program for 36,000 miles, but with almost $300 in taxes. Paying 8,000 more points to save $240 in cash is an easy yes, especially with a budget this tight.
Second, this United price beat Turkish Miles&Smiles, Aeroplan, and the other Star Alliance programs for the same flight. It's rare for United to have the best partner pricing, which is exactly why you should never assume and always check them all.
The damage
Points: 23,000 (Membership Rewards → Virgin Atlantic) + 86,000 (Membership Rewards → Marriott) + 44,000 (Ultimate Rewards → United) + 47,000 (Ultimate Rewards → IHG, across both stays) = 200,000
Cash: $6 (Virgin taxes) + $116 (Transavia) + $405 (Cortina) + $108 (IHG points purchase) + $57.23 (United taxes) = $692.23
Exactly 200,000 points, with not a single one left over.
And with over $1,300 of cash budget left over, buses and trains between the cities are covered many times over, with plenty remaining for food and whatever the mountains talk you into.
What didn't make the cut
American Airlines has great award pricing between the West Coast and Central Europe, as low as 22,500 miles each way. Availability on these dates was bad, so it didn't work.
Air France/KLM Flying Blue can be even better, at 18,750 miles when Promo Rewards line up, and there was a 20% transfer bonus running while I built this.
But this is a peak travel week, and there was simply no availability. Shift your dates a few days in either direction and you'd likely be in the clear.
The bottom line
The Dolomites are the expensive way to do Italy. There's no major airport in the region, chain hotels are scarce, and everything costs more than it should.
I still think it's the best region in the country, and one of the best in Europe. If you like mountains and want to see a side of Italy that isn't a queue outside a museum, this is how you do it.
And if the whole 200,000-points-to-Italy thing still doesn't move you... Albania's right there. 😉
