In the section Basic Travel Planning Advice guess what, I gave some basic travel tips. That section included topics such as language barriers, basic budgeting, pros and cons of self booking and a Checklist. This sections digs deeper into how I plan an actual trip. I just wrapped up a trip plan to Sicily and Greece and you can see my Actual Trip Plan HERE. Last I have the Grumpy Retiree’s view of Online Reviews and how to use them. Planning your dream trip doesn’t need to be hard with some practice!

Basic Trip Planning Process

Here is the basic outline I use.

• Choose Destination, set rough budget (as needed) and timeframe
• Research flights & hotels, adjust timeframe if deals are found and schedule permits
• Check connecting flights, other transportation for multi destination trips
• Verify “must see” attractions are available during your timeframe
• Book flight(s)
• Book critical connecting flights/trains/cars etc.
• Back fill hotels around fights, destinations
• Book tours, miscellaneous transportation
• Research restaurants
• Go On your Trip!

You don’t need to be too rigid with this list. The order can change slightly as you become more comfortable with trip planning. For example, I wanted to go someplace for a Christmas vacation and choose Buenos Aries. While researching flights I found they were quite expensive. Using Google Flight Explorer I searched flights around the world by simply moving the map. I found great flights to Munich around mid-December. Deals were so good I switched my destination to the Christmas Markets in Europe and booked the flights! Stay tuned for those pictures and details in the future!

Destination Unknown!

When selecting a destination I start with places I am interested seeing, my rough dates, expected weather during the trip and length of trip. Do you have a bucket list of places you want to see? If so start there. Or start with a trip within the US (or your home country) if you want a little practice trip planning without straying too far. Below are some places I have traveled that were easy enough to navigate followed by my (very abbreviated) bucket list.

What is your Bucket List? Some suggestions out of hundreds!

• San Francisco, CA – lots to see, good food, close to Napa & Sonoma wine country
• Athens, Greece – Fantastic history, great food & wine, friendly people
• Boston, MA – fantastic history, seafood, close to Cape Cod, sports
• Paris France – easy fly in, French food & pastry, romantic, great metro & so much to see!
• Charleston, SC – lots of history, top US food city, day trip to Savannah, GA, ocean/beaches
• Barcelona Spain – tapas, great architecture, history, nightlife
• Porto Portugal – seafood, Port Wine, Douro River Valley
• Bermuda – Easy from the US, beautiful beaches, top level accommodations, relaxing

My Bucket List

• Vietnam
• Japan
• Argentina
• Sicily (Just returned!)
• Alaska, Montana
• Croatia
• Greece (Just returned!)
• Poland
• Germany (going at XMAS! 2023)
• Stop me now!

For illustration my wife and I wanted to travel early Spring so I want someplace with reasonable sightseeing weather but swimming was not an important consideration. There is a great website call Weather and Climate that lets you check the weather all over the world and offers travel info. Sicily is on my Bucket List and checking the weather it was perfect springtime weather in the 60-70 degree range.

Itinerary: Can I Stay Longer Please!

While working trips were 14-19 days but now during retirement that constraint is gone. Something has to be better as you get older! The longer you stay in one general area, the fewer flights needed saving time and money.

“The longer you stay in one general area, the fewer flights needed saving time and money.”

The Grumpy Retiree

Your itinerary is exceedingly important! Take your time using travel sites, blogs, tours and travel guides to define the length of your trip and time to stay in each area. Consider your personal interests & pace! Rushing is never fun, but being bored someplace for 2 weeks when 3 days is plenty is not good either. You will still make some mistakes. You will fall in love with a place and wish you had stayed longer. With proper research you will reduce this issue.

“The itinerary is exceedingly important! You don’t want to be rushed but being bored someplace for 2 weeks when 3 days is plenty is not good either.“

The Grumpy Retiree

Planning Your Dream Trip: Budget

Flights vary depending on location, but a flight to Europe usually starts at $600 for a great deal in basic economy or if you are lucky regular economy. Travel is going up dramatically in 2023 and prices over $1000 for regular economy flights are becoming common. Plus Seating has started to increase from $1200 to up and over $1500 so I budget $2500 for flights for 2 people to start as I search for deals. An option is to subscribe to The Points Guy or Going to get travel deals sent to your email.

Flights within a destination country can be similar in price to US domestic flights. However inexpensive flights within Europe are common. I sometimes book a flight to a major European hub and use the cheaper flight to my final destination. Plan on $100-$500 for connecting flights per person in most countries.

