Like so many of my friends and family members, I really enjoy vacation planning. I love to think about what the people I'll vacation with love to do, and then look for great places and activities that match their interests. Why do I love vacation planning so much?
My dad loved to vacation plan. Way back, he'd pour over the rental section in The Boston Globe on Sundays looking for that just-right rental for our family of eight. We typically rented different places each year simply to try something new each time. There was something special about every rental from the teeny, tiny cabin in the White Mountains to biking-friendly beach locations on Cape Cod.
My siblings, cousins, and I carry on my dad's love of vacationing today. Typically in the cold winter months, we plan the spring, summer, and fall adventures close by and faraway. When I plan the vacation, I make the following considerations.
Money
Money is always a consideration as like most people we have limited funds. We spend a particular amount on vacations each year, and we stretch that money in ways that bring us the most pleasure.
Location
When I rent a space, I always think about the location and what I'm willing to give up on and what I want. For example, I recently rented a place because it had a great view. I knew that the people traveling with me on that trip would really enjoy a view. I gave up on space in favor of the view. What I'll search for and what I'll give up on depends on who is traveling with us.
Travelers
Who you are traveling with determines the kind of places you'll choose to visit and stay in. For example if you're traveling with people whose plans change all the time, you won't want to invest as much money into the place, but if you're traveling with people who usually stick to their plans, then you might invest a bit more time and money into the choice. Also, if you're traveling with people who like to be active, you'll want to be near the activity. If it's a big, diverse group, you'll probably want to be in close proximity to lots of recreation choices so people can do their own thing now and then.
Timing
With a big, diverse group, I find that three to four days is a perfect amount of time whereas for a more intimate group, a longer stay may work well. The time of year matters too. Off season will allow you to get more for your money, but may limit what you can do due to the weather whereas in-season it likely the best time to travel to locations, but then you're often dealing with the crowds.
Reservations
If you have your heart set on particular activities or food, it's best to make reservations ahead of time.
Research
If you make the time to research the location ahead of time, you'll most likely have a better time.
Safety
Read the travel reports and safety information about the location you are visiting. Also heed the safety warnings at the location. Every year I hear about people who die because they don't pay attention to the safety warnings at vacation locations. That makes me so sad as it is unnecessary and hurtful.
Budget
There's nothing worse than going on vacation and not having enough money to have a good time. It's best to budget ahead with regard to the activities you'll do. You can save a lot of money by including picnics, hikes, free public events, and more low cost options as part of your itinerary.
Have fun
Once your plans are set, be ready to have fun. Know the plans won't go exactly as planned so plan to be flexible and go with the flow. Onward.