Planning a Couples Trip in Maui, Hawaii Hawaii / Travel / United States

Each year, Jen and I take a couples trip together, just the two of us. This year, we chose one of the most paradisiacal places we’ve ever been to – Maui, Hawaii. (Here’s a video of it our 13-year old daughter Marie put together for us).

Maui is so incredibly beautiful! The weather is just about perfect, with a misty rain that periodically falls throughout the day, followed by beautiful rainbows.

On this small island, there are rainforests, deserts, dozens of waterfalls, volcanos (including Haleakala at over 10,000 feet!), beautiful beaches, cute shops, art galleries (we spent hours admiring Vladimir Kush‘s work!), great food, and much much more to love about this place.

It is, however, very expensive. And the roads can be very winding “up country”. But we really loved our time here, especially due to the intention we set.

Our intention for the trip was to connect more deeply together, reflect on and integrate our past experiences, read and learn together, talk for long uninterrupted stretches of time, and experience new adventures together. We rented two separate places. One near the center of the island near Makawao, and one near the beach between Kihei and Wailea.

In the first location, we had a bathtub out on the deck from which we could see the milky way at night!

Having at least a week is important for us, because it tends to take us a couple days to land and orient ourselves, and there is a depth we tend to be able to reach only after several days of focused attention. It’s also important to us that this time is spent without the distraction of computers, work, or meetings. And of course, we want time to enjoy what the place has to offer, such as the breathtaking Road to Hana, the charming town of Lahaina, and the incredible snorkeling right with the coast with sea turtles (Turtle Town near Makena is a great spot)!

One thing we’ve also realized is how important it is to take these kinds of trips with our girls, too. Of course, in our semi-nomadic lifestyle, we’re always “traveling” together, but we’re not usually on “vacation” (or “holiday”). We have work, classes, projects, meetings, planning, and many things that occupy our time and take our focus away from each other.


This is one of the challenges of our lifestyle. Even though I run a literal “4-hour workweek” business, there is a mindset and intention to my time that needs to be crystal clear, or I can easily overload myself with projects and tasks that are less important and meaningful to me than my family relationships.

So in addition to simplifying in the months ahead, we also want to plan regular extended periods of a week or more throughout the year where we can set everything else aside and just focus on each other as a family. It doesn’t have to be in an exotic location, but it must have an intention of connection and fun together.

Something longer than a few days, where work, electronics, and other commitments are set aside with the intention of connecting with each other in a deeper way than we can in shorter periods. What ways have you found helpful to strengthen your relationships as a couple or family? What will you do to connect more deeply in the coming year?

If you’d like help with achieving your family dreams, be sure to check out my Dream Achievement Blueprint program, or get in touch with Jennifer for Embrace Being coaching.

Brandon is a location independent entrepreneur, musician, worldschooling father, and the principal author of this blog. He's all about reaching his potential and enjoying life to the fullest in each moment.