The Grumpy Disclaimer: Planning your own trip isn’t for everyone. There are several reasons people prefer tours and cruises. Simplicity, time, research, what to do if things go wrong and simply not interested. But my wife and I see a lot of way off the beaten path sites that tours and cruises don’t provide and the money saved lets us travel more frequently! We pick highlights that interest us and see more variety than any organized tour. This is our preferred method of travel. If you are interested in planning trips this way start small. As you gain experience navigating the planning process and travel sites, work towards more complicated trips. I hope this inspires you to give travel planning a try. If not I hope it inspires you to seek travel adventures any way you are comfortable. And as always whoooo cares! Your friend, or not, The Grumpy Retiree.

My wife and I love to travel! Given the time and money I would spend everyday on the road. We are not full time travelers but have a lot of first hand travel planning experience. Travel is high on almost every retiree’s to do lists and it makes you less grumpy! I hope to get you started exploring new destination whether it is in the USA or overseas.

There is a lot of information regarding travel planning in this article so it is broken into 2 sections. This section covers the Basic Travel Planning Advice and the second section covers Itinerary Planning Details. Lastly, I provide an actual trip plan I recently did at Itinerary Planning Illustration. Last I have The Grumpy Retiree’s opinion of Online Reviews for hotels and restaurants. Experienced travelers may still pick up a few hints in either section.

We do all our travel planning ourselves including hotels, sightseeing, trains, planes and automobiles. People ask us who books travel for us and are amazed we do it ourselves. Their faces start to look like a Salvador Dali painting as their eyes and face start to melt away. Why do we book ourselves? There are 4 main reasons:

• It keeps my mind busy and engaged and I learn something
• It always saves us money
• We see what we want and eat when and where we want
• And I like seeing peoples faces melt, but who doesn’t!

“Generally we save at least 25-40% over the cost of a mid-range tour when we book independently. I find that substantial and worth the effort. It means we can travel twice as long or twice as often for the same money!”

The Grumpy Retiree

Planning a trip yourself can take several days or weeks depending on the length and number of cites and/or countries visited. Complicated trips can be time consuming, but I enjoy travel planning as it also affords me time to learn about a destination. After you plan a few trips it becomes easier as you learn the travel options and booking sites. Since I retired, travel planning is easier as I have more time without work getting in the way! Below I provide some planning tips. You do not have to plan a complicated oversea trip your first time. Start with a local or week long trip and work your way up if you desire.

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Pros & Cons of Self Travel

Pros

• Keeps my mind active, it is a hobby I enjoy
• Saves Money, sometimes a lot!
• Allows freedom to explore as you want
• Eat when and where you want, eat with the locals
• Stay at hotels you choose
• Tailored to your exact needs, see less touristy places
• Ability to use points for hotels, cars, flights

Cons

• Can be time consuming, especially for beginners
• You can make mistakes! (Take your time)
• Nobody to call when things go wrong, you figure it out yourself
• Can waste time without guidance

Don’t Want to Self Plan? Consider Cruises

We do not go on cruises or take organized tours. I can’t be captive to a schedule and confined to a boat and I don’t follow direction well, ask my wife! I like to poke around and get lost, discover the unexpected. There is not enough time during planned stopovers to explore things the way we want. Just because cruises are not for me doesn’t mean they are not for you. There are many cruise options from basic Caribbean cruises to high end European river cruises. Many retirees love a cruise as everything is planned for you. You unpack once and pack once. If you are interested in a cruise I recommend talking with friends that are active cruisers or research the the offerings online.

“If tours or cruises are your thing, then go for it! Just because I like to travel independently doesn’t mean you must do the same thing. I rather see someone travel and enjoy a trip than become frustrated and stay home.“

The Grumpy Retiree

Don’t Want to Self Plan? Consider Tours

Organized tours are led by a group leader from a travel company and concentrate typically on one geographic location. Group size and prices vary dramatically, but most start at $350 per day per person and go up to over $1500 per day per person or more! Solo travelers pay a “Solo Traveler Supplement” which can add 20-30% per day. Travel to and from the tour start/end points usually is extra. Frequently, some or all meals and all transportation between stops and attractions is provided. If you are interested in just the highlights of a particular area these organized tours are good, though pricey, options. Most tours do allow some free time to explore on your own.

