Wrapping up summer - I have some ideas!

I kind of can’t believe that we’ve only got two weeks left of summer break in our house. I remember being a kid and feeling like it was the longest period of time, and now as a working adult trying to cram in as much fun as we can in that short 2.5 months, it’s just too short. I guess that’s what happens when you get older. Today I wanted to share some ideas for easy-to-plan, kind of last minute type trips you might want to put together before fall gets here and the weather goes to the dogs.

And don’t worry, I’m not going to tell you to head to Alaska on a whim (unless that’s what you’re hoping for). I was just thinking about some of the summer trips we’ve done in the last few years and I always love to put those on the table for others. Thank you for following along and lending a eye to what I share each week. I appreciate it and love the emails and questions that come in after I send out my weekly. :)

I’ve talked before about the difficult with being a parent who works from home (WFH) in the summer, and specifically around the guilt I sometimes feel when the work and deadlines keep me at my desk instead of doing fun things with the kids. I try to break away or set aside time for the fun so we get to enjoy summer break beyond vacation time, and I’ve failed at it this summer. Between our fun trips and a few work trips that I’ve had, it’s left me with more work to do than I should’ve accepted. The kids are chill so they’re fine hanging out with each other when one of us isn’t able to go galivanting with them, but it still feels a bit heavy knowing that there are times that I have to choose my desk over the beach.

Here’s what’s been good about the WFH situation this summer:

• they’ve become more independent, including making their own lunches (they’re big kids)

• we’ve had so many trips together that when we are all home, they have wanted to just be home and do things here at the house

• they’ve gotten good at riding bikes to the library on their own and checking out a range of books, and actually reading them.

What hasn’t been great about the WFH times this summer:

• Even when they don’t necessarily want to hang out with me, I feel guilty that I’m not just in the same approximate area… but also they don’t seem to care

• I haven’t been able to work through deadlines at the pace I need to so I can take more full days off like I had planned on doing

• We haven’t done our usual stack of summer kayaking that we always do when we’re home. We’ve done lots of rafting and kayaking on our trips, but not just around our home territory.

Something that has been great with this summer when we’re home is how the kids’ friends want to hang out and do things. I wish it was more often, but it’s been enough that they’re keeping up on their social skills. Now, we have two weeks left before we’re back in school, so once I publish a few things this week I’ll be able to have the last ten days or so of their time off to just hang out with them.

Okay, here’ are my easy picks for end of summer trips that don’t take a ton of planning and can usually be done on the cheap, or at that you really get a bang for your buck on. Remember that airline miles go the furthest when you’re looking at using them 25 days or more in advance, so if you want to fly somewhere, see if you can use some miles to keep things on a good budget. Below I have fun suggestions for each region of the USA.

First up, the Oregon Coast is awesome in August and September. I remember one September trip we did where we kept joking that we’d driven to Aruba because it was so nice. Oregon Coast Road Trip here

Next idea is a li’l road trip into Montana, because you get easily drive here in less than a day from WA, OR or ID. I think Missoula is a really cool city with lots to do all around the area, but then heading up to Glacier National Park is always awesome, and Glacier Guides Montana Raft can help you put together a fun vacation plan. 5 Day Glacier NP Itinerary here

This summer Elliott and I did a 4 day rafting trip on the Green River in Utah with OARS. It was really fun and they made it an easy trip for us. Since I wrote about it, the OARS team said I could offer a discount to readers if they want to book the trip we did, called the Gates of Lodore in Dinosaur National Monument. If you want to book it or see available days, check out this OARS trip here. Use code OARSFRIEND10 for a 10% discount on bookings made by September 1, 2026!!!

San Diego is always a hit with our family, and if you can slide it right when half the country has already gone back to school, it should be pretty chill and maybe even you’ll find some good deals. I love San Diego because it’s full of fun people, really good food, and fun beaches. 3 Day San Diego Itinerary here

A great last-hurrah of summer for the Midwest or Great Lakes is heading to Wisconsin. Madison and Lake Geneva are really fun and have such good summer vibes. I love how easy it is to be on the water, but then there’s also tons of farm country to explore. My favorite part of Wisconsin though is Door County. It’s so very pretty and between the biking and kayaking, there’s lots to do for every age and energy level. Door County ideas here

Another fun summer trip that Oliver (our oldest) has been hounding me about is Chicago. If you haven’t been, Chicago is actually what I might consider to be the most fun city in the USA. At the end of summer it’s really nice before the fall “windy city” thing really kicks in. The hotels are a little more expensive here, but usually you can find great flight deals. Chicago Trip Guide here

We’ve been really fortunate to get to take the kids to New York several times, and as they’ve gotten older, it’s become more and more fun. I think getting to an age where they enjoy going to Broadway shows has helped, but also they really get into just being in the big city and walking around and doing museums. If you time it right, you can get a hotel and transportation for a sweet deal (usually if you stay 3-4 nights). New York City w/ Kids Guide here

The Maine Coast and Highlands are two totally different areas and you can put them together in the same trip. you can spend four days or you can spend a whole week doing this little trip. I like that you can be on boats one day and then spend the next few days hiking and looking for moose. Maine Road Trip Plan here

I’m not going to tell anyone to come visit us in St Augustine at the end of summer, because it’s hot and muggy like Satan’s armpit. BUT I will say that any beach trip you can do is worthwhile, and we have some great state parks with amazing beaches. So, if you’re looking for a Florida trip on the cheap, plan to be near a beach, chill at the state parks, and enjoy the heat. Heads up though, we’re in hurricane season, so be flexible!

If you’re into history and need to prime kids’ brains before going back to school, you can also plan a fun trip to visit all the forts around Florida and Georgia. You’ve got Revolutionary War and Civil War forts from Savannah all the way to the Florida Keys. Lots to see and do!

Next week I’ll have more to share about all the fun stuff I’ve been writing about. It’s taking a lot to get through photos and polish up all the articles from our Alaska trip. Stay tuned, because there’s a lot of fun and pretty pictures coming next week!

Have a great July, and thank you for reading. If you have any questions about the destinations or trips we suggest, always feel free to leave a comment or send a us a note. Enjoy the sunshine!