Current State Count: 27 states + DC and Puerto Rico.

Hawaii won’t move the needle on my state count but I will never complain about a trip to the Pacific for some fresh air, Aloha, and sunshine.

Trip Background: I got engaged back in August 2015 and my fiancée had asked me to spend the 2015 Christmas holiday with her family. Because it was both her Dad’s 60^th birthday and her sister’s son had just been born, I accepted but I was concerned about price. Christmas is typically the most expensive time of year to fly to Hawaii since everyone else is seeking an alternative to a cold winter and all of the frequent flyer mileage redemption options were horrible.

Instead of paying cash, I redeemed my Citi ThankYou points for a Hawaiian Airlines flight, which cost me more (in equivalent cash value) than my flights to Morocco and Moscow combined! Sigh. But no matter. We were going to see the fam, get some much needed beach time, and take in some Hawaiian food and sights. So we packed our aloha shirts and shorts (and a hoodie) and set off to the Big Island!

Day 1: Transit

Flying Hawaiian Airlines is always a nice experience with its friendly flight attendants and POG juice, but my trip began with a major gaffe. I forgot to add my Known Traveler Number (the ID # you get when you register for Global Entry) in my account, so I did not get TSA Pre Check. #planningfail

After spending a half hour in the security line, I also realized that I had to board in the last boarding group because I don’t have any status on Hawaiian Airlines, I didn’t want to pay extra, and I checked in late. It is indeed humbling to have to wait when you’ve gotten used to breezing to the front of the line and part of me wished I had booked American just for the possibility of an upgrade, but such are #firstworldproblems.

The only highlight, besides the usual good Hawaiian Airlines service, was seeing Air Force One parked on the tarmac in Hilo. I was later informed by an ex-pilot friend of mine that it’s not technically Air Force One unless the President is on it and that plane was likely kept in Hilo for security purposes, as Obama was in Honolulu on holiday. Exciting nonetheless!

Hello Mr. President.

Day 2: Driving the Southern Coastline

In the morning, we set off from Volcano and headed southwest on highway 11 towards the southern end of Hawaii. Along the way you get a pretty nice view of the Pacific Ocean on your left hand side and Mauna Loa on your right side as you pass through countryside and small towns. We stopped at Punaluu, a well-known bakery that makes Portuguese Sweet Bread and malasadas, in addition to a litany of other baked goods. In case you’ve never been to Hawaii, these items are classic staples.

It is indeed the Southernmost Bakery in America!

Portuguese sweet bread (not to be confused with sweetbreads) is soft and chewy, lightly sweetened, and can be eaten as a snack or as a meal. Tear off a piece and just stuff it in your mouth.

Malasadas are fried donuts in which the interior is still doughy and the exterior is dusted in sugar. Make sure you try the regular malasada before adventuring into local flavors like guava or lilikoi (passionfruit). Sure it’s a tourist trap but it also is one of the few sights along the southern coast besides craggy beaches and lava fields.

Delicious, soft malasadas, fresh out of the fryer

As we weaved our way through Naalehu on the southern side of the island, Captain Cook and Kaliua-Kona on the west side, we finally arrived at our home for the first few days – the Fairway Villas Waikoloa by Outrigger. For a family excursion, this is a great way to stay in Hawaii.

The Fairway Villas Waikoloa by Outrigger

A kitchen with all of the cookware you’ll need, fridge and freezer, multiple bedrooms and bathrooms, and a well-appointed living room all make it feel like home. The villas also sit alongside one of the holes on the golf course, which provides a soothing backdrop when you open up your patio door.

Sprawling view from the back patio

If you stay here, dinner options on or near the beach aren’t too plentiful, but if you’re seeking comfortable food with a view, the Lava Lava Beach Club has a nice beachfront from which you can chow down on macadamia crusted mahi mahi or any number of seafood and meat dishes.

Dinner with a Sunset View

Day 3: Beach Time

If you go to Hawaii and don’t spend some time sitting on a beach, swimming, or snorkeling, there really isn’t a great reason to go to Hawaii. I mean sure – you can fly at least 2000 miles for kalua pork and loco moco’s, but that seems like an awfully expensive way to eat comfort food.

We pitched camp on a small, craggy section of Anaehoomalu Bay, which in the landscape of beautiful Hawaiian beaches ranks pretty low. The sand consisted of those sharp, pointy rocks that makes sandal-less walking more of a pain than a joy. The water was a comfortable temperature and we went back to the Lava Lava Beach Club for some lunch and snacks, but there are better and more beautiful beaches on this island to visit.

For dinner that evening, we ambled into Kona for dinner at the Kona Brewing Company. Be forewarned – this is a 25-mile drive and it took us around 40 minutes each way. Kona’s beers are full of flavor and make you feel the aloha spirit, but if you plan to have more than a couple, it might be worth figuring out who the designated driver is in advance!

Day 4: Traversing the Island

So after a couple days of solid beach time, snorkeling, and sleeping, it was time to head back to Volcano where my in-laws live. But before we set out on our 3-hour journey home, we loaded up on supplies and food.

