I know for most people time off can be limited and taking a month long journey through Europe is not feasible, but rather a short trip is more in line with holidays and weekend getaways.
I used to have a regular 9-5 job where I got one to two weeks off a year so I had to maximize every single day off that was available to me. At times it was frustrating that I could not just leave with friends who had more time off with their jobs.
So, I learned the art of taking the short trip and maximizing my time in locations.
I have had the pleasure of visiting all 50 states now and most of the Caribbean and Central America. I believe I am a wealth of knowledge on the topic of travel and the master at planning a short trip.
How to Plan a Short Trip
Believe it or not, I worked full time for almost an entire year while building a social media blog business and social media channels based on travel. Which meant, I had two paid weeks off and 10 federal holidays.
So, 20 days in total to take off in a year plus weekends (there are 105 weekend days in 2019). During this time, I still needed to travel for my business and had to get very creative with time off.
I recognize that not everyone works a Monday thru Friday job and may not always have weekends off, however, just think of those days off as your weekend for planning purposes.
The first thing you want to look at is what days holidays are on. A lot of federal holidays are on Monday or Thanksgiving is always on a Thursday. You will want to look for the ones that move like fourth of July or Christmas and see what day they fall on.
If these holidays do not fall on a weekend, it will be easier to plan a short trip this way by using the holiday, the weekend and then adding one or more days on. Personally, three to four days is plenty for a trip.
Even with the holidays that do fall on a Monday or a Friday (due to moving dates), you can still get a weekend trip out of the deal.
So here are the top ways to plan a short trip with your days:
- Leave on Friday when you get out of work and return late Sunday or early Monday before work
- Utilize a holiday weekend where the holiday falls on a Monday or Friday. You can leave the day before the holiday starts (if it is on a Friday) when you get out of work and come back as late as the morning you return to work. I have done this by flying, driving, taking a bus, or taking the train
- Mix a holiday with a weekend and add an extra day or more to create more time off
- Just add a day or two to a regular weekend
- Do a local 24-48 hour trip – a staycation
- Utilize a Wednesday holiday by adding an additional day off plus the weekend
The way that I would plan a short trip first is with holidays included. Those were my built in days off aside from paid time off.
For example, in November of 2017 I utilized the Thanksgiving weekend to go to Morocco from Washington, D.C.! That probably sounds insane, but the reality is – it was one of the best trips I have ever taken. I used the weekend, Thanksgiving holiday and one day off to make this trip happen. Here is how I did it.
- Discovered I could get to Morocco in about 7.5 hours door to door, so taking an overnight flight put me in Morocco the next morning around noon and I was ready to hit the ground running. I did travel to Morocco solo because everyone else thought I was crazy taking on such a “big adventure” for a short trip. It was perfect. I have plenty of tips for Marrakech for anyone visiting.
- I left Wednesday night when I got out of work and returned from Morocco on Sunday, then went back to work on Monday morning.
- I planned to stay in the Medina for a night to experience the thrill of the city and then stayed at the Four Seasons Marrakech outside the Medina for two nights to experience a different side of the city .. and to get the included car service with my stay.
- I did plenty of research before I left my house on what was open, times, costs, etc. I knew how I was going to spend most of my time and left some time open for spontaneous activities.
- I purchased travel insurance. It can protect you and your trip and I have had many scenarios where I did not purchase travel insurance and it was not pleasant. You can read here about a few times I REALLY needed it.
Best Destinations to Take a Short Trip
I can confirm that Iceland can be done in two days, making it the best short trip I have ever done! Iceland was my first solo trip and to this day, my favorite country.
Flights are now readily accessible from the United States and Europe, making getting there pretty easy! When I went, I flew overnight and the flight was 4.5 hours from Washington, D.C. Easy flight, easy transition in the city and a great place to relax, even with the short amount of time.
I spent 48 hours in Plano and covered a large area of things to do and ate my way through the city. Located just outside of Dallas, Plano has a lot to offer its visitors. It’s not a top destination, but one that took me by surprise when I went to visit. I think above all else, the food really stood out. If you are a foodie – Plano is for you!
One of my absolute favorite cities in America. I have done 1,2,3, and 4+ day trips to the area. I am telling you that you can visit really on any amount of time. The great thing about the area is that there is no shortage of lodging options, activities or fantastic places to eat.
Some of my favorite things to do are hot air ballooning, going to one of the many spas, the Desert Botanical Garden, and visiting Mesa, the neighboring city, to eat at Jalapeno Bucks – get the PB & J brisket sandwich.
Pro tip: go during the summer when the weather is quite hot and you can get insane deals on high end luxury properties! As low as $100 or less.
The Nations Capital. Most of the popular attractions in the city are free. You could get away with just purchasing transportation in, hotel, meals, and getting around the city. On a short trip you probably could not even get to all the Smithsonian’s and Monuments.
