Where to begin

As people begin to travel again, without the restrictions that we’ve had the past few years, a lot of folks have asked me a lot of questions. “How do you decide where you want to go”? “How do you figure out where to stay and what to do”? So I thought I would share my process with you. 

I am lucky enough to be married to someone who loves to travel and have adventures as much as I do. We started our “bucket list“ in the notes app years ago. Some destinations might be small getaways, or staycation ideas. Others might be larger ideas like countries with specific things we want to see.

Like everyone else in the world, we had to push back plans for 2020 and 2021, so we are a little behind on some of the adventures that we had planned. We would like to do international traveling prior to turning 62 years old. I am not saying that 62 is too old to travel, but it is tiring and I am already loosing steam at 56! After 62, will leave time for us to travel within the United States or closer countries like Mexico or Canada.

Creating your bucket list

I would suggest writing your own list of places you want to see, your bucket list. Put it all down either pen and paper or a notes app. Plenty of people have a significant other that does not like to travel, so would you travel with a friend or maybe a child? Note who you would like to take on those trips with you and have those discussions. Throw caution to the wind. If you haven’t traveled with that person before, you might want to do a test run. Maybe a weekend away before you suggest a longer trip.

Traveling as a couple with another couple can be a lot of fun. We have a few couple friends that we have traveled with and have had a blast. The key is to have conversations beforehand about expectations. Most of the time we have “free time” or time for a nap in the afternoon. You don’t want to be frustrated on your vacation so it is best to talk about it. Traveling in a group can be more of a challenge but again conversations and flexibility are key.

I realize that I am fortunate to be self-employed, so I have more time that I can set aside for travel. My husband’s employer is a little more flexible than most. He’s not pulling from a bank of paid time off so it is more about working around events etc. If you are someone who has PTO that you have to consider it is certainly a huge factor. Check with your employer and see if you can either buy vacation time or bank it and roll it over for a longer trip.

Once you figure out where you want to go, I suggest googling the “best time to visit” that particular spot. I like to go on what’s called a “shoulder season”. This means it’s not crowded or as crowded as peak season at that time. During shoulder season, most things are still open versus a total off-season or peak season. There’s nothing wrong with traveling during prime season, especially if that’s the only time you can get off because of your job like being a teacher. If crowds don’t bother you and you have the patience of a saint then I say go for it. As I’ve gotten older, I am less tolerable of crowds, so we take under advisement.

Weather is a factor

I wish that weather wasn’t a factor me for but honestly, it is for sure. Rainy seasons are a big consideration for me. Are you someone who’s going to get totally bummed out if it’s raining and you have to explore carrying an umbrella? If yes, then spring time in certain areas might not be for you. If it doesn’t bother you, then that opens up the time frames a little bit more.

We made a huge mistake, well huge in my book, last year planning to go to Key West in May. I looked at the temperature for that time of year but I did not look at the dew point. Dew point for me is key. Saying it’s going to be easy to 85° sounds perfect but when the dew point is in the 70s, it makes me feel sick to my stomach. We did not do the exploring that we wanted to because I was so uncomfortable. If we ever go back to Key West, that will definitely be a factor.

Be honest about your budget

Budget! Things always cost more than you think they’re going to cost. My suggestion is take your budget and do a mock up of your trip doing everything you want to do. Some major things that can affect your budget are days of travel, season, events going on in location that might boost up the price, etc. Then add 20 percent to that total and you should be in the ball park.

If that is over what you can pay for your trip then you start trimming back. Maybe it is the number of days or time of year that is causing it to be so high. A lot of hotels are super expensive Friday and Saturday night but are half that price the rest of the week. Maybe start your vacation on a Sunday and save some money.

Let’s talk flights. For instance, a lot of airlines charge a different amount, depending on the day of the week that you’re flying. If you are flexible at all when you go to search for flights, choose the option that you’re flexible. You could save a significant amount of money by flying a different day of the week. Take into consideration though if you’re extending your vacation a day or two to get the cheaper flight that you will have to pay for a hotel, etc. Is it really a savings? If you can move everything over one or two days then it might really be worth it to you.

