My strategy for maximizing Hilton Honors points and free award nights

If you read my blog often enough, you’ll know that I’m a recent convert to the Hilton-portfolio brand of hotels. After signing up for a Hilton American Express business credit card which gave me complimentary gold status, and after a few bed Airbnb experiences, I decided to give Hilton a try.

As a remote worker, I was generally opposed to hotels. My main concern was lack of a kitchen — when I’m traveling, I like to cook my own breakfast because it can often take an hour or two to find a place and get served in a new city (plus, I’m pretty cheap when it comes to food, as I would rather spend that money on travel). However, Hilton since gold status comes with free breakfast, this made me less anxious about switching over.

By staying at Hilton properties more and also with credit card bonuses, I’ve managed to rack up a lot of points and a free weekend night (about to hit my second one!).

While there is some controversy around their actual value, Hilton points are valued at ~0.6 cents per point. That said, with my strategy below, I’ve been able to redeem them for as much as 2 cents per point using some of the strategies below.

For the free weekend night, it’s given as a yearly bonus to certain credit card holders (with the Aspire card), and for those with the business card, you can get this after spending $15,000 in a calendar year (if you spend $40,000, you get 2). This can be used on a standard room and can net you a value of over $750, if used correctly.

How to maximize the value of your Hilton points

1) Get a credit card with complimentary Hilton status

If possible, you should sign up for a Hilton credit card that comes with complimentary status — this includes the Hilton American Express business card or the Hilton Aspire card. The main reason for doing this is that elite members receive their 5th award night free (meaning you’ll only need to pay 4 award nights for a 5 night stay).

Which leads me to my second strategy…

2) Wait until you have enough points to book 4 nights (so you can get your 5th night free)

Rather than redeeming points for a night or two at a hotel, if you do obtain Hilton status, you’re better off waiting until you have enough points (and time) to book 4 nights somewhere so that you can get the 5th one for free. The great thing about Hilton Honors is that it’s very easy to earn a lot of points very quickly, and the credit card bonus sign-ups are very nice right now (some are in the 125,000-150,000). A night at a top property is 95,000 miles (more on that below).

Hilton also regularly has sales on points where they give you a 100% point bonus on anything purchased, which can help you get your balance to where it needs to be. This trick can save you as much as 120,000 points for a standard room.

3) Use points at luxury properties

The best way to maximize your points (aside from staying for 5 nights), is to use them for standard rooms at usually pricey properties. This includes the following hotels:

  • Conrad Maldives
  • The Grand Wailea, a Waldorf Astoria Resort
  • Conrad Tokyo
  • Waldorf Astoria Maldives
  • Conrad Koh Samui
  • Conrad Bora Bora

A standard room at most of these hotels will be 95,000 points, which means you’ll need 360,000 points to get the best redemption.

How to maximize the value of your Hilton free weekend night

If you have the Hilton Aspire card, or if you have the Hilton Business or another card that entitles you to a free weekend night after a certain spend threshold, you should strategy 3 above to maximize your points (i.e., trying to stay at luxury properties).

Keep in mind that the free weekend night only applies to standard rooms, and some hotels don’t have any so-called “standard” rooms (here’s a list of excluded properties– but, luckily, all of the above are not excluded).

So far, my redemptions have been for the Grand Wailea and the Conrad Maldives. I wrote about the Grand Wailea here and am definitely excited to check out the Conrad Maldives later this year!

What’s your favorite way to use Hilton points and free award nights? Let me know in the comments.

How I made $1,550 by opening a Chase business checking account

One of the most satisfying parts of my day is checking my mail and throwing all of the junk into recycling. But there was one piece of junk mail I couldn’t ignore — a $300 offer from Chase to open a business checking account.

The fine print was easy enough:

  • Deposit $1,000 within 20 days of opening to account
  • Keep at least $1,000 in the account for 6 months
  • Pay a $15/month fee if my balance goes under $1,500 (essentially, making it so I need to keep $1,500 in the account)

After doing some quick math, it was easy to see that the $300 I would earn would far exceed what I would make if I kept that money in savings. The only downside was that I needed to go to an actual Chase brand to open the account.

I’m not going to lie – it was a difficult process. I called in advance, they said they had space, and I arrived at 4:30pm on a weekday. The process to around an hour and a half, and I found myself leaving at 6pm when the office was closing.

While opening the account, I was told that I was pre-approved for a Chase Ink Business Preferred card and that, if I came back in person a few days later to open the card with the teller’s manager, I would get a 100,000 sign-up bonus instead of the regular 80,000. I couldn’t believe I qualified at all for the card — mostly because I already have the card (and you usually can’t sign up for 2 of the same card).

