How to Plan a Vacation

Co-authored by Greg Guiteras

Last Updated: January 29, 2024 Approved

A vacation is supposed to be a fun and relaxing break from your everyday life. However, a poorly planned vacation can end up being a major headache. Be ready to enjoy your time off by planning your travel, accommodations, and activities ahead of time. Giving yourself plenty of time to plan can be a fun way to build up excitement for your vacation.

Part 1

Part 1 of 5:

Choosing a Destination

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If there are other people traveling with you, have them do the same thing.
If you know why you want to leave home, choosing a destination will be easier. Determining whether your goal is to relax and unwind, have new adventures, see famous or ancient sights, or provide your children with lifelong memories will determine what kind of destination you should choose.^{[1]
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Instead of making this a chore, have it be a fun activity. Over the course of a few days, weeks or other long duration you wish (e.g. 1-3 months), spend some time talking about each place and why it would make a good destination.
If you are traveling with children, someone elderly, or someone with a disability, you may want to consider the destination that would be accessible.
5
Research destination costs. While you may take more time after choosing a destination to find great deals on travel and hotel arrangements, doing a quick online search of approximate costs to travel to each destinations may help you narrow your choices based on your budget.
- Keep in mind expenses to travel, stay, eat, and play while you are developing your estimates.
6
Choose a destination. Ideally, everyone who is traveling will agree on the same place. If there is disagreement, find a way to compromise.
- Consider taking turns selecting vacation spots. If you decide to go with your first choice this year, let another travel partner select the next vacation destination.
- Find a happy medium. If everyone’s first choice for a destination is widely different, find one that everyone would like, even if it is not on the top of their list.
- Pick a destination out of a hat. If there is no compromise on the horizon, let fate choose for you. Write down all of the destinations and put them in a jar or a hat. Then have someone (ideally, an unbiased third party) pull a name out. That’s where you’ll go!
Depending on the season, a destination which is normally too hot or cold for you to consider might have a more enjoyable climate at a different time of the year. This might also be reflected in a lower cost, if you decide to travel out-of-season.

Part 2

Part 2 of 5:

Making Travel Arrangements

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Different airlines can offer widely variant prices for similar flights, so be sure you shop around if you’re planning to fly.^{[2]
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2
Find a flight (and hotel) booking website if you plan to fly. Remember that booking a flight and hotel together may save you money if the website offers specials or discounts.^{[3]
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- These websites often compare flight prices from different websites for you, all in one place.
While flying is the quickest way to travel long distances, other options such as taking a train or bus or even renting a recreational vehicle may be less expensive and more environmentally friendly.^{[4]
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4
Consider all transportation needs. Reaching your destination is only one transportation consideration. Once you have arrived in the area, you will need to figure out how to get from the airport, train station, or bus station to your hotel. You may also have plans to travel locally while on vacation.
- Call the concierge at the hotel you’re staying at and ask whether the hotel offers complimentary or reduced-fee shuttle service to and from the airport. If they don’t, ask for any advice on local ground transportation.
- Rent a vehicle if you will need to get around a lot once you have reached your destination. If you’ll be doing a lot of sight-seeing in areas that are spread out, a rental car will be a better option than taxi services. Be sure you know your hotel’s parking policies and fees.
- If you don’t plan to leave your destination once you get there (for example, if you’re staying at an all-inclusive resort), you may not need a rental car. Consider a taxi or shuttle from the airport instead.
- If you are going to an urban area, search online for the city’s public transportation options. Areas with subways, trains, or bus systems often offer daily or weekly passes that are much cheaper than rental car fees.
5
Perform scheduled maintenance on your car. If you’re planning to drive to your vacation spot, be sure your car is up-to-date on basic maintenance.^{[5]
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- Check the air pressure in the tires.
- Change the oil if it has been 3 months or 3,000 miles (5,000 km) since the last change.
- Be sure that all essential functions are in good working order: check wiper blades, headlights and taillights, brake pads, hoses, and belts.
- Be sure you have a spare tire and working jack.

Part 3

Part 3 of 5:

Finding Accommodations

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This can help you compare hotel prices, ratings, and amenities.^{[6]
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Consider options like free breakfast, free wifi, in-room amenities like mini-fridge, microwave, and television, as well as options like having a good view or being near public transit lines.
For very active vacations, a hotel room is often little more than a place you will sleep at night, and a lower cost will leave you with more money to spend on activities or meals. If you’re planning a more relaxed vacation, you may want a comfortable place to relax in luxury.
4
Consider other housing options. A hotel is not the only option for vacation accommodations. Consider trying another type of housing when making your travel plans.
- Friends or family may have a guest room that you can stay in. If you vacation somewhere that you have connections, ask around. You may be surprised at the hospitality of even somewhat distant acquaintances.
- Local bed and breakfasts often offer more charm and personalized service than traditional hotels.
- Many vacation spots have condos, houses, or cabins that individual owners rent out themselves or through property management services. Try searching online for “house rental” + your destination.
- Renting a recreational vehicle (RV) or motor home may be a good option for traveling. The RV functions as both your travel vehicle and your hotel room.
- Camping is a fun option for anyone who loves being outdoors. Some camping areas and state parks offer amenities such as bathrooms and showers, so it doesn’t have to be “roughing it” completely!

