Essential Guide to Planning a Multi-Island Hawaii Adventure

These eight tips will help you travel between Hawaii’s islands with ease.

The Hawaiian archipelago includes more than 100 islands, atolls, and islets. However, don’t worry if you’re planning a visit; you need not plot a 100-island itinerary. With the majority of the islands uninhabited and inaccessible, you can focus on four of the eight largest islands: Kauai, Oahu, Maui, and the Island of Hawaii (often referred to as the Big Island), with the option to add a few others.

Here are some tips for planning an epic multi-island trip to Hawaii.

Determine travel dates and destinations

Ideally, you should spend at least one week on each of the four islands. However, if you don’t have a full month, planning for four to five days per island is practical, then choose one or two regions within each.

Make a list of activities you wish to do in order of importance. This will help you determine where to base yourself on each island and what to eliminate if necessary. For instance, if visiting an active volcano and night snorkeling with manta rays top your list, consider staying at the historic Volcano House—the only lodging within Hawaii Volcanoes National Park. You can also spend a few nights at Mauna Kea Resort or The Westin Hapuna Beach Resort on the Kona side, where you can join a guided small group night snorkel with Manta Ray Advocates.

Moreover, don’t forget to factor in flight and drive times. Although some islands seem small on the map, weather, road conditions, and traffic can significantly impact overall travel time.

Also, consider when to go. Hawaii has microclimates, meaning weather can vary considerably; generally, summer is warm with minimal rainfall—ideal for beach lovers. However, be informed that it’s also peak travel time, especially during family summer breaks. Expect higher rates and larger crowds during this time, as well as during major U.S. holidays such as Easter, Thanksgiving, Christmas, and New Year’s.

Identify your travel style

Some travelers crave leisurely days at the beach, while others prefer an action-packed itinerary. Additionally, some enjoy vibrant, larger cities, while others appreciate the charm of smaller towns. Therefore, discussing your expectations and interests with travel companions is vital, so you can focus on the regions, tours, and accommodations best suited to your styles.

Conduct thorough research. It’s common for visitors to claim Oahu is “too busy,” yet they haven’t ventured beyond Honolulu. As the capital city with about one million residents, yes, it can be busy. Seek out peaceful locations amidst the hustle, such as Espacio and The Ritz-Carlton Residences, Waikiki Beach, both providing serene retreats. Conversely, if urban life does not appeal to you, skip Honolulu and explore other regions of Oahu.

While tempting to schedule every hour of your itinerary for maximum enjoyment, avoid overbooking. Leave ample time for relaxation between activities; balance is vital to prevent exhaustion. For example, follow an active day of touring with leisure time or a spa treatment.

Plan your route

Although you can begin and end your trip wherever you choose, examining flight schedules aids in mapping an efficient route. Kauai is situated in the northwest while the Island of Hawaii is in the southeast. Thus, starting in Kauai and traveling southeast—first to Oahu, then Maui, and finally the Island of Hawaii—makes logistical sense. This route offers a delightful variety, transitioning from the relaxed pace of Kauai to urban adventures and countryside cruising on Oahu and Maui, culminating with the dynamic atmosphere of volcanic activity on the Island of Hawaii. Moreover, this route aligns with the order in which the islands were formed, granting you the opportunity to experience them from oldest to youngest, observing the geological evolution along the way.

While booking flights, consider opting for a multicity rather than a standard round-trip option. For instance, when traveling the proposed Kauai to Island of Hawaii route, you might arrive in Kauai, then secure interisland flights to Oahu, Maui, and finally depart from Kona. Be aware that some interisland flights are not direct and may require a stopover in Honolulu or Kahului, so check your itinerary thoroughly before booking. You can typically find direct interisland flights by selecting an earlier departure time.

Enlist the help of experts

While exploring the islands independently is feasible, consider booking guided experiences. Native Hawaiian guides and cultural practitioners enrich your visit with personal stories and context that create a more immersive experience. Moreover, by booking with Native Hawaiian experts, you support the perpetuation of Hawaiian culture.

