Vacations I’m planning for a post-pandemic world

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Other than a brief road trip or two, my family and I have been mostly travel-restricted so far in 2020, as has most of the world. While my points and miles balances may be growing, I’m bummed about the trip cancellations and lack of certainty around when and where my family will be able to travel again.

But I’m trying to think positive. With coronavirus vaccines on the horizon and certain international destinations beginning to re-accept healthy visitors, I’m now looking to 2021 travel and starting to plan trips and adventures which my family hopes to take. Hopefully, some of the below ideas can encourage you to start thinking about your next travel destinations — whenever that may be.

Trips I’m planning for 2021 and beyond

Maui in July 2021

My extended family typically does a biannual trip to Maui where we reconnect with cousins, aunts and uncles for a week on the beach. Hawaii has recently introduced a plan for welcoming visitors once again. However, we’ll have to watch closely as regulations differ island by island and the state’s “reopening” date for tourists has been pushed back numerous times.

That being said, I’m optimistic about Hawaii travel being permissible (perhaps with some modifications) 9 months from now. I hope to use British Airways Avios points for a flight on Alaska or American Airlines to get between San Diego and Maui. British Airways is a transfer partner of both Chase Ultimate Rewards and Amex Membership Rewards.

If that doesn’t work, I’m happy to pay cash for flights on Alaska with a companion certificate, which I get from the Bank of America Alaska Airlines credit card.

I could use Hyatt points, transferred from Chase, to stay at the Hyatt Regency Maui. (Image courtesy of the hotel)

Tokyo in May 2021

Japan has among the world’s best infrastructure and will (if I had to guess) be well-prepared to welcome healthy, COVID-free visitors come mid-2021. Japan will also be gearing up to host the 2021 summer Olympics, further suggesting that the Japanese government will be working diligently to safely allow travelers into the country.

[ Read: The best travel credit cards ]

If you’re looking for award flights or hotel awards during the Olympic games, don’t hold your breath. But if you can be flexible and travel before or after the Olympics, you will find numerous award travel options. I have my eyes on the Conrad Tokyo with a fifth-night free Hilton award booking and flights on ANA using Virgin Atlantic miles (which is a transfer partner of Chase Ultimate Rewards, Amex Membership Rewards and Citi ThankYou)

The Caribbean or Mexico in fall 2021

Many countries in the Caribbean have relaxed COVID-19 travel restrictions in favor of re-welcoming tourists. The Bahamas, for example, will no longer require a 14-day quarantine for arriving tourists (starting Nov. 1) if they have a negative COVID-19 test. And Mexico has been perhaps the most travel-friendly country in the past several months for Americans looking to get away.

I have my eye on a long-weekend-trip back to the Waldorf Astoria Los Cabos at Pedregal. This is another phenomenal use of Hilton points (or Hilton Free weekend night certificates) and award nights can be found if you’re flexible with your travel dates. It goes without saying, but Mexico has many other fantastic destinations such as Cancun and Mexico City which could also make for a great visit.

My lovely wife enjoying a poolside margarita at the new Waldorf Astoria Los Cabos at Pedregal last year. We stayed for three nights using Hilton free weekend night certificates earned with Hilton credit cards. (Image by the author)

The Maldives in early 2022

For better or worse, some trips require months or even years of planning. This comes in handy for a potential trip to the Maldives that I’m scheming for early 2022 with my wife and kids. For a trip of this duration (and expense, even in points!), I recommend planning award flights and award hotel nights as far in advance as is humanly possible. This also means an extended runway for the development of a COVID-19 vaccine or additional testing measures to ensure everyone’s safety.

Many airlines and hotel programs make bookings available between 330 – 365 days in advance. I’m starting my planning now by checking on flight options, deciding which hotel to visit (likely the Waldorf Astoria Maldives or the Conrad Maldives, depending on availability) and devising a credit card and miles-earning strategy that will help me save up the points I need.

Using Marriott points for a stay at the St. Regis Maldives can provide great value and awesome views. (Photo by Joseph Hostetler/Million Mile Secrets)

Road trips from Southern California

Last but not least, I’m trying to be realistic about the state of travel and destinations’ reopening timelines. It’s certainly possible that some of the destinations mentioned are not yet ready to welcome visitors when our planned travel dates roll around. Or even if we technically can travel, we can’t be certain how we’ll feel about whether we should travel.

This means that I’m keeping my plans flexible and thinking about road trips to amazing destinations from my home in San Diego. The Miraval Resort in Tucson, bookable with Hyatt points, is about a 6-hour drive and has great award availability for points bookings that provide excellent value (rooms can go for $1000 a night). In Northern California, the Ventana Big Sur, also bookable with Hyatt points, is on my wish list so I’ve started to keep an eye out for award nights (which can be tough to find). And if nothing else my wife and I would be happy to stay at the always-reliable Waldorf Astoria Beverly Hills, perhaps my all-time favorite use of Hilton free weekend night certificates, which is a reasonable two-hour drive from home.

Bottom Line

There’s no question travel planning is tough right now, but some destinations are better prepared than others to welcome (safe and healthy) tourists, albeit with certain restrictions in place.

Personally, I am looking to the future and hoping that travel in 2021 can happen. Hopefully, some of the trips I’ve mentioned inspire you to get to planning!

Featured image by Ron and Patty Thomas / Getty Images

Jake Pearring is a contributor to Million Mile Secrets, he covers topics on points and miles, credit cards, airlines, hotels, and general travel.

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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