Eric Lenson

One of the great things about points is that they make ultra-luxury vacations an affordable reality. In this article we’ll explore some of the most exotic and jaw-dropping destinations that you can book with points.

MALDIVES

Visiting the Maldives is a bucket list item for a lot of people. Fortunately, there are a ton of resorts here that you can book with points.

You can even get an overwater villa, like this one!

BORA BORA

Bora Bora is another bucket list item for a lot of people. It’s a similar tropical paradise to the Maldives, but in French Polynesia. Bora Bora has the added benefit of being close to New Zealand and Australia if you want to add another exotic location to your trip.

EXPERIENCE LUXURY LODGING IN JAPAN

Japan is another hotspot for premium point redemptions. The Andaz Tokyo Toranomon Hills hotel is one of the most spectacular options in Tokyo.

You can check out an in-depth review of this hotel, along with tips on how to book it here.

FIRST CLASS IN THE SKY

For those who love to fly, a first class airborne experience is a must. The majority of airlines allow point redemptions for premium cabins. One of the best is Singapore Airlines’s first class cabin.

This experience features caviar, high-end champagne, a dedicated bed, and your own suite in the sky. You can even combine two beds to make a full size bed if you’re traveling with your partner.

You can check out an in-depth review of this suite here.

NEW ZEALAND

No dream destination post is complete without a nod to New Zealand.

Queenstown, one of the hubs on New Zealand’s South Island, has something to offer for everyone. There’s nightlife, skiing, jet boating, white water rafting, and hiking all within or near the town. The Azur Lodge makes a great luxury home base for your New Zealand adventures.

SKIING

If you prefer a thrill seeking getaway, you’re spoiled for choice. There is an abundance of luxury ski-in ski-out hotels that are bookable with points. One of these is the Waldorf Astoria in Park City, Utah.

FINAL THOUGHTS

Whether you crave the energetic streets of Tokyo or the pristine beaches of a faraway island, dream vacations don’t have to break the bank. Credit card points place unforgettable experiences within your grasp. Check out this article for an intro on how to start earning points.

Booking travel with credit card points and airline miles provides enormous benefits compared to booking cash. Here are the two main advantages:

• Free flights, hotels, and car rentals
• Luxury travel becomes affordable. For example, the $8,165 business class flight I took to Japan that I paid $291 for. That’s even cheaper than an economy flight!

The purpose of this article is to help you decide which booking method is best for you. It’s difficult to find complete information on this topic. A lot of sites provide catchy headlines, but don’t tell you the challenges of booking a 5 star hotel or first class flight.

In this article, I’ll provide an honest comparison of these methods. I’ll include both the highlights and potential pain points that I’ve learned from experience.

For clarity, “points” are what you earn from the credit card issuer when you use your card. Miles are what your points turn into when you transfer them to an airline.

BOOKING WITH POINTS

Booking this way is typically done by booking through your credit card issuer’s travel portal. This enables you to directly pay for travel expenses with points instead of cash. Travel expenses include flights, hotels, and car rentals.

BENEFITS OF THIS METHOD

This method is straightforward. You’re paying with points, not cash. It’s easy to earn significant sums of points for free, making this a low-effort way to earn free vacations. If you don’t already have a stash of points, check out this article on the easiest ways to start earning them.

You can increase the value of your points up to 50%. The details of this are beyond the scope of this article, but know that premium travel cards from Chase make your points more valuable.

DRAWBACKS OF THIS METHOD

This method sometimes requires you to book travel through your issuer’s travel portal. For example, if you have American Express points, you book through the American Express website. Notably, Chase does not require you to book through their portal.

The issue with booking through a portal is that prices are sometimes higher than alternatives. You can still use points to cover your entire purchase, but it will cost more points than it really should.

BOOKING WITH MILES

Booking this way requires you to exchange your credit card points for airline miles, or hotel points. The two biggest benefits of this method are listed below.

• Your points become much more valuable. Sometimes even 15x as valuable, but 2-5x is more common
• Luxury travel. This is how you find yourself sipping champagne in first class 35,000 feet over the Pacific ocean, or at a 5 star resort in the Maldives

The tradeoff is that it adds complexity. Plainly put, it’s more work. If you seek simplicity and don’t care about luxury travel, booking with points is best for you.

