Shannon O'Brien Travel Itineraries

The best destinations

Road to Hana aerial - Maui, Hawaii
Road to Hana aerial - Maui, Hawaii

The Best of Hawaii

#12 best destination in the world

Map view

Hapuna Beach, Hapuna Beach State Recreation Area, Hawaii

Hapuna Beach State Park, Hawai’i Big Island - Aerial View

Walk difficulty: moderate

Best time to visit: Sept-Nov

  • Hapuna Beach is a renowned beach located on the Kohala Coast of the Big Island of Hawaii
  • Visitors can enjoy views of the surrounding landscape, including the Mauna Kea and Hualalai volcanoes

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

Hawaiian Volcanoes National Park - Kīlauea Iki

Best time to visit: Sept-Nov

  • Kīlauea Iki and the Crater Rim Trail are popular hiking destinations located within Hawai'i Volcanoes National Park on the Big Island of Hawaii
  • The Kīlauea Iki Trail offers a hiking experience that takes you down into a solidified lava lake within the Kīlauea Iki Crater
  • The Crater Rim Trail runs along the northern and southern rims of the Kīlauea caldera, offering views of the volcanic landscape, such as overlooks and steam vents

Nāhuku (Thurston Lava Tube) Trail, Hawai'i Volcanoes National Park, Hawaii

Entrance of the Turston Lava Tube in Hawaii Volcano National Park. HDR image created by combining three exposures.

Walk difficulty: easy

Best time to visit: Sept-Nov

  • The Nāhuku (Thurston Lava Tube) Trail is a hiking destination located within Hawaiʻi Volcanoes National Park on the Big Island of Hawaii
  • Nāhuku, also known as the Thurston Lava Tube, is around 500 years old and formed from the flow of low-viscosity lava
  • The lava tube itself is about 600 feet long and offers a unique opportunity to walk through a natural underground cave

Mauna Kea, Hawaii

Milky Way over telescope domes on Mauna Kea, HAwaii.

Best time to visit: Sept-Nov

  • Mauna Kea is a dormant shield volcano located on the Big Island of Hawaii
  • It is the highest point in Hawaii and the tallest mountain in the world when measured from its base on the ocean floor, standing at an elevation of 4,207.3 meters (13,803 feet)
  • Mauna Kea is also significant for astronomy, hosting several observatories due to its high altitude and clear skies, which provide excellent conditions for astronomical observations

Carlsmith Beach Park, Hilo, Hawaii

Small Island and Lava Rock Shoreline, Carlsmith Beach Park, Hilo, Hawaii Island, Hawaii, USA

Best time to visit: Sept-Nov

  • Carlsmith Beach Park, also known as Four Mile Beach, is a public beach located on the Big Island of Hawaii
  • It is renowned for its calm, shallow waters and protected lagoons, making it an ideal spot for swimming and snorkeling
  • The park also offers the opportunity to see honu (green sea turtles) and various fish species in the water
  • It's also possible to spot the occasional humpback whale during their migration season

Heavenly Hawaiian Kona Coffee Farm Tours & Konalani Coffee Bar, Holualoa, Hawaii

Coffee beans in the bag

Best time to visit: Sept-Nov

  • Heavenly Hawaiian Kona Coffee Farm Tours & Konalani Coffee Bar is a renowned coffee farm located in Holualoa, Hawaii, on the Big Island
  • Established in 1994, it specializes in growing, processing, and roasting 100% Kona Coffee
  • The farm provides walking tours that cover the entire coffee production process, and visitors can sample the farm's best coffees during the tour

The Vanillerie, Kailua-Kona, Hawaii

Photo of The Vanillerie

Best time to visit: Sept-Nov

  • The Vanillerie is a vanilla farm located on Hawaii's Big Island
  • The farm invites visitors to explore the world of vanilla through tours where they can see, smell, taste, and feel vanilla growing on the vine in a unique setting
  • The Vanillerie specializes in hand-grown vanilla and offers various products, including vanilla extract

Lydgate Farms Kauai Chocolate, Kapaa, Kauai

Photo of Lydgate Farms Kauai Chocolate

Best time to visit: April-June, Aug-Oct

  • Lydgate Farms is a chocolate farm located on Kauai
  • It specializes in producing high-quality, single-origin Hawaiian chocolate, as well as vanilla and honey sourced from its own farm
  • The farm offers guided tours that include tastings and educational insights into the cultivation and production of chocolate

Waimea Canyon State Park, Kauai

Hawaii Kauai Waimea canyon lookout picnic place

Best time to visit: April-June, Aug-Oct

  • Waimea Canyon State Park is located on the island of Kauai, and stands as a geological formation stretching approximately 10 miles long, reaching depths of up to 3,500 feet, and is about 1 mile wide at its widest point
  • The park features a scenic drive with multiple lookouts that offer views of the canyon and surrounding landscapes

Hanalei Bay, Kauai

Kauai, Hawai, USA - January 28, 2024: Hanalei Pier in Kauai, Hawai, USA. Hanalei Pier is a pier built into Hanalei Bay on the northern shore of the island of Kauai.