Part 4

Part 4 of 5:

Planning Activities

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Even though they may be considered old-fashioned, a printed travel guide can be one of the best companions for your travel. They will have suggestions for activities and ratings for specific companies. The information in reputable guides is usually very accurate.
Make sure you think of all of your travel companions when booking activities. If you are traveling with children, be sure planned activities are kid-friendly. If someone in your group has health or dietary considerations, try to be respectful of those as you plan the trip.
3
Book special adventures ahead of time. If you want to do something special, like a tour of a special collection at a museum, a whale watching trip, a performance, a sunset cruise, or a very fancy dinner, make reservations ahead of time.
- If you are going to a popular place during a busy season, special events may fill up, so you will want to be sure to book ahead.
- Be sure to find out about cancellation policies or rescheduling if you are booking far in advance.
If you are planning a vacation, it’s likely that you are making plans for yourself and other people. It may be fun to plan a surprise—a nice dinner or an exciting excursion—for someone who is traveling with you.
As tempting as it may be to plan every moment of your vacation to be sure you get in every activity you want to do, resist the urge to over-plan. A vacation is supposed to be a break, after all, and a little leisure time or room to participate in an unexpected opportunity can make your trip even more fun and exciting.
6
Prioritize sightseeing or activities. If you have a long list of activities to do or sights to see, rank them based on how important they are to you. That way, you will know to make time for the items at the top of the list.
- If you don’t get to every item, you may be able to return to the same vacation spot in the future and finish your wish list.

Part 5

Part 5 of 5:

Packing and Preparing to Depart

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1
Save money for your trip. The further in advance you plan your trip, the more time you will have to save for it.
- Know how much you will need for each aspect of the trip—transportation, housing, food, tips, activities, and all associated fees—and then plan extra for unexpected expenses.
- For expensive or special trips, consider asking family and friends to chip in to your travel fund in lieu of gifts for holidays or birthdays.
2
Write a list of things you need to pack. Well in advance of your trip, start a list of what you will need to take with you. Keep the list out and add to it anytime you think of something else.
- Think about things that you use every day that you will absolutely need while you are away.
- Be sure to include or even pre-pack very important things, like medications. Be sure to fill any necessary medical prescriptions before leaving for vacation.
- Be sure you know about the weather of your vacation spot so that you can dress appropriately while you are there. You may want to pack a few layers to allow for unusual weather.
- Search online for vacation checklists. There are helpful resources that guide you in packing for different circumstances.
- If you are flying, be aware that many airlines charge customers per bag, so packing light will save you money. In addition to limits to the number of bags, most airlines limit the weight of each bag and will charge exorbitant fees for overweight bags.
- Regardless of your mode of travel, consider packing a first aid kit, snacks, and entertainment for the travel time. Car trips and air travel both involve long periods of potential boredom, so consider bringing along games or activities for the travelers, especially if you are traveling with children.
3
Make a plan for your pets. If you have pets, you will need to be sure they are cared for in a safe environment while you are away.^{[7]
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- If you are driving, you may be able to bring your pet(s) with you. Be sure you know the pet policy of the hotel you’re going to stay at before you get there. Some may charge a deposit or restrict dog breeds.
- Boarding your pet at a vet or a kennel may be an option. Be sure you know about the pickup and drop-off times so you can retrieve your pet appropriately upon your return.
- Hiring a pet sitter to come to your home may be the best option for animals who do not adapt well to new environments. If you have dogs, be sure that the pet sitter has been to your house (several times if possible) while you are home so that the dogs understand that the person is allowed to be in the house.

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Is it cheaper to plan your own vacation?

Greg Guiteras
Travel Specialist
Greg Guiteras is the CEO of Lorraine Travel, LLC, one of the largest privately-owned travel management companies in Florida founded in 1948. With over 34 years of experience, Greg's specialties are in corporate travel management, sales and marketing, contract negotiations, strategic partnerships, and luxury hotel sales. Greg holds a BS in Marketing from Florida State University. Greg has also created WhataHotel!, a website offering exclusive perks on hotel bookings, and CabinMate, an app that matches single cruise travelers with potential cabin matches "in the same boat" to avoid traveling solo on a cruise.

Greg Guiteras

Travel Specialist

Expert Answer

It kind of depends. On one hand, paying a travel planner costs money, so it may be more expensive in that sense. At the same time, a travel planner may be able to find you better deals on tickets, hotels, or activities than what you're capable of finding on your own. It's going to be very situational in that sense.

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What's the first thing I should do if I'm planning a vacation?

Greg Guiteras
Travel Specialist
Greg Guiteras is the CEO of Lorraine Travel, LLC, one of the largest privately-owned travel management companies in Florida founded in 1948. With over 34 years of experience, Greg's specialties are in corporate travel management, sales and marketing, contract negotiations, strategic partnerships, and luxury hotel sales. Greg holds a BS in Marketing from Florida State University. Greg has also created WhataHotel!, a website offering exclusive perks on hotel bookings, and CabinMate, an app that matches single cruise travelers with potential cabin matches "in the same boat" to avoid traveling solo on a cruise.

Greg Guiteras

Travel Specialist

Expert Answer

Look at your budget and figure out how much you have to spend. All of your travel choices need to be constructed around how much you're willing to spend,

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What are the best ways to pack bulky clothes?

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You can roll your clothes, this saves space in your bag and keeps your clothes wrinkle-free. If you need instructions on doing this correctly, check out this article on How to Roll Clothes.

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Be sure to consider number of layovers and time between arrival and departure when booking flights.

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Consider buying travel insurance, particularly if you are booking travel far ahead of time. This may allow you to get refunds for your expenses if you have to cancel your trip unexpectedly.

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Be sure you travel with appropriate identification and know airline policies about acceptable carry on items.

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