5 island getaways you can get to this weekend in 5 hours or less

Jan 28, 2020

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It’s about that time of year when the winter blues start to set in and nothing sounds better than a weather forecast of sunny and 75.

Luckily for those located in North America, a sunny escape isn’t too far away, with plenty of flight options to sandy destinations. Whether you’re looking to explore hidden beaches in the Caribbean or the diverse landscapes of the Hawaiian Islands, there’s an escape for everyone.

Related: Hawaii vs. the Caribbean: Which islands should you visit?

To get you inspired, we’ve put together a list of five island getaways you can get to in five hours or less.

Key West

Photo by Cristian Lourenco / EyeEm / Getty Images.
(Photo by Cristian Lourenco/EyeEm/Getty Images)

This domestic getaway is just a short flight away from most U.S. cities. If you’re traveling nonstop from the Northeast, for example, you can expect about a three and a half hour flight. The temperature here averages around 75 degrees Fahrenheit in the winter, and the water is probably some of the bluest you’ll come across in North America. Basically, there’s a good chance a trip here will wash your winter blues away.

The fastest way to get here is to fly directly into Key West (EYW) although it may be less expensive to fly into Miami (MIA) or Fort Lauderdale (FLL) and then rent a car to drive into the keys. Just be aware that the drive (expectedly) includes lots of overwater bridges, so it is not for those with gephyrophobia. Traffic on the narrow highway through the Keys can also significantly add to the travel time to and from mainland Florida.

The Bahamas

Nassau, Bahamas (Photo by Terrence wijesena/Getty Images)
Nassau, Bahamas. (Photo by Terrence wijesena/Getty Images)

Nassau (NAS) is a quick trip away for both midwesterners and northeasterners, with non-stop flights from cities like Chicago (ORD) and Boston (BOS) running at just three and half hours.

Related: 3 reasons why now is the best time to visit the Bahamas 

The Bahamas offers white sandy beaches, clear blue water and some great points hotel options. For instance, you can book the Grand Hyatt Baha Mar for just 20,000 World of Hyatt points a night. This is another destination that’s typically sunny and 75 in the winter, so be sure to pack your sunglasses.


Honolulu, Hawaii. (Photo by Timur Alexandrov / EyeEm)
Honolulu, Hawaii. (Photo by Timur Alexandrov/EyeEm)

If you’re located on the West Coast, specifically California, then a Hawaiian escape can be done in five hours. (If you’re located east of California, you will probably find flights to the Caribbean will be shorter for that quick sun fix.)

The Hawaiian Islands are comprised of eight main islands — Maui, Oahu, Kauai, Molokai, Lanai, Niihau, and Kahoolawe — though only six openly welcome tourists. Each island offers a unique experience, so be sure to read up on which one matches your vibe. Personally, I’m a fan of the laid-back island of Maui, as it offers a variety of activities. Whether it’s snorkeling, sitting poolside at one of the many points-bookable resorts or chasing waterfalls on the Road to Hana, Maui has it all.

St. Thomas

Caribbean, St Thomas US Virgin Islands. Panoramic view. (Photo by sorincolac / Getty Images)
St Thomas, U.S. Virgin Islands. (Photo by sorincolac/Getty Images)

St. Thomas is a part of the U.S. Virgin Islands, which means U.S. residents do not need a passport in order to visit. Flights to St. Thomas from the East Coast typically run about four hours. The best part about this island escape is that, as of late, it seems like the flight deals here are endless — so be sure to set a Google Flight alert for any dates you’re eyeing.

Related: 7 little-known Caribbean destination you should discover — before others do 

The average high on St. Thomas is 83 degrees Fahrenheit, which is great for thawing out the winter bitterness that starts setting in come February.

Puerto Rico

Old San Juan City Walls in Puerto Rico. (Photo by Maremagnum/Getty Images)
Old San Juan city walls in Puerto Rico. (Photo by Maremagnum/Getty Images)

This is another exotic island escape that doesn’t require a passport, as Puerto Rico is a U.S. territory. Depending on where you’re located, flights to Puerto Rico’s primary airport, San Juan (SJU), from the Midwest and East Coast run four to five hours long. Flights to the island are plentiful, with over 200 flights operated daily.

The recent earthquakes shouldn’t discourage travelers from visiting. In a recent interview, the CEO of Discover Puerto Rico, Brad Dean, told TPG’s Victoria Walker: “The good news for visitors is flights have are operating fully and have not been disrupted,” Dean said. “All three commercial airports are open and operational. The cruise ports are still open — there was a five-day period after the earthquakes where we had almost 60,000 cruise passengers disembark in Old San Juan.”

Featured photo by sorincolac/iStock/Getty Images.

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