Shannon O'Brien Travel Itineraries

The best destinations

Photo of Hawaii
Photo of Hawaii

The Best of Hawaii

#14 best destination in the world

Map view

Diamond Head (Le'ahi) Summit Trail

Photo of Diamond Head

Walk difficulty: Easy

Best time to visit: April-June, Sept-Dec

Cost: $

  • Volcanic tuft cone that resembles the shape of a tuna’s dorsal fin
  • Named diamond head because British sailors in the 19th century mistook calcite crystals on the beach for diamonds

Kīlauea Iki Trail and Crater Rim Trail, Hawai'i Volcanoes National Park

Photo of Hawai'i Volcanoes National Park

Best time to visit: Sept-Nov

Cost: $

  • Pit crater that is next to the main summit caldera of Kīlauea on the island of Hawaiʻi
  • It is known for its eruption in 1959 that started on November 14th and ended on December 20th, producing lava fountaining up to 1900 feet and a lava lake in the crater
  • Today, the surface of the lava lake has cooled and it is now a hiking destination to view the aftermath of an eruption

Polihale State Park, Kauai

Photo of Kauai

Walk difficulty: Easy

Best time to visit: April-June, Sept-Nov

Cost: $

  • Remote wild beach on the western side of the Hawaiian island of Kauai
  • It is the most western publicly accessible area in Hawaii, although the privately owned island of Niihau is further west
  • The park is miles away from the town of Kekaha, and it can only be reached via a poorly marked, dirt sugarcane road, making a four-wheel drive vehicle preferable
  • The beach is several miles long, yet only the area known as "Queen's Pond" offers safe swimming

Waimoku Falls via Pipiwai Trail, Haleakalā National Park

Photo of Haleakalā National Park

Walk difficulty: Moderate

Best time to visit: April-May, Sept-Nov

Cost: $

  • Haleakalā National Park is located on the island of Maui, and is named after Haleakalā, a dormant volcano within its boundaries
  • The land was designated a national park in 1976 and its boundaries expanded in 2005

Hanalei Bay

Photo of Hanalei Bay

Best time to visit: April-June, Sept-Nov

Cost: $

  • Hanalei Bay consists of nearly two miles of beach, surrounded by mountains
  • In the summer, the bay offers excellent mooring for sailboats, stand up paddle boarding and swimming
  • During the winter the surf becomes large and the bay is a favorite surfing location
  • In 1824, King Kamehameha II’s royal yacht, Pride of Hawaii, sank near the mouth of the Waiʻoli River, after its crew struck a 5-foot-deep reef a hundred yards offshore
  • In 1995–2000, archaeologists excavated the wreck and recovered more than 1,200 artifacts
  • During this excavation, a 40-foot section of the stern was discovered, documented, and then re-buried where it was discovered

Wai Koa Loop Trail, Kilauea

Photo of Kilauea

Walk difficulty: Easy

Best time to visit: Sept-Nov

Cost: $

  • The Wai Koa Loop Trail is a hike of up to 8 km (5 mi) to the foundations of the bridge piers of the former railway
  • Trail waiver forms are available that must be signed before the walk, as the trail leads through private property through a mahogany plantation and several smaller family businesses

Koko Crater Arch Trail from Halona Blowhole Lookout, Koko Crater Regional Park

Photo of Koko Crater Regional Park

Walk difficulty: Moderate

Best time to visit: April-June, Sept-Dec

Cost: $

  • Koko Crater is an extinct tuff cone located on the Hawaiian island of Oʻahu
  • During World War II, the US military built bunkers on top of Koko Crater with a railroad leading to its summit
  • Within this park is the Koko Crater Trail, which is a 1.8-mile-long trail that uses the now-abandoned railroad as its pathway

Lanikai Beach

Photo of Lanikai Beach

Walk difficulty: Easy

Best time to visit: April-June, Sept-Dec

Cost: $

  • Beach located in Kaʻōhao, a community in the town of Kailua and on the windward coast of Oahu
  • This small half-mile strip of beach is consistently ranked among the best beaches in the world

