The idea of being on vacation is something we all daydream about, but planning that vacation can often seem like a nightmare. You find yourself asking, “Where do I begin?” “Can I really do this myself?” “How do I know if I’ll like it?”

Here are some things for you to consider when you are planning a vacation to ensure that you have the desired outcome that you are looking for…even if you don’t know what that may be quite yet.

1. Believe in yourself

First of all, a vacation is a major expenditure for most families so it is completely understandable that you would want to get it right. And thanks to the Internet, and Steve Jobs and the many applications that he has enabled to exist, travel planning is merely at your fingertips. Here is my list of helpful travel terms, too. So, have faith in yourself! This is step one.

2. Start with what you don’t want (it’s easier)

Sometimes it’s easier for us to start planning a trip with what we don’t want before we can get down to what we do want out of our vacation. This is true especially when we may not understand all the options a destination or type of trip offers when we first start investigating. Make a list and be honest about the things that you don’t want to do on vacation; don’t want to eat, or see or experience and keep track of the “maybes”, too. Also include the desires of the people traveling with you in your list because traveling with kids is very different than traveling as a couple. This “what I don’t want list” will often begin to paint a clear picture of what you do want out of your vacation.

Here are just a few questions to get you started:

• Do you have a budget?
• Do you want to go far from home?
• Do you want hot or cold weather?
• Do you prefer sun, sand and large bodies of water or mountains, trees, and streams?
• How active do you want to be?
• Does the type of hotel matter to you? Do you want it to be indulgent or bare bones?
• Do you want to eat out for all your meals or do you want to cook?
• Do you prefer destinations/hotels that are family-friendly or no kids allowed?

Once you ask yourself these questions, then you can begin to look beyond your answers for the vacation ideas that support your responses.

3. Time to start booking

When you have chosen a destination or two, it’s time to consider how you will get there. If by air, then you need to look at the flights. While last minute deals are certainly available, it’s always advisable to plan a few months ahead especially if you are trying to use loyalty points or airline miles. School vacations and traditional holidays are going to be your busiest travel periods so expect prices to be higher in most leisure destinations and plan in advance to take advantage of the best availability and pricing. And, factor in the additional fees for checked bags, pets, taxes, etc. when you are comparing ticket prices.

If timing isn’t an issue for you but money is; consider traveling in the off seasons to avoid big crowds as well as those high-season prices. Just remember that there are reasons that it is called the “off-season”. Weather can be adverse and certain restaurants and attractions could be closed or at the very least could have reduced hours.

Trip Insurance is a good option for you if you can’t afford to lose the money you have already spent on the vacation. Read the fine print to understand what is included in the coverage. Do your homework and shop around for a policy that meets your specific needs. If you have to cancel your trip, be sure you follow the exact rules of your policy for cancellation.

Once you have the destination selected, lock in your travel dates, book your flights, and then choose where you will stay based on availability at that time. A site like hotels.com is a great place to start because you can get a broad overview of the type of accommodations available to you in a given locale. Which brings me to the next step…

4. There’s no place like “hotel”

Where you stay during your vacation can really impact your overall travel experience. Sure, a bad road trip can be uncomfortable; a flight could get delayed; but 10 days in a hotel that doesn’t meet your expectations can be downright miserable. Whether you select a big resort, a small boutique hotel, an intimate bed and breakfast, or your own private vacation home, ask yourself these questions that will help you find the right spot for you:

1. Do you prefer big or small resorts?
2. Do you need room service and/or daily housekeeping?
3. Do you need a separate kitchen?
4. Do you want lots of on-site activities and entertainment included or to find your own?
5. Are children’s programs important?
6. Do you want a romantic setting?
7. Do you want it to be pet-friendly?
8. Do you want a place to gather with friends?
9. Do you want to be close to area attractions (beach, theme parks, museums)?

If your heart is set on staying at a particular resort then check rate calendars to determine the best time of year to get the accommodations you are looking for at the price that works for you. And be honest with yourself, if sun and warm water are a pre-requisite for your trip then visiting your desired resort in its coldest season may not be worth the savings to you.

5. Plan for the fun

Once your travel arrangements are secure, you can fill in your trip itinerary as much or as little as you desire. Every city in the world (practically) has a website for visitors to glean information on area tours and sites of interest. Hotels.com has a nice selection of travel guide articles to use as a reference. Just remember to allow time for the unexpected and some relaxation. Don’t be afraid to ask questions and to make specific requests of a resort or a tour company. If you don’t get the response that you are looking for then decide if you are okay with the answer or simply find another option. There is always another option.

After all, this is your vacation so make it great!

If you have any specific questions for me about trip planning, comment here on the blog and I will get those answers to you!

 

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