I originally posted this article in 2017, but it seems timely to share it again as we embark on a 52-day journey to Europe. We chose a repositioning cruise sailing to Portugal instead of flying and couldn’t be happier that we made that choice. After the events of the past few weeks, we need some time to relax and be pampered. If you would like to know more about repositioning cruises, please read here and here. In the meantime, I hope you will add your thoughts and recommendations to my growing list of resources and tips.
Original Post 2017 – updated
When we were working, our vacation destinations were highly predictable – anywhere in the US or the Islands that could be reached within two to four hours by plane. Typically, we choose a resort in the Caribbean, a ski village in Colorado, or a visit to Mickey’s house in Orlando. We could never be away for more than nine days (constraints of business ownership), so it was important not to use precious time getting there. We also did not have the luxury of time to plan and execute a vacation that included multiple destinations and intricate details. Vacations were expressly for relaxing and having family fun, which meant one destination, one hotel, and built-in activities. Everything changed when we sold our business and retired.
For the first time in our lives, we could go beyond a one-week vacation and really travel. We took our first trip abroad when our daughter was sixteen and on summer vacation. That was the beginning of a love affair that will never fade. Malcolm took months to meticulously arrange travel plans. We traveled throughout France and Italy for one month, packing our bags for departure every fourth day. It was an ambitious and aggressive trip. We made some rookie mistakes, but we had one of the most memorable trips of our lives, and we learned how to travel.
Since that trip, Malcolm has become “travel agent extraordinaire” for our family, with more than nine trips abroad, numerous cruise/land vacations, and countless stateside adventures. I trust him to take us anywhere in the world seamlessly. Whether it’s Amtrak across America or a series of trains across Europe, he makes it seem effortless, which, of course, it is not.
It takes patience, time, and the ability to stay organized. While Malcolm does most of the planning (with my input), I am the organizer. I keep a master calendar, download train tickets, event tickets, and printed hotel confirmations. Every train, plane, automobile, and hotel room is accounted for. Not everyone has the luxury of time to devote to the process, but when you do, you can create an experience tailored specifically to your expectations. Sure, you can hire a travel agency, and there are many good ones out there, like Gate1Travel and Tauck Tours, but our experience has been that it is possible to save literally thousands of dollars by doing it ourselves. You just have to be willing to do the work.
Recommended Checklist
- determine a destination, or multiple destinations
- determine the number of days (weeks) to travel
- research Visa requirements
- know Schengen rules and requirements (for longer stays in Europe)
- set a budget
- know weight restrictions for all flights and pack accordingly
- consider traveling a week or two before or after high season to some destinations (cost savings)
- research your destination – culture, climate, things to do, geography
- fully understand the logistics of traveling between countries (time changes, etc.)
- consider a transatlantic, or repositioning cruise as an alternative to flying to or from Europe
- prepare a travel notebook, complete with an itinerary, confirmation numbers, addresses, phone numbers, pre-purchased tickets and copies of passports
- make decisions about phone use while abroad (call your carrier to discuss options)
- select which electronic devices you will take with you
- make sure your passport is valid and has at least 6 months remaining for your return
- research and understand the transportation system in each country you will visit
- book train tickets in advance whenever possible (huge savings)
- use good resources – Hotwire, VRBO, Trip Advisor, Viator, etc. for hotels and excursion recommendations
- Secure your home, prepay bills, forward mail, etc. for extended travels
- purchase some currency for each country you plan to visit (exchange rates will be better at your home bank)
- apply for a Global Entry card if you plan to travel often
Our Favorite Travel Assistance Websites
Seat61 for train travel
Trip Insurance.com – don’t leave home without it
Vacations to Go – compare cruise fares
Hotwire.com – for discounted accommodations
Trip Advisor – user reviews of hotels, restaurants, things to do
Cruise Plum – for searching cruises worldwide
Cruise Critic – for ship reviews
Chase Travel – for booking flights, hotels, etc. (Chase Sapphire is a great card to own for travel benefits)
VRBO – accommodations for long-term stays
Viator – for booking small group tours
This list continues to grow. Please add your suggestions and ‘go to’ apps or websites in the comments.
Happiness; when the bucket list becomes the to do list
Picture Retirement 
Thanks for your post! It is a ton of work to plan a trip. I planned our Alaskan cruise with two cities before and one city after – including all the transportation, hotels and activities. I was pleased it all went off without a hitch. I also felt that by planning it myself, it prepared me for the trip. I’ve thought about using a travel agent for any future big excursions, but after reading this, I think I’ll stick with doing it myself. I hope you have a wonderful time on your trip to Europe. Safe travels, and have the best time! I look forward to reading your posts about it.
