• Russell Levinson

Livin it up! The big travel hacking payoff

Updated: Oct 18, 2021

What I love most about getting points, miles, and cool travel benefits from credit cards, is using it all to get extreme value back. Hotels and airlines continuously make it difficult to get high value from your points and miles such as a $10,000 first class flight across the world for a low number of miles (still possible, but hard to find). Hotels are even tougher.

The American Express Hilton Aspire Card in combination with the pandemic, proved to help me get my best free hotel nights ever.

Apply yourself with this link. We can both get rewarded if you're approved!

Opportunity arose from this card and the extension of free night certificates. Hilton's Amex Surpass ($95/year annual fee) and Hilton's Amex Aspire ($450/year annual fee) each gives you one free weekend night per year. Due to the pandemic, Hilton not only extended the expiration dates on these for everyone, but they also are allowing the free nights to be ANY day of the week. This card also gives you a Hilton resort credit of $250 per year that can be used at any Hilton resort for any room charges.

I piled up three of these certificates and when I was finally able to travel and put them to use, I searched for the most expensive Hilton resorts with availability. One property really stood out with paid rates over $1500/night and points rates at 120,000/night. That hotel is the Waldorf Astoria Pedregal in Cabo San Lucas, Mexico.

I also looked at other properties in Europe, but the value there was no more than $500/night.

So, I decided to look at what flights there were from NYC. I quickly noticed non-stop flights from Newark daily priced very low. I also saw that business class was fairly reasonable as well. The airline was United, and wouldn't you know it, I had $450 in my United account. That $450 was from using the $250 airline credit with the Hilton Amex Aspire, and then another $200 from my Citibank Prestige airline credit. I simply made four separate purchases from United's travel bank, and the money is then stored in my account and can be used for any flight. All $450 was credited back to my Amex and Citi cards within a few days of purchase.

The stars were starting to align for this hotel and flight to Cabo.

The reviews and pictures were all amazing and every room has its own plunge pool. Check out the 3D tour:

First, I booked the business class flight and paid with the United credit. I called Hilton and they had rooms available on my dates, so I booked it as well. My flight was a one-way, as I didn't know where I would go after my three free nights.

The Cabo area is a bit confusing as it is broken into three parts, San Jose Del Cabo has the airport and then a beach town, Cabo San Lucas is 30 miles away and is also a beach town, and lastly is the tourist corridor which runs between the two and has scattered condos time shares, and beach resorts without much else.

To get from the airport to the Waldorf costs anywhere from $25 for a shared shuttle to $160 for a VIP private ride. Many options in between those included taxis and Uber. I didn't want to spend a lot of money on the transit, but I also wanted to get to the resort quickly to enjoy it as much as possible. My flight was landing around 1pm. Google maps showed no public transportation, but I didn't believe it and further research showed a bus route called Ruta Del Desierte that would cost about $4 and drop me fairly close to my hotel, although I would have to walk in the heat for at least 20 minutes (I do stuff like this all the time to save money).

Sounds crazy, right? Well, I love these kinds of challenges and saving money is important to me, even when staying at a 5 star luxury resort.

Fast forward to landing in San Jose Del Cabo Airport, it turns out the bus leaves from Terminal one, and I landed in terminal two. There is a walkway between the two which took about 10 minutes. Both terminals are very small, and I could see the purple busses as i walked into the terminal and purchased my ticket for 80 pesos ($4). I was then on the bus and the journey was a bit longer than expected, as the bus stops a lot! I was the only tourist on the bus, as it stopped to pick up and drop-off locals. The bus was safe and air conditioned, and the total time was 95 minutes. A taxi would have taken no more than 45minutes , but cost about $100! I got off at a mall and walked until I was at what looked like private roads to some condos. I told the security guard I was looking for the Waldorf and he pointed me to the left. I actually thought I was going to have to lug up a small mountain to get to the hotel, but as i rounded the corner I was happy to see this:

The gates to the hotel are huge and I was quickly welcomed in, offered water, and a seat. Soon, a golf cart pulled up and whisked me away through a tunnel that I didn't know existed because google doesn't really show it correctly. As I emerged from the other side of the tunnel, I was greeted with a margarita, my luggage whisked away to my room as I checked in. I thought the hotel was on top of the small mountain, but most

of the hotel is at the base near the water, with some buildings built into the mountain. I was then walked to my room which was less than 4 minutes from the lobby and once inside, I could not wait for the guy to leave so I could jump in the plunge pool. My room had been upgraded to a sea view due to my Diamond status (which you can get with the Amex Asire), and it was gorgeous! Constant crashing of waves and riptides make the water completely un-swimmable for miles, but that didn't bother me at all.

The hotel offers all guests a daily dose of salsa, guac, and chips along with two Coronas or two margaritas at 4pm. You communicate with the hotel via text or whatsapp, and the staff are all trained to try and say yes to all guests needs.

Over the 4 days I spent a ton of time in the room because of the plunge pool, the view, and the sounds of the waves. I also enjoyed the fitness center, the infinity pool, room service, and a meal at the pool. I was driven by golf cart several times to the main entrance that is a 5-minute walk from the town. I also walked through the tunnel a few times, just to get a little extra exercise. I enjoyed the free continental breakfast each day, as well as paying $9 the second day to upgrade to the fancier breakfast that included more like custom omelets. The continental breakfast included delicious muffins, bagels, homemade yogurts, toast, fruits, coffee, fresh juices, and cereals. On my last day, I asked for a 4pm checkout, which was granted, and I spent the last few hours with a second room service breakfast, and extra time in the plunge pool.

