The Great Big and Hugely Awesome Summer Travel Cheat Sheet

Summer is closer than you think

It may be January, gents, but if you’re booking travel, summer is closer than a Kentucky cousin.

If you haven’t booked yet, the time is nigh.

Like, very nigh.

Why? Pretty simple, really. Summer is a popular time to travel.

That means increased demand for everything, from plane tickets to hotel reservations to tourist attractions (Taking the family to see the Sistine Chapel? Better book now, bud).

But, if you book your travel in the next few weeks, you’re more likely to get the seats you want on your plane. Don’t be the dude stuck in the middle.

And you’re more likely to find vacancies at hotels and resorts, not to mention the type of room you want.

Because what good is a romantic getaway if you’re sleeping, Lucy and Desi-style, in twin beds?

So book now.

Here’s how.

How to Find the Best Flight, Period

1. Use a private (incognito) browser window. Search engines use cookies to raise prices while you search.

2. Start by using a metasearch engine. KayakHipmunkSkyscannerITAMatrix. They search the widest amount of airlines. (ITAMatrix is also a good way to find fares that stop in specific cities, which is one way of finding “hidden city” fares).

3. Don’t start with Orbitz, Expedia or Priceline. They’re inventory holders. They buy inventory, mostly from hotels, then resell to you. 

4. Unless you’re taking a family. In that case, you may have more incentive to take advantage of hotel deals. Also definitely search, which has the best small hotel inventory and prices for Europe.

5. When searching, try to find the lowest prices along your desired routing.

6. Set price alerts for those routes. Or use AirfareWatchdog.

7. Try to be flexible on travel dates. Could mean a big difference in price.

8. Pay attention to gateway airports, like London’s Heathrow. They often have the lowest prices.

9. Some airlines, like American, let you put holds on flights for 24 hours. United lets you pay to do a weeklong hold. This option is more likely with U.S. carriers.

10. Most searches take 7-12 days. Be persistent.

11. Remember: there is no “the price” or “the time” to buy. The price and time to buy depend on your preferred price and time.

12. FWIW, the top-searched summer destinations for 2015, so far, in Europe, are London, Dublin and Paris, according to Chris Slowe, the data wizard at Hipmunk. Amsterdam isn’t as popular this year. Says Slowe: “No need to travel to Amsterdam if you can just go to Colorado!”

13. Most popular In Asia: Bangkok. North America: Orlando. South America: San Juan.

Further Reading:

The One Place You Should Visit in 2015
How to Avoid Checked Bag Fees
8 Ways to Save on Travel in 2015
Can I Travel to Cuba Now?

How to Book Award Travel

1. Don’t have award miles already? Skip this. You won’t get them in time to make a difference this summer.

2. First ask yourself: Where do you have miles — a credit card or an airline?

3. A credit card company will let you transfer miles to select partners. Chase Reward Points, for example, transfer to United and British Airways, among others.

4. If you have points with an airline, you can use those points for that airline and its partners. American Airlines, for example, is in the OneWorld Alliance with British Airways, Qatar, and many more.

5. Then ask yourself: can you use your miles to get to your preferred destination?

6. If you’re going to Asia, American or United miles will treat you better.

7. Going to Paris? Delta miles will treat you better, because they partner with Air France.

8. Spain? American, because they partner with Iberia. Germany? United, because they partner with Lufthansa.

9. There are always optimal airlines to use for every destination. Comparison shop.

10. With your destination in mind, search award travel on your preferred airline.

11. Airlines and credit card companies usually value miles at 1-1.25 cents per mile. If you can redeem your miles for a per mile price above that, you’re winning.

12. For example: if a flight costs $1,800, but you can get it for 60k in award miles, then you’re getting 3 cents per mile.

13. Business class always offers a higher per mile redemption value.

14. Ask yourself: Do you want to take two free round-trips to Asia in coach, or one free round-trip drinking Champagne?

15. Don’t wanna deal with all this hassle? Use Book Your Award or Points Pros. They charge a nominal sum (~$149) to book awards itineraries.