If you’re intrigued by this option despite the extra work, you’ll want to know just how much extra work we’re talking about here.

THE REALITY OF AFFORDABLE LUXURY TRAVEL

There are many considerations when maximizing the value of your points for luxury travel. Discussing them all will make this post too long, so we’ll focus on the biggest hurdle.

The booking process is complicated. Here’s an example. I recently exchanged my American Express points for Air Canada miles, in order to book a United Airlines flight. 

Seems silly, doesn’t it? The reason you can use the miles of one airline for a flight on a different airline is because they are in the same “alliance”.

But, how do you keep track of which airlines are in which alliance? How do you know where to find the best deals? Starting from scratch, this will take a lot of googling to figure out.

HOW TO MAKE IT EASIER

We invite all of our readers to reach out to us directly. The Life of Points team has spent countless hours researching this topic. We have learned many best practices from real world experience.

The best way to get in contact with us is by joining our discord, but you are also welcome to send us an email at [email protected]. Our mission is to help our readers craft unforgettable vacations, so we are happy to help!

HOW TO MAKE IT EVEN EASIER

The simplest option is to pay a third party to do all of the legwork for you. You provide them with the details of your trip (route, number of passengers, desired cabin, point balances) and they provide a list of your best options and guidance on how to book.

These services charge roughly $200 per passenger. With how much you’ll save on the flight itself, the total cost will still be quite reasonable.

FINAL THOUGHTS

Credit card points provide huge savings for anyone with travel plans. If you don’t mind some extra work in planning your next trip, luxury vacations are within your grasp.

If you want to keep things as simple as possible, booking directly with points, or a cashback strategy is a low-effort way to make your next vacation free.

A little bit of guidance goes a long way when it comes to both quantity and ease of points earned. In this article I’ll discuss why you should start earning points, and describe an excellent way to get started.

WHY YOU SHOULD START EARNING POINTS

This blog focuses on free and heavily discounted travel. However, credit card points can also be used for significant amounts of cashback. Over time, this will add thousands to your bank account with little effort from you.

UNLOCK LUXURY DESTINATIONS AND FREE TRAVEL

It doesn’t take a lot of points to start redeeming free flights and hotel rooms. Within a few months you can easily have enough points for two round trip domestic flights and several nights at a nice hotel.

A stash of points also makes aspirational travel realistic and affordable. Cash prices for luxury destinations like the Maldives and Bora Bora are often $10,000+. With points, the cash price goes down to $1,000-$2,000.

Another example is my recent business class flight from Los Angeles to New Zealand. This flight only cost 75,000 points and $94. You can earn 75,000 points with just one welcome offer. The cash price for the same seat that I flew in was an unbelievable $7,400.

EARN CASHBACK

While you will earn several hundred in cashback upfront from welcome offers, the idea with a cashback approach isn’t to quickly make thousands of dollars. Instead, the idea is that a small amount of work now (figuring out which cards are right for you and then applying for them), will earn you thousands over time.

BOOST YOUR CREDIT SCORE

A remarkable side effect of building a stash of credit card points is the impact it has on your credit score. In the short term, the hard pulls from applying for new cards will negatively impact your score. However, in the medium to long term, applying for new cards and using them responsibly will significantly boost your score.

The most important factor in calculating your credit score is your credit utilization rate. Simply put, this is how much credit you use compared to how much credit you have. Getting new cards increases the total credit available to you which quickly improves your utilization rate.

SAVE BIG ON LARGE PURCHASES

The biggest benefit of boosting your credit score is getting lower interest rates on loans for big purchases. If you have plans to buy a home or car, having a better credit score can save you thousands. If you already have a big ticket loan, a great score will put you in a better position to save big on better refinancing rates.

EXCELLENT STARTER CARDS

In my opinion, the best two cards to start with are the Chase Freedom Flex (CFF), and Chase Freedom Unlimited (CFU). These cards are complementary to each other, which we will explore later in the “Perks” section.

Neither are premium cards, which means they have no annual fees and they are easy to get approved for. They are both issued by Chase, which is a reputable company with a great app that makes managing your account simple.

WELCOME OFFERS

Both the CFF and CFU currently have $200 welcome offers. To get these $200 bonuses, all you need to do is spend $500 in the first 3 months of having the account.