A cautionary note about much organized travel. Many advertised prices can seem low at first, but to get the full experience there may be add-ons that increase the prices. Frequently tours, both large and small, bring you to places such as shops and restaurants that provide the operator or guide with kickbacks. Tours like this may be more interested in the largest kickback than providing a great local experience. In some cases it is hard to avoid. Even small food tour operators are likely getting free food. A complementary meal I am fine with, but unwanted shopping destinations are a waste of time for me. Just be aware this is how many tours operate and supplement their income so read the fine print regarding tour add-ons vs. included itineraries. You may reduce this issue with larger well respected tour companies, but it is reflected in the price.

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Itinerary Planning and Ideas

Don’t be shy about using travel blogs to gather basic information and itineraries. I use these all the time to rough out my trip! Most of these itineraries will start to sound the same. Pick and choose attractions for your style and speed of travel.

Look for travel blogs that provide first hand knowledge and fits your travel style. It makes no sense to follow an outdoor adventure blog if your interested in fine dining. This blog will lean towards active adults, retired or not, that want to explore on their own. You don’t have to do everything I suggest or do. Pick what makes sense for you. The last thing this world needs is two of me!

Rick Steves is a great choice for information and is one of the original travel bloggers before they called them bloggers. There are many contributors to a site like his so you can get multiple hotel and restaurant recommends in a given geographic area. Also, Rick Steves’ site has a lot of information, Q&A and reviews from actual travelers in the Rick Steves Forum. Rick has several great videos and an app online detailing how to travel overseas. He actually encourages people to use his information and travel independently. If I was ever to book a tour I feel his price, quality and group size may be the best value you can find.

Tour groups Tauck and Overseas Adventure Travel are a high/mid end escorted tour companies. A high end tour like Tauck offers a different perspective than a budget tour and may give you a different perspective. Trip Advisor also has many 3 day or 5 day itineraries for hundreds of destinations. It costs nothing to get itineraries and travel planning ideas from multiple sites to help plan a trip or research future travel.

Build and Itinerary, Subject to Audit

When considering your itinerary make a basic outline of all the places you want to see. You can fine tune stop duration later. Place the number of days to stay next to each destination and simply add them up. If you have 21 days of vacation and 30 days planned, well Euclid it’s time to adjust! I don’t stay less than 2 days at a location unless it’s just a quick overnight stop on a route. You don’t see much packing/unpacking or parking and getting in/out of the vehicle all the time.

A big city like London can be 5 days to a week or more, its is all up to your travel style and what you want to see. Use the travel itineraries you research as a good starting point and adjust as needed. Don’t cram in too much! It is better to save a stop for a different trip than to rush and not enjoy your vacation.

Dress & Clothing

Go out and buy a mirror. Look in the mirror. You go out like that? If you are over 5 years old no pajamas or pillow at the airport. Are buttons on a shirt a complex math problem for you? Save the “I’m with Stupid” T-shirt for BBQ in the back yard or to wash the car. I can dress down, but I like to look at least reasonable when traveling. And you wonder why I am grumpy? Remember, assault and battery on the eyeballs is a crime enforceable by life in prison.

Travel planning includes clothing research before you travel. Churches, mosques, houses of worship may require long pants, no bare shoulders and head coverings. You don’t have to like it or agree, but you are a guest and you may not be allowed inside many places. Cancun verses Milan? Think clothing appropriate, it doesn’t take much effort. Also, sticking out as a tourist targets you for scams and pickpockets. You don’t need suits and ties, but some nice casual clothing goes a long way.

