Planning the Ultimate Dream Vacation on Miles and Points!

If you are reading this post, I assume you have some interest in traveling and have a couple of dream destinations in mind. Traveling with miles and points can help you get astounding value and amazing travel in premium class cabins and hotels for almost no cost. Here’s how you can book a vacation for 2 on Miles and Points.

The Maldives are within reach with the power of points!

Table of Contents

Start Saving Early

No, you’re not saving cash in a savings account, but rather you are growing your stash of miles and points about 18 months in advance in preparation for a dream vacation. I would focus on earning flexible currencies such as Amex, Chase, or Capital One points. These currencies hold solid value and at worst have a minimum redemption value if utilized properly. Flexible currencies are also “flexible” as you can transfer those points to a variety of airline and hotel loyalty programs.

For a dream vacation for you and a significant other, having around half a million points total should be sufficient enough. Ideally, you want to have your points saved and ready for use 12 months in advance and to lock in flights before award capacity dries up. Dream destinations often fill up fast, but will vary based on your home airport and ideal destination.

Build a Credit Card Signup Strategy

Credit card signup bonuses continue to play an important role in the miles and points game. Think of a plan to meet a couple of credit card sign up bonuses, refer your significant other, and even dip your toes in manufactured spending. All these methods can help you rack up some miles and points in preparation for your dream vacation.

Just remember to track your spend and meet those signup bonuses before you open another card.

Some of the best credit cards for those starting out include:

  • Chase Business Ink Cards
  • Chase Sapphire Reserve/Preferred
  • Chase Freedom Unlimited
  • American Express Platinum
  • Citi AA Business Card
  • Capital One Venture/VentureX
  • Capital One Saver

Pick a Few Brands

Everyone has their favorite brands, mine in Hyatt

Once you’ve received those heard earned sign up bonuses, pick a few brands(airlines and hotels) that you would like to fly or stay with. Having an idea of which brands you would like to try can help narrow down your trip planning. For example, if you want to fly to Asia, pick a few airlines you would like to try. Since you are planning an aspirational award and dream vacation, I would try to splurge a little more of your hard earned points for luxury hotels and premium cabins.

Having brand loyalty isn’t necessary, but rather knowing which brands or specific hotels you would like to stay at can go a long way in trip planning. While some like to make last minute plans, I find that award availability is extremely scarce when flying from major hubs.

Take Advantage of Rakuten and Other Shopping Portals

American Express credit cards are a must have as you unlock several unique transfer partners (ANA) and the ability to earn cashback via Rakuten at solid rates which are then converted in Amex points 1 for 1. This amazing partnership has allowed me earn over 1 million American Express Points in the last 2 years!

The rule of thumb is to always shop through an online shopping portal to maximize your savings. If you’re unsure which portal is currently offering the best rates, check out Cash Back Monitor. This site does a wonderful job comparing cash back rates!

Give Yourself Time and Options when Planning

If you want to go to the Maldives last minute only during a certain week of the year, chances are you may struggle to find flights and hotel award space. Award flights to highly sought after destinations can fill up fast so start looking 300 days in advance. In order to plan your “Dream Vacation”, give yourself ample time to pick the desired flights, hotels, resorts, or destinations that you want.

On the other hand, if you’re someone with a really flexible schedule, you may be able to pull off a last minute dream vacation. As a general rule of thumb, some airlines may open award space as soon as their flights are scheduled, while others may open award space closer to the departure date. Generally, airlines will release seats in batches, with more seats becoming available as the departure date approaches. Airlines will also release more seats for offseason travel when demand is much lower. Some airlines such as Lufthansa will only release first class awards to partners closer to departure date.

Final Thoughts

Planning a dream vacation can be pricey and tedious. Thanks to miles and points, premium cabins and luxury resorts are more accessible than ever. With the right strategy, planning, and mindset, you can go anywhere including places such as Tokyo, the Maldives, Rome, Paris, and much more. Happy Traveling!

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