Further Reading:

The Points Guy — The respected authority on how to maximize your award points
Milepoint — Educational forums on optimizing your award values
AwardWallet — Keep track of your miles across multiple cards and airlines
NerdWallet — Optimize your travel financials
TheFlightDeal — Exactly what it sounds like. Crazy good deals on flights.

For Your Destination:

HitlistYou pick places you’d like to go. The app sends you price alerts when the price is to your choosing.

Hopper: Know where you’re going? Hopper tells you the best time to go (and when to buy).

Valet: View curated city guides and snag exclusive rates at luxury hotels

Routehappy: Pick your flight based on a “happiness” factor — from legroom to WiFi

TripIt: A master itinerary. Keeps all your flight/hotel/car rental info in one app.

Skift: The travel industry’s bible; useful for consumers, too (their one place to visit in 2015: Oman)

Roads & Kingdoms: A great off-the-beaten-path travelogue/idea generator for your next vacation

For Your Flight: 

: reveals exactly which seats you want to reserve.

Global Entry: Apply now, and you’ll never wait in line at customs (it also automatically qualifies you for TSA Precheck, saving you time in domestic security lines).

LoungeBuddy: Once you have your itinerary, figure out which airline lounges you can use via membership status or one-time fee

Before You Arrive:

Telestial: Order international SIM cards for your phone/tablet in advance

Karma: If you’re traveling domestically, this little device’ll get you WiFi anywhere. And you only pay for what you use.

Trakdot: A tiny device to keep track of your luggage

Viator: Book curated, small-group tours far in advance

The Best Places to Stay


1. Start with Kayak (meta-search, compares five other deal engines) and Expedia (good hotel inventory).

2. Europe-bound? (also covered in Kayak’s comparison search) has the most properties and thus usually the best deals.

3. Hotel sold out? Call them. Search engines only have access to part of a hotel’s inventory.

4. For boutique and romantic hotels, we recommend Mr and Mrs Smith.

5. Last-minute? HotelTonight has the best day-of deals. Hipmunk helps here, too.

6. For precision room selection, use Room77.

7. Give the hotel a reason to upgrade you. Call them directly. Join their loyalty plan. Flash your card. Convince them you’ll bring back more business.

Rental Properties

1. Start with Airbnb.

2. Recently listed properties with fewer reviews tend to be cheaper to attract guests.

3. Create a thorough, likeable profile. Homeowners aren’t required to accept your reservation, so put a presentable foot forward when requesting a stay.

4. Look for watermarked photos. Means Airbnb’s photographers have visited.

5. When possible, book a property where the owner is on site. Helps immensely with getting to know your neighborhood.

6. Beware scammers. Never accept a request to book outside the platform, never pay security upfront without first seeing the property, and never pay cash or money order.

7. If you had a nice experience, leave a nice review. Helps the property owner. Greases the palm for next time.

8. Beyond Airbnb: OneFineStay and HomeAway Luxury Rentals. Options are limited, but you may rethink your plans when faced with, say, a Parisian pied-à-terre or oceanfront Malibu mansion.

Further Reading:

The Master List of Worldwide Hotel Openings in 2015

The Best Hotel Credit Cards
The Startups Built Around the Airbnb Ecosystem

British Airways/ Lorenzo Agius

The Art of the Upgrade

1. Stick to one airline. Airlines, like rappers and dog owners, value loyalty.

2. Get elite status on that airline you’re sticking to. Flying 50k miles/year helps here.

3. Arrive early.

4. Check in early.

5. Dress nice. Dignified. Impressive.

6. Get to know your gate agents. Get to know your flight attendants.

7. Two words: Kindly Brontosaurus.

8. Flight overbooked? Offer to be bumped. Family needs to sit together? Offer to move.

9. Just buy the upgrade. The later you do this, the better deal you’re likely to get. It does not benefit the airline to have an empty first-class seat.

10. Use your frequent-flyer miles. Is this cheap? No. But the value usually beats the hell out of buying a first-class seat, especially on long flights.