30 days in Hawaii Itinerary

30 days in Hawaii Itinerary

Created using Inspirock Hawaii Trip Planner

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Route & dates

30 days in Hawaii Itinerary

Start: Tallinn
+3
ferry + tram + bus + Fly:  9​h 30​min
1
Honolulu, Oahu
— 8 nights
Fly:  2​h 30​min
2
Kapaa, Kauai
— 6 nights
Fly:  1​h 30​min
3
Kihei, Maui
— 6 nights
Fly:  3​h
4
Hilo, Island of Hawaii
— 2 nights
Drive:  1​h 45​min
5
Kailua-Kona, Island of Hawaii
— 5 nights
Drive + Fly:  31​h
End: Tallinn

8
nights
Honolulu, Oahu

Honolulu ©
In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Attractions like USS Arizona Memorial and Hanauma Bay Nature Preserve make great kid-friendly stops. Explore the numerous day-trip ideas around Honolulu: Kailua (Kailua Beach Park & Lanikai Beach), Laie (Malaekahana State Recreation Area & Polynesian Cultural Center) and Sea Life Park Hawaii (in Waimanalo). There's still lots to do: tour the pleasant surroundings at Waikiki Beach, steep yourself in history at Iolani Palace, go for a walk through Diamond Head State Monument, and explore the activities along Waimea Bay.

To find photos, ratings, and tourist information, go to the Honolulu tour itinerary planner.

Tallinn, Estonia to Honolulu is an approximately 23-hour combination of ferry and flight. The time zone changes from Eastern European Time (EET) to Hawaii Standard Time (HST), which is usually a -12 hour difference. Plan for warmer temperatures traveling from Tallinn in February, with highs in Honolulu at 32°C and lows at 24°C. Wrap up your sightseeing on the 13th (Sat) early enough to travel to Kapaa.

Things to do in Honolulu

Parks Outdoors Beaches

Side Trips

Kailua, Laie, Haleiwa, Sea Life Park Hawaii, Makapu'u Point
Highlights from your plan
USS Arizona Memorial ©
USS Arizona Memorial
Waikiki Beach ©
Waikiki Beach
Diamond Head State Monument ©
Diamond Head State Monument

6
nights
Kapaa, Kauai

Kapaa ©
Noted for its low-key beaches, Kapaa is a small town with a high concentration of tourist-oriented hotels, shops, bars, and restaurants.
You'll visit kid-friendly attractions like Poipu Beach Park and Anini Beach. Change things up with these side-trips from Kapaa: Ke'e Beach (in Haena), Hanalei (Hanalei Valley Lookout & Hanalei Beach) and Poipu (Spouting Horn & Allerton Garden). And it doesn't end there: take in breathtaking views at Waimea Canyon State Park, trek along Kalalau Trail, kick back and relax at Anahola Beach Park, and tour the pleasant surroundings at Tunnels Beach.

For reviews, photos, maps, and other tourist information, read Kapaa trip planning site .

Traveling by flight from Honolulu to Kapaa takes 2.5 hours. In February, daytime highs in Kapaa are 30°C, while nighttime lows are 22°C. Wrap up your sightseeing on the 19th (Fri) early enough to travel to Kihei.

Things to do in Kapaa

Parks Outdoors Beaches

Side Trips

Kauai, Poipu, Hanalei, Waimea, Anahola Beach Park
Highlights from your plan
Poipu Beach Park ©
Poipu Beach Park
Hanalei Beach ©
Hanalei Beach
Spouting Horn ©
Spouting Horn

6
nights
Kihei, Maui

Kihei ©
Stretching over 9.7 km (6 mi) of pristine south Maui coastline, Kihei is the island's driest and sunniest region, making it a perfect location for water activities and beach leisure.
Family-friendly places like Maui Ocean Center and D.T. Fleming Park will thrill your kids. Go for a jaunt from Kihei to Haleakala National Park to see Haleakala Crater about 1h 25 min away. And it doesn't end there: immerse yourself in nature at Iao Valley, kick back and relax at Wailea Beach, see the world from above with Maui Flight Academy, and see Maui Waveriders.

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

Traveling by flight from Kapaa to Kihei takes 1.5 hours. In February, daily temperatures in Kihei can reach 32°C, while at night they dip to 21°C. Wrap up your sightseeing on the 25th (Thu) to allow time to travel to Hilo.

Things to do in Kihei

Outdoors Parks Tours

Side Trips

Wailuku, D.T. Fleming Park, Wailea Beach, Haleakala Crater, Surfing Goat Dairy
Highlights from your plan
Maui Beach Boys ©
Maui Beach Boys
Maui Ocean Center ©
Maui Ocean Center
Wailea Beach ©
Wailea Beach

2
nights
Hilo, Island of Hawaii

Hilo ©
One of the island of Hawaii's major towns, Hilo contains a mix of Asian and Polynesian cultures and is known for its proximity to a national park encompassing two active volcanoes.
Start off your visit on the 26th (Fri): admire the sheer force of Rainbow Falls, learn more about the world around you at Mokupapapa Discovery Center, and then take in the dramatic scenery at Akaka Falls State Park. Get ready for a full day of sightseeing on the next day: get curious at Imiloa Astronomy Center, then admire nature's wide array of creatures at Panaewa Rainforest Zoo and Gardens, and then admire the natural beauty at Liliuokalani Gardens.

To plan Hilo vacation without wasting time, ask Inspirock to design an itinerary.

Fly from Kihei to Hilo in 3 hours. Alternatively, you can do a combination of flight and bus. February in Hilo sees daily highs of 32°C and lows of 21°C at night. Finish up your sightseeing early on the 27th (Sat) so you can go by car to Kailua-Kona.

Things to do in Hilo

Museums Parks Childrens Museums
Highlights from your plan
Imiloa Astronomy Center ©
Imiloa Astronomy Center
Akaka Falls State Park ©
Akaka Falls State Park
Liliuokalani Gardens ©
Liliuokalani Gardens

5
nights
Kailua-Kona, Island of Hawaii

Kailua-Kona ©
Thanks to its favorable location near a mountain range blocking the northeasterly trade winds, Kailua-Kona gets little rainfall, allowing adventure seekers and nature lovers a chance to enjoy over 300 days of sunshine each year.
Kids will enjoy Hapuna Beach State Recreation Area and Kahaluu Beach. Venture out of the city with trips to Pu'uhonua O Honaunau National Historical Park (in Honaunau), Captain Cook (The Captain Cook Monument & Kealakekua Bay) and Papakōlea Green Sand Beach (in Naalehu). The adventure continues: discover the deep blue sea with Kona Diving Company, take in the spiritual surroundings of Mokuaikaua Church, stop by Waikoloa Beach Resort, and get close to the beloved marine mammals with Big Island Divers.

To find where to stay, other places to visit, photos, and more tourist information, refer to the Kailua-Kona trip itinerary planner.

You can drive from Hilo to Kailua-Kona in 2 hours. Alternatively, you can take a bus. February in Kailua-Kona sees daily highs of 32°C and lows of 24°C at night. Cap off your sightseeing on the 3rd (Thu) early enough to travel back home.

Things to do in Kailua-Kona

Parks Outdoors Nature

Side Trips

Waikoloa, Captain Cook, Pu'uhonua O Honaunau National Historical Park, Kahaluu Beach, Papakōlea Green Sand Beach
Highlights from your plan
Hapuna Beach State Recreation Area ©
Hapuna Beach State Recreation Area
Papakōlea Green Sand Beach ©
Papakōlea Green Sand Beach

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