Baggage: Pack Light!

I pack very light when traveling. My goal is 1 carry on bag for my clothing, and a second carry on like a knapsack, regardless where I go and for how long. Occasionally I have 1 checked bag if I need a large variety of clothes. Hauling bags around is a pain in the ass especially when maneuvering trains in a place like India! There are exceptions such as cold weather clothes that are bulky and take up room.

Have clothes washed via the hotel or have it done at a laundry service. In places like Thailand or Mexico it is very inexpensive to have clothes washed, dried and folded. Regardless, it is better to pack light and do laundry than cart 42 pairs of bloomers around for a week trip. Mix and match clothing.

One important consideration for baggage is to have enough room for anything you buy, especially when flying. You can have items shipped home, but it may cost more than the item itself. Also, liquids such as a bottle of wine or olive oil, etc. cannot be in your carry on baggage. Check all the rules of the airlines and counties visited.

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Budget: General Tips

Everybody’s budget is different. Travel can be expensive and is getting more expensive by the day as everyone wants to travel and that bids prices up. Besides flexibility, saving money is a big reason to plan trips yourself. I can’t tell you how to budget a trip as it depends on your resources, style of travel and location, but I do have a few basic pointers.

Most trips I budget $250-400 per day for my wife and I which includes room and food roughly 50/50. That is an average price based on 2023 prices. Some days I go over but it is hard to go much below $250/day, my ballpark. I adjust this based on the location. Check hotel & restaurant prices online of your destination to get some guidelines. Thailand had inexpensive rooms and great cheap food, while everything in Switzerland was very expensive. Adjust your figure as you feel necessary and multiply by the duration. Airfare, cars, trains, sightseeing are all added on top of the per day amount. Budget more and spend less is better than budget less and spend more!

“Budget more and spend less is better than budget less and spend more!”

The Grumpy Retiree

Hotel Tips

Major tourist cites are always more expensive. Think Rome, Paris, Tokyo, London or San Francisco. Two weeks in Paris, France costs more than 3 or 4 weeks in many other destinations. World class cities are typically more expensive than off the beaten path secondary locations, but you won’t see the Eiffel Tower or Musée d’Orsay without going to Paris.

Apartment style rooms can save money. AirBnB apartments frequently have a kitchen, bedroom, washer & dryer and living room/balcony. Cooking and laundry facilities can save money in the long run. A bottle of wine and some local pastries on your balcony is way less expensive, and more enjoyable, than the hotel bar. 2023 prices have increased, but deals still can be found. Countries like Mexico, Thailand, India and even Sicily can have inexpensive rooms based on US prices. You can moderate your budget by staying in clean, comfortable mid-range accommodations when in cities and splurge when outside the pricey places.

Frequently hotels and B&Bs offer a reduced price if you select Non-Refundable rooms. For the extra few dollars I usually book refundable room, especially if booking well in advance as things happen.

I find myself staying at small local hotels and Bed & Breakfasts more frequently than large US based hotels. I feel you get a better value and more authentic experience at these accommodations. While I have a lot of US hotel points I use them where it makes sense. Lately I started using Hotels.com more as they have a great variety of hotels all over the world. Hotels.com also offers loyalty points and a credit card for those interested.

Marriott, IHG (Holiday Inn) and Hilton hotels offer deals when using points: Stay 5 nights at one Marriott hotel on points and you only use points for 4 nights. Essentially the 5th night is completely free. Many Airbnb rentals are cheaper for long term stays, which is a great way to live like a local for a month in a foreign country.

Travel Planning : Location is as important as Destination!!!

Location is everything! Don’t stay far away from places you want to see to save money. Time wasted getting to a site may not be worth the cost. When in a large city I want to be near the metro station or walking distance to the attractions. If you need to stay further away to moderate the budget, transportation options become more important. Make sure to take into account the added time getting around. Getting stuck in rush hour traffic doesn’t make for a good trip.

