Island-Hopping in Hawaii

Anniversary Escape, part 2 

“Island-Hopping in Hawaii”

After a relaxing weekend in Los Angeles (see “part 1”) we headed out on Sunday morning to catch our flight to the Big Island (an easy 5 ½ hour flight from LAX).

The Kailua-Kona airport is adorable, and you know right away that you have arrived in the islands 🙂  You deplane down some roll-up steps and walk across the tarmac to an open-air terminal with just one baggage carousel.  We had an easy ride on the shuttle to the car rental lot, with no lines at the counter, and we were in our Jeep in no time. The landscape surrounding the airport is really stark – it reminded me very much of arriving in Reykjavik (Iceland) – a barren moonscape of black lava rock. Our hotel was about 35 minutes away, along the one main highway leading northeast to Waimea.

pebbly beach and ocean surrounding the Fairmont Orchard hotel in Hawaii

The beautiful Fairmont Orchid is in the Mauna Lani development, on a small cove-style beach with historic fish ponds and lots of rugged lava rock. The hotel itself centers around a pool that was closed for renovation (a recurring theme on this trip, as it appears that September is a popular time to do maintenance and construction) so they were offering some discounts on spa treatments to make up for it. It really didn’t impact our quick one-night stay, but would have been a bummer if we were staying for the week.

We had a drink at the pool bar, and went out to explore for a little bit, then ate dinner at a casual brewpub in the Waikoloa development (Tropics Ale House), and called it an early night.

On Monday we were up and out by 6 am (still getting used to the multiple time changes!)  We checked out, stored our bags, and got on the road to Hilo. It is about a 2 ½ hour drive across the interior of the island, through a very foreign-looking landscape, to the wetter eastern side of the island. We started at Rainbow Falls, made a quick pass through Hilo, and continued on to Volcanoes National Park. You could easily spend a whole day in the park (especially if you wanted to see the lava flows at night) but we only had a few hours, so we stopped at the info station, and at a couple of the main overlooks, and then we drove the scenic Chain of Craters road down to the coast. This provided lots of great photo ops, and we were very glad that we had gotten an early start because we only encountered one tour bus along the way.

steam rising from a crator at the volcano park in Hawaii

a couple with a hawaiian waterfall in the background

Afterwards, we took a southern route back towards Waikoloa, stopping at the beautiful Punalu’u black sand beach (where we saw a whole bunch of turtles sunning themselves!) and at the popular Punalu’u Bakery (serving malasadas, plate lunches, sweet bread, and more) Total time on the road was about nine hours, and over 200 miles, and it was fabulous!

seaturtles on a black sand beach in Hawaii

black-sand-beach in Hawaii

We retrieved our bags from the Fairmont and checked into the nearby Marriott Waikoloa Beach for the rest of our time on the island. The resort was a little more casual than the Fairmont, and had more of a mix of business/leisure clientele, but it was lovely. There was some renovation going on in the lobby and the function rooms, but the pool, restaurants, spa, etc. were all open, and the staff could NOT have been nicer…everyone from the front desk to the valet and bell staff were top notch. Our room was garden view, but comfortable and spacious.

We had dinner reservations that evening at the Canoe House (to celebrate my husband’s 50th birthday).  The restaurant is lovely, and the setting (right on the water, with stunning sunset views) is fabulous, but be prepared for sticker shock. You are definitely paying for the view and the atmosphere…not the portion sizes or attentive service. All in all, the birthday boy loved it, and that’s all that matters 🙂

Tuesday morning my husband had a full-day fishing charter, so I grabbed breakfast from the coffee shop and hit the pool.  There were romantic daybeds all around the perimeter that could be rented for $50/day (including two mai tais) but they were all already reserved. I would definitely have enjoyed that if I had planned ahead.  The Marriott’s small beach is a short (scenic) walk from the pool  – past lava rocks and fish ponds – and they have a water sports shack for kayaks, paddleboards, etc. I ate lunch at the open air restaurant, and then headed over to the nearby Mauna Lani Bay to do a site inspection and meet with the destination wedding staff. If you’re interested….it was fabulous.

mauna-lani-bay hotel in Hawaii

When Everett got back from fishing, we had cocktails at the hotel before heading over to the Lava Lava Beach Club for our dinner reservation. It’s a popular spot, and people were piling in there at sunset, but we got a decent table with a view, and I had a delicious coconut Mai Tai 🙂 The dinner menu was casual (burgers, salads and fish) but it was really all about the setting, and I’d go back there in a minute.

