Miami, FL

10 Best Holiday & Winter Vacation Destinations in 2020

Jordan Hinsch

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Author's Note: The inspiration for this article came from the utter failure of every other 2020 Winter Travel recommendation article I've come across. None of them take Covid-19 into effect, it's just robotic and auto-filled with typical trending destinations from previous years. This article is real and is written by a human, please read.

Covid-19 is really putting a damper on nearly all aspects of our lives. One of the biggest, is travel. As I write this (December 3rd, 2020), cases of coronavirus are surging in nearly every state and hospitalization is at an all-time high. Any holiday traditions you have probably need to be altered, and this includes traveling home for the holidays or flying somewhere for a nice vacation with the family.

Personally speaking, being a New Yorker now living in Miami, I was unable to travel home for Thanksgiving due to the virus and I won't be traveling home for Christmas either. It's very sad, but I immediately began exploring vacation ideas for the week of Christmas (I've been outside of New York on Christmas only twice since I was born!). While it's tough to break strong traditions, it's also exciting to start exploring alternatives.

My go-to for airfare inspiration is Google Flights. Google Flights allows you to search on a blank canvas for the best airfare to various locations from your nearest airport (I chose MIA). The photo below shows you just how glorious this technology is and yet another incredible product by Google:

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The first idea I had, was Colorado, Utah, or Wyoming, to partake in some skiing or snowboarding (neither of which I've tried yet). Wow, that airfare is cheap! Then I took a hard look at the facts and the reality of this current situation of utter madness.

Important questions you should ask while selecting a city or country to travel to this holiday season:

  • Is there anything open and accessible in the town/city that you'd like to stay in?
  • How has the city/state/country fared with Covid-19?
  • What are the quarantine policies of such city/state/country?
  • What are the procedures to enter the state/country? PCR test needed? Letter from Embassy?
  • What if Covid-19 gets worse after you book your travel and everything closes? You'd be in for a boring vacation.
  • Particularly for the ski states, what if the slopes close before you arrive?
  • When choosing a hotel, are their amenities open? PRO TIP: Reconsider booking a high-end hotel if their amenities are not accessible.
  • Research crime stats since crime has increased in many areas since Covid-19 began.
  • If you travel outside the US, what if there is a lockdown in that country and you can't return? It's unlikely, but you need to consider it. Although, just about anywhere is better than the US right now.

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Why?

The state of Quintana Roo has fared very well with Covid-19 lately and has seen a surge in visitors while maintaining a low amount of new cases.

COVID-19 Entry Procedures:

Click here for the latest updates from the Embassy.

Where to stay:

  • Beach
  • Town
  • Jungle (the area in between the town and beach)

See top hotels in Tulum

How to get there:

Search flights here.

Tips:

  • Crime in Quintana Roo is very low compared to the rest of Mexico. Having said that, it's recommended you have the ability to lock the doors of your hotel or AirBnb. If you don't, then consider staying elsewhere.
  • Buy tickets to Cenotes! They can get busy.
  • The public beach is very rocky. The private beach is sandy.

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Why?

The Bahamas have done very well with Covid-19 since their spike over the summer when they re-opened. They implemented a 14 day quarantine program which is no longer in effect as of November 1st.

COVID-19 Entry Procedures:

Click here for everything you need to know.

Where to Stay:

  • Eleuthera (highly recommended)
  • Paradise Island
  • Elbow Cay
  • Andros Islands

See top hotels in the Bahamas.

How to get there:

Search flights here.

Tips:

  • I recommend the island of Eleuthera not just for it's beauty, but for it's quiet & chill way of life. It's not busy or gimicky like Nassau. You can stay in North Eleuthera (Dunmore Town), Governor's Harbor area, or the Rock Sound area.

This photo is from a previous trip to Eleuthera. Just wow!

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Why?

