Our Travel To-Do List for the Next Few Years


You might say I have a problem. When I’m not on vacation, I’m usually looking forward to the next vacation.  And on the off chance that we don’t have another vacation planned, well then I’m starting to plan the next vacation.  My wife’s the same way.  I’ve been like this since I started planning cross-country road trips about fifteen years ago.

I know what you’re thinking. We must not like our home life and jobs if we always think about getting away.  That’s not true at all, though.  We recently moved into a gorgeous new house and we love it.  I love my wife, kids, and dog.  Heck I even love my Ram truck.  I like my job and Ashley would probably say she loves hers.  We also love where we live, but we wouldn’t mind a shorter winter season.  So, in other words, we love our life; but we also include travel as being an important piece of the life we love.

We recently started to try planning out our vacations for the next several years. We usually go on at least one big family trip per year and, if possible, try to go on a second vacation as well.  We like to go somewhere warm in the winter for a week or so; usually a cruise or Florida.  Then, in summer, we feel it should be a good time to visit just about anywhere we’re interested in.

This year we’re already half done. We went on a Caribbean Cruise with our kids and a bunch of Ashley’s family in early February.  Then this summer we’re renting a big house in the Poconos in Pennsylvania with some friends.  There will be four couples and seven kids.  The house has a little beach on a small lake, so we think it should be a lot of fun for us and our children.

This is what we’ve started planning for the more distant future:

  • February of 2019 – We’ve begun planning a return trip to Disney World (we went in the winter of 2017). This time we’re going to go with two other couples who have two children each. Unlike last time, we’re going to stay in one of the Disney Resort Hotels and have a partial meal plan. I think we’re going to spend six nights there, but only book park passes for four days. That way we can guarantee some calmer time by the hotel pool and be sure to visit the Disney Boardwalk area for a day or two (because we loved it so much last time).


  • Summer of 2019 – I’m in the early stages of planning a New England road trip. I haven’t worked out all the details yet, but there will likely be stops in Lake Placid (NY), Newport (RI), and Bar Harbor (ME). We may also include another stop in Maine and perhaps somewhere in the Green (VT) or White Mountains (NH). Since we’ll be driving and have multiple stops we’re thinking we’ll have the trip last somewhere between seven and nine days. My in-laws will probably be joining us on this trip.

  • Summer of 2021 – ALASKA! We don’t have any plans for 2020 yet, but we’re thinking we’ll go to Alaska the following summer. Alaska is at the top of my Bucket List, so we thought it would be the perfect place to go to celebrate my 40th birthday. There’s a good chance we’ll take an Alaskan cruise and maybe even add on a cruisetour package at the end of the cruise that could include a bus trip to Denali National Park.
  • Summer of 2022 – Drive up the California coast. This trip would be to celebrate our ten year anniversary. We have plenty of time to plan this one, but we’re thinking that we could leave the kids home with their grandparents on this one if possible. I would like to at least include Big Sur, Monterrey, San Francisco, Point Reyes, and Redwood National Park. I’m sure Ashley would like to include a couple of wineries. If possible I’d like to add in Yosemite, Sequoia, and Kings Canyon National Parks.
  • Winter of 2026 – HAWAII! We have a few years in between planned vacations here, but that’s ok; we don’t want to have everything planned out already. Ashley would like to go to Hawaii to celebrate her 40th birthday. I’m all for that idea, because Hawaii is also high on my Bucket List. Ashley will likely want to take a cruise to Hawaii for the trip.


So, those are the vacations we have planned so far. I’d call this a Travel To-Do List instead of a Bucket List at this point, because we wholeheartedly plan on making all of these trips at these times.

We do have other places we’d like to visit, but we’re just not sure when we want to fit them in yet. Here’s what else we’ll try to fit in over the next several years (in addition to cruises to the Caribbean and another visit to Disney, I’m sure):

  • Cape Cod. I’ve been interested in Cape Cod for a while. I just picture it being a relaxing beach setting unlike Virginia Beach or Myrtle Beach. I get the feeling those places are busier and crazier. I don’t know for sure, but I think Cape Cod would be more my style.
  • A trip to Yellowstone and Grand Teton National Parks. I’ve been to these parks three times each and think that Yellowstone is the perfect place to introduce my kids to National Parks. I’m hoping it will make them love the National Parks like I do. I’m also certain that my wife and I will enjoy some time in Jackson, which is a great mountain resort town.
  • Atlantis. I’m talking about the nice resort in the Bahamas, not the lost city under water. We walked around Atlantis on a cruise once, and would love to take our kids there when they’re a little older.  Us at Atlantis
  • The Outer Banks. You can pretty much apply everything I wrote about Cape Cod to the Outer Banks. We both think this would be a nice place to rent a big beach house with family or friends.
  • The Pacific Northwest. I’ve been up that way before and loved it. I’d like for this to be more of a National Park trip with stops at all three parks in Washington (Olympic, Mt. Rainier, and North Cascades). Ashley’s cousin recently moved to Seattle, so we could visit her, too.
  • A European cruise to England, Ireland, and Scotland. This vacation will likely be the farthest into the future of anything I’ve written about here. One day we’d like to take a cruise to these places, but we have no idea when. I don’t know if this would be something to do with our children or if it would be better if it’s just the two of us.


Do you have any thoughts on our rather ambitious list? Any recommendations dealing with what I’ve listed or suggestions of other places to visit?  Please let me know in the comments section below.  Thanks!


9 thoughts on “Our Travel To-Do List for the Next Few Years

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  1. We’re in a similar position – we both enjoy our jobs but also really love to travel. Sometimes it’s hard to balance both (mainly because we wish we had more vacation time). But I think it’s good to always have a trip on the horizon. It’s something to look forward to. Your upcoming travel list looks amaaazing. Alaska and California are pretty high up on our lists as well! Looking forward to reading all about your adventures.


  2. I do the same thing. I have our trips planned from this summer through 2021 which is our 25th anniversary.


  3. Love your list. We went on many cruises with groups of friends before but we truly enjoyed the last one we did a couple years ago with just the four of us to Europe (Italy and Greece). It was for my daughter’s graduation trip and they were at the age to be able to enjoy the European culture and lifestyle. The Alaska cruise/cruisetours that start from Vancouver B.C. will get you further north to see the glaciers.


    1. Yeah cruises are definitely a good time. We went to France and Italy on a cruise a while back. Alaska is the one I’m really looking forward to. I’m sure we’ll go on many others too. Maybe Europe, New England, or Hawaii.

      Liked by 1 person

  4. What a great list!

    For what it’s worth, my advice for Cape Cod is to avoid 3-day weekends (and probably weekends at all, if possible) in the summer because it’s crazy. We went over Labor Day and there were just people everywhere. That being said, you can definitely escape the crowds if you’re willing to hike. Rather than paying the $20 to park at one of the beaches, we parked for free and hiked about 2 miles out to a beach and there were only 4-5 other people there!


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