A Procrastinator’s Guide to Summer Vacation Planning

See recent posts by Margot Bigg

If you still haven’t planned where to go (or how to get there) this summer, fear not. We’ve whipped up a guide to summer vacation planning that will help even the biggest procrastinators. Read on -- it’s not too late to plan the perfect summer getaway.

One Month Out

The beach at Hotel Bellevue Dubrovnik.

Beach at Hotel Bellevue Dubrovnik

If you’ve got a whole month to plan your next trip, you’re doing alright. But the key is to start planning sooner rather than later. Once you’ve decided where you want to go, you’ll want to prioritize transportation. If you’re looking to fly somewhere and have a bit of flexibility around exact departure dates, most airfare sites will let you search for the best deals over a certain time range. If you’re fixed on your dates, set up a fare alert that will notify you of any fare changes, but don’t wait too long! Airfares often start to rise dramatically about three weeks out and continue to get more and more expensive. Once you have your flights locked in, it’s time to start looking for hotels. If you’re visiting a popular destination, you may want to book something that’s fully refundable as soon as possible and keep looking for better deals and more suitable places in the weeks ahead. This way, you have something booked, in case nothing else pops up.

Where to Go: Consider Croatia, a country with beautiful beaches, gorgeous architecture, and abundance of “Game of Thrones” filming locations. 

Our Dubrovnik Hotel Pick:

Two Weeks Out

Old Lahaina Luau, Maui

Old Lahaina Luau, Maui

With two weeks, you might have a tough time finding a deal, and you may want to start looking at destinations closer to home, particularly if you’re on a tight budget. A road trip might be a better option at this point, but you can still score decent airfares, especially if you are willing to travel midweek. Make sure to prioritize transportation; booking on a Tuesday can often bring good bargains. Once that’s sorted out, it’s time to solidify your hotel. 

Destination Pick: If you want some beach time and only have two weeks to cobble a trip together, Hawaii is a good bet. You won’t have to worry about passport issues, and you may be able to nab some last-minute deals on hotels and resorts. 

Our Hawaii Hotel Pick:

One Week Out

Streets in San Francisco

Streets in San Francisco

With only a week before your trip, you’re going to have to act fast. Given the tight timing, you might want to opt for a big-city destination. Cities tend to have a solid amount of hotel inventory, as well as plenty of flight options. Book your flight ASAP, or consider using mileage if flight prices are too high. The same goes for hotels, though if you do choose a big city, you can shop around a bit. 

Destination Picks: If you’re in the Midwest or on the East Coast in the U.S., you can never go wrong with New York. Meanwhile, San Francisco is a good option for those in western states. Both cities have multiple airports with tons of routes and plenty of hotels to choose from. 

Our San Francisco Hotel Pick:

Next Weekend

Street at Inn at the 5th, Oregon

Street at Inn at the 5th, Oregon

With only a few days to go, you’re best off going on a road trip, as you may have to drop a small fortune to fly somewhere. That being said, it’s a good idea to check travel booking sites for last-minute deals. Plus, don’t forget to search for error fares, particularly if you don’t have a set destination in mind. Also note that you may face a shortage of hotel availability in popular vacation spots. However, college towns make a great choice for last-minute summer vacations, as they tend to have more hotel rooms sitting empty when school is out of session. If you’re coming by car, make sure to look for hotels with their own parking lots or in areas with free street parking. 

Destination Picks: East Coast and Midwestern travelers should consider Ann Arbor, Michigan, a city with a fantastic food and beer scene. Meanwhile, those out west may like Eugene, Oregon, which hosts great summer festivals and provides easy access to outdoor adventure in the Pacific Northwest.

Our Eugene, Oregon Hotel Pick:

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