The 9 tricks I’m using to have a five-star vacation (worth $8,000+) for ~$95 per day

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I’ve been toying with a trip to California for a while now. As coronavirus restrictions begin to lift in the state, I’ve gone ahead and made speculative bookings. I’ll show you what that looks like below — every single tactic can be used at your favorite destination.

If you’re new to miles and points, you can use it as a template for your own dream trip. I’ll show you which travel credit cards you need to make it happen. Yes, the credit cards I use to get this trip for cheap do come with annual fees. But I keep them year after year because of their stellar ongoing benefits anyway — so I’m not factoring annual fees into the price of this trip.

1) AutoSlash: $70+ in savings

If you’re not familiar with AutoSlash, it’s one of the greatest tools in the miles and points enthusiast’s utility belt. No, it doesn’t have anything to do with miles and points. But it’s saved everyone in this hobby hundreds and hundreds of dollars over the years. Read our AutoSlash how-to here — and also check out our general post on how to save on car rentals.

There are many shrewd ways to find discounts on rental cars, but I tend to just leave it to AutoSlash. They always find better deals than I ever could. I booked a nine-day full-size car through Sixt (I have elite status because I have a World Elite Mastercard). The total came to a laughable $366 after taxes. I can do way better than that. I reserved the cancellable rate anyway), and entered my info into AutoSlash. Literally within 10 minutes the site emailed me with the same car for $90 cheaper.

Still, the price is too high for my liking. I’ll cancel my current Sixt reservation and rebook at this lower rate. Then, I’ll have AutoSlash monitor this new rate.

Having used AutoSlash dozens of times in the past, I know its amazing capabilities. I expect to receive an email within a couple days of an additional $70+ off that new lower rate.

UPDATE: AutoSlash has emailed me a new price of $175.78. Not bad, I’d say!!

2) Chase Sapphire Preferred: Primary rental coverage = $120+ in savings

You know how rental car agencies violently foist their $12+ per day in-house car insurance upon you when picking up your rental? If you have one of the best credit cards for car rentals, you don’t have to pay it.

For example, I have the Chase Sapphire Preferred® Card, which automatically covers me for damage due to theft or collision, as long as I waive the rental car agency’s CDW. For my 10-day rental, I will likely save at least $120 by not having to pay for the rental agency’s insurance plan.

You can read our post on the Chase Sapphire Preferred benefits and perks to learn everything you need to know about this benefit. And skim my story about how Chase reimbursed me $2,300 when I wrecked my rental car in Ireland. They were amazing about it.

3) Priority Pass: Food credits at two airport restaurants = $112 in savings

Did you know that Priority Pass lounge membership gives you gigantic discounts at 50+ airport restaurants?

Domestically, there are only 29 locations where you can use this benefit for free food. By simply presenting your Priority Pass to the server, you and a guest will generally get $28 in free food, per person. Note that Priority Pass membership earned through an American Express card does not qualify for this benefit. You’ll have to use a card like the Chase Sapphire Reserve®. Read our Priority Pass guide for exhaustive information on what each card offering Priority Pass can and cannot do.

Two restaurants at San Francisco International Airport participate in the Priority Pass discount:

• San Francisco Giants Clubhouse
• Yankee Pier

Both are temporarily closed due to coronavirus — hopefully, they’re up and running in a couple of months! My wife and I will stop at one of these restaurants when we arrive to receive $56 in free food, and we’ll do the same when we depart. I don’t even care if it’s inconvenient — I’m not passing up $112 in food.

If you’re traveling to an airport that doesn’t have participating restaurants, note that Priority Pass lounges often have free food and alcohol anyway — definitely duck into a lounge if there’s one nearby.

4) Ritz-Carlton Half Moon Bay: 2 Marriott Free Night Certificates = $1,819 in savings

Cards like the Marriott Bonvoy Brilliant™ American Express® Card and the Chase Ritz-Carlton Card (not available to new applicants) come with an annual free night certificate worth up to 50,000 Marriott points. Per the Marriott award chart, Marriott Category 6 hotels cost 50,000 points per night. There are many excellent four-star hotels in this category that cost many hundreds of dollars per night, such as the Westin Snowmass Resort, which can cost $650+ during ski season. This is an excellent use of a free night certificate!

However, you can also reserve even better Category 7 hotels during off-peak dates. This category is rich with five-star hotels that can cost $1,000+ per night. I have both the Marriott Bonvoy Brilliant and the Chase Ritz-Carlton Card, which gives me two 50,000-point certificates per year. So, I booked two nights at the Ritz-Carlton Half Moon Bay during off-peak dates. The rooms are currently just 45,000 points per night through this promotion, so it was no problem using the certificates.

The same rooms I’m reserving with my certificates cost $909 per night, after taxes. Note that Marriott charges you the resort fee (but not taxes) even if you’re staying on points.