Best time to visit: April-June, Aug-Oct

  • Hanalei Bay is the largest bay on the north shore of Kauai, where it features a crescent shape and is renowned for its picturesque views and beaches
  • The bay is home to several beaches, including Hanalei Beach, which is favored for swimming, kayaking, and other water sports
  • The Hanalei Pier, built in the late 19th century, served as a transportation hub for rice and sugar and remains a popular gathering spot

Tunnels Beach, Kauai

Aerial shot off the coast over Tunnels beach on Hawaiian island of Kauai with Na Pali mountains behind

Best time to visit: April-June, Aug-Oct

  • Tunnels Beach, also known as Makua Beach, is located on the North Shore of Kauai
  • The beach gets its nickname from the extensive network of lava tubes that can be found within its coral reef
  • Tunnels Beach is famous for its exceptional coral reef teeming with marine life, including turtles, fish, and even Hawaiian monk seals

Nā Pali Coast State Park, Kauai

An aerial helicopter tour view of Kalalau Beach and the Kalalau Valley on the famous Na Pali Coast on the northwestern side of the island of Kauai, Hawaii, United States.

Best time to visit: April-June, Aug-Oct

  • Nā Pali Coast State Park is a park located on the northwest side of Kauai, that encompasses a 16-mile stretch of dramatic coastline characterized by towering sea cliffs, lush valleys, and pristine beaches
  • The cliffs, known as pali, rise up to 4,000 feet above the Pacific Ocean, creating a rugged landscape
  • The park is a destination for outdoor activities such as hiking and kayaking
  • Access to the Nā Pali Coast is limited; it can primarily be reached by hiking or by sea, with guided tours available during the summer months

Poipu Beach Park, Poʻipū, Kauai

the afternoon on the Poipu beach, Kauai, light sand, pure ocean

Best time to visit: April-June, Aug-Oct

  • Poipu Beach Park is a beach located on the southern shore of Kauai
  • The park is well-suited for swimming, snorkeling, bodyboarding, and surfing
  • It has areas designated for both calm swimming and more challenging surf breaks for experienced surfers

Princeville Botanical Gardens, Kauai

Princeville Botanical Garden, Princeville, Kauai, Hawaii

Best time to visit: April-June, Aug-Oct

  • The Princeville Botanical Gardens are a botanical garden in Kaua'i
  • The area farms chocolate, honey, and a variety of fruits, giving tours and tastings of them
  • Most of the plants that reside in the gardens are a combinations of tropical, canoe, medicinal, and endangered/rare plants

Haleakalā Crater, Haleakalā National Park, Maui

Caldera of the Haleakala volcano (Maui, Hawaii)  - HDR image

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

  • Haleakalā Crater is a prominent geological feature located at the summit of Haleakalā, an active shield volcano on the island of Maui
  • Contrary to common belief, Haleakalā Crater is not a volcanic caldera formed by collapse but rather a large erosional valley, which was shaped primarily by erosion over approximately 145,000 years
  • The crater's unique structure results from the erosion of lava flows that erupted around the volcano's summit

Waiʻanapanapa State Park, Hana, Maui

The famous black sand beach and crystal blue water at Waiʻanapanapa State Park, in Hana on the eastern side of the island of Maui, Hawaii, United States.

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

  • Waiʻanapanapa State Park is a park located in Hana, on the island of Maui
  • It features a dramatic volcanic coastline, renowned for its black sand beaches, freshwater caves, and panoramic coastal views, making it a popular destination for visitors along the famous Hana Highway

Road to Hana, Maui

Road to Hana aerial - Maui, Hawaii

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

  • The Hana Highway, also known as the Road to Hana, is a scenic 64.4-mile (103.6 km) route located on the coast of Maui,
  • It connects the town of Kahului to Hana and is known for its coastal views, winding roads, lush rainforests, and numerous waterfalls
  • The highway is known for its narrow, twisting roads with many turns and over 50 bridges, some of which are one-lane
  • The road is dotted with cultural and historical landmarks, providing insight into Maui's heritage

