Travel – set yourself up for success

On By Suzanne@PictureRetirementIn packing tips, road trips, travel

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!

27 thoughts on “Travel – set yourself up for success”

  2. Lots of great advice here! We’re that couple where one of us is the travel planner (me!) and the other just goes along for the ride, then wonders what he’s doing there 😃 I do however often rely on a trusted tour company when booking more ‘exotic’ destinations, as it’s great to have their advice and also their back-up should things go wrong.

    I’ll be interested to hear all about your New Zealand adventures as it’s very much on our radar, though I doubt we would opt to cruise – but never say never!

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    1. Sarah, I admire folks like you, and Phil and Michaela who visit the most exotic places on the planet. I would only do that with the assistance of a tour company. I need the security and confidence that places have been ‘vetted’, so to speak, for tourists. A NZ land adventure is the way to really see both the North and South Islands thoroughly, but the cruise will at least provide food for thought – for next time. Thanks for stopping by.

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      1. We’re far less adventurous than Phil and Michaela. They organise everything themselves and often travel with only a rough plan and few places pre-booked. We prefer to do as you describe and rely on a tour company for many ofour trips, booking almost everything in advance.

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  3. You sound so well prepared, and so aware of what you need and don’t need. It’s been a while since we’ve travelled and it seems to get harder to get the ball rolling – especially since neither of us wants to be the planner/researcher. You’ll love NZ – I’ve never heard of a single person who has visited and not come back raving about the scenery etc. I think a cruise is a good way to do a non-driving trip when the driving doesn’t appeal – it may be the way we do it one day too. Have fun!

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    1. Leanne, NZ is just a stone’s throw away from you guys. Hop on a nice boat and drift away. Cruising is a great way to kick-start a travel deficit, or just a great place to get started for anyone on the fence about travel. I have no doubt we are in for a treat. The photos and videos we’ve seen are breathtaking.

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  4. Great tips!! We are staying close to home this year. My husband has a knee replacement on March 2 and we want to focus on his recovery. He seems to think it will limit him longer than I do!!I love your pictures. I’ve been experimenting with AI too, using CoPilot. It helps me create fun pictures for my posts, but I haven’t used any yet. More fun creating the pictures than writing the post!! 🤣

    Have a great trip.

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    1. Hi Linda, we are trying to get as much travel in as possible before the parts need replacing. Malcolm is still in rehab for his shoulder, but we are taking a chance that he will not have a setback while we are away. I am spending way too much time playing with Chatty Cathy, but it is fun to test what she can do. I miss connecting on your blog. How’s life? Well, besides getting ready to nurse your patient after the knee replacement? Thanks for stopping by.

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  5. Excellent travel planning advice, Suzanne. Your physical trip binder is essential back-up when digital technology fails. I always bring physical and digital versions of important documents and the physical documents have saved me a few times.

    I also bring some cash in addition to my credit cards. On one of my trips, there was a network outage that lasted almost two days. ATMs were down and the local businesses accepted cash only as they couldn’t process credit card transactions. The unthinkable happened and I was so glad I had cash to buy food!

    I always think of each trip as an adventure that starts the minute I leave home. With good planning, a few things may still go different than expected but most will go right and give memories of a lifetime. That’s been my experience. Have a wonderful trip! I look forward to reading your February wrap-up post.

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    1. Natalie, that is a good point. Malcolm picked up our NZ $$ from the bank last week. We always bring some local currency, and we always need it. Surprisingly, there are lots of places that don’t accept credit cards. We always joke that the trip begins at the airport lounge, but the adventure starts when we arrive at our destination. We love to travel but hate ‘getting there.’

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    2. Excellent points for your travels, Suzanne! I LOVE my travel journal for notes, calendars, addresses! I also keep my outlook calendar up to date. We begin our 6 week road trip this week, and packing for our sweet dog is like a whole other person! I’m the main planner and navigator.

      Love your pics, I’ll have to check out ChatGTP! Enjoy your trip…I’ll wave at you from Arizona and California!

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      1. Terri, you chose the perfect time of year for a road trip to Arizona and California. Are you pulling your RV or staying in hotels? Can’t wait to hear all about it. I personally enjoy being the keeper of the documents and details. The more I know, the more relaxed I am. Have a wonderful trip.

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  7. We carried collapsible hiking poles for NZ. There will be lots of opportunities for hiking on rough trails.

    We only use shore excursions booked through the ship as the ship won’t leave without you.

    The wine in NZ is great and very affordable.

    Have a great trip.

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    1. John, our first few days in NZ are on Waiheke Island (lots of wineries), so we will be drinking some good wine as we acclimate to the time difference. Walking poles are a good idea. We had planned to get them before we go to Greenland in September, but it might be a good idea to get them now. We booked a few tours through Viator and GetYourGuide, and trust them to get us back on time, but you never know what can happen. They always fall well under the price of the ship’s tours. Thanks for stopping by and have a great week.

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  9. Enjoy your time in and around New Zealand, Suzanne! I applaud you for knowing your limitations and being able to throw in the towel when certain realizations set in. I’m way to stubborn for that. Yet. 🙂

    I’m all for traveling light – for financial reasons and for the flight reasons you mention. At the moment, Mark, Maya, and I are in Europe for the foreseeable future (without a camper yet) and we “restricted” ourselves to two carry-on suitcases and two personal items (backpacks).

    We are making it work, but when you add Maya’s dog food and all the spices and ingredients for meals we have gathered, it will be hard to travel by train to Belgium from Lisbon to Brussels once we have to return the rental car, haha.

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