How to Take a $10,000 Vacation for $1,000
I recently spent two weeks spread across The Swiss Alps at The Matterhorn, The Italian Dolomites, Milan, Rome, and New York City for less than $1,000, all expenses included. To those following along on Instagram, I’m sure I look like a millionaire. How else would one afford such a trip? This article can hopefully provide some insight into how to make your own dream trips come to fruition. As always, my greatest recommendation is to ABSOLUTELY AVOID credit cards if you can’t pay off the balance in-full each month and/or lack the discipline to impulse buy unnecessary items.
The only things I’d booked prior to departing were: a 9.5k point American Airlines (AA) flight from Steamboat Springs to NYC, 39k Delta points w/$53 for taxes direct RT flight JFK-MXP, 12k Southwest points to fly back to Steamboat, 15k AA points for my friend’s sister to meet me in NYC, an IHG $99 annual fee credit card night at Hotel Kimpton Eventi in NYC that got me a $500 a night high floor corner suite looking at the Empire State Building, and two nights in a respectable 3 star hotel with a spacious balcony looking at The Matterhorn and free breakfast (in Switzerland breakfast costs roughly $Mexico) using 30k Chase points provided by my $95 annual fee Chase Sapphire Preferred card that comes with a $50 annual hotel credit. The Preferred’s protections for travel can’t be beaten for a card in its class. Trip delay, baggage delay, trip insurance, trip interruption, primary rental car insurance, purchase protections, 5x points on Lyft, 3x on dining, 2x on travel, and 1x on other purchases.
Beyond that, I had another week of unplanned travel. This whole trip came about after purchasing the Ikon Snowboard Pass on the last day of its availability. It happened to have Zermatt Matterhorn and Dolomiti Superski resorts included in the hefty $1400 price tag, and I’m always searching for a reason to return to Europe.
Two nights in Zermatt wouldn’t suffice, so I added another night while I was there. I paid $200 out of pocket for it as well as the 3 nights of CHF city tax. Earning 2x points on that travel purchase with my Chase Visa Preferred. Considering I couldn’t get my rental car, I’d spent $100 to get there and $85 to get back to Milan on trains.
On the train back to Italy, I accidentally paid for my night at the Holiday Inn with another 9k Chase points instead of the $113 that would’ve earned me 5 points per dollar back. Oh, well. That hotel wound up being surrounded by streetcars shaking the hotel throughout the night. As relative sickness had set it due to lack of sleep and every European coughing on me in Zermatt, I decided (despite my lack of fervor for carrying my snowboard bag, carry-on, and backpack weighing 120 pounds on public transit again) to take the street car which had kept me up all night to a new hotel.
The STRAF by Marriott offered a view of the Duomo Cathedral for the low, low cost of only my $95 Marriott Bonvoy anniversary night’s 35k points. The room was a blend of Orwell’s 1984 meets The Fifth Element, and at $500 a night on a Saturday was a hell of a utilization of my 35k point free night. Plus, being right next to the Duomo was a killer central location for food and photography.
Without any other plan forward, it was time to make having brought my snowboard bag truly worthwhile. Using Chase’s travel portal, I found a solid 3-star hotel a one minute walk from a valley grocery store, with phenomenal reviews, a sauna/spa, free breakfast, and five minutes from the lift that would take me to the Dolomiti Superski, allowing access to 29k+ skiable acres. Grand total for two nights — 30k Chase points.
My $23 train ticket from Milan took me out to the Dolomites, where I’d attempt to do the Serra Gordo — a 40km touring trek around Superski Dolomites scenic alpine terrain touching 18 resorts.
For once on the trip, I planned ahead by booking a $56 train down to Rome for two nights using 16k Choice Hotel points total. My Choice Credit Card got me 90k points after spending $3k, and my $95 annual fee gets offset by a 30k point injection each anniversary. Effectually the $400 worth of two nights at the Clarion Collection in Rome is already worth quadruple what my annual fee costs me, with 14k points to spare. Choice Hotel points have extraordinary value in Europe. I’ve gotten similar worth in Vienna using 8000 points for a $200+ hotel near the palace. 8000 points will get your Rodeway roach motel guaranteed complimentary scabies in the states.
My trains were about $150 for the voyage from Dolomites to Rome and back to Malpensa Airport to fly out after a $100 Marriott Moxy night to wake up in peace of only needing to get through security and sit in a lounge with free breakfast before flying back to the states thanks to the Priority Pass Lounge access offered by my Amex Platinum, where my Global Entry (TSA Precheck for the world) allowed me to clear customs in less than 30 seconds. I scanned my passport, then told the customs agent my name as I passed through, glancing back at the folk in regular customs line, remembering my first attempt at reentry a decade prior in LAX, which took two hours.