“Location is everything! Don’t stay far away from places you want to see to save money. Time wasted getting to a site may not be worth the cost.”

The Grumpy Retiree

Rental Car Tips

Shop prices on rental cars like anything else. The big major US based rental car companies are sometimes overseas, but not always. Cars are priced the same as the US as bigger and fancier cars are more expensive. You will pay more for an automatic transmission outside the US and gasoline is also typically much more expensive outside the US. Consider public transportation in larger cities which is quick, reliable (usually) and inexpensive. One way car rentals, while more expensive, can be advantageous if it save time during the trip. NOTE: Larger groups may benefit from a rental car or taxi over the cost of public transportation. It will depend on the size of the group, alternative options and destination(s).

Rental cars are a great option to see a lot and have freedom to explore and come and go as you please. They can be very cost effective depending on location. I use them primarily when I am not in a city or to drive between destinations. In many European cities parking can be difficult and very expensive. Look for free parking at hotels but don’t be surprised with $30 or more a night parking. Rent the car when leaving the city if possible. Have a valid non expired International Driver’s License which you can get at AAA. Honestly it is seldom checked, but if it is requested and you don’t have one your plans are ruined.

Dining Out Tips

Food is similar to hotels. The cost of a meal at a Michelin star restaurant in New York city will feed you for a week or a lot more in Chang Mai, Thailand. And I prefer the food in Chang Mai!

You can moderate your food budget if you want. Some people love simple street food that can be inexpensive yet very good. I like to walk around eating a little here and there when possible as I get to sample more food that way. However, I still like a great meal at a nice restaurant, so don’t miss dining just to save money. In general I stay away from large US hotel restaurants.

My budget tends to be $100-150/day for eating depending on location. Breakfast at the hotel and street food can reduce that amount dramatically. A meal with wine for 2 in Europe can be $40-100. Drinks are always a killer! If I stopped drinking so much wine I could save a lot of money, but damn it, I would be grumpier! Coke outside the US can be as expensive as wine in some countries, so I may as well have wine! On a recent trip some days we spent as little as $40 for food eating street food and getting free B&B breakfast. A couple of days we broke $100 on a great meals.

Hotel Meals & Cooking

Be careful with hotel breakfasts. Breakfast at the Intercontinental in Madrid ran $32 per person when I was there several years ago. I have a hard time justifying an expensive breakfast. Eggs, coffee, fruit and yogurt approaches $100 for two people with tax (and tip depending on location) at that rate. I usually can find a coffee shop or restaurant much cheaper, and you eat with the locals! Hotels that provide breakfast can save you a lot of money especially if you are just a coffee and muffin person.

While I don’t cook many meals I do cook breakfast frequently. I like Airbnb or apartments with kitchens as I can make my own breakfast early. Breakfast in Europe starts too late for me so this saves time and money and beats the crowds to my 1st stop! Cooking at an apartment or AirBnB can be fun. Incorporate a day shopping at a market like a local. Many markets are destinations in their own right. Buy some local food and cook a new meal. And don’t forget the bottle of wine!

Airfare

Airfare deals can be as low as $600/pp to many destination in Europe or South America in economy class if you are vigilant. Lately prices have been stretched, but if you are flexible there are still deals. I usually plan $1000-1300/pp for Economy Plus or Comfort seating if the trip is long. After 2000+ flights I just cannot do economy any more for flights over 4-5 hours unless I have to! Don’t be afraid to check major carriers from other countries during travel planning. TAP Portugal for example flies to the US and throughout Europe and has some great deals. I use Kayak to search flights and unless I want to use airline points, I pick the airline with the best price/itinerary combination.

One way to decrease airfare cost is to fly to and from a hub and then book feeder flights to your destination. If I find a great price on a flight to Paris Charles de Gaulle Airport, I book that and take an inexpensive flight to my final destination. In Europe short flights can be $99 or lower one way. Using this strategy has saved over $500 on airfare in 1 trip. One caveat, you will have 2 separate flight tickets on 2 separate carriers if you do this! This makes flight cancellations, baggage transfers and flight delays more problematic. Frequent flyers understand these intricacies, but inexperienced flyers may want to avoid this strategy.