Barbados was offering relocation packages for Americans shortly after COVID-19 hit to entice them to move there if they have the capacity to work remotely. It's safe to say that they've handled things well-enough to attract ex-pats!

COVID-19 Entry Procedures:

Click here for the latest updates from the Embassy.

Where to Stay:

See top hotels in Barbados.

How to get there:

Search flights here.

Tips:

  • The west coast of Barbados is luxurious. The east coast is rugged and natural.
  • Crime is low, but always remain alert and aware.

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Why?

St. Kitts has handled Covid-19 very well and cases are low. They do require a quarantine, so I'd recommend booking a 2 week stay as opposed to 1 week. Your first week there requires you stay on hotel property. Once you test positive on day 8, you can roam about.

COVID-19 Entry Procedures:

Click here for the latest updates from the Embassy.

Where to Stay:

See top hotels in St. Kitts.

How to get there:

Search flights here.

Tips:

  • Hike Mount Liamuiga!

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Why?

Aruba is currently wide open and accessible as long as you provide a negative NCR test. There is no quarantine and the island has handled Covid-19 very well.

COVID-19 Entry Procedures:

Click here for the latest updates from the Embassy.

Where to Stay:

See top hotels in Aruba.

How to get there:

Search flights here.

Tips:

  • Aruba has alot of top-notch all-inclusive resorts, if you're into those.
  • Rent a Jeep and explore!

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Why?

145 Covid-19 cases as of December 3rd. No quarantine. Do it!

COVID-19 Entry Procedures:

Click here for the latest updates from the Embassy.

Where to Stay:

See top hotels in Curacao.

How to get there:

Search flights here.

Tips:

  • Get scuba certified and go diving in some of the best reefs the Caribbean has to offer.

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Why?

Airfare is cheap, and if you really want to ski or snowboard badly, this is your best shot. Arrive at the airport, rent a car, and drive to Breck, Aspen, or Vail. Just note what I said in my intro.

COVID-19 Entry Procedures:

None (unless required by your airline), but I'd get a negative NCR test anyway, for the sake of others.

Where to Stay:

See top hotels in Breckenridge.

See top hotels in Aspen.

See top hotels in Vail.

See top hotels in Telluride.

How to get there:

Search flights here.

Tips:

  • This is my favorite hotel in Telluride! Service level is 15 out of 10.

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Why?

Skiing, the great outdoors, Yellowstone National Park. Do it!

COVID-19 Entry Procedures:

None (unless required by your airline), but I'd get a negative NCR test anyway, for the sake of others.

Where to Stay:

See top hotels in Bozeman.

How to get there:

Search flights here.

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Why?

As crazy as it sounds, Key West has had very few cases of Covid-19. Escape the cold and visit the southernmost point in the continental USA!

COVID-19 Entry Procedures:

None (unless required by your airline), but I'd get a negative NCR test anyway, for the sake of others.

Where to Stay:

See top hotels in Key West.

How to get there:

Search flights here.

Tips:

  • Visit Dry Tortuga's National Park if you can!!

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Why?

Like St. Kitts, St. Lucia has handled Covid-19 very well. They also have a quarantine and are a bit more strict. However, St. Lucia is an island which is not the easiest to get around and most visitors tend to stay on resort for the majority, if not all of their stay. That's the only reason why I'm including St. Lucia on this list (aside from the fact that it's beautiful).

COVID-19 Entry Procedures:

Click here for the latest updates from the Embassy.

Where to Stay:

See top hotels in St. Lucia.

How to get there:

Search flights here.

Tips:

  • Ladera Resort is my favorite! Please check it out.

This photo is from my trip to St. Lucia.

#nbholidaycheer

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Jordan Hinsch is a sales expert, blogger, investor, photographer, videographer, and outdoors enthusiast. Primarily known for unique travel and bucket list related content, Jordan also specializes in lifestyle, fitness, and finance. Follow him here on NewsBreak and on Instagram & Pinterest @neverjordinary.

Miami, FL
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