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The Ultimate Guide to Planning Your Dream Vacation

I love to travel. The one thing I enjoy almost as much the trip itself is all of the excitement and anticipation that comes along with planning the vacation and choosing where to go and what to see and do.

Whether you are planning a two week destination vacation or a long weekend getaway, taking the time to research where to go, where to stay and how you’re going to get there makes all the difference between a travel nightmare and a dream vacation.

But as I write this, I am guessing that not everyone shares my love for planning and organization. So…since I am in the middle of planning a three week trip to Europe, I thought I would share some tips and advice on the best way to navigate the whole process.

When to Go?

Choosing the right time of year to travel can make or break your overall experience. Most accommodations will list their rates for high, low and shoulder season. If you can plan far enough in advance and your vacation time is flexible, traveling during low season means lower hotel costs and fewer crowds. This can affect your entire trip, from the ability to get a reservation at a restaurant, to avoiding traffic snarls (especially at popular destinations and national parks), and more open space at the beach or poolside. Weather is also a major factor. Of course, no one wants to travel in rainy season or the dead of winter. Book your trip during that sweet window of opportunity, such as late May or early June before kids are out of school or in the fall after most people have taken their vacations. Check the average temperatures and rainfall amounts at your destination to ensure you are choosing an optimal time.

Where to Stay?

It has never been easier to find the best and most cost-effective places to stay. If you like researching and have the time to spend online and compare costs, there are plenty of travel websites that provide comparisons for accommodations, things to do in the area, restaurant reviews and travel forums. My favorites are Airbnb, Rick Steve's, TripAdvisor, and Kayak. I will look up the same hotel/accommodation on at least 2-3 different sites and compare ratings to make sure I’m getting consistently high reviews for where I want to stay. Sure, it takes time, but you will thank yourself when you get there. If you know friends and family who have taken vacations where you are going, be sure to get their advice too. Once you’ve done your research and found your favorite accommodation, you can often get the best rate by calling the hotel or vacation rental directly.

How to Get There?

I use Travelocity (owned by Expedia) to compare flights and car rentals. There are many other sites you can use, but the website is easy to use and I find their rates are generally the best. After you have done your comparisons, it may be cheaper to call the airline directly to book your flight. If you want to know the best way to get from point A to B (especially outside the U.S.), there is a really cool site called, Rome2Rio. It will tell you if it’s cheaper to take the train, rent a car, take a bus/ferry or fly and includes the time it will take to get there.

As you compare transportation options, also consider what kind of traveler you are and your preferences. Personally, I would rather rent a car and have the flexibility to stop wherever I want along the way. For others it may be too stressful to drive and getting from point A to B quickly is more important. If you’re renting a car, remember to factor in gas, tolls and parking costs. If you’re traveling by air or train, remember to factor in the cost of an Uber or taxi to your hotel. When traveling between cities, allow additional time before departure: two hours before a flight and at least 30 minutes for trains.

Getting Around the Area

Traveling in an unfamiliar place can be a challenge. You can rent a car with GPS or download offline maps on your phone before your trip so you don't use all of your data. Here is a quick guide:

On your Android phone, open the Google Maps app

  1. Tap your profile picture or initial. Offline maps.

  2. Tap Select your own map.

  3. Adjust the map according to the area you want to download.

  4. Tap Download.

For iPhones:

Open the Maps app on your iPhone. Tap your picture or initials next to the search field, tap Offline Maps, tap Download New Map, then enter a location in the search field or tap Current Location.

What to See & Do?

Google points of interest and activities along the way. A great way to start is to search: “Top 10 Things to do in… (your destination).” You can also use ChatGPT to plan activities based on your interests. Enter something like, "I am looking for a travel destination that has sunny sandy beaches, great restaurants, and an overall relaxing vibe. Can you help me figure it out by giving 5 recommendations worldwide?" Or, search: "I am planning to visit Tuscany. Tell me more about it and give me recommendations on why I should choose it."

You may want to visit your local bookstore and pick up travel guides to research specific things on your trip so you can find specific places to go while you’re there. Seeing the photos in the travel guides and online may inspire you to check out places you may not have heard about. Once you are at your destination, ask the locals. I have received the best advice on restaurants, best beaches, picnic spots and local festivals just by asking a waiter, concierge or shop owner.

Don’t Have Time for all of this Research?

Leave the planning to travel experts. Find your nearest AAA office, tell them where you would like to go and let them plan it for you. I can’t recommend them enough. They can help you choose great destinations and arrange everything from flights, cruises, transportation and accommodations. They can usually get better rates than you can on your own. Anyone can join. I’m a member and the benefits are well worth the membership. Another stress-free vacation option is choosing an all-inclusive resort or cruise. You’ll pay for most of your trip up front and let them take care of the itinerary, meals and activities.

What to Pack?

One of the best things I’ve learned over the years is to keep one standard packing list you can refer to for every trip. Lists make me happy. They free up space in my head so I don’t have to think or try to remember things. For your convenience, download my packing list from my Resources page and save for future trips. There may be differences here and there depending on where you’re going, but generally, you tend to want or need the same things on every trip. You may also like this more specific list for your carry-on bag and this checked bag list.

Sometimes you need to bring along the little comforts from home. Here is a list of “extras” that have saved the day on some of my trips.

  • Pillow

  • Reusable water bottle

  • Small backpack

  • Laundry soap

  • Candle or room freshener (for rental cars or hotels)

  • Heating pad

  • Garbage bags

  • Space saving Ziploc Big Bags and Packing Cubes for organizing your suitcase

  • Corkscrew

  • Notebook or Post-it pads

  • Binoculars

What is the one must-have thing you pack for your vacations? I would love to know!

Wishing you safe and happy travels,



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