Although I didn’t want to head back to Chase, and was originally fine with the $300 offer, the opportunity to get 100,000 Chase points (roughly valued at $0.0125/point, or $1,250) was too good to pass up and worth the $95/year annual fee.

I was completely unsure that I would qualify to get the same card twice, so I had the teller write down a note saying that I would for sure get this card, that I would receive 100,000 Chase points, and, optimistically, that my visit would only take 15 minutes. My friends that it was so cute that I was being this optimistic.

But, having just left Chase, I have to report that it all worked out, my new Chase Ink Business Preferred card is on its way (and, as soon as I get it, I’ll be canceling the “old” one), and I am currently one happy customer.

If you’re looking to get this offer, login to your Chase account and, under accounts, you may see a banner advertising this promotion. It’s a targeted offer, so not everyone qualifies and you need to have a business to open an account. But if you do qualify, it’s an offer worth considering.

Los Angeles Trip Deal: $410 round-trip from LAX to Barcelona on Air Canada

Air Canada is putting Europe on sale and one of the best deals active right now is LAX to Barcelona, Spain. Flights start at $410 round-trip, after taxes with open availability in September and October 2018.

Sample dates:

  • September 12-19
  • September 19-26
  • October 14-21

For most of these flights, there is a 1 hour layover in Montreal on the way over and a 2 hour layover in Toronto on the way back.


8 places I would visit if I had paid time off

I realize that I am very lucky — getting to work remotely while traveling the world is, in my ways, a dream come true for me. But, as I frequently write about, this type of travel means that the destinations I visit need to have reliable WiFi and be in time zones which are conducive to working with American clients.

Because of this, I sometimes catch myself dreaming of the day that I can go completely off-the-grid on a trip. Below are some of the top destinations I’d like to visit if I ever got some paid time off.



Located just south of Croatia is Montenegro, a gorgeous country bordering the Adriatic Sea.

I first decided that I needed to go to Montenegro while traveling down the Dalmatian Coast, from Split to Dubrovnik. As I kept heading further and further south, I could not believe that the landscape kept getting more and more beautiful. I took out a map (because maps were a thing back then), and saw that if I kept going south, I’d hit Montenegro, and set my goals on visiting the country.

While it is stunningly beautiful, WiFi is not yet reliable in the places I’d like to visit in Montenegro, which is why this trip has been put on hold. But hey, I’m told delayed gratification can be a good thing… right?



It’s my own fault that I haven’t visited Patagonia yet — I’ve actually had 2 trips planned there that I’ve canceled at the last minute (the first time, I went to Mendoza, Argentina instead and the second time, after checking the forecast in Patagonia, I decided to instead visit the Atacama Desert in Chile).

I am still aching to go, however, particularly to Bariloche and Ushuaia in Argentina.

While WiFi in those destinations is actually decent, the types of activities that I want to do (hiking, camping, and some adventure sports) would be difficult while working remotely.



Guatemala, particularly Antigua, is increasingly being a hub for remote workers. Known for its stunning landscape, Mayan history, and low cost of living (for Americans), this Central American country has been a top dream destination of mine for years now.

Although there are spots where you can find reliable WiFi, I want to stay on Lake Atitlán, which was formed in a massive volcano crater and is supposed to be one of the most beautiful lakes in the world. WiFi is spotty in this area of the country, though, so my visit will have to wait!



I love taking the road-less-traveled and there are few places that are more “remote” than Mongolia.

While the capital, Ulaanbaatar, has reliable infrastructure, my dream isn’t to stay in the city – it’s to go to the windswept plains and Gobi Desert and to get completely off-the-grid.

As a remote worker, this isn’t possible (at least not yet), meaning I’ll have to keep Mongolia on my bucket list for now.



There’s an old saying amongst seasoned travelers: “When you’ve seen the world, there’s always Greenland.”

Located at the tip of the world, I first decided I needed to travel here after taking in an amazing view of the country on a flight from Norway to California. Since then, I’ve used Instagram to follow a few individuals who live in Greenland and have been captivated by their pictures.

While WiFi is reliable in towns and certain villages, I would love to be out on a boat and on hikes, neither of which are conducive to remote work.



It’s not hard to see why this is a dream destination of mine – with crystal clear water, idyllic beaches, and some of the most luxurious accommodations in the world, the Maldives is one of the most aesthetically pleasing places on the planet.

The tourist infrastructure is set up for honeymooners rather than remote workers, though, and while many hotels have decent WiFi, it’s often in the public areas and the time zone can be difficult to work from with American clients.

With global warming and the chance that the islands will soon be under the sea, I’m definitely in a rush to visit (and hope that I can disconnect when I do).



With the Atlantic Ocean to the west, Rwanda to the east, and the Namid desert in between, Namibia offers a mix of stunning landscape and incredible nature/wildlife.