Still, it’s a great deal to be able to use a free night certificate at this hotel. We estimate Marriott points are worth 0.8 cents each, meaning a 50,000 point certificate should net you about $400 in value. But this reservation is giving me more than double that value — 1.8 cents per point!

5) Alila Ventana Big Sur: 90,000 Hyatt points = $3,680 in savings

Ventana Big Sur, an Alila Resort, is a property in the rugged wilderness of California’s Big Sur region. It’s in a forest of redwoods. It’s a five-star resort. It’s even all-inclusive (except for alcohol!). If you want a totally free five-star vacation, you could just spend a bunch of Hyatt points for an extended stay here!

The resort costs a load of money. The dates I’ve booked cost $1,226 per night after taxes.

The hotel otherwise costs 30,000 points per night for double occupancy. Not bad for six collective free meals per day. We estimate that Hyatt points are worth 1.5 cents each, so receiving a $3,679 stay for 90,000 points is a staggering deal. I’m getting a value of 4+ cents per point with this reservation!

To earn Hyatt points quickly, check out Hyatt’s own credit card, The World Of Hyatt Credit Card. And because the hotel chain is also a Chase Ultimate Rewards transfer partner, Hyatt points are extremely easy to earn with cards like:

• Chase Sapphire Preferred® Card
• Chase Sapphire Reserve®
• Ink Business Preferred® Credit Card

If you haven’t already, read our post on how to become a Chase points earning machine. Most of us in the miles and points hobby abide by that strategy.

6) InterContinental Mark Hopkins: IHG Ambassador free night = $231 in savings

You can buy Intercontinental Ambassador status for $200. It comes with benefits such as:

• IHG Platinum status
• Guaranteed room upgrade (if you book the room category right below a suite, you will be upgraded to a suite)
• Guaranteed 4:00 pm late checkout
• $20 credit per stay in select hotels, good towards minibar and on-site restaurants/bars
• One free night certificate, valid for the second night of a paid stay of at least two weekend nights

If you stay even a few times per year with InterContinental, this status is worthwhile. Or, if you find an expensive hotel to redeem your free night certificate, Ambassador can be well worth it.

I did not find a super expensive hotel that I want to visit before my free night expires, so I’m using it at the InterContinental Mark Hopkins in San Francisco. The hotel is right at the top of the famous Nob Hill, which means the views out the window are of cable cars struggling to climb 80° hills. It’s exactly stereotypical San Francisco.

The Ambassador Complimentary Weekend Night comes as a rebate after checkout, so I’ll earn points for $462, but I’ll only pay $231. Note that you can only use this perk at InterContinental hotels — not just any IHG hotel, like Holiday Inn.

7) Hyatt Regency San Francisco: 40,000 Hyatt points = $700+ in savings

The Hyatt Regency San Francisco isn’t the fanciest hotel in town, but it’s got one of the best locations for beautiful views of the bay. The historic Ferry Building is literally 500 feet from the hotel. It’s also sort of reasonably priced most of the year. My rate is $225 per night after taxes, or 20,000 Hyatt points.

We estimate that Hyatt points value to be about 1.5 cents each — and if you know how to use them, you can get way more value. So at first glance, using them for a stay that costs $449 doesn’t deserve a standing ovation. There are a couple reasons why this stay is worth more to me, however:

1. I have a Club Lounge Access Award, which I can use at this hotel for free food (you can receive two Club Lounge Access Awards by staying with Hyatt at least 10 nights in 2021)
2. I have Hyatt Globalist status, which comes with free parking on award stays — among a ton of other benefits (you can earn Globalist status by staying with Hyatt at least 15 nights in 2021)

The hotel charges $35 per night for parking. By using points, I’ll save $70 for this stay. That means I’m getting a value of 1.3 cents per point.

The Hyatt Regency Club Lounge can be the real money-saver here, however. It serves daily continental breakfast, as well as light snacks in the afternoon. In the evening it lays out hors d’oeuvres and even dessert. It’s open until 9:00 pm daily.

I’ll be working these two days, so I’ll probably eat at the lounge often. I know I don’t have the willpower to return to the lounge for all three meals — otherwise I could avoid spending a dime on food during these two days. Still, I’ll value this lounge perk at $100 per day for my wife and me. That’s two free breakfasts and two desserts per day — and perhaps an hors d’oeuvres plate one day.

It’s not necessarily that I’d pay $50 per person per day for the food the lounge is offering but keeps me from spending money elsewhere in San Francisco. Plus, the panoramic views from the lounge look stunning.

8) Alcohol from home and camping meal pouches: $500+ in savings?

My wife and I do this whenever we’re going somewhere that’s out of our social status tier. For example, we did this when we stayed at the St. Regis Maldives in 2019.