Based on 2023 prices, $300 average per day room & food is possible. You can easily go above that figure, but I don’t budget under that amount. Rooms usually average $150-$200/day depending on location leaving $100-$150 for food per day. Adjust your budget to your travel lifestyle.

Air Fare, Hotels and Food are the major part of my travel budget. After those items car rentals, miscellaneous transportation and sightseeing are the next budget variables. I budget $50/day for a car rental if needed.

Trains, taxis, busses etc. for me are not a big budget item. I usually add about $500 into the sightseeing budget for miscellaneous transportation based on a 2-3 week trip.

Sightseeing also is variable. Many sights, such as a museum, can be as low as $20/person. Food tours, cooking classes and day trips vary greatly. You can easily spend $150/person for a food tour or cooking class. We don’t do a lot of organized tours, so our budget may be lower than yours as organized tours are more expensive. I start with $500 for sightseeing per week which for me is more than enough.

Planning Your Dream Trip: The Search Is On

Once I have a destination in mind I concurrently search hotels and flights (if needed) for my preferred dates. Why do I do that first? Food is somewhat variable everywhere, so that budget can be managed if absolutely needed. Most attractions and group tours are a fixed price or within a narrow range. But, flights and room accommodations can vary greatly so I want to know if my assumptions about the costs are in the ballpark. I also want to know if hotels are plentiful across my price range or are being booked quickly and are in scarce supply. Hotels in popular destinations, or centered near a special event, can book well in advance. If budget is of little concern you can minimize this step. I want to know if my budget assumptions are correct or if I need to adjust my expectations.

Trip Advisor has a lot of information about a destination including attractions, hotels and restaurants. First I narrow down a neighborhood within cities, or a geographic location if outside a city. Large cities are spread out and each neighborhood can have a vastly different feel from vibrant nightlife to cultural to modern or historic. Find the must see attractions and if possible stay nearby. In a large city such as Paris or Rome, you will find that attractions are spread throughout the city. In locations like those I put emphasis on the neighborhood, hotel quality, local dinning options and proximity to public transportation.

“Choose accommodations close to major attractions and transportation options, especially in cities.”

The Grumpy Retiree

Next, using Google Maps I search “Hotel” or “B&B” in my selected area. You can scan prices and star ratings just by hovering over a hotel bypassing anything below a rating of 3.5 stars. I narrow hotels to 3 or 4 choices in my price range and desired location. Cross referencing rating sites like Trip Advisor, Hotels.com or Google Reviews I pick my favorite of the bunch.

By this time you understand the budget and have used your calendar to define the daily itinerary. It is time to move into the booking process!

Flights are fun! Right?

I use Kayak or Google Flights to search for flights around my preferred dates. You can find airline price bargains if your dates are flexible, so don’t be afraid to look for flights on different days, weeks or even months if your schedule permits. Unless I am hoping to use miles for a free flight on my preferred carrier I book any airline with a good flight and price.

Most airlines offer Basic Economy tickets. I don’t book them as they are too restrictive for me, but if you are OK with the restrictions you can save some money. Read everything carefully! Checked bags are never included and usually you cannot select seats. I recently saw $150 checked bag fee on a Basic Economy flight! That may not make for a cheap ticket in the end! Basic Economy tickets prices are usually quoted on travel sites unless you specify otherwise in the filter options. Regular economy and premium seats are more expensive, so pay attention!

While you can look for flights about 1 year in advance, I usually look at least 3-6 months prior to a trip. Airline prices are dynamic and deals come and go faster than the damn planes fly! When I see a good deal, I book it. For a complicated trip with several destination and flights it is too difficult to book last minute. Last minute deals are only good for a simple single destination trip in my opinion.

Why We HATE Airlines (one of many reasons)

This is where things can get messy as airlines play a shitty game when you want to book a free flight. Many times you will see the perfect paid flight, but when you try to use miles that flight is not there. Where the hell did it go? You think you are just stupid and searched incorrectly. While you may be stupid that isn’t the reason … this time. Frequently the “best” flights are not available on the date desired as a free ticket. Flights with long layovers or multiple stops will show up, or nothing at all. Maybe the great flight is available, but for substantially more airline miles than the crappy flights.

When this happens you have a couple of choices. I personally won’t take a crappy, long layover or multi stop flight to save a few dollars or points. Time is too important! More flight stops and layovers means more chances someone at the FAA, TSA or airline will have gas that day and all your flights are delayed. You can either pay for the better flight and save the points for another day or try searching the same itinerary again a day or 2 later. I cannot tell you how many times I grabbed great free flights searching 2 or 3 days later. Clearing “cookies” or using “Private Mode” on your browser can also help searching flights. Airlines use dynamic pricing which means the price, whether paid or points, can change daily.