If you are going to check luggage, is there a cost? If so, does that amount open up the door to possibly taking a different airline? All of these factors need to be taken into consideration.

Are a member of the airlines frequent flyer program? I highly recommend that you join them for sure. Even if you never get enough points to fly for free, some airlines in larger airports, have specific lines for people in their rewards program for problem-solving purposes. It doesn’t cost anything, so why not?

Speaking of points a lot of credit cards give points or cash back for booking with them. They also sometimes offer travel insurance. These are the details that are helpful to look at prior to actually booking your vacation.

Hotels

Booking a hotel, you do not want to cut off your nose to spite your face. Let’s say it’s $100 cheaper to just stay 5 miles from the center of everything that you’re going to do. Are you going to end up paying that in public transportation or Uber‘s? Is the convenience of being located near where everything is worth it to you to pay the extra money? What are your non-negotiable items? I have to have a bathroom in my room. This is a major non-negotiable in my world. There are plenty of cute bed-and-breakfast that do not have private bathrooms and unfortunately that is a hard pass for me.

Another consideration is what size hotel do you like? Are you a national chain person that wants their breakfast buffet with special K and a waffle maker or would you prefer a bed-and-breakfast experience or perhaps a boutique hotel? We usually prefer smaller hotels, especially when we’re going to a new location. I will splurge for the breakfast to be included if it’s an additional price or better yet finding a hotel where the breakfast is included. We don’t eat a lot for breakfast and to me that is time during the day that I don’t have to be spending waiting. I prefer to go out to lunch, apertivo, and dinner and save breakfast for the hotel.

If traveling with children, something I used to look at was more of a suite situation. If there was some type of kitchen, it was perfect. A kitchen will be helpful, especially when traveling for sports, tournaments, etc. You can eat breakfast in the room and make sandwiches for lunch and/ or dinner, to save time and money.

Transportation

Car rental prices have gone through the roof since the pandemic started. When you’re traveling in the city do you need a car? Can you get by with Uber’s, taxis, or a train? When traveling in Europe, we do not rent a car. We travel by train or hire a car for special visits or transfers between hotels.

I know that sounds like it could be expensive, but hear me out. Transfers are very common in Europe. A lot of people do not own cars because of the cost to maintain a car in Europe is outrageous. My husband and I have decided that we would rather spend the money on having someone drive us so we don’t park we’re not supposed to park or drive where we are not supposed to drive.

Drinking and driving is a huge no-no wherever you go. Unless one of you is going to be the designated driver it might be worth it to you to hire a driver for the day. Our most recent trip to Italy we were there for 11 days. We only got into a car 4 of those 11 days and on two evenings we used an Uber. The car rental actually would have been more expensive than hiring the drivers for those occasions. Just something to think about.

Let’s go!

OK, you have figured out your destination, the dates of travel, your travel companion, budget and any non-negotiable things. Now what? When I am planning my trip, I open the notes app on my phone and enter the dates that we will be there. I fill in the dates as I go. Here is an example of what that can look like for you.

I know a lot of people base decisions using online review platforms. Online reviews are a base line but not the whole enchilada. I want to share my experience with you to help give some perspective. In my former life I managed a restaurant. I would welcome anyone’s feedback when it came to the food or service. Making rounds and constantly talking to the patrons and inquiring about their satisfaction with their meals. If they were not happy with their meal or experience, I would do my best to remedy the situation right then.

If someone does not take the opportunity to have that conversation with a manager then that is on them! If someone doesn’t know, how can they fix it? Going back home and writing a review when you didn’t try to fix the problem in person to me, is being a keyboard warrior and not a problem solver. I know conflict can be uncomfortable but if you are kind in your complaint, everything should work out. Being clear is being kind.

This is why I tend to not put a lot of weight on negative reviews on Yelp, Google and other review websites. There is a saying “if you have a good experience, you tell two people, but if you have a negative experience, you tell ten”.