lava-lava beach club restaurant sign painted on surf boards in Hawaii

Wednesday we were up and out early (again) for a day of fishing. I had agreed to accompany Everett for one out of his two days, and I apparently chose the right day!  The weather was picture-perfect, we got to enjoy the sunrise as we headed out of the harbor, and Everett caught an 800 lb blue marlin!

fishing rods on a boat with mountains and a sunset in Hawaii

Back at the hotel that evening, we grabbed some celebratory frozen drinks and went for a swim. It was so relaxing to lounge in the pool listening the Marriott’s luau happening nearby. For dinner that evening, we took the fishing mate’s recommendation and went to Sansei Sushi at the nearby Queens Shops. It was absolutely fantastic!! Wish we had discovered it earlier in the week, as we would have eaten there more than once.

Thursday morning we checked out and did some shopping at the Kings and Queens Marketplace shops, all of which are within walking distance of the hotel, which is super convenient.  We picked up some souvenirs and gifts, and then headed to the airport for our flight to Maui.  Check-in at the cute little airport was really quick, and waiting at the open air gates is very relaxing 🙂 The Hawaiian Air flight was only 30 minutes…barely enough time to settle into your seat!

When we arrived in Maui, we picked up another Jeep and drove about 50 minutes to our hotel. Like the others before, the Hyatt Regency Maui was undergoing some renovations, and there were some services that were impacted (a couple of restaurants were closed). Overall, it was a much bigger and busier resort than the others we stayed in on this trip. The main lobby area has retail shops, eye-catching water features, and even some penguins on exhibit! The grounds are lushly-landscaped, with flamingos and swans roaming about. The clientele was a mix of families and honeymooners, and there were lots of younger couples around the pool and the bars. We enjoyed a deluxe ocean view room on the sixth floor, with views over the grounds to the ocean beyond, and we saw some great sunsets from there!

hyatt-selfie the front garden with lake and pathway of the Hyatt beachfront hotel in Hawaii

The resort is very conveniently-located on Kaanapali Beach, and we strolled down to Whalers Village for dinner most evenings. That first night we ate at Leilani’s on the Beach and, because we had early reservations, they were offering a special prix fixe menu (appetizer, entree and dessert for $29pp) We watched the sunset, walked back, and went to bed early.


Friday morning we were up and out by 6:30 am for our full day on the Road to Hana.  We picked up breakfast and bottled water in one of the lobby shops, and brought some towels from the hotel in case we decided to swim anywhere along the way. By far the best decision we made was to plan ahead and buy the GyPsy Guide app that synced up with our GPS and walked us through the whole route, with tips, directions, commentary, and history. We loved it!! It was a long day (9+ hours) and we skipped a lot of the stops, but we saw some breathtaking scenery, enjoyed some cool local snacks, and had fun exploring on our own. The drive was narrow and twisty, but totally manageable. Not nearly as scary as I had feared.  I would definitely recommend a stop at the Nahiku Marketplace for coconut chips and smoothies!

lush green mountains and blue sea on the road-to-hana in Hawaii

waterfall surrounded by lush greenery in Hawaii

Dinner that night was at the Hula Grill, which we loved. It’s in Whalers Village, so we were able to walk there, and we grabbed last-minute reservations on Open Table. It’s worth noting that for this one, and for Leilani’s, if you make reservations you eat in the fine dining part of the restaurant, and if you walk up you can eat in the more casual area. We loved the (more expensive) fine dining menu, and were happy to have reservations and not have to wait for a table. It had a very romantic atmosphere, with tiki torches and live music, and a great “locavore” menu.

Saturday morning we arranged a private paddle board lesson with Paddle On Maui, which departed from Polo Beach in Wailea (about 45 minutes from our hotel).  They do an early morning (7 am) paddle and a later (9:30 am) departure, which is what we booked. Peg was a fabulous instructor, and was very patient with two complete beginners 🙂 We both eventually managed to balance and stand up — it was a gorgeous morning on the water, and it was well worth the time and effort. They do offer other tours as well (kayaking, photo sessions, SUP yoga) and will even do vow renewals on paddleboards!


Peg recommended that we have lunch at the nearby Five Palms at the Mana Kai, which was a great suggestion. The hotel is a casual little condo-style resort on a pretty stretch of beach, with great views, and the open air restaurant is just steps from the sand. We enjoyed our fish tacos, and a couple of local beers!

