It used to be so easy. We’d take a two-week vacation in summer and a one-week vacation in winter. One destination, one hotel room, one flight there, one flight home. Now that we are retired and have time for extended stays, involving multiple destinations, planning is a little more involved – and a little more complicated. We have the time and the desire, so why not make the most of it while we can?

When it comes to planning a vacation, most couples have one person who is a researcher and organizer and one person who goes along for the ride. We are not that couple. Malcolm and I both enjoy researching, planning, and sorting the details of every adventure we undertake. We scour through YouTube videos, travel vlogs, tour company offerings, FB groups, and even Instagram photos for inspiration and encouragement.

These days, planning is made easier with internet search tools such as AI(ChatGPT, Gemini, etc.), organizational tools like Monday.com, Google Maps, and websites like What’s In Port and The Man in Seat 61.

“Every great vacation begins with an honest conversation”.

First Things First

• Discuss your travel ‘style’ and expectations
• Choose a destination
• Know your limitations
• Determine start date and length of stay
• Set a budget

In just two weeks, we will be on a flight to New Zealand. We started planning this trip (which is actually one of the easiest we have ever planned) almost one year ago. That is mostly because the trip consists of three back-to-back cruises, no rental cars or trains to consider, only three hotel stays, and just four flights. We have traveled often enough to know that we both enjoy cruising (seeing a glimpse of a new place is often enough), and we are getting tired of multi-prong travel, which requires constant logistical calculations, good upper body strength (think luggage) and lots of energy. When we originally considered NZ, we thought we would rent a car, book multiple hotels, and spend a month discovering both the North and South Islands. I tossed in the towel within weeks of the initial planning. Malcolm agreed that it might be aggressive for us at this age, so rather than choose another destination, we started looking at cruise options. Hiring a tour company was also a consideration, but that can get expensive, and like cruising, itineraries tend to be restrictive.

Get Organized

Even with websites like Monday Morning to keep everything organized in a spreadsheet that is easily accessible on a cell phone, we still like the comfort of physical documents. Our trip binders are legendary! Besides, it is much easier to misplace a cell phone than a trip binder. Call me old school, but I still like to have printed copies of hotel confirmations, rental car reservations, and airline reservations. Even with the holy grail (my trip book), I store event tickets in Apple Wallet, collect barcodes like precious gemstones, and save screenshots of anything deemed useful.

Don’t Book the Flight – until

• You have researched the best airfare to the destination you will visit
• You have determined if this will be round trip, or one way
• You have determined additional flights (leaving room for flexibility)
• You have checked and applied any applicable reward points
• You know baggage restrictions for every flight
• You have considered downtime

We are fortunate to live within one to two hours of four major airports in Florida. When we travel, we check flights on multiple airlines and from each airport. Once we have narrowed the field, we look for applicable points. Sometimes it makes sense to purchase tickets with points, and sometimes not. We tend to use points on international flights or upgrades. If you are a frequent traveler, Chase Sapphire is a good credit card to have on hand.

When traveling abroad, multiple flights are often the norm. For example, we recently flew from Florida to London and then took another flight to Edinburgh. This was a separate flight, not a connecting flight where our luggage would be checked through to our final destination. We collected our luggage and boarded a much smaller plane for the trip to Edinburgh. The weight allowance for our baggage was determined by that specific flight, not the previous one. We also researched the airline’s carry-on luggage policy in advance to prevent any issues. In fact, having multiple flights on a single trip is my best argument for packing light. I’m not always successful, but the prospect of having to ship things home is a good motivator!

What to Consider When Packing

• the weather
• the season
• weight restrictions on flights
• activities (dressy nights on cruises, snorkeling outings, bungee jumping, climbing Machu Picchu)
• the availability of laundry facilities
• a color palette for mix and match outfits
• shoes (functional, practical, easy to pack)
• medications

If you are constantly telling yourself, “I might need this,” you should probably leave it at home. Take what you need, and try to stick to a color palette that supports multiple mix-and-match outfits. I pack for approximately 1/3 of the days we will be traveling and plan to wash whenever I have laundry facilities. I also pack Tide sheets and use a sink to wash underwear and other lightweight clothing.

Housekeeping Items – literally

• Consider a Housesitter
• Hire a Handyman to check in regularly
• Enlist the help of a friend, neighbor, or family member
• Place a hold on mail delivery
• Decide how you will pay bills, tend banking, etc.
• Purchase travel insurance
• Have prescription medication filled for the duration of the trip
• Make sure your passports have at least six months remaining from the date of your return
• Secure necessary Visas for each country you plan to visit

We use several combinations of these suggestions to secure our home, depending on the time away. A one-week trip will merit leaving a key with a trusted neighbor, turning off the water, raising the AC temperature, and canceling the mail.

Even with the best laid plans, things can go wrong. We plan to arrive in San Franscisco one day early for our flight to Auckland, rather than catching a connecting flight on the same day. There are still no guarantees, but we try to minimize the risk when possible. It’s all a house of cards…

I will be back with a February wrap-up, and then you likely won’t hear from me for a while, unless you follow us on Instagram. I will be posting photos and updates there for the duration of the trip.

Images for this post were created using ChatGPT.

Even if you have strong feelings about Ai, I encourage you to download the ChatGPT app to your phone and have a go at it. I’ve named my bot Chatty Cathy, and she advises me almost daily on matters of concern. Just be advised that once you go down that rabbit hole, you may become addicted!