Many hotels, including ‘Alohilani Resort and Waikiki Beach Marriott Resort & Spa on Oahu and Ka’anapali Beach Hotel on Maui, increasingly offer complimentary, Native Hawaiian-led activities, encompassing hula lessons, Hawaiian language sessions, lei-making practices, and sunrise ceremonies. Other properties, such as Timbers and Kukui’ula on Kauai, provide farm tours that introduce guests (and their taste buds) to local plant and produce varieties. Certain hotels, including Halekulani, also offer private tours or discounted/free entry to local cultural sites, such as Bishop Museum, Iolani Palace, and Shangri La Museum of Islamic Art, Culture, and Design. Be sure to inquire about such offerings before securing your hotel accommodations.

For adventurous activities like hiking, engaging a reputable tour operator such as Kauai Hiking Tours can enhance safety and enjoyment. Additionally, select tours provide access to remarkable locations, including Hualalai crater, a sacred site only accessible through specific tour operators—Uluha’o O Hualalai and Hawaii Forest & Trail.

Some expert-led trips from operators like Kailani Tours can help you maximize your experience by taking you to various sites in a single day, allowing you to relish the views while sidestepping logistical concerns.

Make reservations

Many popular spots like Hanauma Bay on Oahu now require reservations, and sought-after tours including sunrise at Haleakalā on Maui and sunset at Mauna Kea on the Island of Hawaii often book out, meaning it’s wise to make reservations as far in advance as possible. For instance, Arnott’s Adventures provides sunset and stargazing tours from Hilo, while on the Kona side, you might check out Hawaii Forest & Trail’s Summit & Stars Give Back Experience.

Furthermore, securing dinner reservations ensures you don’t miss top dining options or waste time waiting for a table. Additionally, consider car rentals for each island too; these often sell out, and with the exception of Honolulu, where shuttles, public buses, and ride-share options are accessible, having your own vehicle is generally necessary for convenient travels.

Pack your bags

One common mistake people make when traveling to Hawaii is assuming it’s perpetually sunny and warm. If you’re planning to visit multiple islands, you’ll likely face a variety of microclimates and changing weather conditions. Therefore, come prepared with layers and proper footwear for your activities, and always include a rain jacket. And, of course, pack a Hawaiian shirt or two.

Don’t forget to bring binoculars for better viewing of wildlife, such as endemic birds and migrating whales, plus Hawaii’s stunning landscapes. If you’re fortunate to witness volcanic activity, you’ll appreciate having them for a closer look at bubbling lava. Some tours provide outdoor gear and equipment, so inquire when booking.

Consider additional islands

If you have time and wish to incorporate another island into your trip, several options await visitors. For instance, you can take a ferry from Maui to Lanai for a day trip or spend a night or two there to submerse yourself in the relaxed island experience.

If you’re interested in visiting Kalaupapa National Historical Park on Molokai, allocate a few extra days for exploration. Note that flights to Molokai are limited, and as the island is home to vulnerable kupuna (elderly residents), it’s gradually reopening to visitors post-pandemic.

For an exclusive tour of a neighboring island, Four Seasons Resort Maui at Wailea can charter a yacht or helicopter from Maui to Lanai or Molokai.

While stepping ashore on Ni’ihau, the “Forbidden Island,” requires an invitation, you can snorkel the surrounding waters via a Holo Holo Charters Super Tour.

Travel with aloha

For you, Hawaii may be a dream destination. For many residents, it’s home and sacred. Travel with respect: Stay on marked trails, do not enter private property, heed warnings (from posted signs, lifeguards, and law enforcement), and remember that the environment is delicate, with the land holding cultural, spiritual, and ecological significance.

Remain flexible, too. Don’t cling too tightly to specific expectations or activities. Plans may shift due to unforeseen meteorological conditions—for instance, that time I traveled to Kauai to see the famed cliffs of the Nā Pali Coast and the colors of Waimea Canyon, only to find it enveloped by clouds and fog. If you’re fortunate enough to visit Hawaii, embrace the unexpected, stay present, and aim to enjoy the experience—rain or shine.