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 chose 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 arrange travel plans that included planes, trains, automobiles and several hotel reservations. We traveled for a month throughout France and Italy and packed our bags for departure every fourth day. It was an ambitious and aggressive trip. He 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” with more than six 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 Eastern Europe, he makes it seem effortless. Which of course, it is not.

It takes patience, time and an ability to stay organized. Not everyone has the luxury of time to devote to the process, but when you do, you can create an experience that is tailored specifically to your expectations. Sure, you can hire a travel agency and there are a lot of very 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.
Lessons We’ve Learned
- determine a number of days (weeks) to travel
- set a budget
- pack light and know weight restrictions for all flights
- consider traveling a week or two before or after high season to some destinations
- research your destination – culture, climate, things to do, geography
- fully understand the logistics of traveling between countries (time changes, etc.)
- consider a transatlantic, or re-positioning 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 devices you will take with you
- make sure your passport is valid – months in advance
- 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, etc. for hotels and excursion recommendations
- Secure your home, prepay bills, forward mail, etc. for extended travels
- Consider buying some currency from your home bank prior to the trip (exchange rates may be better in advance)
- apply for a global entry card if you plan to travel often

Malcolm’s Favorite Websites – the short list
Seat61 for train travel
Trip Insurance.com – this one is obvious
Vacations to Go – cruises
Hotwire.com – for accommodations
Trip Advisor – user reviews of hotels, restaurants, things to do