We haven’t managed to get away for a proper family vacation in the past two years. Since I’m feeling a bit out of practice when it comes to this type of trip I’ve had to think hard about what to bring. As a family we have so much stuff we need for the kids and everything — it’s going to be important that I do my best to limit my personal luggage.
Since I’m packing I thought it could be fun to share some of what I like to travel with here. It’s a bit late in the game to to talk about a lot of summer stuff but this should be helpful either now or in the future.
Hawaii as a destination demands some slightly different and specific things versus what I normally take on a trip. It’s going to be warm, sunny and the time will be full of activities and I want to maximize versatility for activities and maximum relaxation. Hawaii is a bit sportier and more informal than where I typically go, so I need to think differently about what to bring. Hope this is helpful.
Bags: The few times a year I will travel with a backpack is when we go to Hawaii or on family vacations. I don’t love backpacks generally speaking, but it’s important to have my hands free to carry kids, kid stuff and everything else. My two favorites for backpacks —which both happen to be Montana companies —are either from Evergoods or Mystery Ranch. The Black Hole bags from Patagonia are popular (along with some other bags from The North Face) but they are all just too logo strong for me. If I need a duffle I typically bring my Goruck Kit Bag which is one of my all time best purchases. Those Kit Bags are modeled after bags that military special forces use and the 57L is well-made and huge. These bags are also a great overflow bag to pack just in case you need some flexibility in coming home. MIS CALIF makes a simple and light tote to bring as a simple everyday bag while around town.
I still really love bags that are made in the USA — specifically nylon bags. Some favorite brands are DSPTCH, Tom Bihn, Flowfold, Mission Workshop, Drifter, 1733 and of course the quirky Tough Traveler.
Swimwear: My preference for swim is from Outerknown. These Huckberry exclusives are good and if you like a more traditional board short then I would go for the Apex trunks or these Apex hybrid shorts. Other good options: Meriggi or Patagonia Baggies. These RØ shirts from Patagonia are great if you spend any time out on the water surfing, on an outrigger canoe or standup paddle board.
Clothes: The Riviera Polo from Sunspel is perfect for trips like this because it looks nice in any situation and feels good in hot weather. Beyond a shirt from Sunspel, or the famous Sid Mashburn polo, I really take the opportunity in Hawaii to break out relaxed shirts which I would likely not wear in everyday life. When in Hawaii you need to wear Aloha shirts and the best are from Kahala which still manufactures on Oahu. Considering history and make — these are the real deal Hawaiian shirts. The other shirt brand I like is Portuguese Flannel that makes some nice camp shirts. I own several of these and love them. Everything ships from Europe but everything is sent via DHL and arrives quickly. Other options: Corridor and the Original Madras Trading Company.
There’s really no need for layers in Hawaii, but I always want a hoodie for post swim moments. This sweatshirt from Western Hydrodynamic Research is perfect and the brand is one of my recent favorites. I will bring my WHR hat with me as well.
Shorts. My goal is to find shorts that can cover a variety of different activities. These Buck Mason Trail Roam shorts are great for hiking, working out and other active stuff. You never need pants in Hawaii so these other Buck Mason Carry-on shorts are all I need for any other situation including dinners etc. I also like these hybrid shorts.
Hiking shoes: Hawaii has some incredible hiking. Depending on how serious your hiking is going to be there are a few options. If it’s casual hikes I wear either these Hoka hiking shoes or these Nike Trail running shoes.
Golf Clothes: It can be hot and sweaty in Hawaii and you likely need some tech fabric. My favorite summer golf polos are the Holderness & Bourne Performance Pique. Everything H&B makes is great and I love the sweaters and other layers from them. These guys are the only brand out there making a polo shirt with a real collar. It’s all very classic menswear inspired and it’s exactly what I want to wear.
I still can’t find golf shorts I like more than these J.Crew Tech Shorts. I wish they would come in an 8” length so I wouldn’t have to have them hemmed myself. My golf shoes are either FootJoy Premiers, or when I play in Hawaii I do also like the new golf collection from Oluaki which are pretty clean and simple.
Books: I’m planning on bringing a few books to read while we are in Kauai. The first is Four Thousand Weeks by Oliver Burkeman, which my wife recommended and loved. Another one is 21 Lessons for the 21st Century by Yuval Noah Harari. Lastly, I’m hoping to get to read Anna by Amy Odell (who also has a great Substack). I’m not one to obsess over the happenings at Vogue, but I love Amy’s writing and there are certain people I will read regardless of subject matter and Amy is one of those people.
Camera: I always want to bring a non-iPhone camera to document the trip. My plan is to bring the Fuji X-Pro3 because I can’t seem to ever let myself buy a Leica. I shot a bunch of my Scotland trip with this Fuji and loved using it and the images it produced.
Odds & ends: This is the sunscreen I use based on buying only buying stuff like this in Europe for the past decade. It’s worth the money to pay for good sunscreen as it’s easy to apply which to me means I will actually use it. When you travel make sure to put this in a ziplock and then into your checked luggage. Having to abandon an expensive thing of sunscreen at TSA is as annoying as getting a parking ticket.
I’ve been swimming laps here in LA and like to swim for fitness when I travel. Roka is my go-to for goggles, caps, fitness swimwear. All of my sunglasses are either from Salt or from the new brand Rose & Co.
Recently I’ve been able to get away with only bringing my iPad Pro and Magic keyboard and no laptop. It pretty much works for 99% of what I need to do and it’s versatile and light. I carry this simple charger and this cord to keep the program simple and streamlined. I also always have one of these powerbanks on me for every trip because I don’t like sitting on the floor at airports while charging my phone.