Consider Open Jaw flights. That is flying to one city and returning via a different city. I booked a free Delta flight flying to Rome but flew home from Athens for no difference in price (points). There is no reason to travel back to the start of your trip if unnecessary. Open Jaw flights save both time and money!

Travel Planning: Climate

It sounds simple but check the climate at your destination as part of your travel planning. Perfect sightseeing climate may not be warm enough for swimming. Nothing worse than scorching hot or freezing cold weather you are not prepared for physically, mentally or clothing wise.

Travel Planning: Time-frame

Allocate time to see everything you want to see. I cannot stress this enough! You don’t want to be rushing from site to site and not enjoy the trip. Be realistic about your pace. Do you walk fast, talk fast and eat in the shower or are you a sloth and breakfast starts at 10am and takes 2 hours? Are you traveling alone or is your partner’s style of travel faster or slower than yours? My wife can stay in an art museum for half a day. I would core my eyes out with an apple peeler after an hour, so I head into the street to take photos giving her more time. Balance you travel style(s).

Add a few days for relaxation and unexpected paces to explore or delays. Consider starting the day early as you usually beat the crowds, saving time and frustration. Realize in many other countries breakfast starts later than the US, plan accordingly.

Time-frame boils down to your travel style, budget and destinations. Take into account your activities when determining time-frame. How many attractions do you want to see? How far apart are they? Do you have mobility issues? Streets in Europe and old world countries may be cobblestone or uneven footing. Walking may be more difficult for some people for that reason. Consider flights or long train/car rides between destination as a lost travel day.

Budget and time-frame are closely related as the longer you stay the more it costs. We almost exclusively travel during the shoulder seasons as it is frequently less crowded, less expensive and more enjoyable. Retirees have flexibility with dates and days of travel. A small change on your departure date may you save money, and less crowded attractions means more time to explore or relax.

It is better to add an extra week or more and see another place than fly 2 times to a geographic location. Combining counties or stay longer when possible saves time & money, especially when flying.

Note: Many credit card companies no longer require travel notices. Check with your credit card company which can usually be done online. However, I find ATM cards associated with banks or other financial institutions still need a notice. Make sure to advise your ATM card provider to access cash outside the US. I usually have no trouble with foreign ATMs as most provide English menus. I did have to try 2-3 ATMs in India to find one that worked, so be prepared in remote locations.

Staying In Touch

Electronics are a big part of daily life. While it is nice to get away from your laptop or phone, they are very handy travel assistants. You seldom need a voltage converter outside the US. Electric shavers are one exception. Phones, laptops and iPads charge fine on electrical plugs outside the US with an adapter plug. I always have 3 or 4 country specific adapters with me.

Phone plans vary, but some sometimes you can make calls & texts overseas on your phone. Check with your carrier for overseas rates or temporary overseas plans. You may be in for a costly surprise upon return if you don’t check and I hate costly surprises! As an alternative you can purchase a local SIM card on arrival or purchase a cheap local phone for calls. WiFi is available at most hotels and B&Bs.

I use a VPN all the time to help protect my identity which is even more important on public WiFi anyplace. To avoid public or hotel WiFi completely I carry a portable WiFi hotspot that works in over 130 countries. This is a small device that multiple users can connect to anywhere there is service, similar to your home WiFi. You load this up with megabytes which are usually good for 1 year. If I have to make an online banking or credit card transaction I use my hotspot avoiding hotel and public WiFi altogether.

Get Going!

I find travel planning fun. I have been doing it so long for work and vacation it is second nature now. Independent travel isn’t for everyone and that is fine. It is better to see the outside world than to see the inside living room, however you choose to get there!