That afternoon we strolled through Lahaina, which is a fun and funky little town (feels a little bit like Key West). We bought some souvenirs for the kids, and Everett had his first shave ice 🙂 We had dinner at Lahaina Pizza, and it was delicious. The restaurant was very crowded right at sunset, so it would be a good idea to go before 5:30 or after 7:00, but the deep dish pies were yummy and quite reasonable (for Maui).

Sunday was our last full day on Maui, and we planned a thorough exploration of Upcountry! We started with breakfast at a funky cafe in the surfer-town of Paia (Everett’s first acai bowl, lol), and then we headed inland through Makawao towards Haleakala. We wound our way through the hairpin turns leading up the mountain, marveling at the bikers speeding past us downhill (I’m really glad we didn’t do that tour!)  The weather at the top was too cloudy/rainy to see much (it’s better to be there at sunrise) but we were happy to have experienced the drive.

The first stop after that was the Alii Kula Lavender Farm, a peaceful oasis of sights, smells and even tastes (be sure to try the lavender coffee!)  We wandered the garden paths and enjoyed the views, and I was excited to see that they have a wedding gazebo for those who want something a little different than the usual beachfront ceremony. The farm would make for an amazing photo backdrop!

Suitably relaxed, we set off for some winetasting at Tedeschi Vineyards (and purchased a few bottles to bring home.)  We popped into the nearby ‘Ulupalakua Ranch Store to check out some of their tasty treats, and then made our way to the Surfing Goat Dairy Farm. We just missed the last tour (bummer!) so it would have been smart to have checked that timing in advance, but they have a take-out window and we did NOT miss out on sampling some of their specialty cheeses!  The last stop in our Upcountry Adventure was the Hawaii Sea Spirits Organic Farm and Distillery, home of Ocean Organic Vodka and Deep Island Hawaiian Rum. We did a tour and tasting, picked up a little “sample” to bring home (along with some inspiring recipes), and wandered the scenic grounds (which are ALSO available for weddings and events).

Anne on a bench amoung the flowers on a lavender farm in Hawaii

sea-spirits signs in Hawaii

When we eventually wound our way back down to Kaanapali, we picked up our bags from the Hyatt and moved over to our final hotel, the Royal Lahaina, which is about a mile down the beach. Older, smaller, more casual and more traditional than the flashy Hyatt, the Royal Lahaina was a lovely low-key way to end our trip. We had a deluxe oceanfront room with the most amazing views – it felt like we were right ON the water, on a boat – and the stretch of beach out front was arguably the best we saw the entire trip.

royal-lahaina hotel room view looking from the room out to the balcony and the ocean sunset in Hawaii royal-lahaina-beach

It’s hard to believe that we had any appetite after a full day of tasting Maui’s finest local products, but we had a dinner reservation at Duke’s Beach House, and we wanted to make the most of our final evening. Dinner was yummy, the service was attentive, and the beachfront setting (at the Honua Kai resort) was beautiful.

Monday morning we slept in, packed up, and drove back to Paia to do some window-shopping at the cute little boutiques and shops. We watched the surfers at Ho’Okipa Beach Park, and then enjoyed a decadent lunch at Mama’s Fish House. Mama’s is always the most-recommended restaurant on Maui, and I now know why. The beachfront setting is gorgeous, the interior is interesting and eclectic, the history is tangible (there are old photos and letters from celebrities on the walls) and the service is impeccable. Our meal was to-die-for, and I didn’t even care when the bill came.


After lunch, it was time to face the inevitable. We drove back to the airport, returned the Jeep, and boarded our overnight flight back home 🙁

If anything, this trip made me love Hawaii even MORE than I did before, because I got to see so much of the interior of the islands, beyond the beaches. For my husband, who was making his first visit to Hawaii, I think his main takeaway might be that it was SO worth the long flight. We’re already talking about when and how to go back. The next trip has to include Kauai and Oahu, so that he can see Pearl Harbor!

You provided excellent guidance for us. I appreciated that you really had us think about what was most important to us when we were selecting the right cruise – and not to totally focus on what other people had to say. THANK YOU for helping to make this a memorable trip for our family! It really was a trip of a lifetime!

Clare and Mark (family cruise to Alaska)

The level of service we experienced was out of this world (and we did NOT make it easy on Ann). We weren’t quite sure where we wanted to go, when we would be able to go, or what “vibe” we were going for. After asking us some key questions (what we liked, didn’t like, why, etc.) Ann helped us narrow down our trip details and planned the honeymoon of our dreams. She helped book some of our excursions, answered some emergency questions while abroad and was always available/willing to help. I think it’s safe to say we won’t be using anyone else for future travel planning – Ann is a rockstar!

Carli (Italy and Spain)