While the country is starting to attract more and more visitors, WiFi is still fairly unreliable and the time zones are difficult to work from with American-based clients.



Nestled between India and China is Bhutan, a Buddhist kingdom on the Himalayas’ eastern edge.

Featuring jaw-dropping landscapes, temples built on the sides of mountains, and in a region known for its incredible food, Bhutan is a dream destination of mine. As an American, it can be difficult (and costly) to obtain a visa to travel here and the time zones/WiFi aren’t ideal for a remote worker.

Let me know what you think of this list in the comments below!

5 steps to take before visiting a new country

Whether you’re new to travel or a regular globetrotter, visiting a new country is always exciting. It can also be a bit nerve-wracking, particularly for solo travelers, as you may be worried about safety, maximizing your time while visiting, and making sure you have a good time.

Below are some tips for steps to take after you’ve booked your adventure but before you step foot in a new country:

no one deals like we do!

1. Learn basic phrases in the local language

Aside from my love of unlimited soda refills, probably the most American thing about me is that I am terrible at learning foreign language. After taking almost 8 years of Spanish and spending 4 years living less than 100 miles away from the Mexican border, my Spanish language skills are still very basic (though get better with alcohol consumption).

That said, before traveling to a new country, I always make sure that I learn how to say the basics, which include:

  • Hello
  • Thank you
  • Sorry/excuse me
  • Goodbye

While it would be great to know more (and see tip #4 here for help with that), I’ve found that knowing these words in a local language, a smile, and some body language are often all that I need to traverse a new, foreign destination.

2. Figure out currency conversion rates

One great way to save money when you travel is to use local ATM’s rather than currency exchanges to get your money, as the rate your bank charges is often lower. To do this, you should have an idea of how much money you need to get out by the time you land.

A trick that I like to use is looking up typical currency denominations and their corresponding value in USD, and writing down what it amounts to. For instance, in Colombia, here’s a list of the bills they have and current value in USD:

  • 5,000 Pesos = $1.75 USD
  • 10,000 Pesos = $3.50 USD
  • 20,000 Pesos = $7.00 USD
  • 50,000 Pesos = $17.50 USD

Knowing the exact worth, in USD, of these bills helps me avoid math (or really, getting the currency conversions wrong) when I’m out and about and possibly with no internet/cell service.

3. Learn about the local public transit system

If you’ve ever been to a new country and tried to hop on a local, non-tourist focused train/bus, you’ve probably experienced some anxiety related to it. Are you going the right way? Do you have enough money to cover the fair? Will there be signs for where you need to get off?

Even with proper research, a new city’s public transit system can be intimidating. I was in Tokyo a few months back for the annual cherry blossom festival, and Shinjuku station was hectic and confusing enough that, even with a plan, I almost had an anxiety attack.

But if you plan on using public transportation at all (and you should!), you should download a copy of the city’s local transit map and look into things like day passes, cost of public transit tickets, and hours of operation. Sometimes, you’ll find that private options (such as cabs or Uber) offer better value for your time and provide a way of saving time for you to explore.

4. Download “Google Translate” and “Google Trips” apps

Recently, I wrote an article about how Google Trips is my new favorite travel tool. I’ve linked to the article itself but, basically, it provides amazing day trip itineraries based on your interests.

Although Google Trips is my new favorite travel tool, Google Translate has been a favorite travel tool of mine for years. You can use Google Translate in a few ways, including entering a phrase you’d like to say in English and having the app tell you how to pronounce it in a local language to placing your phone over a menu (or anything in a foreign language) and having it auto-convert into English or another selected language.

5. Look into visa requirements

A few years ago, I was flying from Lima, Peru to Buenos Aires, Argentina when, at the Lima airport, I overheard 2 Americans talking. Apparently, they hadn’t realized that travel to Argentina required a visa for Americans, and because the system to apply for a new visa was down, they were stuck in Lima until they could get the visa approved.

Now, admittedly, I’m not the best at this — I’ve got a trip to Georgia planned in 7 weeks and I haven’t looked into the visa… yet. But you can save yourself a big headache by having the visa situation figured out a few weeks before your trip (or potentially a few months out for places that are known to have a difficult visa process, such as China).

Are there steps you take when you traveling to a new country? Let me know in the comments!

Why Google Trips is my new favorite travel tool

This April, I went to Japan for cherry blossom festival (which was one of the coolest trips I’ve taken in recent memory). Before arriving, my friend Shawn had mentioned a new app that he loved — Google Trips. I decided to give it a whirl.

Only having a few days in Kyoto, the app presented me with a few options and I selected “Day Trips.” From there, I have the option to pick between a few options and, based on my hotel’s location, I went with “East side highlights.” There were also options which included “Kid-friendly attractions” and historic monuments.

