33 days in Hawaii Itinerary
Created using Inspirock Hawaii route planner
Start: San Jose
Fly
1
Honolulu, Oahu
— 12 nights
Fly
2
Koloa, Kauai
— 6 nights
Fly
3
Lahaina, Maui
— 6 nights
Fly
4
Hilo, Island of Hawaii
— 3 nights
Drive
5
Kailua-Kona, Island of Hawaii
— 4 nights
Fly
End: New York City
Thu, Apr 27 - Mon, May 29
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Honolulu, Oahu — 12 nights
Big Pineapple
Get some cultural insight at Waimea Valley and USS Bowfin Submarine Museum & Park. Head to Ko Hana Distillers and Aloha Stadium Swap Meet & Marketplacefor some retail therapy. Explore the numerous day-trip ideas around Honolulu: Pupukea (Banzai Pipeline, Shark's Cove, &more), Haleiwa (Laniakea Beach, Wys Galleries, &more) and Waimanalo Beach (in Waimanalo). There's lots more to do: take in the dramatic scenery at Manoa Falls, examine the collection at Bishop Museum, identify plant and animal life at Wildlife Areas, and enjoy the sand and surf at Kapiolani Regional Park.
For more things to do, maps, traveler tips, and other tourist information, read Honolulu trip planner.
San Jose, Costa Rica to Honolulu is an approximately 17-hour flight. Due to the time zone difference, you'll gain 4 hours traveling from San Jose to Honolulu. In April in Honolulu, expect temperatures between 33°C during the day and 25°C at night. Wrap up your sightseeing on the 9th (Tue) to allow time to fly to Koloa.
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For more things to do, maps, traveler tips, and other tourist information, read Honolulu trip planner.
San Jose, Costa Rica to Honolulu is an approximately 17-hour flight. Due to the time zone difference, you'll gain 4 hours traveling from San Jose to Honolulu. In April in Honolulu, expect temperatures between 33°C during the day and 25°C at night. Wrap up your sightseeing on the 9th (Tue) to allow time to fly to Koloa.
Side Trips
Highlights from your trip
Koloa, Kauai — 6 nights

Do some cultural sightseeing at Old Koloa Town and Tabora Gallery. Step out of the city life by going to Maha'ulepu Heritage Trail and Shipwreck Beach. Change things up with these side-trips from Koloa: Kapaa (Sleeping Giant Trail, Kauai Path, &more).
To find maps, where to stay, other places to visit, and other tourist information, use the Koloa journey app.
Getting from Honolulu to Koloa by flight takes about 2.5 hours. Expect a daytime high around 32°C in May, and nighttime lows around 25°C. Cap off your sightseeing on the 15th (Mon) early enough to catch the flight to Lahaina.
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To find maps, where to stay, other places to visit, and other tourist information, use the Koloa journey app.
Getting from Honolulu to Koloa by flight takes about 2.5 hours. Expect a daytime high around 32°C in May, and nighttime lows around 25°C. Cap off your sightseeing on the 15th (Mon) early enough to catch the flight to Lahaina.
Side Trips
Highlights from your trip
Lahaina, Maui — 6 nights
Crown Jewel of Maui
Maria Lanakila Catholic Church and Lahaina Printsellers are good opportunities to explore the local culture. Visiting Ho'okipa Beach Park and D.T. Fleming Park will get you outdoors. Explore Lahaina's surroundings by going to Kihei (Kalepolepo Beach Park, Kamaole Beach Park III, &more), Haiku Mill (in Haiku) and Art On Market (in Wailuku). There's lots more to do: trek along Kapalua Coastal Trail, relax and rejuvenate at some of the top local wellness centers, see some colorful creatures with a scuba or snorkeling tour, and stroll through Baby Beach.
To find more things to do, maps, ratings, and tourist information, go to the Lahaina travel itinerary planner.
Traveling by flight from Koloa to Lahaina takes 2.5 hours. May in Lahaina sees daily highs of 32°C and lows of 24°C at night. Wrap up your sightseeing on the 21st (Sun) early enough to fly to Hilo.