Destination Transportation: Plan the Connections carefully!

A single destination trip is always easier to plan. Once you determine how to get to your destination you only need to figure out sightseeing in 1 area. That can be walking, a car rental, daily tours, metro, buses or taxis. When there are multiple destinations on a trip you must consider how to get from point A to point B.

“You can’t get there from here.“

Credited to a wise old Mainer

An important variable is the timetable of the transportation. If you are planning sightseeing in Milan and are only there 2 nights, you don’t want to arrive late afternoon on day 1 and leave early morning your last day. You have effectively cut your time in Milan to 1 day of sightseeing. When I expect 2 days of sightseeing, I either arrive early, leave late or both. If transportation options don’t allow enough time to see everything, don’t rush! Add an extra night to accommodate the transportation. This means before you finalize your itinerary you are not done until you understand all the connecting transportation.

“Before you finalize your itinerary you are not done until you understand all the connecting transportation. Add sufficient time into your schedule and stops to account for this transportation.”

The Grumpy Retiree

Destination Transportation Options: Car Rentals

Car rentals are always the most flexible transportation option. I use them in particular between cities or sightseeing around a destination. They do have other costs such as fuel & parking, but while we were in Sicily staying at 5 towns, and seeing many more in between, a car was perfect. Determine your comfort level driving in a foreign country. To map routes I use Google Maps and have never had an issue, but make sure Google Maps will work on your device wherever you’re traveling. GPS from the rental company is another viable option.

Destination Transportation Options: Trains & Planes

Trains in Europe and many Far East Countries are very efficient and many times as fast as planes depending on the destination. Also, trains are usually a cheaper options than a plane. Many European cities are connected by fast trains and connect to smaller feeder routes. Occasionally you will need to use a bus to get to a final destination in more remote areas. I frequently pick hotels near the train station so I can walk to the hotel on arrival and use the train/metro as needed when local.

In South America busses are more prevalent. There are trains along select routes, but they are not as widespread as in Europe. Since South America is very large geographically, you may find yourself flying between destinations.

Train tickets can be purchased online or at the station. Purchasing tickets online well in advance offers a discount in counties such as Italy. I purchase tickets online if I want to ensure I have a ticket on a specific train to related to my planned itinerary.

European Train Notes: A Euro Rail Pass is available which has several options allowing you to travel on trains whenever you want. You can buy this online in the class of service you desire before your trip. I have never used trains extensively enough to make this a cost effective option. Do the math before deciding.

Long Distance Transportation Options: Planes & Still Trains

Planes make sense for long distances, but don’t forget to include the time to get to and from the airport and the need to arrive early for bags and security lines. If I am traveling over 4 hours I consider planes unless a good train option is available.

For longer journeys a train can still be a viable option. Many destinations are connected by overnight trains. You can sleep on the train overnight saving both valuable sightseeing time and eliminating the need for a hotel room that night. This may not be for everyone, but for the right traveler it is a great option.

Sightseeing & Attractions: Defining Your Trip

Start looking at attractions along your route to determine the length of stay in every city or town and adjust the itinerary if needed. Don’t forgot to account for transportation time and method between stops to leave enough time for sightseeing. Make sure sights you want to see are open during your visit and that tickets are available, especially for popular places. Don’t book tickets until you know how everything fits into the schedule to avoid conflicts.

“Sightseeing is very personal and it is what makes or breaks a trip. See what you enjoy and you will enjoy what you see.”

The Grumpy Retiree

Sightseeing is very personal and it is what makes or breaks a trip. When I started traveling I always wanted to see every “must see” place everyone talked about. Now I like to wander the places I visit for a more local experience. I still see the highlights, but I make sure there is plenty of time to explore. Figure out what is important to you. Food, architecture, art, history or a little of all. See what you enjoy and you will enjoy what you see.

Tie Everything Together

At this point you have an itinerary, flights (if needed), connecting transportation and some sightseeing figured out. Once I am very solid on the itinerary, I start booking the flights and connecting transportation. I then fill in the hotels and add rental cars if needed. I book critical sightseeing and may book a train or other local transportation.

At this point I will research local food and some restaurants at my destinations. If you must eat at a special place consider a reservation in advance. I use The Fork or Open Table to search restaurants and make reservations. Google is another alternative and a phone call for reservations works like in the old days.

When you are ready to leave, make sure to double check your Checklist. Have all your tickets either on your phone, paper copies or both. Make sure your partner knows at least the names of hotels in case you get separated, unless the plan was to ditch them on purpose!

Have fun planning and traveling!