For the sake of clarity, this offer is available for both cards. Most people will naturally spend more than $1,000 in 3 months, so applying for these cards and then using them earns you a quick $400.

THE PERKS

The welcome offer is only the beginning. Both of these cards are designed to provide significant value over time.

FREEDOM FLEX

The CFF’s primary draw is the 5x rotating calendar. Every quarter, Chase picks a few categories in which, for every dollar spent, you earn 5 points instead of the usual 1 point. Common categories include grocery stores, amazon, streaming services, and gas stations.

There is a limit for earning increased points in these categories of $1500 per quarter. If you meet that limit, you will have earned 7,500 points and will then earn 1 point per dollar until the next quarter.

It is important to know that you need to activate this offer each quarter. All you have to do is tap the offer in the app, or click “Activate” on the reminder email that Chase sends you.

FREEDOM UNLIMITED

The CFU’s primary draw is the 1.5 points per dollar spent on anything. Unlike the CFF, there is no limit, and no activation is required.

Additionally, this card earns 5x points on travel booked through the Chase travel portal, 3x points on drugstore purchases, and 3x points on dining.

HOW THESE CARDS WORK TOGETHER

The idea is that you use the CFF whenever your spend falls into one of the 5x categories, and the CFU for all other purchases. This is a simple and easy to manage strategy to maximize the number of points you earn.

FOR THOSE WHO LOVE TRAVEL: ONE MORE OPTION

These two cards are a powerful duo on their own, but for those with lots of travel plans, there is one more option to consider.

Adding the Chase Sapphire Preferred (CSP) or Chase Sapphire Reserve (CSR) multiplies the amount of free travel you can redeem. The combination of these three cards is called the “Chase Trifecta”.

The Trifecta has been written about extensively online, so I’ll keep things brief. With this setup, you primarily use the CFF and CFU to earn points, and then you transfer those points to the CSP or CSR. This allows you to take advantage of the 25-50% travel redemption bonus offered by the Sapphire cards.

FINAL THOUGHTS

Whether you’re interested in travel or cashback, a little bit of credit card planning now will pay off big in the long run. In the time saved by skipping that Sunday movie you plan to watch, you set yourself up for thousands of dollars or free vacations.

If you’re unsure which cards are best for you and would like our opinion, join our discord server and ask away!

My recent business class flight to Tokyo granted me access to the United Polaris lounge at the San Francisco airport (SFO). You can read more about this $8165 flight and how I got it for $291 here. This article will review the superb SFO Polaris lounge.

This is the type of lounge that is an attraction on its own. I actually chose the earliest flight into SFO to spend as much time as I could there.

Simply put, this lounge is an all inclusive premium haven. Equipped with shower suites, a buffet, a la carte dining, and a full bar, it has everything you’d want at an airport.

THE ONE ISSUE: FINDING QUIET SPOTS

At 28,000 square feet, this is one of the biggest airport lounges in the US. Regardless, due to high traffic, the hotspots can get uncomfortably crowded.

Having spent 20 hours there, I’ve found two spots that are quiet even at the busiest of times. There is one spot on the first floor, and one on the second.

On the second floor, proceed away from the dining area to the opposite side of the lounge. The area past the escalators will be less crowded and has seating with both privacy dividers and power outlets. If you continue all the way to the opposite end of the lounge, you’ll also find a secret snack bar.

The quietest spot in the entire lounge is on the first floor. This area is just outside of the shower area, near the entrance to the lounge.

DINING HIGHLIGHTS

Unlike the food provided for Polaris passengers in the sky, the food in the Polaris lounge is excellent. Two options are provided, a buffet, and a la carte dining.

A LA CARTE

Nestled at the far end on the second floor sits a modestly sized dining area. Despite its size, the staff does a great job at minimizing wait times. That being said, you should put your name on the list before you actually want a table. Even if there are open tables, there will always be a wait. In my experience, the wait time is usually half of what they say.

Outside of being refused a cocktail in the dining area, the staff have been excellent. I found this odd as the dining staff in the LAX Polaris lounge were happy to provide cocktails. To be fair, the LAX lounge was much less crowded.

Despite the cocktail refusal, my champagne flute was kept filled to the brim. I can’t complain!

I took the waiter’s recommendations for all 3 courses and was not disappointed.

