21 days in Hawaii Itinerary

Step off the beaten path and head to Lanikai Beach and Waimea Valley. Your itinerary includes some good beach time at Kailua Beach Park and Ala Moana Beach Park. Get out of town with these interesting Honolulu side-trips: Waimanalo Beach (in Waimanalo), Shark's Cove (in Pupukea) and Haleiwa (Laniakea Beach, Sunset Beach Park, &more). There's lots more to do: hike along Koko Crater Railway Trail, contemplate in the serene atmosphere at Byodo-In Temple, admire the sheer force of Manoa Falls, and get to know the fascinating history of Makapuu Lighthouse Trail.

For more things to do, reviews, and other tourist information, you can read our Honolulu vacation planner.

Seattle to Honolulu is an approximately 7.5-hour flight. The time zone changes from Pacific Standard Time (PST) to Hawaii-Aleutian Standard Time (HST), which is usually a -2 hour difference. In May, Honolulu is a bit warmer than Seattle - with highs of 84°F and lows of 71°F. Finish your sightseeing early on the 16th (Tue) to allow enough time to fly to Lihue.

You'll get in some beach time at Hanalei Beach and Kalapaki Beach. Take a break from the city and head to Wailua Falls and Sleeping Giant Trail. Venture out of the city with trips to Na Pali Coast State Park (in Wainiha) and Aloha Spice Company (in Hanapepe).

To find where to stay, ratings, reviews, and tourist information, read Lihue trip planner.

You can fly from Honolulu to Lihue in 2.5 hours. Expect a daytime high around 82°F in May, and nighttime lows around 71°F. Finish your sightseeing early on the 19th (Fri) to allow enough time to fly to Kailua-Kona.

Relax by the water at Pu'uhonua O Honaunau National Historical Park and 49 Black Sand Beach. Get in touch with nature at Fishing Charters & Tours and Manini'owali Beach (Kua Bay). Change things up with these side-trips from Kailua-Kona: Kealakekua Bay (in Captain Cook) and Hapuna Beach State Recreation Area (in Puako). It doesn't end there: look for all kinds of wild species at Kanaloa Octopus Farm and experience rural life at Hula Daddy Kona Coffee.

To see more things to do, reviews, where to stay, and tourist information, you can read our Kailua-Kona trip itinerary builder tool.

You can fly from Lihue to Kailua-Kona in 2.5 hours. In May in Kailua-Kona, expect temperatures between 83°F during the day and 73°F at night. Finish your sightseeing early on the 22nd (Mon) to allow enough time to drive to Hilo.

Kick off your visit on the 23rd (Tue): enjoy the sand and surf at Richardson Beach Park, see the interesting displays at Pacific Tsunami Museum, then admire the natural beauty at Hawaii Tropical Bioreserve and Garden, then admire the natural beauty at Liliuokalani Gardens, and finally take in the dramatic scenery at Rainbow Falls. Keep things going the next day: take in the dramatic natural features at Thurston Lava Tube (Nahuku), hike along Kilauea Iki Trailhead, and then get impressive views of Kīlauea.

For more things to do, other places to visit, maps, and more tourist information, read our Hilo trip planner.

Getting from Kailua-Kona to Hilo by car takes about 1.5 hours. Other options: take a bus. Traveling from Kailua-Kona in May, you can expect nighttime temperatures to be a bit cooler in Hilo, with lows of 67°F. Wrap up your sightseeing on the 24th (Wed) early enough to fly to Kihei.

Discover out-of-the-way places like Zipline and Ho'okipa Beach Park. Your itinerary includes some good beach time at Kapalua Beach and Napili Beach. You'll find plenty of places to visit near Kihei: Parasailing & Paragliding (in Ka'anapali), Lahaina (Hale Pa'i Printing Museum & Kapalua Coastal Trail) and Haliimaile Distilling Company (in Makawao). Next up on the itinerary: stroll through Kamaole Beach Park III, enjoy the sand and surf at Kamaole Beach Park II, sample the tasty concoctions at Maui Brewing Company, and get engrossed in the history at Story of Hawaii Museum.

Plan a Kihei trip in moments using our itinerary builder.

You can fly from Hilo to Kihei in 2.5 hours. In May in Kihei, expect temperatures between 86°F during the day and 68°F at night. You will have some time to spend on the 29th (Mon) before leaving for home.