Traveling around the holidays, especially during the Fourth of July, can be cause for a major headache. Between tracking down the best flights to figuring out how to dodge travel fares, there’s plenty left to the unknown. We’re setting out to make sure that you make the most out of America’s favorite celebration, so we caught up with Cheryl Rosner, CEO of Stayful, a travel site that helps you book some of the best independent boutiques around the world. Scroll on for Cheryl’s top tips on how to make the most out of travel this holiday season.


1. Three words: Location, location, location: When it comes to booking your hotel, think outside the box of where you might typically choose to stay. Cheryl says, “Stay in hotels located in the financial district on the weekends, and stay in hotels located in leisure tourist districts midweek. This strategy will save you a lot of money and endear you to boutique hotels.”

2. Plan ahead. Normally, you might think booking your stay months ahead of your Fourth of July trip will guarantee you the best deal. But Cheryl doesn’t see the same thing, adding, “At Stayful, we’ve seen our community getting the best deals when they book boutique hotels with us seven days out.”


3. Don’t ask for an upgrade. When you’re looking to score a little extra for your stay, it’s all about how you frame your ask. Instead of asking for an upgrade, ask for an experience. “While I am staying in boutique hotels in need time periods, I will ask, ‘If you happen to have a suite available, I would love to experience it.’ As a result, I get upgraded a lot. The hotel knows because I’ve asked if I can experience it that I intend to share my experience. Who knows, a simple upgrade could get you a better view of the fireworks,” says Cheryl.

4. Get the best flight possible. “Choose the plane. When you have several options around the same time you plan to travel, check the type of aircraft offered. A 767 has fewer middle seats due to the configuration, 2-3-2,” notes Cheryl. She adds, “Choose your seat, even if it is not your ideal choice. Seats free up as you get closer to the flight. Check the airline’s app on your way to the airport for last-minute seat availability. As upgrades are granted, additional seating becomes available. Check the cost of checking bags and leave most of your stuff at home.”


5. Don’t forget about transportation. You might think hailing a cab or checking in with Uber will be a breeze when you step off the flight, but that might not always be the case. Cheryl agrees, adding, “Check transportation from the airport to your destination. In urban destinations, this can mean big savings. Flying into Newark Airport can save you on fares instead of flying into LaGuardia or JFK. In addition, you can take Air Train, which connects to Amtrak, taking you to Penn Station in the city. The cost is $12.50, versus $50-$75 by taxi.” Basically, a little research and a willingness to go slightly out of your way can mean more money saved for the important things, like blue wine.

Tweet us your holiday travel tips @BritandCo!

(Photos via Stayful)