Ka'anapali Beach, Lahaina, Maui

Looking down on Kaanapali Beach, Maui, Hawaii

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

  • Ka'anapali Beach is a renowned beach located on the coast of Maui
  • The beach is flanked by several resorts, restaurants, and shopping areas
  • Ka'anapali Beach is known for its diverse recreational activities, including swimming, snorkeling, and cliff jumping
  • It is also a location for spotting marine life, such as Hawaiian green sea turtles

Nāpili Bay, Lahaina, Maui

Photo of Napili Bay

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

  • Nāpili Bay is a beach located on the coast of Maui, known for its crescent-shaped sandy shoreline, which is fringed by coconut palms
  • The bay is sheltered by a reef, making it ideal for swimming, snorkeling, and other water activities like kayaking and stand-up paddleboarding
  • Nāpili Bay is a great spot for observing marine life, including tropical fish and sea turtles

Maui Pineapple Tour, Makawao, Maui

A pineapple still on the plant

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

  • The Maui Pineapple Tour is a popular attraction located at the Maui Gold Pineapple Farm in Upcountry Maui
  • This tour offers visitors a unique opportunity to explore one of the only working pineapple plantations in the United States
  • Guests can walk through the pineapple fields, learn about the history and cultivation of pineapples, and see the harvesting process
  • Each participant receives a boxed, airport-ready pineapple as a souvenir

Big Beach, Makena State Park, Maui

Big Beach at Makena State Park in Maui Hawaii

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

  • Big Beach, also known as Makena Beach or Oneloa, is one of the largest beaches located within Makena State Park on the coast of Maui
  • The beach is particularly known for its large shore breaks, making it a favorite spot for experienced surfers and boogie boarders
  • The park features scenic landscapes, including cinder cones and black lava outcroppings, enhancing its natural appeal

H.A. Baldwin Beach Park, Paia, Maui

Baldwin beach, maui island, hawaii, united states of america, north america

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

  • H.A. Baldwin Beach Park is a beach park located on the North Shore of Maui
  • The park is ideal for bodysurfing, bodyboarding, swimming, and other beach sports
  • Originally a private recreation area for employees of the Hawaiian sugar industry, H.A. Baldwin Beach Park became public in 1963

Hoʻokipa Beach Park, Paia, Maui

Ho'okipa Beach Park in Maui Hawaii, renowned windsurfing and surf site for wind, big waves and big Turtles drying on sand. Snorkeling paradise for coral reefs.

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

  • Hoʻokipa is a beach on the north shore of Maui
  • The beach is perhaps the most renowned windsurfing site in the world
  • A combination of large, well-shaped waves breaking across a system of reefs that extend across the bay and consistently strong winds make it ideal for the sport
  • Ho'okipa Beach is occasionally a tourist attraction in the winter time because of spectacularly large surf

Wailea Beach, Maui

Pathway to Maui Wailea Beach

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

  • Wailea Beach is a renowned beach located in Wailea, Maui
  • Wailea Beach is popular for swimming, sunbathing, and snorkeling, making it suitable for outdoor enthusiasts
  • Visitors can enjoy views of nearby islands like Kaho'olawe and Molokini, especially during the winter months when whale sightings are common

Hanauma Bay, Honolulu, Oahu

An aerial view of Hanauma Bay on the island of O'ahu in Hawaii

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

  • Hanauma is a marine embayment formed within a tuff ring and located along the southeast coast of Oʻahu
  • Hanauma Bay is known for its abundance of Green sea turtles and coral reefs, making it ideal for snorkelers
  • The park requires online reservations for all non-residents
  • Upon entry, first-time visitors are required to watch a 9-minute video about the bay, its history, its delicate ecosystem, and how to sustainably visit the Bay, causing as minimal damage to the area as possible

Manoa Falls, Honolulu, Oahu

the falling waters of Manoa Falls surrounded by lush green trees, plants and foliage in Honolulu Hawaii USA

Walk difficulty: moderate

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

  • Mānoa Falls is a 150-foot waterfall along the Manoa Falls Trail in Honolulu
  • Since the area surrounding the waterfall is considered a tropical rainforest, it is prone to heavy rainfall often making the ground damp and muddy
  • The high amount of precipitation leads to a high amount of plant life near the falls

Waikīkī Beach, Honolulu, Oahu

Honolulu, Hawaii. Waikiki beach and Honolulu's skyline.

