Planning Your Spring or Summer Vacation?

Mar 5, 2026 | Newsletter

As an estate planning attorney, many of my conversations with clients focus on planning ahead and being prepared. That mindset applies not only to your legal and financial affairs, but also to everyday parts of life like travel. With spring break and early summer trips coming up, a little planning can help you travel smarter, stay organized, and avoid unnecessary stress.

Below are a few travel tips that can help you make the most of your travel dollars while keeping your trip smooth and enjoyable.

BEFORE YOU LEAVE: A quick planning check before heading out of town is always a good idea to make sure things at home are in order. Confirm that your estate planning documents are up to date, particularly your healthcare power of attorney and living will. If you are traveling internationally, you may also want to review your health insurance coverage since some policies provide limited or no coverage outside the United States. In those situations, travel medical insurance may be worth considering.

WHEN TO GO: Consider traveling during off-peak times, such as late April to early June or September to mid-October, to save on costs and avoid crowds.

FUNDING YOUR TRIP: If you’re using travel credit cards, make sure you’re maximizing sign-up bonuses and taking advantage of transfer partners. Some programs offer a better value when transferring points to airline partners instead of booking directly. Also, try to transfer points during bonus promotions, which might provide up to 30% extra miles.

BOOKING YOUR FLIGHTS: Using an AI tool, like Google Flights or Hopper, can help you identify optimal booking times and receive real-time price alerts for flights and accommodations.

  • For hotels and rental cars, book refundable rates early. Then check prices 30–60 days before departure. If rates drop, rebook and cancel the original reservation.
  • Start tracking flights 3–6 months before domestic trips and 6–10 months before international trips.
  • Fly midweek (Tuesday or Wednesday) for lower fares.
  • Compare nearby airports — sometimes a 1-hour drive saves hundreds.

PACKING: It’s never been more important to “pack smart and light,” given the baggage regulations and fees now in place. Have you heard of the “3-3-3” packing rule? Basically, it is 3 outfits, 3 pairs of shoes, 3 accessories – ensuring you don’t overpack. Travel expert Rick Steves has lots of information on his website about smart packing, including:
·         Fold and roll your clothes before zipping them up in packing cubes.
·         For maximum bag space, consider a clothes compressor.
·         A lightweight mesh bag is handy for small items like socks, a sewing kit, etc.

FINANCES DURING YOUR TRIP: Look into contactless payments via your smartphone (make sure to take a portable power bank) to manage transactions and currency without physical cards or cash.

WHILE YOU’RE THERE:  Take advantage of AI tools like mapping walkable daily routes and avoiding tourist traps. Find and enjoy non-touristy local restaurants where the food is more authentic and probably less crowded. Create backup rainy-day plans to make the most of every day of your vacation.

A little preparation can make travel more enjoyable and far less stressful. It is also a good reminder to keep that same mindset at home by making sure your estate planning documents are current and that someone you trust can assist if needed.

Wishing you safe and enjoyable travels.

Regards, 

David