Florida, Caribbean Lead Labor Day Weekend Travel

AUGUST 13, 2020

It’s been, well, an odd summer travel season: road trips have seen a resurgence, most international travel is off the menu, and many popular US destinations for Americans require a 14-day quarantine upon arrival (hello, New York and Hawaii).

Now, with the end of summer right around the corner (it’s been a long March!), we wondered if US travelers might make one last grab for a hint of summer vacay normalcy. But where do Americans go when the usual locales are off limits? Turns out, wherever they can.

Labor Day Weekend Flight Destinations

We analyzed the top 100 destinations for US-origin roundtrip flight reservations made from Jan 1 – Jul 30, 2020, with a travel date between Sep 4 – 8, 2020, and compared that to an equivalent booking and travel window in 2019.

Here’s a look at the top 25:

Labor Day Weekend Hotel Destinations, Top 25 Arrival City Rankings

While large metros continue to rank in the top flight destinations, more interesting is how destinations have shifted in popularity YoY:

Top 25 Labor Day Weekend Travel Destinations, Rank change by arrival city for LDW from 2019 to 2020

While big metros like NYC, SF, Chicago, LA, and ATL still rank in the top 25 destinations, each of these cities have dropped in rank, most notably NYC, which dropped 14 spots — from No. 5 for Labor Day travel in 2019 to No. 19. (Newark dropped 43 spots, from No. 17 in 2019 to No. 60 this year.)

As to be expected, destinations where travel for Americans has been restricted or which have been hit hard by the pandemic have seen some of the largest drops on the list:

Covid-19 Restrictions' Affect on LDW Travel, Rank change by arrival city for LDW from 2019 to 2020

Destinations with the biggest rank place increases? Florida, Mexico, the Caribbean and Hawaii dominate the list. (United Airlines recently announced increased service to Mexico, the Caribbean and Hawaii, despite Hawaii’s two-week quarantine, which is in-place through Sep 1).


Florida this year is claiming the lion’s share (plurality) of Labor Day flight reservations, with 12 percent of all plans including a destination in the Sunshine State. In 2019, Florida’s share of LDW flight reservations was 4 percent, representing a 200 percent year-over-year increase.

Florida, Rank Change by Arrival City fopr Labor Day Weekend

The Caribbean and Mexico

After spending the majority of last year recovering from hurricane damage, many Caribbean and Mexico destinations are allowing Americans to visit with the caveat that visitors adhere to strict COVID policies, such as Aruba, which requires in-flight masks and a negative PCR test within 72 hours prior to departure or at arrival.

The Caribbean and Mexico, Rank Change by Arrival City for Labor Day Weekend


Originally due to start on August 1, a pre-travel testing program was pushed back and is now scheduled to begin on September 1 (as with the Caribbean, out-of-state travelers will need to show proof of a valid COVD-19 test within 72 hours of departure and show proof of negative result in order to avoid a 14-day quarantine). Meanwhile, United’s announcement that it was planning to increase its services to Hawaii in September is bolstered by the 50 percent YoY increase in flight booking share for Labor Day Weekend travel.

Hawaii, Rank Change by Arrival City for Labor Day Weekend

Labor Day Weekend Hotel Destinations

So, what about accommodations? With fewer travelers flying and an increase in road trips, we wondered if hotel reservations might show a more varied destination list than in years prior. As with flights, we analyzed US hotel reservations made from Jan 1 – Jul 30, 2020, with a travel date between Sep 4 – 8, 2020, and compared that to an equivalent booking window in 2019.

We found that Florida cities dominated that list, as well — nabbing 5 out of the top 10 spots, with four (Orlando, Lake Buena Vista, Bay Lake, and Kissimmee) located in the immediate Disney World vicinity. In 2019, only Orlando cracked the top 10.

Labor Day Weekend Hotel Destinations, Top 10 Hotel Destinations Rankings

Methodology: TripIt analyzed the top 100 destination cities for US-origin RT flight and US hotel reservations made from Jan 1 – Jul 30, 2020, with a travel date between Sep 4 – 8, 2020, and compared that to an equivalent booking and travel window in 2019.

Travel Well

You already had enough to worry about when you traveled—and that was before COVID-19. If you’re planning on traveling this Labor Day Weekend (or any time), TripIt is here to equip you with the tools you need to help you make the best decisions for your trip. With your health and safety in mind, we’ve created new health and safety resources—and enhanced some of your most-trusted features—so you’re better prepared for each step of your journey.

TripIt Traveler Resource Center Icon

TripIt Traveler Resource Center
From public health and safety advisories to cancellation policies and new travel guidelines, the TripIt Traveler Resource Center makes it easy to find the latest travel advisories, restrictions, and guidelines, alongside other helpful resources, so you have the information you need to make the best decision for your next trip.

Neighborhood Safety Scores

Nearby Places
Nearby Places—the TripIt feature that makes it easy to find places close to where you’re staying—now shows the locations of the nearest medical facilities, including hospitals, clinics, and pharmacies.

Neighborhood Safety Scores

Neighborhood Safety Scores
TripIt’s Neighborhood Safety Scores help travelers learn about the safety of the neighborhood they’re visiting, including a Health and Medical score that factors in COVID-19 data.

About TripIt:
TripIt from Concur, the world’s highest-rated travel-organizing app, instantly organizes all travel plans in one place. Simply forward confirmation emails to plans@tripit.com, and TripIt will create a master itinerary for each trip—for free. The premium service, TripIt Pro ($49/year), has all the organizing power of TripIt plus additional features that help members stay one step ahead while traveling. Real-time flight alerts, refund notifications, and the ability to track reward points and miles are just a few of the additional benefits TripIt Pro members receive.