Tip #1: Fly nonstop if you can, especially in the winter

We’ve learned the hard way after a few missed or canceled flights that leaving Denver early with a connecting flight is a bad idea at this time of year. Fortunately, United offers a couple of nonstop options daily from Denver. We took the mid-afternoon flight so we could avoid the morning rush of holiday travelers and any weather-related issues that might have cost us a day on the island. The downside was we landed pretty late – at 9pm local time. Luckily, since we were staying in Po’ipu, we had just a 25-minute drive from the airport to our resort. If you have the option to take a nonstop flight when traveling in the winter, we strongly suggest you do it. The cost may be a little higher, but you will avoid a lot of potential hassle.

Tip #2: Split Up at the Airport

Arriving in Lihue at any time usually means you first get your luggage at baggage claim, and then you head to the car rental agency. All of the car rentals at LIH are accessed by a shuttle across the street from the arrivals and departures drop off area. Most of the car rentals are located on-airport, and just a 5-7 minute drive from the shuttle stop. They run pretty frequently as well. Depending on your status and car rental agency, you may then have to stand in line at the counter to get your vehicle. To make this process more efficient – and possibly beat the rush of travelers headed to the same place, we recommend you split up as soon as you arrive and deplane. We’ve been doing this for years. One of us will head straight to the car rental agency while the other collects bags at baggage claim. This speeds up our ability to get out of the airport quickly, no matter the time of day.

Tip #3: Pre-Order Groceries for Pick Up for First Morning

We tried something new on this trip that you may want to consider. Since we were arriving so late in the day, I knew we wouldn’t want to stop at a store to pick up any groceries on our way to the vacation rental. I usually like to grab a few essentials for breakfast on the first morning, so on this trip, I decided to try to pre-order groceries from Safeway. I knew pick up ends at 10pm, and once I knew our flight was on schedule, I placed the order just after we boarded our flight. This gave us the ability to grab some items we’d need for breakfast in the morning. Unfortunately, a number of key items were out of stock and since we were on a plane with sketchy WiFi, we didn’t get notified to approve substitutions. Most of the items we needed were left out of the order, making it much less helpful. So my added tip if you want to try this is to make sure you specify alternatives when placing your order.

Tip #4: Take a Whale Watching Tour in Winter

Tip #5: Try the surfing canoe at Kalapaki Beach

During a beach day at Kalapaki Beach in Lihue, we tried the outrigger surfing canoe ride at Kauai Beach Boys. This was a ton of fun, especially if you want to catch a wave without learning to surf. The outrigger canoe accommodates four people plus a guide. After a brief lesson, we set out from the beach, journeying east along the shore toward the lighthouse before turning south to find the waves. Our team had no trouble catching waves. Mike sat in front and took a lot of water in the face – so be warned. Overall, the experience was fantastic. It’s easy to paddle, easy to surf, and a lot of fun.

Book in advance to ensure your spot – though we nabbed a couple seats just as another couple was getting ready to leave. The cost is $69 per person, which is double the cost of a SUP or kayak, but well worth it if you’re feeling more adventurous.