Traveling the world (in style) this winter for $900 and 90k in points

It’s only the beginning of January and I already have so much travel planned to look forward to.

As a freelancer, it’s hard for me to plan my travel too far ahead, since it’s hard for me to predict what my revenue and workload will be like. As a result, I don’t like to plan trips out more than a few months in advance, unless I find an incredible deal to a location I’ve been dying to visit.

That said, I felt comfortable enough to book my travel through April. I not only wanted to go to amazing destinations, but I wanted to be comfortable while traveling. As a result, I looked for trips where I could get good deals on business/first class, focusing mostly on either using miles or booking flights where it’s likely I will get upgraded.

My 4 trips, which include 2 confirmed international first/business class legs and 3 additional legs which are likely to be in first/business class, cost  a combined $907.90 and 90,000 United MileagePlus award miles. My 4 trips are:

Caye Caulker, Belize

I’m starting off my travel this year with a trip to Caye Caulker in Belize, which I scored for 35,000 miles and $66.91 in fees on United.


I booked this trip pretty randomly. A person I follow on Instagram was there a few weeks back, and it looks really stunning. It’s very cold and rainy in San Francisco right now, and I was dreaming of a tropical beach, so, I made Caye Caulker my first trip of 2017. I haven’t been to Belize since a cruise in 2007, so I am really excited to head back.

Flights from San Francisco were around $450 at the time I booked (they have gotten cheaper since then), so I decided to go with miles for this trip. As a United Premier Silver member, I qualify for upgrades on Complimentary Premier Upgrade (CPU) eligible flights, and all of the flights in this reservation are CPU eligible (the flight is from San Francisco to Houston to Belize City, and home the same route). Based on current capacity, I expect, at the least, to get a complimentary upgrade to Economy Plus for all of these flights and to be upgraded on at least 2 of the flights.

Approximate business/first class legs: 2

Chile and Uruguay

In winter months, I like to chase summer, and there’s no better way to do this than to visit South and Central America (particularly if you’re an American freelancer who needs to stay close to a specific time zone).

Santiago, Chile from San Cristobal Hill

My friend Julie is living in Uruguay right now, so I was looking up ways to visit her. While searching for different South American hubs to fly to, I found an amazing deal: 55,000 miles and $49.86 in fees on United to fly international business class from Santiago, Chile to San Francisco (with a layover in Toronto).

Notably, international business class on Air Canada comes with lie flat beds.

I still haven’t figured out how I’m going to get to Chile, though I am considering jumping from Mexico City to Bogotá, Colombia to Uruguay, before eventually heading to Santiago. This route would cost about $200 for a direct flight from SFO to Mexico City and 40,000 in miles to fly business from Mexico City to Montevideo, Uruguay with a long layover in Bogotá.

Full disclosure that this will, of course, add to the overall cost of my trip, but because I can book this completely with miles or with Chase points, and because I’m too excited about the travel to wait to post this, I haven’t included this cost in the total yet.

Confirmed business/first class legs: 2

Puerto Vallarta, Mexico

As a San Francisco gay, I would be remiss if I went more than a year without visiting Puerto Vallarta. Puerto Vallarta is one of my favorite destinations to visit for many reasons, including my love for Mexico and the Mexican people, its ease to get to from San Francisco (usually around $300-$400 and a 4-5 hours direct flight away), the great weather, good infrastructure for remote work, and one of my favorite hotel pools in the world.

My happy place in Puerto Vallarta

Having a friend already going in March, I tagged along to his trip. I purchased this ticket outright on United there and Alaska on the way back. I had a $125 voucher to use on Alaska from a flight to Portland that was delayed 3 hours, which brought the total for this flight to $229.27 total.

The flight I’m taking to Puerto Vallarta is still very empty and it qualifies for a Complimentary Premier Upgrade, so I am sure I will get Economy Plus and am also expecting to be upgraded to United First.

Approximate business/first class legs: 1

England and Italy/Spain/Portugal/Morocco

Maybe it’s cliché, but I love Europe. I also love flying direct on an airline I have status with. So, when I saw a $561.86 direct SFO to London ticket on United, I booked it for April. Really, I would have rather booked it for May, June, or July when the weather would be better but, as mentioned earlier, it’s hard for me to predict my life in May enough for me to book travel out that far.


So, my plan is to celebrate my friend Bob’s birthday in London and visit with some friends, and then fly south to either Portugal, Morocco, Spain, or Italy to thaw out. Full disclosure that these flights could add to the cost of this trip, but as nothing is booked and I could end up staying in England (unlikely), I haven’t included these costs.

My guess is that I’ll be able to upgrade to Economy Plus for these routes, but they aren’t CPU eligible, so I almost certainly won’t be in business or first.

Approximate business/first class legs: 0

I feel like I made out pretty well for my winter travel and am excited for the adventures ahead!

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