The stay at this hotel was the best I have ever had and the cost of a room here is at least $1300 per night, easily making this my best redemption ever!

During my stay, I was constantly trying to figure out where to go and stay next and I ultimately decided to try the other side of Cabo....San Jose Del Cabo, 22 miles away.

I chose the Hyatt Place Los Cabos, which is very basic, but close to the beach.

I used both Hyatt points and cash here in order to reduce the price. My time here was also enjoyable, but obviously very different from the Waldorf. It was fun to explore the area, walk on the beach, and while looking for a dinner spot, I discovered what tuned out to be one of my favorite memories of the trip. The photos turned out pretty amazing and reflect what a nice little place Mama Mia's turned out to be (especially at sunset):

I debated trying an all-inclusive hotel for a few days after this stay (Cabo is full of them), but soon decided to head to the big city...Mexico City that is! The 6th largest city in the world with over 21 million people. So, I booked an Aeromexico flight for August 7th and used 35,000 IHG points for a Holiday Inn for the first four nights. IHG gives you the fourth night free when booking with points.

Upon arriving in the evening, I used Uber to get to my hotel and booked a food/bike tour for the next day. The hotel was very modern, but not in the best neighborhood in the world, but the price was right.

I walked about 40 minutes to the bike tour starting point the next morning and a small part of the walk felt a little unsafe, but no real issues. As always, I highly recommend bike tours as a great way to get acclimated to visiting a new city. This tour combined food and bikes and was a fantastic experience. These tours always force me to try new food and drinks that I would not normally try on my own. The guides are local experts and valuable resources for tourists.

Riding on a Sunday afternoon on some of the busiest streets of this great city is a lot of fun.

I wound up using the city bike share after this quite a bit. One week unlimited usage costs $15 with a 45 minute max per ride. The bikes are heavy and clunky, but they get the job done and the app will guide you to all the stations and bike availability.

After my week of biking was up, I switched to walking because the streets are full of energy and I found it a lot safer than I thought it would be. I moved to the Hampton Inn in the Central Historic area, also know as Zocalo. This hotel was $57/night plus tax. The area is lively with many historical and government buildings. It is also among the safest. Zocalo Square is the second largest public square in the world. It hosts many holidays, tourist events, local events and protests, and government functions. One of my favorite moments was this one:

A surprising scene on a Friday afternoon in Zocalo Square...

I wasn't really sure what I was seeing, but I loved it. This was a great start to a day exploring the city.

A few nights later:

A special holiday remembering The Fall of Tenochtitlán which led to the fall of the Aztec civilization. A huge symbolic pyramid is built in the square and the story is told with images and video cast onto the pyramid and the entire square is adorned with decorations and lights.

I then realized the area I wanted to stay in for the remainder of my trip was the Roma and Zona Rosa neighborhood. I was hoping to use some of my hotel points for a nice hotel that included a club lounge that would give me opportunities for some free breakfast and dinners. You can sometimes get access to these lounges with elite status such as Hilton Diamond or in this case, I booked the Marriott Reforma and was granted access with my platinum status. I researched the recent reviews on google and tripadvisor before booking and several people said that the club lounge was closed but the hotel was providing a nice selection of food in the evenings. When I checked in, I was shocked and what they actually offered:

Free breakfast in the restaurant, and then anything on the bar menu (besides alcohol) from 5pm-10pm. The bar menu included a small selection of appetizers, soups, salads, entrees, and desserts. The entrees included pastas, burgers, and even filet mignon!

I booked five nights at this hotel for 95,000 points and got free breakfast and dinner daily. The dinners included delicious and huge meals because they let you order as much as you want. My first night's dinner: Chicken and rice soup, Fish tacos, Filet Mignon, and cheesecake. My bill each night was zero (plus a tip).

The room was great and the hotel had a nice gym, hot tub, sauna, and a terrific location.

I was able to walk out of this hotel any time of day onto Reforma Street which is gorgeous and runs through the heart of the city. I took long and short walks into many of the best neighborhoods in the city. I never had any safety issues.

So, to recap: I flew United business class from Newark to Cabo where I started my trip in a 5-star hotel with a private plunge pool and a private tunnel inside a mountain. I arrived and departed that hotel on a public bus. I followed that up with several 3-star hotels and an economy flight to Mexico City. My last five days were spent at the 4-star Marriott where I got some amazing free perks from my Marriott status. Mexico turned out to be better than expected and Mexico City is undoubtedly one of the most underrated cities in the world.

Let's go over the costs:

Flight (Business Class) one-way to Cabo: $453 - $450 United credit from credit card airline reimbursements ($250 used from Amex Hilton Aspire & $200 used from Citibank Prestige) - Total = $3.00

Bus from Cabo airport to hotel $4.00

3 Nights at Waldorf Pedregal - $0 (3 free night certificates used from Hilton Amex credit cards & $125 used on food/drinks from Amex Aspire resort credit)

2 Nights at Hyatt Place Los Cabos - 5000 hyatt points + $110

Flight to Mexico City - $154

Uber to Hotel - $11

4 nights at Holiday Inn Buenavista - 35.000 IHG points

4 nights at Hampton Inn Centro Historico - $285

5 nights at Marriott Reforma - 95,000 Marriott points

Food/Bike Tour - $55

Transportation in Mexico - $39

Food/drinks - $300

Covid at home test - $33

Uber to airport - $9

Flight (Business Class) to Las Vegas - $368



Tips: Always try and get maximum value for your points, free night certificates, and miles. Look at the dollar cost before booking. Sometimes its best to pay cash when rates are very low, but everyone's situation is different. Just do you homework!

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