If you visit during Cherry Blossom season the city is very crowded and prices on hotels are high. I recommend coming in August when it is warm and considered low season. You can pretty much stay where you want and the city is pretty empty compared to other months.
Traverse City, Michigan
The Cherry Capital! I would be doing you a disservice if I did not mention Traverse City as one of the best trips one can take on a limited time frame. You can fly right into the city and get your day started immediately.
I would highly recommend checking out Brys Estate Vineyard and the other wineries on the peninsula. Additionally, the Sleeping Bear Dunes are close by AND you can get just about any cherry food you want.
I think this goes without saying, New York is a short trip most anyone can do, it is also what you make it. If you live on the east coast, a bust or train can get you there relatively quickly and cheap.
I have paid $1 for a one way bus ticket before – think about all the bourbons I was able to have by saving on that ticket!
New York does take some planning, especially if it is around the holiday or New Years. Book hotels in advance, tickets for shows and leave some free time to just walk around Time Square.
I don’t know what it is about Orlando, but I can get in and out in under three days AND still do what I want. If you just want to take a quick trip for parks or to just have a holiday, Orlando is usually cheap to fly into.
If you are planning to go to Disney, just book everything through them and they will pick you up at the airport and take care of everything until you go home.
Pro tip: if you are going during the summer or over a holiday – beware of the crowds! It will be insanely busy and could make your trip feel overwhelming.
Mackinac Island, Michigan
While Mackinac Island is a seasonal destination (April-October), it is worth the weekend escape. The easiest way to get there if you do not live in Michigan, is to fly into Traverse City airport and then make the two hour drive to Mackinaw City and take the ferry to the island.
I know that sounds like a lot of work, but I promise, it is not and once you get to the island, you’ll know it was worth it.
This charming island nestled between the upper and lower peninsulas in Michigan is just over eight miles around and has no cars allowed on it. Everything is done by foot, bike or horse and carriage.
Fortunately, most of the tourist stuff is located in the downtown area and very walk able. You will find the island has no chain hotels and several bed and breakfasts to choose from.
You could technically get away with just spending a day on the island, but I would recommend at least one night so that you can take a carriage tour, experience afternoon tea at the Grand Hotel, do some shopping, ride a bike around the island, eat all the fudge, and feel like you have stepped back in time, momentarily.
Santa Fe, New Mexico
I spent two full days in Santa Fe and fell in love hard. It is the cutest town with so much to offer its visitors. From art museums, chocolate tastings, Meow Wolf art experience, the downtown, and incredible dining.
The city is easy to access as well with their own airport OR you can fly into Albuquerque and make the two hour drive up (which is really easy).
From experience, I can tell you that I have visited almost every country in the Caribbean on a short trip and they were all marvelous. In cases like this, depending on where you live, try and book the earliest flight out to your destination and the latest flight back so you can get the most time possible.
When I go to the Caribbean, I take 5-6am flights and tend to land by 12:00pm. I still have the entire day and I sleep on the plane.
Getting the Best Bang for your Buck
If you are open to going anywhere, I suggest going to the Skyscanner website and plug in your dates and what airport you will be leaving from. In the “to” section type “everywhere” and a list of places with the cheapest airfare will come up first.
This is a great way to end up somewhere you were not expecting and to be budget friendly.
Look for destinations that are in a shoulder season AKA in between busy seasons. I like to travel often during off season to places I love because my money goes so much further.
One of my favorite off seasons destinations is Scottsdale/Phoenix. It gets very hot in the summer (over 100 degrees) but it is dry heat. It is still hot, but you can get very nice hotels with add ons for very low prices.
If you love to travel and plan to continue to travel. Make sure you have a credit card that is working for you for points and miles AND make sure that you are signed up to get status with your favorite airlines and hotel companies. It pays to be loyal.
The Short Trip that Turned into a Long Trip
Most years there is a sweet spot in December between Christmas and New Years where within a two week period there are two federal holidays and four weekend days. For 2019, you could get 12 days off for the price of SIX vacation days.
In theory, 12 days is enough time to really take any trip you would like. You would have to sacrifice your holidays (if you participate) but think of what 12 days off could really get you. You could take multiple short trip adventures or one big trip.
For example, you could take a cruise in a lot of destinations around the world, work on your European bucket list destinations, have a relaxing week long all inclusive vacation in Barbados, take a Christmas river cruise with Viking, or you could even go to Antarctica!
So you see, there are many places to visit, even if only for a day, making short trips work in your favor even if you have time working against you. Nearly every trip I take is 2-3 days in length and I can cover a lot of ground in that time. However, if you do have more time or can work out a longer holiday, there are a lot of wonderful places around the world to consider that would be more in reach.
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Disclaimer: this article was written in Partnership with Allianz Travel Insurance. As always, opinions are entirely my own.
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