Skip to content

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

Jan. 28, 2020
5 min read
St. Thomas, USVI.
The cards we feature here are from partners who compensate us when you are approved through our site, and this may impact how or where these products appear. We don’t cover all available credit cards, but our analysis, reviews, and opinions are entirely from our editorial team. Terms apply to the offers listed on this page. Please view our advertising policy and product review methodology for more information.

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)

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 (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.

Daily Newsletter
Reward your inbox with the TPG Daily newsletter
Join over 700,000 readers for breaking news, in-depth guides and exclusive deals from TPG’s experts

Hawaii

Scenic View Of Sea And Mountains Against Sky
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

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)

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 image by Getty Images/iStockphoto

TPG featured card

Best for businesses with high spending
TPG Editor‘s Rating
4.5 / 5
Go to review

Rewards

2 - 10X miles

Intro offer

LIMITED-TIME OFFER: Earn up to 400K bonus miles

Annual Fee

$395

Recommended Credit

740-850
Excellent

Why We Chose It

The Capital One Venture X Business Card has all the Capital One Venture X Rewards Credit Card has to offer and more. It offers an incredible welcome bonus and requires an equally impressive spend to qualify. In addition, the card comes with premium travel perks like annual travel credit. (Partner offer)

Pros

  • The Capital One Venture X business card has a very lucrative welcome offer.
  • In addition, the card comes with many premium travel perks such as an annual $300 credit for bookings through Capital One Business Travel.
  • Business owners are also able to add employee cards for free.

Cons

  • The card requires significant spending to earn the welcome offer.
  • Another drawback is that the annual travel credit can only be used on bookings made through Capital One Business Travel.
  • LIMITED-TIME OFFER: Earn up to 400K bonus miles: 200K miles when you spend $30K in the first 3 months, and an additional 200k miles when you spend $150k in the first 6 months
  • Earn unlimited 2X miles on every purchase, everywhere—with no limits or category restrictions
  • Earn 10X miles on hotels and rental cars and 5X miles on flights and vacation rentals booked through Capital One Business Travel
  • With no preset spending limit, enjoy big purchasing power that adapts so you can spend more and earn more rewards
  • Empower your teams to make business purchases while earning rewards on their transactions, with free employee and virtual cards. Plus, automatically sync your transaction data with your accounting software and pay your vendors with ease
  • Redeem your miles on flights, hotels and more. Plus, transfer your miles to any of the 15+ travel loyalty programs
  • Every year, you'll get 10,000 bonus miles after your account anniversary date. Plus, receive an annual $300 credit for bookings made through Capital One Business Travel
  • Receive up to a $120 credit for Global Entry or TSA PreCheck®. Enjoy access to 1,300+ airport lounges worldwide, including Capital One Lounge locations and Priority Pass™ lounges, after enrollment
  • Enjoy a $100 experience credit and other premium benefits with every hotel and vacation rental booked from the Premier Collection
  • This is a pay-in-full card, so your balance is due in full every month
Apply for Capital One Venture X Business
at Capital One's secure site
Terms & restrictions apply. See rates & fees
Best for businesses with high spending
TPG Editor‘s Rating
4.5 / 5
Go to review

Rewards Rate

2X miles2 miles per dollar on every purchase
5X miles5 miles per dollar on flights and vacation rentals booked through Capital One Business Travel
10X miles10 miles per dollar on hotels and rental cars booked through Capital One Business Travel
  • Intro Offer

    LIMITED-TIME OFFER: Earn up to 400K bonus miles
  • Annual Fee

    $395
  • Recommended Credit

    740-850
    Excellent

Why We Chose It

The Capital One Venture X Business Card has all the Capital One Venture X Rewards Credit Card has to offer and more. It offers an incredible welcome bonus and requires an equally impressive spend to qualify. In addition, the card comes with premium travel perks like annual travel credit. (Partner offer)

Pros

  • The Capital One Venture X business card has a very lucrative welcome offer.
  • In addition, the card comes with many premium travel perks such as an annual $300 credit for bookings through Capital One Business Travel.
  • Business owners are also able to add employee cards for free.

Cons

  • The card requires significant spending to earn the welcome offer.
  • Another drawback is that the annual travel credit can only be used on bookings made through Capital One Business Travel.
  • LIMITED-TIME OFFER: Earn up to 400K bonus miles: 200K miles when you spend $30K in the first 3 months, and an additional 200k miles when you spend $150k in the first 6 months
  • Earn unlimited 2X miles on every purchase, everywhere—with no limits or category restrictions
  • Earn 10X miles on hotels and rental cars and 5X miles on flights and vacation rentals booked through Capital One Business Travel
  • With no preset spending limit, enjoy big purchasing power that adapts so you can spend more and earn more rewards
  • Empower your teams to make business purchases while earning rewards on their transactions, with free employee and virtual cards. Plus, automatically sync your transaction data with your accounting software and pay your vendors with ease
  • Redeem your miles on flights, hotels and more. Plus, transfer your miles to any of the 15+ travel loyalty programs
  • Every year, you'll get 10,000 bonus miles after your account anniversary date. Plus, receive an annual $300 credit for bookings made through Capital One Business Travel
  • Receive up to a $120 credit for Global Entry or TSA PreCheck®. Enjoy access to 1,300+ airport lounges worldwide, including Capital One Lounge locations and Priority Pass™ lounges, after enrollment
  • Enjoy a $100 experience credit and other premium benefits with every hotel and vacation rental booked from the Premier Collection
  • This is a pay-in-full card, so your balance is due in full every month