BUFFET

The buffet is a great option for those with limited time. There are a wide selection of dishes to choose from, and the staff did a great job at keeping the dishes full. Both hot and cold food is provided, and there are plenty of options for vegetarians.

Hot dishes:

• Seafood adobo
• Hainan chicken
• Roasted broccoli and cauliflower
• Red pepper rice
• Ramen
• Ginger lemongrass broth bowl
• Winter squash bisque

THE EXCELLENT POLARIS BAR

This is the best open bar I’ve ever been to. I am still on my quest to find green chartreuse in an airport lounge, but they had everything else I asked for.

Tipping is not required or expected anywhere in the lounge, but a $5 tip went a long way. My bartender was friendly and talented. He gave great recommendations based on my previous orders. If you’re a fan of bourbon, ask for an Inside Job.

The problem with the bar in the past is that it was way too small. A bar that seats about 8 people in a lounge the size of multiple mansions never made sense. I am happy to say that they addressed this and made the bar roughly 3 times bigger.

Over the course of the day, I had a French 75, Espresso Martini, Sazerac, and Inside Job. They were all well balanced and delicious.

PRIVATE SHOWER SUITE

The lounge is equipped with 8 high quality shower suites. I was 3rd in line when I went for my shower at 8pm. I waited only 5 minutes.

The towels provided are made by Saks Fifth Avenue, and the soaps are from Therabody. Suffice it to say, the amenities are excellent.

My airport shower pet peeve is a suite that quickly steams up due to lack of ventilation. For a reason I don’t understand, most airport showers suffer from this problem.

It is quite annoying to step out of the shower and have the mirror be completely unusable due to condensation. Not to mention the uncomfortably hot room.

I’m very happy to say that the ventilation in these private suites is excellent.

FINAL THOUGHTS

Unlike most lounges, you can’t buy an entry pass. However, I would gladly pay a pretty penny to spend a day there with friends. If your ticket grants you entry, treat yourself and start your vacation off in luxury.

For many, a trip to Japan is a once in a lifetime aspirational vacation. But it doesn’t need to be. With just one or two credit cards you can secure the airfare for free.

In this article we’ll look at a few credit cards that will cover the expense of those round trip tickets. These cards also provide benefits to make those long travel days breeze by.

HOW IT WORKS

Here’s the bottom line on how you get to Japan for free with credit cards.

• Apply for a travel credit card with a high welcome bonus
• Meet the spend requirement to earn the welcome bonus
• Use the perks of the card to make your travel more comfortable, affordable, and easy
• Move your everyday spend to the travel card, or a sister card that is mutually beneficial with the travel card

There are multiple cards that meet all of the points listed above. All you need is a decent credit score and the financial responsibility that comes with having a credit card. There are no guarantees, but credit scores in the low 700’s often see approvals.

These are the credit cards we’ll look at in this article:

• Chase Sapphire Preferred
• Chase Ink Business Cards
• Capital One Venture X

We’ll also look at sister cards to the ones listed above. These cards work together to help you earn more points and get more free travel.

OPTION 1: CHASE

SAPPHIRE PREFERRED

The Sapphire Preferred has a welcome bonus that fluctuates between 60,000 and 100,000 Chase points. If you apply when the bonus is 80,000, you’ll have at least 84,000 points when you finish earning the welcome bonus.

This card provides a 25% bonus when you book travel via Chase, so your 84,000 points are worth ($840 * 1.25) $1050 towards travel. Round trip Japan tickets roughly range from $700 – $2k, so this bonus is enough to cover the cost of the tickets in the low season.

It is worth noting that this card has an annual fee of $95. Sometimes it is waived for the first year, but usually not. For almost all travelers, the value of the benefits far outweigh the annual fee.

CHASE INK BUSINESS CARDS

The Ink cards are a suite of 4 business cards from Chase. Welcome offers for these cards range from 75,000 points to 100,000 points. Even the Ink cards with no annual fee have had welcome offers as high as 90,000 points!

If you get the 90,000 point bonus, you will have 96,000 points by the time you are done with the welcome offer. This is at least $960 towards travel.

Currently, the Chase Ink Preferred has an outstanding and all time high 100,000 point welcome offer. This card provides the same 25% travel bonus that the CSP does. So, 100,000 points is worth $1250 towards travel!

The Ink cards also have an incredible referral bonus of 40k Chase points. This means you can be rewarded with $400 of travel simply for referring someone.