If you’re on the western side of the Big Island, a must-go place is Umeke’s, a small restaurant with an outdoor seating area and nondescript signage. But don’t let its shabby interior or plain exterior fool you. You don’t get a 4.5-star rating on Yelp with ~700 reviews unless your food and drink are solid – and both were outstanding. We decided to get a poke bowl (with an extra serving of poke because, well, Hawaii) and a kalua pork bowl for some variety. My recommendation: get the seaweed salad as your side and make sure to add furikake, a Japanese seasoning mixture of seaweed, sesame seed, and assorted other niceties that make white rice delicious. We opted for a mason jar of strawberry lemonade but it was way too sweet.

Kalua Pork Bowl with furikake

If you want to get around the Big Island, you can basically take one of three routes: Go around the north side, go around the south side, or cut through the middle on what is called Saddle Road. Saddle Road is well known for being…well, boring as hell. You’ll find some stretches with stunning visuals and some that will bore you to tears. My advice: bring some good music, a movie, or a good book. And if you’re driving this stretch: soda, gum, and anything stimulating will be your best friend.

Day 5: The Volcano

Hiking anywhere around Volcano National Park will give you a vista of a lifetime, but start your adventure at the Kilauea Visitor Center where the rangers will provide some great context around the natural landscape around you and where the best places are to go.

Families live on the park and one such family put up an adorable Despicable Me themed holiday display

The beautiful crater

As you hike around the crater, you may see steam vents here and there. Don’t be too concerned – and if you are, have a read. If, however, you have asthma or breathing issues and you come across one of the Sulphur Banks, I would consider finding a different place to hike! But don’t let this deter you. The views are magnificent and on clear days, the blue skies make for a stunning contrast against the crater.

The stunning crater

The only other thing to note is that rain has a sneaky way of finding you on this island. We got caught out in a surprise rainstorm once or twice…and they have a way of moving fast and soaking you to the bone! Bring a rain jacket regardless of when you’re here…it will likely come in handy!

If you’re looking for a place to see the crater at night, consider stopping at Uncle George’s Lounge at Volcano House to look out over the crater while you sip cocktails.

The crater at night – apologies for the bad photo quality!)

Day 6: Christmas Day

Since this was a holiday trip, we opted to spend December 25^th sleeping, eating, drinking, and engaging in the typical mirth of the holiday season.

Day 7: Green Sand Beach

For my second to last day, we somehow convinced ourselves that a hike to Green Sand Beach on the southern tip of the island was an adventure worth undertaking. What should have been a red flag was my future brother-in-law (who is a park ranger at Volcano) recommending we bring hiking shoes and prepare ourselves for an exhausting physical activity. But vacations somehow have a way of dampening common sense and we set off.

When you arrive at the main parking lot for the beach, you can either pay locals who have off-road capable SUVs and trucks or you can hike the 2.5-mile distance along somewhat rough and muddy terrain. Being a slightly frugal and adventurous group, we chose to hike and instead paid the price in facial pain and sore legs. The day we hiked happened to be an extremely windy day and we kept getting slapped in the face with stinging sandy gusts.

If I didn’t tell you the scale here, would you know if this is a walking path or an aerial shot of craggy 400-foot tall hills?

Despite the pain, the view at the end was actually quite nice. And yes, the sand is quite green.

Green Sand Beach

Green Sand Beach

Once you arrive, you’ll need to traverse a small winding set of steps to get to the bottom, so be careful if you’ve got young kids or seniors or anyone with a fear of heights in your group. You may not find the swimming as relaxing as on other beaches and you should guard your hats carefully. The winds picked up a half dozen tourist hats and swept them up the cliffs in the pic above. As a result, I would only encourage people visit Green Sand Beach if they have the time to spend a half day to an entire day hiking to and from this place.

If you’ve not yet satisfied your hunger for vistas, then venture over to South Point. It’s not only the southernmost point in the United States, but there’s a small structure from which adventurous people can dive off the cliff into the water below and then climb back up. Definitely not for the faint of heart!

My fear of heights = NONONONONO

Day 8: Time to go Home

Saying goodbye to any vacation is always a sad moment but being sent off with some greasy Hawaiian food sure softens the blow, and Ken’s House of Pancakes is an excellent way to end your time on the Big Island. It’s an old school diner that’s open 24 hours a day and a meal at Ken’s can fix a hangover, be a good first date night, or give someone a solid introduction to Hawaiian comfort food. Take my advice: have the loco moco (two scoops of white rice covered in a hamburger patty, fried egg, and gravy) or saimin (a rich, heartwarming noodle soup).

Final Thoughts

The Big Island is definitely not the prettiest of the Hawaiian Islands nor the most cosmopolitan, but it is the most laidback of them all. It provides a wonderful balance of activities and places to disconnect, fancy foods and street foods, and a naturally clean air from the trade winds and rainy seasons. And if you happen to be there at Christmas time, it’s a simply magical place.