Okay let’s get back to happy talk. Matt and I have finally figured out how we are going to get home from Thailand for our summer anniversary vacation. Remember our parameters: using only miles for business class tickets. It’s a game, and part of the thrill of it is seeing what kind of luxury you can get for very little cash!

 If y’all recall this July we were originally spending a week in Thailand and another few days in Israel to reposition ourselves to earn a better redemptions home. Unfortunately due to tragic world events we had to cancel the Israel portion (we will do Israel the right way for a longer period of time in the future as it is an important place to us for family reasons) which left us stranded in Thailand.

May I introduce you all to our new 10^th Anniversary Vacation. Get ready for this whirlwind of an itinerary. Every flight and hotel are booked on miles and points besides a few short-haul flights which are cheap within Asia.

2 Nights in Bangkok

We arrive in Bangkok late in the evening after two very long flights around the world. Our plan for these two days is to get ourselves together and if we have the energy check out the night scene…but it is us so don’t count on it.

Hotel: St. Regis Bangkok

Flights: Japan Airlines: Boston-Tokyo-Bangkok-Business Class-Cathay Pacific Miles Transferred from Capital One

5 Nights in Koh Samui

If you have never heard of Koh Samui, that will change as season 3 of the White Lotus takes place there. It is an island known for its beaches, forests, and elephant sanctuaries! We will be celebrating our anniversary here. @Matt says he is working on it….

Hotel: Vana Belle a Luxury Collection Hotel

Flights: Short 45 minute flight on Bangkok Airways. We are paying for this, but cheapie cheapie

1 Night in Bangkok

I know this is getting nuts, but we have a real early flight the following morning to our next destination and we did not want to risk it. This also gives us the opportunity to spend a day in Bangkok and see the city while not recovering from jet lag.

Hotel: St. Regis Bangkok

Flights: Short 45 minute flight on Bangkok Airways. We are paying for this, but cheapie cheapie

Okay now this is about to get ridiculous…..

5 Nights in the Maldives

How the heck did we go from Tel Aviv for 3 days to the Maldives for 5 nights?  Well, we were kind of desperate, but remember business class is a must at no (money) cost. Matt had a lot of United miles and I had a lot of American Airlines miles. The problem was we needed to find a location that was not in East Asia or Japan to get home in business on miles. This is tricky, particularly if you are gay as the Middle East is the really only option to keep the mile redemption reasonable while also not being too far from Thailand. With Israel ruled out I started looking at random cities in Asia, Middle East and  Eastern Europe. I could not believe I found a saver pass in miles on United from Male’, Maldives to Portland ME!  Thankfully Fly Dubai is a partner of United, so it is all one ticket.

How does one get from Bangkok to the Maldives? Easy, 3.5 hour direct flight on the same cheap airline as we were taking to Koh Samui. Low and behold we even had enough Marriott points for 5 nights at the St. Regis Maldives. For Marriott points redemption, you always get the best value with 5 nights as the 5^th night is free using Marriott points. With the Maldives being significantly closer than Israel and our willingness to add a day on the backend of the trip, we were able to squeeze 5 nights in the Maldives. We were set.

5 Night Maldives

This is exciting because we were debating between Thailand vs the Maldives and now we get both.

Hotel: St. Regis Maldives

Flights: Fly Dubai to Dubai, United from Dubai to Newark and Newark to Portland

Is this vacation nuts? Are we nuts? We also get half a day in Dubai as a bonus in between flights. A perfect opportunity to see a few of the sites (the fountains!!!), get some good Arabic food, and visit one of my oldest friends and finally meet his family!

Fun Fact: All in we are spending less than $1,000 on all these flights and hotels. For sh*ts and giggles I priced this same itinerary with the same hotels/room categories and flight….$39,574 dollars. I think we did well doing this for <$1,000. I told you this was a happier post! I am so excited to celebrate our 10^th anniversary on this whirlwind trip.

PS I hope Matt doesn’t like it too much as we will never likely do this one again 😊

Bon voyage,

Andrew

PSS If you need free advice on how to book something similar, check out this post and  and part 2.