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Betty, travel planning is a lot of work. But, once we have our flights and at least one accommodation in place, we take our time filling in the rest. Trains are the most sensitive component since tickets are released for purchase on a schedule. We set numerous calendar alerts which prompt us to tend those.
I can forsee using a travel company in the future, but for now, we like the flexibility of constructing our own experience.
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Safe travels! I appreciate the list of resources. We’re the opposite of you. We used to go vacations with multiple destinations, much planning— but now we look for one place to land and use as a home base.
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Ally, we all gravitate to what works for us at each stage of life. I have never met anyone who travels exactly as they did twenty or thirty years ago. I’m sure this will not be the last evolution of how we travel. Have a great week.
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You’ve clearly found a travel style that works for you and it’s great that you’ve seized the opportunity that retirement offers to travel more widely. I am both planner and organiser! For trips in Europe and the US I do as you do, planning everything myself and booking travel, accommodation etc. But when we go to Asia, Africa or South America, for instance, I prefer to book with a travel company that specialises in the region we want to visit. However I still research myself to make sure we have an itinerary that will meet our needs and expectations.
On the subject of websites, personally I prefer not to rely on Trip Adviser reviews as I know some are written by people paid to do so. Also, a hotel or restaurant willing to pay can have negative reviews taken down! For accommodation I often book through Booking.com, and I trust the reviews there as you have to have stayed in the place to be able to review it
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Sarah, I agree that not every site can be completely trusted. That’s why it is so important to read a lot of reviews, and cross-check on other sites. We use Booking.com often and find it reliable. I will add that one to the list.
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Suzanne, enjoy every moment of your trip!
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Thanks Beth. We will.
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I always make sure to have an emergency supply of aspirin, anti-acids, an eye glass repair and cleaning kit and ear plugs. Those things tend to be expensive on cruises. I used to refer to Rick Steves but gave up on him after he recommended driving in the UK! You are so thorough!
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Jan, Malcolm is in charge of our first-aide kit and it is well stocked. The last thing we want is to have to visit the ship’s doctor. $$$
Rick Steves is a good resource, even though he recommends driving in the UK. We are hesitant to venture to the ‘other side.’ Unfortunately, it is the biggest reason we haven’t visited the Cotswolds. Have a great week.
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Suzanne, Thank you for your list of travel resources. One of the travel resources that I’ve found helpful is the destination tourist office. I usually visit their website as part of my pre-trip planning and in-person when I’m there to pick up maps, ask for recommendations, etc. The staff are usually multi-lingual. On my recent trip to Italy, I booked a couple of English guided walking tours organized by the local tourist offices and led by local guides. The tours were all excellent and inexpensive.
I also use booking.com to look up accommodations. However, I book directly with the hotels and usually get a discount that gives even better pricing than booking.com.
I resubscribed to your blog as I didn’t get a notification for this post. I found it while reading another blog. Wishing you and Malcolm a wonderful trip!
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Hi Natalie, I appreciate your travel tips. Local walking tours are often overlooked but so beneficial to discovering a new place. Thanks for letting me know about the notifications and for resubscribing. I have been sensing something is wrong. WP is such a joy!
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Have a wonderful, wonderful time, Suzanne! We’ll be floating along a bit behind you, although in a different direction. 😊
Like Natalie above, increasingly I use Expedia to do quick research, but then book directly for as much as the pricing makes sense to do so. It makes dealing with hiccups much easier I’m finding.
Although, I do still use Expedia when traveling in a country where communications can be problematic due to distance or language barriers. It does provide a layer of protection that might otherwise be challenging.
Have you been to Portugal before? I believe so, if which case you already know that anything already at, or brought to your table, in a restaurant that you did not order is not free, the exact opposite of what we experienced in nearby Spain. I do so love the things that make each country unique and special, and that was Portugal’s for me, well that and their lovely and lightly effervescent vino verde!
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Third party bookings often end up being a headache. Sometimes a ‘good deal’ just isn’t. Yes, we learned that cultural lesson the hard way on our first visit to Lisbon. Something arrived with plastic wrap over it. We thought that odd, but opened it anyway. Surprise, surprise, there was a charge on our bill.
Where are you guys heading next?
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To the Caribbean via Oceania, 11 days around the BVI and USVI area, then to Iceland for a week in August, after which we’ll board a ship a cruise back to Boston by way of upper western Iceland, Greenland, and several Canada Maritime provinces.
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Sounds wonderful. Enjoy
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