Hawaii, Kauai, Maui, Travel

Five Tips to Survive Traveling with Extended Family

Our trips to Hawaii are always very special, and the more we travel the more we realize that those islands in the Pacific firmly hold the top spot as our favorite place on Earth. We’ve crisscrossed the globe in a never-ending search for adventure and along the way we’ve been lucky to explore many stunning places, but that siren’s call continues to bring us back to our beloved islands each and every year. Don’t worry, I am completely dedicated to the arduous process of exploring other amazing places on Earth just to make sure that Hawaii is still our favorite — the things I do for you guys. 😉

Road to Hana5-1

A few years ago Cody and I explored Norway with my grandmother and cousins, and since that trip we have often discussed how much fun it would be if our family joined us in Hawaii. So when my parents expressed interest in traveling to Hawaii for my stepmom’s 50th birthday, I was head-over-flip-flops excited!

We are a close family and get along quite well, so I knew that we would have an amazing time together, however, it goes without saying that traveling with a group is significantly different than traveling with your spouse or traveling solo, so today I wanted to share a few simple tips to help your next family vacation go as smooth as possible.

Heart Rock in Maui
Sweetheart Rock, Maui
  1. Planning: The Early Bird Gets the Coconut

    We started planning this trip two years ago when my stepmom brought up the idea of a birthday trip to Hawaii. Of course Cody and I were immediately on-board, and I thought the best way to start the trip was to have the birthday girl decide which island(s) we would visit. (I tried to minimize the pressure of her decision by sending her magazines from Hawaii’s tourism board, and followed up with a, “It’s Hawaii, you can’t make a wrong choice” pep-talk).
    That first year of planning was really just a lot of dreaming and discussion, but once the calendar changed to 2015 (about a year out), we confirmed the dates for our trip and chose the islands we would explore.
    *The key is to start early so family members have a chance to save their pennies, accumulate PTO, and arrange vacation.

  2. Planning: Communicate!

    When it comes to planning a trip with multiple people, communication is so important. Talk about the budget. Talk about the kind of trip that each person envisions. Talk about everyone’s must-see activities and sights.
    If you can get everyone around the kitchen table for an afternoon, give each person a chance to add their two cents and start creating the itinerary.

    Kauai Sunrise
    A serene sunrise in Kauai
  3. Traveling: Be Flexible

    And I’m not talking about upping your yoga game with this tip. 😉 If you travel a lot than you already know that most of the time things don’t go exactly as planned — and those kinds of days are completely okay! Some of the family may decide to stay at the beach or go to the spa instead of going on that excursion, sometimes people get sick and don’t feel up for adventure that day, and sometimes people just want a little alone time for a romantic dinner or moonlight stroll along the beach. Being flexible keeps everyone light-hearted, easy-going, and understanding.
    *At the end of the day you’re at an incredible location hanging out with your loved ones and that’s what matters.

  4. Traveling: E ‘ai kakou (Let’s Eat!)

    Depending on the size of your party, you may want to schedule your dinner reservations before you arrive at your destination. Reservations will take the guess-work out of  the “where do we want to eat for dinner?” discussion, and more importantly it will allow better use of your time. The last thing I want to do is spend my precious vacation time sitting outside of a busy restaurant when I could have spent an extra hour or more at the beach.

  5. Traveling: Hakuna Matata

    I spent a lot of time organizing this trip and therefore, I also spent a lot of time worrying about if everyone was having fun. I felt responsible for everyone’s happiness and because I spent so much time worrying, the first couple of days were a little stressful.
    Thankfully, early into the trip my husband reminded me that we had created an amazing itinerary and that everyone seemed to be enjoying themselves, so in the nicest way possible, he suggested that: maybe I should stop worrying and enjoy the trip. 🙂
    At that moment I was able to let go of the smothering pressure of presenting an amazing once-in-a-lifetime-trip to my loved ones, and as the self-imposed-weight lifted off my shoulders I was able to truly enjoy the precious time with my family.
    *Hakuna Matata. Be present and in the moment. Don’t overthink it. Take time to relax.

Old Lahaina Luau
My cute Family at the Old Lahaina Luau

Cody and I loved every moment of showing off our favorite islands to our sweet family, and as my parents left for the airport we all got a little emotional while saying our goodbyes. We flew to Hawaii as a close-knit family and we left the islands with an even stronger bond, and I couldn’t have asked for more.

Have you traveled with family? What other tips would you add?

12 thoughts on “Five Tips to Survive Traveling with Extended Family”

  1. Good tips and thankfully I learned much of this by traveling in our Tom, Dick and Harry group. We had a wonderful time and remain good friends, even though some of our trip plans didn’t work out and we were a little bummed about it. It is all in “do you want to have a good time or do you want to complain? ” There is a time for disappointment, but no time for complaining.

  2. Back in 2002 we took our whole family to hawaii, as part of a 3 week once in a lifetime trip. We decided on a week each on kauai and big island, then a week in Orlando at the theme parks. Our daughter was just 6 and flying from the UK is a long haul, a total of about 17 hours flying time. With so much flying time (and waiting in airports) it was important to keep our 6 year old occupied. She had lots of colouring books and a Nintendo gameboy (remember those?) . To your point about planning, we missed our connecting flight from kauai to big island due to an administrative error by the holiday company, but the local rep soon had us back on track. It was a fabulous 3 weeks, so much so that we returned in 2005 and visited kauai and maui. We love hawaii and hope to get back their again soon. Thanks for bringing back some happy memories.

    1. That sounds like a great trip with your family, Tony. What beautiful memories! That is a great tip to add, keeping the kids occupied. My little brother had his iPad and cell phone to keep him distracted while we traveled. He almost fainted when I told him Hawaii was a 5.5 hour flight from LAX. I do remember the Nintendo Gameboys 🙂 Those were so fun!
      Hope you get back to Hawaii soon as well.
      Have a great day.

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