Owen Park
Planning a 2-week trip to destinations within the USA or around the world differs significantly from planning a 4-week sabbatical to far-flung lands or a 3-day weekend getaway. Over the years, I have run trip plans for staff and clients with the exact 2-weeks per year constraint, and have a keenly observed what can be done and what quickly goes awry when trying to cram too much into limited time. Below is a simple primer to running an optimal 2-weeks trip.
Pick destinations that fit the time window
Traveling within a two week time window creates constraints that affect your choice of destinations more than you might think. In general, the farther afield you travel, the more time you spend on planes. So if you’re traveling all the way to Australia or New Zealand, or even all the way to Southeast Asia from the US, you can expect to spend 2 to 3 days traveling to and from your destination, in and out of airports, dealing with jet lag. That’s 2 to 3 days that could have been spent exploring a region, which, when spread across a 14 day vacation, leaves you with only 8 to 10 days to explore your destination. If you’re traveling within a region, on the other hand, you’ll find that you preserve more of your days for traveling within the region. For example, traveling to Mexico, the Caribbean or Western Europe from the East Coast of the US, you might lose a day each way, but then you’ll have 8 to 10 days to travel within your destination. It’s worth noting that within a two week time window, it makes sense to take a long haul flight one year and then travel within a region the next year, as opposed to splitting your two weeks into two 7 day trips, or saving up for years to take one really long trip.
The R/Sat-Sat-Sun trick
I call this trick stretching weekend days into your vacation. It’s a very inexpensive way to lengthen your trip. By departing on a Friday evening and returning on a Sunday evening you will extend your 14-day vacation by 1-2 days or create a 16-18 day vacation, all without using any of your vacation time. The catch is that you may be booking flights that cost more on the outbound than they do on return. To take advantage of this trick it would help if you’re flying into a hub, a large airport which offers many flights, and have one major stop on the way to your first night’s accommodation. For example, on a trip to Peru I took, I departed from JFK airport on a Thursday evening. My first night was in Miami where I was able to spend some time with a friend, and I departed from Miami on a Friday morning on a short flight to Lima. The reason that this worked well for me is that my friend lived in the Miami airport, so I was able to have a evening of accommodation without incurring any extra costs, and I was able to depart from the airport on Friday morning for my flight to Lima. That worked well for me, but I can also imagine a circumstance in which I am departing from New York City on a Friday evening and flying into a hub airport and spending the Friday evening in transit and then continuing on to my first night’s accommodation on a Saturday morning. In that circumstance, the entire Friday evening would be lost to transit. But the following Saturday would be a full day. This approach clearly needs to be tailored to your specific circumstances and planned out ahead of time, but it is an inexpensive and effective way to add days to your vacation.
I have really only struggled with this point in the past and have come to a conclusion. But I have no idea where this is going to end up.
Anchor and explore is better than circle
Finally, on longer trips, there is an optimum number of locations to visit. A “circular” route, back-tracking between different cities, loses too many days to traveling between locations. For example, 14 days in Italy might cover Rome, Florence, Venice, Cinque Terre, Tuscany and Amalfi. A “circular” trip such as 5 nights in Rome, then 4 nights in Florence and then 4 nights in a village in the Tuscan countryside would achieve the same core locations with 2 less days of transit between locations. Small countries, such as Iceland, Croatia, or Switzerland can be circular, because each leg of the trip takes about half a day. Large countries, like the U.S. or Italy are best done as an “anchor” with excursions.
Where to splurge with limited time
When you only have two weeks per year to travel, you can make different trade-offs than when you have more time to travel. For instance, I would pay for an upgrade to premium economy or even business class for the long-haul outbound flight, but then return in economy, since you would otherwise lose a day to recover from jet lag. In the connecting airport, a one-day pass to the lounge or even a Priority Pass through a credit card can turn a 4-hour wait into productive time. And when booking your accommodations for the trip, it is worth splurging on a small hotel or even a private room at a hostel for the nights you do have booked, since the cost difference over 14 nights can add up to $300-$600, but that does not have to equal a trip cost.
Pre-trip prep for two-week trips
Because you’re traveling for only two weeks, for every day you spend getting familiar with a place (researching a destination before you arrive so you can hit the ground running instead of wasting days figuring out the basic things you need to survive) you are throwing away space on a 14-day trip for a 2-day learning curve that a 6-week trip could absorb with ease. This is where you would reserve the harder things in advance (more popular restaurants and museums which require advance reservations, individual train tickets which are subject to dynamic pricing). Your on-the-road planning can then be very loosey-goosey, with a rough outline of each day that has one really solid thing planned and the rest of the time to wander around as you wish, but, overplanning a two-week trip can make it feel as though you’re on a rigid schedule and end up being just as un-flexible and unhappy as you would be on a circle trip, while planning no trip at all would be to waste the days on the basic things that you’d be needing for the trip in the first place. Most travelers find this out the hard way, after having made all the mistakes on a couple of trips.
I double checked my notes for two of my past trips, one in 2024 and one in 2026. The principle of anchor and explore holds true for both trips.
How to Apply When You Plan Your Next Trip
Be sure to include a contingency line is built into your trip plans as if part of them. I suggest that you include a contingency day in your itineraries per week, offer refundable cancellations on at least 40% of your bookings and have a little money aside as contingency. In the long run, this will save you so much money as compared to trying to recover from a problem whilst on the trip. As with planning any trip, start with the fixed items – the dates of travel and the trip budget – and work from there. Don’t let the idealistic list of possible places for your trip dictate your planning, instead, plan within the confines of the basic items – dates and dollars – and then let the rest of the items on your trip plan lists expand out as if part of a trip plan within the boundaries of the hard dates and fixed budget established from the get go. Lock in the largest bookings – flights, primary lodging – first. This will set the ‘booked’ anchor for the rest of your trip planning for the sections that do not have to be locked in as tightly.
—Tara Singh; checked against author’s notes for 2024 and 2026 trips.
Editor’s Notes: Our article was reviewed by Tara Singh and found to be accurate based off of primary sources, data, and traveler interviews. The prices, routes, and conditions for flights, etc. were reviewed for accuracy prior to the article being published. If there are any errors in the article or if you have any other feedback please contact us through our Contact page. Our articles go through a rigorous Editorial Standards and Fact-Checking process prior to publication.