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To find more things to do, maps, ratings, and tourist information, go to the Lahaina travel itinerary planner.
Traveling by flight from Koloa to Lahaina takes 2.5 hours. May in Lahaina sees daily highs of 32°C and lows of 24°C at night. Wrap up your sightseeing on the 21st (Sun) early enough to fly to Hilo.
Side Trips
Highlights from your trip
Hilo, Island of Hawaii — 3 nights

America's Wettest City
Step off the beaten path and head to Liliuokalani Gardens and Kīlauea. You'll get in some beach time at Richardson Beach Park and Carlsmith Beach Park. You'll find plenty of places to visit near Hilo: Hawaii Volcanoes National Park (Pu'u Loa Petroglyphs & Holei Sea Arch), Steam Vents (in Pahoa) and Epic Lava Tours (in Volcano). There's still lots to do: take in the dramatic scenery at Rainbow Falls, explore the striking landscape at Lava Viewing Area, take in the exciting artwork at Banyan Gallery, and stop by Hilo Coffee Mill.
Ask Inspirock to suggest an itinerary and make planning a trip to Hilo fast, fun, and easy.
You can fly from Lahaina to Hilo in 2.5 hours. In May, daily temperatures in Hilo can reach 32°C, while at night they dip to 22°C. Wrap up your sightseeing on the 24th (Wed) to allow time to drive to Kailua-Kona.
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Ask Inspirock to suggest an itinerary and make planning a trip to Hilo fast, fun, and easy.
You can fly from Lahaina to Hilo in 2.5 hours. In May, daily temperatures in Hilo can reach 32°C, while at night they dip to 22°C. Wrap up your sightseeing on the 24th (Wed) to allow time to drive to Kailua-Kona.
Side Trips
Highlights from your trip
Kailua-Kona, Island of Hawaii — 4 nights
Heart of the Kona Coast
Escape the urban bustle at Pu'uhonua O Honaunau National Historical Park and Scuba & Snorkeling. Your itinerary includes some good beach time at Manini'owali Beach (Kua Bay) and 49 Black Sand Beach. Step out of Kailua-Kona to go to Captain Cook and see Kealakekua Bay, which is approximately 30 minutes away. There's lots more to do: kick back and relax at Magic Sands, tour the pleasant surroundings at White Sand Beach, admire the majestic nature at Kahalu'u Beach Park, and identify plant and animal life at Wildlife Areas.
For photos, more things to do, where to stay, and more tourist information, refer to the Kailua-Kona journey builder app.
You can drive from Hilo to Kailua-Kona in 2 hours. Alternatively, you can drive; or take a bus. Traveling from Hilo in May, expect somewhat warmer with lows of 26°C in Kailua-Kona. Finish your sightseeing early on the 28th (Sun) to allow enough time to fly back home.
more
For photos, more things to do, where to stay, and more tourist information, refer to the Kailua-Kona journey builder app.
You can drive from Hilo to Kailua-Kona in 2 hours. Alternatively, you can drive; or take a bus. Traveling from Hilo in May, expect somewhat warmer with lows of 26°C in Kailua-Kona. Finish your sightseeing early on the 28th (Sun) to allow enough time to fly back home.
Side Trips
Highlights from your trip
Hawaii travel guide
The Aloha State
An archipelago of hundreds of volcanic islands located in a geological hot spot in the middle of Pacific, Hawaii offers diverse natural scenery and a warm tropical climate. The six major islands open to tourism draw visitors with their sun-drenched public beaches and craggy natural trails. Thanks to their mid-Pacific location, the islands boast a vibrant native culture influenced by both North America and Asia. You can spend your vacation basking in the modern comforts of the big hotels, but to experience the true spirit of these islands, remember that real Hawaiians live outdoors. Encounter nature by surfing, swimming, fishing, and picnicking, or join a guided tour across the ancient lava flows to the top of Hawaii's rugged volcanic peaks.