Now, I’m not saying that every negative review is not warranted. Honestly, there are a lot of bad reviews because some people enjoy bashing businesses. Most people don’t fully understand the place that they are visiting or how restaurants works. They blame the business vs realizing they didn’t do their research. I recently saw a review for a restaurant. The only negative thing they could say was that it was raining so they couldn’t sit on the patio, but the food was great, the service was great, but they gave them one star. See where I’m going with this?

Travel arrangements are first on the list

Ok, the first step is to book your flights, car rental, train etc. If you are flying to a city and not renting a car you also need to consider transportation from the airport to your hotel. In some cities, Uber and other ride share companies, are no longer allowed at the airport. Taxis are still available in a lot of cities though, so you will have to find your way to the taxi stand. Next step, hotel.

Choosing your home away from home

What is your favorite type of place to stay in? A big hotel chain? An AirBnB? Boutique hotel on a quiet side street? A true bed and breakfast? Whatever your desire, this is the next step in planning your vacation. Things to take into account are the type of atmosphere you want to be around. Do you like to stay up late and party? Then being in Times Square might be the perfect spot for you. You want to feel like you are a part of the city? A small boutique hotel or airbnb might be your jam.

Figure out the vibe that you are going for and factor in if you need a car. If there are certain things you want to be near, like a square, monument or concert hall put in that address and then search “hotels nearby”. This will give you a jumping off point for research.

You can always do an internet search by location. Search the city and include in the search the word neighborhood and other keywords of things you want to be near. For peace of mind, I want to see photos! I don’t mean the ones the hotel or airbnb share, but photos others have taken. Google the name of the hotel for photos and if there is a huge difference in what they post and what visitors have posted, I would steer clear.

See my tips below on searching for restaurants and you can apply some of the same principals to finding a hotel.

For me, it is all about the food

First step is an internet search for “highly recommended restaurants blog in xxx”. I read four or five recommendations by bloggers and see if there is are any common threads. Why bloggers? I feel that they have knowledge enough about the industry to be honest.

Second step is searching some well known sites like Eater, Thrillist, Travel and Leisure, Bon Appetit magazine etc. using that location in the search. This is a great way to find out well known, good restaurants in that area. Take that list and compare the blogger recommendations.

Once you google the restaurant you will see the Yelp, Google and other review sites come up. Skim through them and find the most negative review. Read the review and decide whether this is a valid or not. Then click on the reviewers name and read other reviews they have written. If you only see a few negative reviews and they don’t hold water then I wouldn’t really consider them. If there are a lot of reviews that are commenting negatively about the same things, I tend to put that restaurant at the bottom of my list.

Once I have created my list, I will review the menus, double check the days of the week and hours they are open and confirm if they take reservations or are first come, first serve only.

I am sure you have heard me say if you don’t set expectations, then you can’t be upset when you are disappointed in your experience. This is why I highly recommend reservations, especially for dinner. There are a lot of restaurants out there that book up months in advance so keep that in mind.

Some restaurants don’t take reservations and that is their decision. I honestly might try to go to that restaurant for lunch of plan my day so I can arrive early enough to get a table. It depends on how much I want to go to that particular establishment.

After all of these factors, I look at the restaurant I want to go to the most and will book that one first. Recording my reservations along the way in my notes app. My calendar on my phone is where I record all of my reservations. Also, I save all of the emails for this trip in a file on my gmail account.

Things to do

There is so much information out there on places to see when you are visiting a new area. I use Viator and Get Your Guide to plan what we want to see. You enter the city and a few key words and there are the recommendations for you. A lot of busy cities with famous museums and churches will have long, long lines so please plan ahead. You can buy tickets so you don’t have to wait in those lines. Wouldn’t it stink to make it all the way to Rome but not be able to see the Vatican? Plan ahead! Again, setting expectations leads to a successful trip.

In conclusion

That is a wrap. It can be a lot of work but I promise it will be worth it in the long run. If you have any questions please put them in the comments or send me a DM on Instagram.

Bon Voyage!