DO I QUALIFY FOR BUSINESS CARDS?

The scope for what qualifies as a business is wider than most expect. You don’t need a LLC or Corporation to be considered a business.

For example, if you resell items online, provide photography services, or do nearly anything that generates revenue, you can apply as a Sole Proprietorship.

OPTION 2: CAPITAL ONE

VENTURE X

The Venture X is Capital One’s flagship travel credit card. The welcome bonus varies from 75,000 points to 90,000 points. This is $750 or $900 towards travel.

The Venture X has a ton of benefits that any traveler would be sure to enjoy. Check out this article for a more detailed look at the Venture X, and a comparison with the Sapphire Preferred.

POOLING POINTS: EARN POINTS FASTER FOR FREE

The bottom line with mutually beneficial cards is to earn the most points for every dollar you spend. Specific non-travel oriented cards earn points at an accelerated rate. These points can still be redeemed for travel.

For Chase, the mutually beneficial cards are the Freedom Flex, and the Freedom Unlimited. The Freedom Flex earns 5 points for every dollar spent on certain categories. These categories change every quarter and often include things like gas, groceries, or Amazon. The Freedom Unlimited earns 1.5 points for every dollar spent, regardless of category.

The idea with these Chase cards is to use the Sapphire Preferred on travel expenses, the Flex on the 5x categories, and the Unlimited on everything else.

For Capital One, the sister card is the Savor Rewards. This is a cashback card, but Capital One allows you to transfer cashback rewards into travel rewards. The Savor Rewards card has excellent cashback rates on popular categories. Most notably it earns 4% back on dining, and 3% back on groceries.

WHAT TO DO IF YOU ARE SHORT ON POINTS

Here are three options if you’re short on points:

• Get the cards far in advance and transition your everyday spend to them
  • Why not use expenses that you’re going to incur regardless to bring you closer to a free vacation?
• Consider applying for sister cards, or more than one travel card
  • Not all travel cards provide the same benefits. Depending on your situation, getting multiple travel cards might make sense for you
• Take advantage of referral bonuses
  • Referral bonuses are a great way of easily scoring a big point bonus. If you’re traveling with friends or family this is practically a must do

FINAL THOUGHTS

In conclusion, embarking on your dream vacation to Japan is more attainable than ever with strategic credit card planning. By leveraging welcome bonuses and maximizing travel perks, you can turn your travel aspirations into reality. Start planning today and pave the way for unforgettable experiences and cherished memories in the Land of the Rising Sun.

Join our Discord server for expert guidance on maximizing credit card points for travel and start your journey today!

Back in March of 2023, fueled by boredom, I spent several hours looking for fun flight deals. As one does… It didn’t matter where or when, I was just enjoying the search. I wound up finding a great deal on business class award flights to Tokyo and back. On a whim, I booked them.

I was able to book these tickets on a whim for two reasons. First, I had over a 250,000 United miles that I got from the United credit cards offered by Chase.

Second, United offers free award flight cancellations and changes. I didn’t know if I’d actually go or not, but with cancellation being free, why not book them?

In this article I want to do two things:

• Provide a glimpse into what an $8,000 seat on one of the world’s best airlines looks like
• Share some important considerations when it comes to booking expensive flights with points

LUXURY FOR LESS: THE POINT PRICE

Not only did this trip happen, but I re-booked both of my tickets when I found even better deals. My new outbound flight cost 45,000 miles and $291, and my return flight cost 70,000 miles and $47. 

By using points and putting in effort searching for award flights, I was able to get business class tickets for less than what economy costs!

My outbound flight was particularly exciting for two reasons. First, it was operated by All Nippon Airways (ANA), which arguably has the best business class product in the world. Second, the cash price for the exact seat that I booked with miles, was an astonishing $8165!

THE $8,000 ROOM IN THE SKY

First, let’s look at what a standard long haul business class seat looks like. Pictured below is a seat in United’s Polaris business class cabin.

Here are some of the highlights:

• The seat extends into a lie-flat bed
• Every seat has direct aisle access. The narrow passageway at the bottom of the picture leads directly to the aisle
• A reasonable amount of privacy for some seats
• Extra storage for personal belongings

Now let’s take a look at ANA’s “The Room”.