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

  • Waikiki Beach is a renowned beach located in the Waikiki neighborhood of Honolulu, in Oʻahu
  • Once a playground for Hawaiian royalty, Waikiki has transformed into a center for surfing, swimming, and snorkeling
  • The beach offers views of Diamond Head, a volcanic crater, and one of Hawaii's most recognizable landmarks

Pearl Harbor National Memorial, Honolulu, Oahu

Aerial view of USS Arizona Memorial, World War II Valor In The Pacific National Monument in Pearl Harbor Honolulu Hawaii

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

  • Pearl Harbor National Memorial is a unit of the National Park System on the island of Oahu
  • The site commemorates the events of the attack on Pearl Harbor on December 7, 1941, which killed over 2,400 Americans and sank twelve ships
  • The site includes the USS Arizona Memorial, the USS Utah memorial, the USS Oklahoma memorial, six chief petty officer bungalows on Ford Island, mooring quays F6, F7, and F8, which formed part of Battleship Row, and the visitor center at Halawa Landing
  • Visitors can take a ferry to the Arizona memorial

ʻIolani Palace, Honolulu, Oahu

Ali'iolani Hale or House of the Heavenly King was designed as a palace and built in 1874. It was never used and now houses the Supreme Court of Hawaii.

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

  • The ʻIolani Palace was the 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
  • It is located in Honolulu, on the island of O'ahu
  • 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
  • ʻIolani Palace is the only royal palace on US soil

USS Arizona Memorial, Honolulu, Oahu

Aerial view of USS Arizona Memorial, World War II Valor In The Pacific National Monument in Pearl Harbor Honolulu Hawaii

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

  • The USS Arizona Memorial is a significant national memorial located at Pearl Harbor in Honolulu
  • It commemorates the lives lost during the attack on Pearl Harbor on December 7, 1941, specifically honoring the 1,177 sailors and Marines who died aboard the battleship USS Arizona
  • Built in 1962, the memorial spans 184 feet across the sunken ship
  • The memorial attracts thousands of visitors daily, offering a solemn space for reflection and remembrance

Koko Crater Arch Trail from Halona Blowhole Lookout, Honolulu, Oahu

Koko crater arch, honolulu, hawaii

Walk difficulty: moderate

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

  • The Koko Crater Arch Trail is a scenic hiking trail located near the Halona Blowhole Lookout on Oahu
  • The trail offers hikers a chance to explore a natural rock formation known as the Koko Crater Arch, which has been shaped by wind and erosion

Diamond Head Crater (Lēʻahi) Summit Trail, Honolulu, Oahu

Honolulu, Hawaii - December 27, 2022:  Tourists hiking on the Diamond Head lookout trail.

Walk difficulty: moderate

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

  • The Diamond Head Crater (Lēʻahi) Summit Trail is a hiking trail located in the Diamond Head State Monument on the island of Oahu
  • The trail is renowned for its panoramic views of Honolulu and the surrounding coastline
  • The hike includes two sets of stairs (totaling 175 steps), dark tunnels, and remnants of old military bunkers, reflecting its historical significance as part of Oahu's coastal defense system established in 1908

Lanikai Beach, Kailua, Oahu

Drone photo of Lanikai Beach on the island of Hawaii

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

  • Lanikai Beach, also known as Kaʻōhao Beach, is located in the community of Kaʻōhao on the coast of Oahu
  • The beach is particularly famous for its picturesque views of the Mokulua Islands, which are visible just offshore

Duke's Beach, Oahu

Diamond Head Crater seen from Duke Kahanamoku  Beach, Honolulu Oauhu

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

  • Duke's Beach, also known as Duke Kahanamoku Beach, is located in Waikīkī, Oahu
  • The beach is part of the famous Waikīkī Beach and is situated in front of the Hilton Hawaiian Village and the Duke Kahanamoku Lagoon
  • It is named in honor of Duke Paoa Kahanamoku, an Olympic swimmer and a celebrated figure in Hawaiian culture

Makapu'u Point Lighthouse Trail, Waimānalo, Oahu

Trail to Makapu'u Point Lighthouse, Oahu, Hawaii

Walk difficulty: moderate

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

  • The Makapu'u Point Lighthouse Trail is a hiking trail located on the southeastern coast of O'ahu, Hawaii
  • The trail offers stunning views of O'ahu's coastline, including sights of Koko Head, Koko Crater, and the Pacific Ocean
  • The Makapu'u Lighthouse dates back to 1909 and was established following the grounding of a ship in 1888, which highlighted the need for a lighthouse in the area