16 days in Hawaii Itinerary

16 days in Hawaii Itinerary

Created using Inspirock Hawaii trip planner
Make it your trip
Honolulu, Oahu
— 2 nights
Fly to Lihue, Taxi to Poipu
Poipu, Kauai
— 4 nights
Taxi to Lihue, Fly to Lahaina
Lahaina, Maui
— 5 nights
Kailua-Kona, Island of Hawaii
— 4 nights


Honolulu, Oahu — 2 nights

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
Kick off your visit on the 29th (Fri): stroll the grounds of USS Arizona Memorial, appreciate the history behind King Kamehameha Statue, and then buy something for everyone on your list at Ala Moana Center. Get ready for a full day of sightseeing on the next day: steep yourself in history at Iolani Palace and then stroll through Waikiki Beach.

To see more things to do, where to stay, maps, and tourist information, use the Honolulu trip app.

San Diego to Honolulu is an approximately 7-hour flight. The time zone difference when traveling from San Diego to Honolulu is minus 2 hours. Prepare for somewhat warmer weather when traveling from San Diego in July: high temperatures in Honolulu hover around 88°F and lows are around 75°F. Cap off your sightseeing on the 31st (Sun) early enough to travel to Poipu.
Outdoors · Parks · Beaches · Historic Sites

Poipu, Kauai — 4 nights

You'll enjoy a bit of beach vacationing at Poipu Beach Park and Hanalei Beach. For shopping fun, head to Coconut Marketplace or Poipu Shopping Village. Venture out of the city with trips to Na Pali Coast State Park (in Wainiha) and Waimea Canyon State Park (in Waimea).

To find traveler tips, other places to visit, where to stay, and tourist information, go to the Poipu day trip planner.

You can do a combination of flight and taxi from Honolulu to Poipu in 3 hours. Another option is to do a combination of flight, bus, and shuttle. In July in Poipu, expect temperatures between 84°F during the day and 74°F at night. Wrap up your sightseeing on the 4th (Thu) to allow time to travel to Lahaina.
Parks · Outdoors · Wildlife · Nature
Side Trips

Lahaina, Maui — 5 nights

Once the booming capital of the Hawaiian Kingdom, the tropical paradise of Lahaina still remains one of Maui's top vacation attractions, providing both culture and recreation.
For shopping fun, head to Moana Glass by Ryan Staub or Karen Lei's Gallery. Your itinerary includes some good beach time at Ka'anapali Beach and Kapalua Beach. Venture out of the city with trips to Hui No‘eau Visual Arts Center (in Makawao), Alexander & Baldwin Sugar Museum (in Puunene) and Hale Ho'ike'ike at the Bailey House (in Wailuku). There's lots more to do: see some colorful creatures with a scuba or snorkeling tour, steep yourself in history at Lahaina Jodo Mission, kick back and relax at Napili Beach, and take a stroll through Lahaina Front Street.

For maps, reviews, where to stay, and more tourist information, read our Lahaina trip planner.

Traveling by combination of taxi and flight from Poipu to Lahaina takes 3 hours. Alternatively, you can do a combination of shuttle, bus, and flight. August in Lahaina sees daily highs of 86°F and lows of 74°F at night. Finish your sightseeing early on the 9th (Tue) so you can fly to Kailua-Kona.
Outdoors · Parks · Beaches · Museums
Side Trips

Kailua-Kona, Island of Hawaii — 4 nights

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.
Pu'uhonua O Honaunau National Historical Park and Puako Petroglyph Archaeological Preserve will appeal to history buffs. Your cultural itinerary includes sights like Puukohola National Historic Park and Holualoa Village. Venture out of the city with trips to Kealakekua Bay (in Captain Cook), Hapuna Beach State Recreation Area (in Puako) and Papakōlea Green Sand Beach (in Naalehu). The adventure continues: fulfill a lifelong dream with a swim-with-the-dolphins experience, enjoy the sand and surf at Kahaluu Beach, stroll through Mauna Kea Beach, and contemplate in the serene atmosphere at Mokuaikaua Church.

To see maps, more things to do, reviews, and tourist information, read Kailua-Kona trip maker tool.

Fly from Lahaina to Kailua-Kona in 2.5 hours. Alternatively, you can fly. In August, daily temperatures in Kailua-Kona can reach 87°F, while at night they dip to 77°F. You'll have a few hours on the 13th (Sat) to wrap things up before traveling home.
Parks · Outdoors · Beaches · Nature
Side Trips

Hawaii travel guide

Scuba & Snorkeling · Beaches · Zipline
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.