The seat, bed, and in-flight entertainment screen are bigger than what you would find in most first class cabins. Having a seat like this makes flying immeasurably more comfortable and enjoyable. Instead of dreading an 11.5 hour flight, I was excited to experience a terrific and luxurious product.

My favorite part of “The Room” is how incredibly private it can be. With the touch of some buttons, you can slide two doors closed and get your own mini room on a plane. What more could you ask for?

One of the great things about flying business class and having a lie-flat bed, is that it is a jet lag cheat code. On this 11.5 hour flight I got a solid 8 hours of sleep and still had time to have breakfast and coffee before landing. This effectively added a day to my vacation as I was well rested and ready to go when my flight landed in Tokyo at 5am.

CHALLENGES OF BOOKING WITH POINTS

$291 is nothing to pay for a flight across the Pacific, let alone an ultra-luxurious seat. So, what is going on here? What is the catch?

As mentioned above, this flight cost 45,000 miles in addition to the cash fee. We’ll put this aside for now as miles are not difficult to attain, and it is not the most important consideration. We’ll write about best practices for accumulating points and miles in other articles.

The “catch” is that booking big ticket award flights is not easy. The process can be complex and availability is limited. You have to invest time to learn how to book them, and search for availability. There are resources online to help you learn the process, and in-depth guides are currently in the works by the Life of Points team.

This is the reality of big ticket award flights. They will rarely be as easy to book as a traditional cash fare.

For those who want a quick and simple booking experience, or for those who don’t care about flying business, points still provide excellent opportunities for you. There are other ways to use points to make travel free or heavily discounted. This topic is not the focus of this article, but it will get its own, dedicated post in the future.

FINAL THOUGHTS

Premium travel experiences are attainable even for those without $8,000 to spend on a flight. Any type of traveler will benefit from racking up points, but those willing to put in a bit of research can unlock luxury travel experiences.

The Shimanami Kaido is quite literally, a bicycle ride over the sea. Between the main island of Japan and the smallest major island in Japan, Shikoku, is the Seto Inland Sea. The ride goes from Imabari in Shikoku, to Onomichi in Honshu.

Along the route are several small islands linked together by enormous suspension bridges. The ride is 42 miles, but with our many detours along the way, we rode 60 miles in 3 days.

As opposed to a guide or an in-depth review, this article will serve as a brief overview of what the Shimanami Kaido is all about.

The Shimanami Kaido rests in a sleepy part of Japan. In fact, Shikoku has the lowest population density in all of Japan. This adds to both the allure of the trip, and the safety.

A large portion of the route is on bicycle only roads. Even the parts on main roads do not feel unsafe as there are few cars and many sidewalks. Every suspension bridge crossing has bicycle only lanes on the side of, or beneath the bridge.

The remoteness of this adventure adds a special magic that can only be found off the beaten path. The majority of people we saw and interacted with were locals. Nowhere else in Japan was I greeted with such big, authentic smiles, and gifts!

HOW TO GET TO THE STARTING POINT

Despite its remoteness, it’s easy to get to the Shimanami Kaido. From Tokyo, it is only a 90 minute flight down to Matsuyama. From Matsuyama airport, you have public transportation options as fast as 60 minutes to Imabari station. The bicycle rental shop is located immediately next to Imabari station, a mere 30 second walk.

Alternatively, if you are in the Osaka / Kyoto area, you are looking at about 2 hours on the bullet train (Shinkansen) to get to Onomichi.

SUPPORT FOR CYCLISTS

The infrastructure for this epic adventure is excellent. They make it very easy to get started and feel comfortable that you have all the resources you need to safely make it from beginning to end. Let’s look at some of the highlights.

• There is a wide selection of bicycles and helmets with suitable sizes for tall individuals and those with large heads
• The route is clearly and consistently marked
• There are 8 stations along the way where you can switch out your bicycle if you encounter mechanical issues
• There is a baggage transfer service so you don’t have to carry your cumbersome belongings with you
• There are plenty of accommodations along the way that provide the same level of service you’d expect anywhere else in Japan
• There are plenty of konbinis (convenience stores), restaurants, and vending machines to keep you fueled throughout the day

EVALUATING THE PHYSICAL CHALLENGE

With how much you can customize your route and schedule, the physical challenge can be whatever you’d like it to be. All of the ascents to the bridges have their own pathways specifically designed for bicycles. This means there is nowhere on the main path that has a significantly challenging slope.

