Itinerary

Aloha! An important Hawaiian word of many meanings, that’s what you’ll hear people say upon greeting you to the islands. You’ll be landing in the capital, Honolulu, Hawai’i’s largest city where tropical nature blends seamlessly with urban living, and local life is rooted in both Hawaiian tradition and the unique melting pot of cultures that call Hawai’i home.

Collect your rental car and make your way to your hotel. You’ll be staying at the edge of the world-famous Waikīkī Beach just beneath the breathtaking Diamond Head (Lē’ahi) Crater. Get settled in and if you have the energy after your flight, stroll Waikīkī’s golden shores or stop somewhere locally for dinner. Island cuisine generally features fresh ingredients from both the land and sea, and features influences from Polynesian, Asian (i.e. Japanese, Chinese, Filipino), Portuguese and American cultures.

Honolulu has a rich past, from royal and missionary history to both natural and living culture – so spend today exploring at your own pace.

Tour ‘Iolani Palace, the only royal palace in the United States, where ornate rooms and carefully preserved artefacts tell the story of Hawai’i’s monarchy and its final reigning sovereigns. Nearby sits Kawaiaha’o Church, the oldest Christian church in the islands, built in the 1840s from massive coral blocks and a designated National Historic Landmark.

Alternatively, head to Bishop Museum. The state’s premier natural and cultural history institution, here you can explore immersive exhibits showcasing ancient Hawaiian navigation, royal artefacts, feather work and stories of Polynesian voyaging alongside fascinating displays on volcanology, native ecosystems and Pacific Island cultures. If time allows, finish your visit with a planetarium show for a deeper look at the stars that once guided Hawaiians across the Pacific.

This morning, you might like to experience one of O‘ahu’s classic highlights: a hike to the summit of Diamond Head, the island’s iconic volcanic crater. The well-marked, easy-going trail climbs steadily along switchbacks and past historic military bunkers, with a few staircases and tunnels adding a sense of adventure. If you choose to make the ascent, you’ll be rewarded at the top with sweeping panoramic views stretching from the turquoise shoreline of Waikīkī to the rugged slopes of the Ko’olau Mountains.

In the evening, you’ll head to a historic hillside estate overlooking Honolulu for an intimate luau. Rather than a large stage production, this evening combines storytelling, traditional games, music and the Hawaiian dance form of hula with sweeping views from downtown Honolulu up to the Wai’anae Range for a more immersive and participatory experience. Afterwards, you’ll be treated to a feast of traditional Hawaiian dishes to round off the night.

After the fun of last night, you’ll spend today relaxing and unwinding on the beautiful shores of Kailua Bay. One of O’ahu’s most breath taking spots for swimming, sunbathing or simply relaxing with your toes in the sand, you’ll start with a two-hour kayak adventure across the bay’s calm, clear waters – usually filled with Hawaiian green sea turtles – to nearby Popoi’a Island, a protected seabird sanctuary just off the main shore. Here, you’ll stop for an easy guided walk along the island’s coastal trail before returning to Lanikai Beach in Kailua Bay to spend the rest of the day relaxing in the postcard-worthy scenery.

Today, you’ll take a short flight for your next destination: Maui. Often considered Hawai’i’s most charming island, Maui boasts beautiful beaches, incredible greenery and friendly, laidback towns for whiling away the day and night. Once you arrive, you’ll collect your rental car and get settled into your hotel in Kīhei on the tranquil south shore of the island.

Come late afternoon, you’ll be picked up by a guide who will drive you through Maui’s charming Upcountry towns and farms before ascending the summit of the dormant volcano in Haleakalā National Park. In Hawaiian mythology, the demigod, Māui, lifted the Hawaiian Islands from the depths of the sea by lassoing the sun from the island’s highest peak, Haleakalā, bringing daylight to the islanders—and on today’s tour, you’ll get to see the spectacular sunset from that very same peak.

You’ll also get to witness some of the best stargazing in Hawai’i once the sun sets, and hear stories of Hawaiian history, geology and ecology from your guides. A picnic-style dinner completes this unforgettable evening experience.

Today you have the option of taking a scenic, self-guided drive around West Maui via the Honoapi’ilani and Kahekili Highways where rugged coastline, calm beaches and small villages offer a taste of old Hawai’i.

We suggest an early stop at Napili Bay for tranquil waters and picturesque views, before continuing to Honolua Bay to walk the shoreline trail and search for sea life in the clear waters of the reef-fringed cove. Then, as the road narrows and the landscapes turn wilder, pause at Nakalele Blowhole to watch ocean swells surge through lava rock, and, when conditions are safe, respectfully admire the vivid basalt and tide-fed basins at the Olivine Pools. Finish with a stop in Kahakuloa for a taste of fresh banana bread or browse the local art galleries and roadside stands before winding back along cliffside roads and sweeping overlooks. The drive takes around 2.5 hours, but you can make a full day of it allowing time for all the incredible stops.

Alternatively, spend the day relaxing by the ocean in Kīhei – you’ll be hard pressed to find a more beautiful area to go to the beach.

Today you have the option of taking a scenic, self-guided drive around West Maui via the Honoapi’ilani and Kahekili Highways where rugged coastline, calm beaches and small villages offer a taste of old Hawai’i.

We suggest an early stop at Napili Bay for tranquil waters and picturesque views, before continuing to Honolua Bay to walk the shoreline trail and search for sea life in the clear waters of the reef-fringed cove. Then, as the road narrows and the landscapes turn wilder, pause at Nakalele Blowhole to watch ocean swells surge through lava rock, and, when conditions are safe, respectfully admire the vivid basalt and tide-fed basins at the Olivine Pools. Finish with a stop in Kahakuloa for a taste of fresh banana bread or browse the local art galleries and roadside stands before winding back along cliffside roads and sweeping overlooks. The drive takes around 2.5 hours, but you can make a full day of it allowing time for all the incredible stops.

Alternatively, spend the day relaxing by the ocean in Kīhei – you’ll be hard pressed to find a more beautiful area to go to the beach.

Alternatively, choose to extend your stay in the Hawaiian Islands or at a destination of your choosing on the USA mainland before returning home.

Contact us for ideas and inspiration.