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  • Jordan Hinsch

10 Best Holiday & Winter Vacation Destinations in 2020

Updated: Jan 6, 2021

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:

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.


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.


  • 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.


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.


  • 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 Instagram post is from a previous trip to Eleuthera. Just wow!