There are people who do the entire route in one day, so I think most people can do it comfortably over 3 days with little to no training. That being said, you are sure to enjoy yourself more if you put in some work beforehand.

THE BIGGEST OBSTACLE YIELDS THE BIGGEST REWARDS

If you’re up for a challenge, you can stop at the Kirosan Observatory along the way. Located just off the main route on the island of Oshima, this is the most difficult obstacle on the Shimanami Kaido. The grade along the ascending road goes as high as 9%. Unless you are an experienced cyclist, you will have to get off and push like we did.

Waiting for you at the top is a local specialty, salt ice cream! It sounds odd, but I can promise you it is delicious. Additionally, the view from the top makes the hard slog to the top well worth it! Pictured below is the longest suspension bridge along the route, and the first that you traverse if you start in Imabari like we did.

FINAL THOUGHTS

I cannot recommend the Shimanami Kaido highly enough. It is the most spectacular thing I’ve done in Japan, and one of the coolest things I’ve done in my life. Plus, the extra calories burned by cycling means you can eat that much more Japanese cuisine. If you want to add some adventure to your Japan trip, do the Shimanami Kaido.

We started our recent Japan trip with the Shimanami Kaido, a 42 mile bicycle ride across Japan’s Seto Inland Sea. I’ll write more about the Shimanami Kaido in another article, but it required us to relocate to northwestern Shikoku after landing in Tokyo.

Domestic flights in Japan are known for being inexpensive. For the most part, they are priced the way that domestic flights within Europe used to be priced before COVID. Unfortunately, we quickly ran into an exception. The only option to fly from Tokyo to Matsuyama was $151.

THE POCKET CHANGE OPTION

Within 5 minutes of searching, I found an excellent alternative. United was offering a seat on the exact same flight for a mere 5,500 United MileagePlus miles and $2.50!

This is an absolutely massive savings! Additionally, when you book a flight with points instead of cash, you will usually get main cabin economy instead of basic economy. This has several benefits. My favorite of these is the ability to choose your seat for free! I like to choose a window seat over the wings to minimize turbulence and provide a view of the landscape.

The fees required in addition to the miles (in this case $2.50) give you an opportunity to pay with your favorite travel credit card. I choose the word “opportunity” here intentionally.

Paying for airfare with certain travel cards provides several types of complimentary travel insurance. For example, you will get trip delay reimbursement, lost or delayed luggage reimbursement, and others.

EARNING MILES WITH EASE

Now, you might be asking, how hard is it to get 5,500 United miles? In short, it is easy, but let’s dive just a bit deeper. There are many ways to earn airline miles and credit card points that can easily be converted into airline miles. Let’s take a brief look at 3 of them.

THE FIRST METHOD

The quickest way to earn a large amount of miles is credit card welcome bonuses. The smallest welcome offer currently available that would earn you United miles is a surprisingly hefty 30,000 miles. There are also several larger offers that would net you north of 100,000 miles.

THE SECOND METHOD

If you don’t want to apply for a new credit card, there are simpler and more passive ways to earn miles. For example, in quarter 1 of 2024, the Freedom Flex card from Chase is offering 5 points per dollar spent at grocery stores. Spending $1100 across these 3 months would net 5,500 Chase Ultimate Rewards points.

The Freedom Flex has no annual fee and is easy to get approved for. This makes it a great long-term option for earning points without needing to get new cards.

Chase points can be converted into United miles at a rate of 1:1. Simply changing which credit card you use at the grocery store can get you a free flight! Small changes in how you allocate spend can yield tremendous results.

THE THIRD METHOD

You can earn a significant amount of points without spending any money. Most credit cards have a refer a friend program, and referral bonuses can be as high as 40,000 points!

We’ll write more about this outstanding 40,000 point offer in another article, but that can be as much as $400 cash, or $600 towards travel. This is a great win-win as you earn a referral bonus, and the person you refer can earn a generous welcome bonus.

FINAL THOUGHTS

If you take anything away from this article, it should be the value of making small changes in how you pay for things. Spending a small amount of time to create a credit card strategy can yield significant results over time.

It doesn’t get much better than getting free flights from using a different credit card, or referring a friend!