Poipu Beach Park

Photo of Poipu Beach Park

Walk difficulty: Easy

Best time to visit: April-June, Sept-Nov

Cost: $

  • Poʻipū Beach Park is located in the community of Poʻipū on the southern coast of Kauaʻi island
  • Amenities include swimming and snorkeling areas, and a surf break over a reef for experienced surfers only

USS Arizona Memorial

Photo of USS Arizona Memorial

Best time to visit: April-June, Sept-Dec

Cost: $

  • The USS Arizona Memorial, at Pearl Harbor in Honolulu, marks the resting place of 1,102 of the 1,177 sailors and Marines killed on USS Arizona during the attack on Pearl Harbor on December 7, 1941, and commemorates the events of that day
  • The attack on Pearl Harbor led to the United States' involvement in World War II
  • Accessible only by boat, it straddles the sunken hull of the battleship without touching it
  • Historical information about the attack, shuttle boats to and from the memorial, and general visitor services are available at the associated USS Arizona Memorial Visitor Center

Waikiki Beach

Photo of Waikiki Beach

Walk difficulty: Easy

Best time to visit: April-June, Sept-Dec

Cost: $

  • Beach and neighborhood of Honolulu on the south shore of the island of Oʻahu
  • Waikiki is most famous for Waikiki Beach, which is almost entirely man-made

Duke Kahanamoku Beach

Photo of Duke Kahanamoku Beach

Best time to visit: April-June, Sept-Dec

Cost: $

  • Sandy, curved beach that offers swimming, surfing, and paddle-boarding

Hawaii Tropical Botanical Garden, Hilo

Photo of Hilo

Best time to visit: Sept-Nov

Cost: $

  • Garden and nature preserve located in a scenic valley opening out to Onomea Bay, that features streams, waterfalls and a boardwalk along the ocean
  • Opened in 1984, today the garden contains over 2,000 plant species, and some of the garden's mango and coconut palm trees are over 100 years old

Kaanapali Beach

Photo of Kaanapali Beach

Walk difficulty: Easy

Best time to visit: April-May, Sept-Nov

Cost: $

  • Beach featuring resorts, eateries, shopping, plus a scenic beachwalk, swimming, and snorkeling

Kauna'oa Beach

Photo of Kauna'oa Beach

Best time to visit: Sept-Nov

Cost: $

  • Kaunaʻoa Bay has one of the few white sand beaches of the Kohala Coast, the western side of the island of Hawaiʻi
  • A historic hotel, the Mauna Kea Beach Hotel, is located on Kauna'oa

Kualoa Ranch, Oahu

Photo of Oahu

Best time to visit: April-June, Sept-Dec

Cost: $$

  • 4,000-acre (1,600 ha) private nature reserve and working cattle ranch, as well as a tourist attraction and filming location on the windward coast of Oʻahu
  • Kualoa is open for guided tours and tours on horseback

Hana Highway

Photo of Hana Highway

Best time to visit: April-May, Sept-Nov

Cost: $

  • The Hana Highway (colloquially referred to as The Road to Hana) is a 64.4-mile-long (103.6 km) stretch of Hawaii Routes 36 and 360 which connects Kahului to the town of Hana in east Maui
  • Although Hana is only about 52 miles (84 km) from Kahului, an uninterrupted car-trip takes about 2.5 hours to drive, since the highway is very windy, narrow, and passes over 59 bridges, of which 46 are only one lane wide
  • Many of the concrete and steel bridges date back to 1910 and all but one are still in use

Wailea Beach

Photo of Wailea Beach

Best time to visit: April-May, Sept-Nov

Cost: $

  • Sandy public beach with activities such as swimming and snorkeling

Puaʻena Point Beach Park, Haleiwa

Photo of Haleiwa

Best time to visit: April-June, Sept-Dec

Cost: $

  • Rocky, sandy shoreline with tide pools and small waves suitable for those new to surfing

