21 days in Hawaii Itinerary

Step off the beaten path and head to Lanikai Beach and Koko Crater Railway Trail. 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: Shark's Cove (in Pupukea), Haleiwa (Laniakea Beach, Sunset Beach Park, &more) and Waimanalo Beach (in Waimanalo). There's much more to do: have unforgettable encounters with a shark diving experience, examine the collection at USS Bowfin Submarine Museum & Park, enjoy the sand and surf at Turtle Bay Beach, and admire the sheer force of Manoa Falls.

Plan trip to Honolulu with our itinerary maker to find out where to go and what to do.

Seattle to Honolulu is an approximately 7.5-hour flight. You'll gain 2 hours traveling from Seattle to Honolulu due to the time zone difference. Traveling from Seattle in May, things will get a bit warmer in Honolulu: highs are around 84°F and lows about 71°F. Wrap up your sightseeing on the 16th (Tue) to allow 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 Hanalei Bay. 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 Hapuna Beach State Recreation Area. Get in touch with nature at Fishing Charters & Tours and 49 Black Sand Beach. Go for a jaunt from Kailua-Kona to Captain Cook to see Kealakekua Bay about 30 minutes away. There's much more to do: identify plant and animal life at Kanaloa Octopus Farm, tour the pleasant surroundings at Manini'owali Beach (Kua Bay), and relax in the rural setting at Hula Daddy Kona Coffee.

For photos, other places to visit, maps, and other tourist information, use the Kailua-Kona trip itinerary builder.

Getting from Lihue to Kailua-Kona by flight takes about 2.5 hours. May in Kailua-Kona sees daily highs of 83°F and lows of 73°F at night. Wrap up your sightseeing on the 22nd (Mon) early enough 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 Kapalua Beach. Your itinerary includes some good beach time at Ho'okipa Beach Park and Kamaole Beach Park III. You'll find plenty of places to visit near Kihei: Haliimaile Distilling Company (in Makawao), Lahaina (Hale Pa'i Printing Museum, Napili Beach, &more) and Parasailing & Paragliding (in Ka'anapali). There's lots more to do: stroll through Keawakapu Beach, enjoy the sand and surf at Wailea Beach, get engrossed in the history at Story of Hawaii Museum, and sample the tasty concoctions at Maui Brewing Company.

For more things to do, ratings, other places to visit, and tourist information, use the Kihei trip itinerary planner.

You can fly from Hilo to Kihei in 2.5 hours. Expect a daytime high around 86°F in May, and nighttime lows around 68°F. On the 29th (Mon), you'll have the morning to explore before heading back home.