The app provided me with a map of all of the destinations I’d visit, including opening/closing times, a brief history, and transit options (see screenshots below).

This turned out to be the perfect day trip, hitting all the major spots with plenty of incredible views and sakura. When I’d get lost in the map, I could click a destination and the app seamlessly integrated with Google Maps, which was also very helpful. Picking the route I should travel was very helpful and turned out to be super efficient, even though I walked instead of taking cabs and public transit as the app suggested.

The experience was an upgrade from the Lonely Planet walking guides and, while those are still pretty great, I’ll be switching those out for Google Trips for the foreseeable future.

What are your favorite travel apps?

The 5 best destinations for Americans traveling abroad for the first time

This blog is meant to inspire others to travel more and, for some Americans, that may mean their first trip abroad.

There are many factors that can stop a person from traveling overseas: finances, family, and work are just a few. I believe that with an eye for deals, a desire/ability to play the “points” game, and by following blogs like Josh Trips, international travel has been opened up to people who may have otherwise never considered it.

On that note, I wanted to write this post about the 5 best destinations for Americans planning to leave the country for the first time.

5. Montreal, Canada


Our neighbor to the north is an amazing place to begin your adventures abroad. Canada is a very safe, diverse country with great medical care and friendly people.

While there are a handful of great places in Canada to choose from (Toronto, Vancouver, and Banff among them), Montreal is located in French-speaking Québec, making it feel more foreign. Even with that, you will still be able to communicate effectively in English, which is especially important many first-time international travelers.

Another advantage Montreal has is that it caters to all kinds of travelers – the city is as well known for its culture and architecture as it is for its strippers and poutine.

Advantages: Very safe, feels foreign
Disadvantages: Can get way too cold

4. Cabo San Lucas, Mexico


Full disclosure: I struggled a lot with this. Mexico has a number of excellent options for your first trip abroad, including Cancún, Puerto Vallarta, Tulum, and even Mexico City. What put Cabo San Lucas over the top, though, is that many establishments in this Mexican resort town accept U.S. dollar and English is more commonly spoken here than anywhere else I have visited in the country.

Not having to convert money will help first-time international travelers (pro trip: it’s almost always better to get cash from a local ATM than to exchange the money in advance, particularly at the airport where the fees are ridiculous).

But practical reasons aside, Cabo San Lucas is an amazing first-time (and for me, ongoing) destination because of it’s near perfect weather, its beautiful beaches, amazing resorts, and the quick flight from the West Coast.

Advantages: Safe, can use U.S. dollar, can get by with English
Disadvantages: Americanized, not a ton of culture

3. Paris, France


Gay Paree!

One thing is for sure: if your first international trip is to Paris, you will be planning another in no time. The City of Lights is a must-visit destination for anyone, and its solid tourism industry means that it has the perfect structure for first-time travelers.

Those who like to plan their trips can easily find free guides online and learn from others mistakes. Budget travelers also have a host of options due to the size of the city and the number of backpackers who visit.

As amazing as Paris is, recent terror attacks may cause additional anxiety for first-time international travelers, which is the only reason this glorious city isn’t ranked higher on the list.

Advantages: Safe, world-class city, amazing sights
Disadvantages: Foreign language, recent terror attacks

2. London, England


Like Paris, London is a world-class city. But also like Paris, recent terrorist attacks have made it less friendly for first-time international travelers, many of whom are already a bit skittish. Despite this, London is still an excellent choice for Americans going abroad for the first time.

Many Americans already know some English history and a bit about the royal family, which is helpful when exploring. The Tube is easy to use and effective, and there is an amazing mix of culture, fun, and food that will keep any first-time traveler happy.

What puts London over Paris, though, is that its an English-speaking country, which is helpful for many first-time international travelers.

Advantages: English speaking, familiar history/culture
Disadvantages: Strong-ish Pound, recent terror attacks

1. The Caribbean


The other selections for this list were specific cities, but for the number 1 spot, I picked an entire region. The reason is simple: for all intents and purposes, if you’re visiting a beach destination with the goal of relaxing and enjoying the vibes, most islands in the Caribbean are very similar.

Particular islands that come to mind include The Bahamas, Jamaica, Barbados, Aruba, and St. Kitts. Assuming you stay at a hotel/resort, your experience will likely be very similar.

The Caribbean boasts amazing beaches, world-class service, a tourism industry which caters towards English speakers, and safety in and around its touristy parts.

It’s important to time your trip to the Caribbean right; June through November is hurricane season, so the winter months are usually “safer” for a first-time international trip.

Advantages: English speaking, easy flight (from the East Coast), postcard pictures
Disadvantages: Not usually cultural, Hurricane prone