There are these freeze-dried food packs at Bass Pro called AlpineAire, and they’re actually pretty good. All you do is pour boiling water into the bag, close the bag’s press seal, and agitate it a bit by squeezing or shaking the bag. We boil water in the in-room kettle and pour it into the bag. We usually make two meals out of them during a luxe vacation. And because we have to stifle every fiber of YOLO coursing through our veins as fancy restaurants beckon us, we make those meals count. In other words, we eat them at times that will save us the most money.

During this trip, we’ll be eating them at the Ritz-Carlton Half Moon Bay. If we eat one for dinner on the first day, we could potentially save hundreds of dollars versus eating nearby or at the hotel. The on-site restaurant charges $125 per person for a three-course dinner — not including alcohol or tip. If I have a freeze-dried meal my first night, I can less guiltily swallow a $125 per person meal on the second night.

And, of course, if we stuff a couple of bottles of liquor from home in our checked bag, we can save untold hundreds of dollars over buying overpriced mixed drinks at the bar.

9) Capital One Venture miles: 100,000 points = $1,000 in savings!

Before we embark on our trip, my wife will open the Capital One Venture Rewards Credit Card. You can redeem Capital One miles to wipe away just about any travel-related expense, including all those annoying little purchases:

• Parking fees
• Resort fees
• Airfare
• Hotel stays
• On-site hotel restaurants (usually)
• Rental cars
• Lots of other stuff

The card currently comes with 100,000 bonus miles when you spend $20,000 on purchases in the first 12 months from account opening, or still earn 50,000 miles if you spend $3,000 on purchases in the first 3 months. Read our post on how to use Capital One miles for all the details — it’s literally the easiest points currency to redeem, and it’s great for beginners. We’ll use this gigantic bonus to pay for the following:

• Two nights parking at Ritz-Carlton Half Moon Bay – $65 total
• Two nights resort fee at Ritz-Carlton Half Moon Bay – $100 total
• One night stay at InterContinental Mark Hopkins – $232
• Two nights parking nearby InterContinental Mark Hopkins (I’m not paying their exorbitant parking fees) – $70 total
• Dinner for two at the Intercontinental Mark Hopkins – $150 total

Another big (yet unsung) benefit of this card is that you don’t have to earn the bonus before your travel starts. You can earn it long after you’ve returned from your trip, and use your miles retroactively!

What am I actually paying for?

Food

During a 10-day trip, with about three meals per day (give or take for the arrival and departure dates), I’m estimating that my wife and I will each have 28 meals during this trip. Here’s what I’m getting for free:

• 2 meals at airport restaurants thanks to Priority Pass
• 11 meals at the all-inclusive Alila Ventana Big Sur
• 4 meals at Hyatt Regency San Francisco Club Lounge
• 2 meals out of a freeze-dried camping pouch
• 1 meal at the InterContinental Mark Hopkins with Capital One miles

That leaves 8 meals each that we need to pay for, I’ll estimate it’ll cost:

• 3 breakfasts – $25 average per person
• 3 lunches – $40 average per person
• 2 dinners – $75 average per person

Total food cost: $690 (or $34.50 per day average, per person)

Transportation

The annoying fees like parking and rental car insurance are eliminated with Capital One Venture miles and the Chase Sapphire Preferred built-in travel insurance. For transportation, I’ll only need to pay:

• 10-day rental car – $210 (estimate)
• Gas – $50 (estimate)

Total transportation cost: $260 (or $26 per day average)

Bottom line

These nine techniques can work just about anywhere you want to go — it’s certainly not just San Francisco-specific! With a good mix of credit card benefits and a few credit card welcome bonuses, you can save thousands and thousands (and thousands) of dollars on a vacation. If I were starting from scratch, I’d have to open the following cards to make (almost) this exact trip possible:

• Marriott Bonvoy Brilliant™ American Express® Card
• Chase Sapphire Preferred® Card
• Ink Business Cash® Credit Card
• Capital One Venture Rewards Credit Card

Mind you, that’s a total of over $700 in annual fees! But most of the above cards have such good ongoing benefits that you can’t help but keep them. For example, the Marriott Bonvoy Brilliant annual fee is $450 (see rates and fees), but it comes with perks like:

• $300 in Marriott statement credits each cardmember year (good towards room rate, food, etc.) on eligible purchases at hotels participating in the Marriott Bonvoy program
• 50,000-point free night certificate (as discussed above)
• Priority Pass lounge access to 1,300+ airport lounges (worth $429 per year) (enrollment required)

Let me know if you’ve got any post-coronavirus travel plans — and tell me how you’re doing it! You can subscribe to our newsletter as well if you want more trip ideas like this delivered to your inbox once per day.

For rates and fees of the Marriott Bonvoy Brilliant, click here