Everything considered, not having the rental car probably helped me considerably as I would’ve paid $75 to stash it in Tasch for 3 nights while i was at Zermatt, at least $50 in Milan, and probably $100 in Rome. In addition to tolls, gas, and the roughly equivalent of what i spent on trains for the car itself, I probably saved $200 (although there was an Amex offer for spend $350 get $90 back at Hertz).
Returning to the United States, I’d booked a room at The Beekman using my American Express Platinum points, as they were offering a buy 2 nights, get a 3rd free promotion at a hotel nominated by Travel + Leisure as “The World’s Best.” The Platinum is seemingly an absurd card at $695 a year. That said — it offers me yearly $240 in digital credits for free Audible/Sirius XM radio, $179 CLEAR credit, $100 Global entry/TSA Precheck reimbursement, $100 Saks credit, $200 airline credits, $200 in Uber credits, and $200 back when booking a Fine Hotel & Resort (which is the case with The Beekman). Fine Hotel and Resorts offers — 12 PM check-in, 4 PM checkout, $100 experience credit (food or spa), free daily breakfast for two, and complimentary room upgrade. Grand total for that stay — 90k Amex points.
My friend Maci flew into New York utilizing my 15k American Airlines points. Flying out of tiny Stillwater Regional Airport on less than two weeks’ notice, those flights would’ve been over $1100 out of pocket. She’d never seen a Broadway play. I got us two close Book of Mormon orchestra tickets for $180 (a hell of a deal for 10 rows back on Broadway).
These cards constantly have offers available from 10% off hotels to some massive ones with the Platinum (spend $200 at Hilton get $80 back & $300 get $120 back at Marriott)
All travel expenses considered, I spent roughly $1000 ($800, if you count the $200 Amex cash back for the hotel) for 2 weeks’ worth of travel across my home continent to Europe. Staying 3 nights at 5-star hotel in New York City, 2 nights in 4 stars at the Empire State Building & Duomo, 3 nights in a 3 star with Matterhorn view, 2 nights at a 4 star in central Rome on the executive level, 2 nights at a 3 star in the Dolomites, a Holiday Inn at Garibaldi Station, and a swanky airport hotel. I flew over 10,000 miles with a snowboard bag, carry-on, and big backpack at no extra cost thanks to my AA, Southwest, & Delta (which actually gets me 15% point redemption discount on flights) airlines credit cards.
I got mine and Maci’s food a few times, subway trips, and bought a $100 book at The Met for her so she didn’t have to carry cash. She gave me $600 when she left, bringing my grand total for my trip down to about $700.
What I spent would’ve cost as much as my 3 nights at 5-star hotels in NYC. What I would’ve spent, I calculated, would have been just shy of $10,000. And the beauty part is, I still have a massive point bank worth over $10k across 5 airlines, 5 hotel chains, 2 agnostic ecosystems (which i can transfer points from), my new IHG free night just hit, along with the one I get for my $49 a year card (Chase no longer offers, for good reason).
All in all, I spend about $1500 a year on credit card fees. That may seem absurd, but the return I get on them is astronomical. A world of luxury is at my fingertips for far less than the value I receive from the price. I’ve rarely not turned a $99 hotel credit card anniversary night into at least $400 worth of a room. The $99 Choice card will provide an $800 return yearly in addition to the 90k points I got from spending $3000, properly used will net me $2500 back for money I was going to spend anyway. My American Airlines and Delta cards paid for themselves with luggage on this trip alone. My $99 Southwest card offsets itself with 6000 points each anniversary (and the companion pass is available to those who sign up by 3/10/24 and spend $4k within 3 months). I also got one referral away from earning the companion pass for an entire year with the SW card last year. I actually didn’t pay for any of the $2000 in SW flights I flew in 2023.
I was terrified of credit until about a decade ago when I applied for a Target RedCard with a $200 limit that I still have and haven’t requested a limit increase. My total credit limits are now over $150k. In that decade, I’ve had over 30 cards. Some I’ve closed unwisely, others I’ve downgraded to keep the line of credit open, and once i violated the Patriot Act by adding a Polish friend with her Polish address. I’ve made all of the mistakes yet done well enough to have a credit score over 800. Please let me know if there’s anything I can do to help you.
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