Making up for lost time: How I'm booking my biggest trip of 2021

While I've done a bit of traveling this year, I haven't actually been anywhere new. I've made a handful of trips around the U.S. and even one international trip, but all were to visit friends and family. I've been longing to see a new place since the coronavirus pandemic grounded my international travel, and my sights have been set on an early 2021 trip to a country that's accepting American tourists.

The country in question? South Africa. The country recently announced that it's reopening to all tourists — including Americans — later this year. The only stipulation is that you need to bring a negative COVID-19 PCR test and follow extensive safety protocols. Obviously, these seem totally worth it for what looks to be one of the most beautiful places on the planet.

I have been putting together an itinerary over the past week or so and finally have the majority of the trip pieced together. In planning the trip, I've also tacked on another new country, making the adventure even grander. Being a points traveler, the flights and hotels will be mostly covered by points and miles that have gone unredeemed during the pandemic.

In this article, I'll show you what I've planned and how I plan on booking my biggest points and miles trip of 2021. I'll start by walking you through the outbound leg of the trip and then discuss hotels and how I plan to return to New York City. In the end, you'll have a complete look at how I'm booking a trip to South Africa and hopefully some inspiration for your next big trip.

Let's get started!

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Flying to South Africa via Dubai in style

This flight will be my first of 2021, so it needs to be a good one. Likewise, my girlfriend will be joining me on the adventure. She's never flown international first-class before, so I want to make this trip one to remember for both of us. With that in mind, I settled on draining my Alaska Airlines Mileage Plan balance to book one of my bucket list flights: Emirates first class.

Yes, I may be the only points and miles writer left who hasn't flown Emirates first — but I'm glad I waited. In looking for award space in early 2021, I was pleasantly surprised to see a reasonable amount of award space from Newark (EWR) to Dubai (DXB). In fact, there are many days in March and April that have wide-open space for two.

I have a huge stock of Alaska Airlines Mileage Plan miles that I've been waiting to use for a trip in Emirates first too. Unfortunately, Emirates will start restricting its first-class award space to its own loyalty program next April. This isn't a huge deal as Emirates Skywards is a transfer partner of all the major transferrable points programs, but the program adds mild fuel surcharges and higher redemption rates on some tickets when compared to booking with Alaska miles.

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Further, Alaska Airlines offers a free stopover on all international award tickets. With that in mind, I plan on spending a few days in Dubai on the way out. The United Arab Emirates is also allowing American tourists into the country, so this seemed like an excellent way to explore yet another new city on the way to South Africa.

From a points perspective, however, this flight isn't cheap. The total out of pocket for two passengers is a whopping 400,000 miles — just about everything in my Alaska account — plus a low $104.40 in taxes and fees. That said, it's considerably cheaper than if we were to pay cash (just under $8K per person) for the flights, which would be way outside my price range.

In the end, I think blowing my Alaska mileage balance for this trip of a lifetime is completely worth it. It gives my girlfriend and I flights to two new cities in an excellent first-class product for little cash out of pocket. 2021 truly can't come soon enough.

Related: How to earn miles with the Alaska Airlines Mileage Plan program

Hotels in Dubai, Johannesburg and Cape Town

I want to start this section by saying that we're not completely finished planning our itinerary in South Africa. Right now, we know that we need hotels in both Johannesburg and Cape Town, and possibly Durban or Port Elizabeth. For this section, however, I'll show you the hotels picked in the cities we've confirmed as well as in Dubai for our layover.

Another quick disclaimer: I'm a Marriott guy, so all of the hotels featured here are Marriott properties. I'm using this trip as a way to earn elite nights towards keeping my Marriott status and use Marriott Bonvoy points my girlfriend and I have earned over the year.

Related: Battle of the hotels: Why I think Marriott is the best

Renaissance Downtown Hotel — Dubai

There are a ton of hotel options in Dubai — so much so, that this three-day stopover was actually the most complicated leg to plan. That said, we finally settled on the Renaissance Downtown Hotel. The hotel is located smack-dab in the middle of Downtown Dubai, giving us easy access to the rest of the city. Plus, it's a relatively new property with posh and modern rooms.

We plan to pay out of pocket for this stay. A three-night stay is 170,000 Marriott Bonvoy points or $788 after taxes and fees. This would've given us just 0.46 cents per point in value, which isn't a great deal for Marriott points. I'm a Marriott Platinum member as well, so we'll earn 50% bonus points (15x per dollar) for this paid stay, which makes the somewhat high cost of the stay easier to justify.

Related: 3 ways to do Dubai on points and miles

African Pride Melrose Arch, Autograph Collection - Johannesburg

Marriott has a handful of properties in Johannesburg, but we settled on this one because of its unique design and location. The hotel rooms feature posh modern design, with exposed brick, wood floors and unique accents. Plus, the hotel is located in the Melrose Arch shopping district, which gives us quick access to great eateries, shopping and transit to the rest of the city.

As far as cost goes, we'll use 65,000 Marriott Bonvoy points to cover the entirety of our stay. Since it's a five-night stay, we're using Marriott's infamous fifth-night free benefit to shave one night off of the total points cost of the stay. This gives us a cool 1.15 cents per point in value — higher than TPG's valuation — as the total for a five-night stay is $752 after tax.

Related: Want great value for your Marriott points? Go to South Africa

AC Hotel Waterfront - Cape Town

We plan on ending the trip with four nights in Cape Town. We settled on the AC Hotel Waterfront because of its proximity to the water, reasonable price and modern design of the hotel. I've always been a big fan of the AC brand because of how fresh they feel, especially for a mid-tier hotel brand. Plus, the hotel is just steps from the coast, which will be a great way to end the trip.

Five nights cost just 75,000 points with Marriott's fifth-night free benefit at this property. This would have otherwise cost $565.44 after tax, so we're getting a cool 0.75 cents per point in value. This is slightly less than TPG's most recent valuation, but a good redemption for us since we don't have to pay anything out of pocket.

Related: Best Marriott credit cards

Flying back to NYC with Turkish Airlines

On the way back, we plan to fly Turkish Airlines business class from Cape Town (CPT) to Newark via Istanbul (IST). We will book this flight with Avianca LifeMiles and pay 78,000 LifeMiles per person with minimal taxes and fees. We plan on booking the flight by transferring American Express Membership Rewards points to LifeMiles. This is a solid deal, especially since the flight has just a quick layover in Istanbul.

Turkish Airlines business class is a new product for both of us and I've heard nothing but good things about the product and service. The entire itinerary is operated by the carrier's 787-9 aircraft as well, so barring any equipment changes, we should be in the airline's new business class product.

We toyed with the idea of hanging out in Istanbul for a couple of days as the county is also open to Americans, but decided against it as we'll likely be exhausted from just over two weeks of adventure. I do plan on returning to Istanbul later in 2021 for a trip, however, as I've never been to Turkey before.

Related: Turkey is open to tourists – here’s how to get there on points and miles

Bottom line

After being grounded for the better part of 2020, I'm super excited for a trip to two new countries and three new cities. It gives my girlfriend and I some much-needed time away from New York City after being here for almost the entirety of the coronavirus pandemic. Obviously, things could change given how the pandemic continues to evolve worldwide, but it's something nice to look forward to in 2021.

Feature photo by Deyan Denchev/Shutterstock