Hapuna Beach State Recreation Area

Photo of Hapuna Beach State Recreation Area

Walk difficulty: Easy

Best time to visit: Sept-Nov

Cost: $

  • Large park and sandy beach on the Big Island of Hawaii
  • It is one of a few other white sand beaches on the west coast of the Big Island

Iolani Palace

Photo of Iolani Palace

Best time to visit: April-June, Sept-Dec

Cost: $

  • Former royal residence of the rulers of the Kingdom of Hawaiʻi beginning with Kamehameha III under the Kamehameha Dynasty (1845) and ending with Queen Liliʻuokalani (1893) under the Kalākaua Dynasty
  • After the monarchy was overthrown in 1893, the building was used as the capitol building for the Provisional Government, Republic, Territory, and State of Hawaiʻi until 1969
  • The palace was restored and opened to the public as a museum in 1978
  • ʻIolani Palace is the only royal palace on US soil

Maui Tropical Plantation, Kahului

Photo of Kahului

Best time to visit: April-May, Sept-Nov

Cost: $

  • Tropical working farm offering tram ride tours on how sugarcane and pineapples grow

Lanikai Pillbox #2, Kailua Beach Park

Photo of Kailua Beach Park

Walk difficulty: Moderate

Best time to visit: April-June, Sept-Dec

Cost: $

  • Area known for its white, powder-like sandy beach and its hiking trail along the Kaʻiwa Ridge to the World War II military bunkers commonly known as the "Lanikai Pillboxes"

Lake Waiau via Mauna Kea-Humu'ula Trail

Photo of Mauna Kea

Walk difficulty: Moderate

Best time to visit: Sept-Nov

Cost: $

  • Dormant volcano on the island of Hawaiʻi, its peak is 4,207.3 m (13,803 ft) above sea level, making it the highest point in the state of Hawaiʻi and second-highest peak of an island on Earth
  • Mauna Kea is unusually topographically prominent for its height: from its underwater base, it is greater than Mount Everest's height above sea level of 8,848.86 m (29,032 ft), and some authorities have labelled Mauna Kea the tallest mountain in the world
  • Mauna Kea last erupted 6,000 to 4,000 years ago and is now thought to be dormant

Papakolea Beach

Photo of Papakolea Beach

Walk difficulty: Moderate

Best time to visit: Sept-Nov

Cost: $

  • Papakōlea Beach (also known as Green Sand Beach or Mahana Beach) is a green sand beach located on the island of Hawaiʻi
  • It is one of only four green sand beaches in the world, the others being in Guam, Floreana Island in the Galapagos Islands; and Norway
  • It gets its distinctive coloring from olivine sand eroded out of the enclosing volcanic cone (tuff ring)

Punalu'u Bay Trail

Photo of Punalu'u

Walk difficulty: Moderate

Best time to visit: mid April-early June, Sept-mid Dec

Cost: $

  • Also called Black Sand Beach, Punalu'u Beach is on the Big Island of Hawaii
  • The beach has black sand made of basalt and created by lava flowing into the ocean which explodes as it reaches the ocean and cools
  • Punaluʻu is frequented by endangered hawksbill and green turtles, which can often be seen basking on the black sand

Tunnels Beach Track

Photo of Tunnels Beach

Walk difficulty: Moderate

Best time to visit: April-June, Sept-Nov

Cost: $

  • Low-key sand beach backed by picturesque tropical vegetation, with shallow reefs for snorkeling

Waimea Canyon Lookout, Waimea Canyon State Park

Photo of Waimea Canyon State Park

Walk difficulty: Easy

Best time to visit: June-Aug

Cost: $

  • Waimea Canyon, also known as the Grand Canyon of the Pacific, is a large canyon, approximately ten miles (16 km) long and up to 3,000 feet (900 m) deep, located on Kauaʻi
  • The canyon was formed by a deep incision of the Waimea River arising from the extreme rainfall on the island's central peak, Mount Waiʻaleʻale, among the wettest places on earth