14 days in San Diego & Hawaii Itinerary

14 days in San Diego & Hawaii Itinerary

Created using Inspirock United States visit planner

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San Diego
— 1 night
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Kailua-Kona, Island of Hawaii
— 2 nights
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3
Lahaina
— 4 nights
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4
Honolulu, Oahu
— 3 nights
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San Diego
— 2 nights
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San Diego

— 1 night

America's Finest City

Divided into neighborhoods with distinct characters and cultural heritages, San Diego sits just north of the Mexican border and offers visitors a blend of tourist attractions, including a lively nightlife, diverse cuisine, and a thriving musical scene.
For more things to do, ratings, traveler tips, and other tourist information, refer to the San Diego planner.

Washington DC to San Diego is an approximately 7-hour flight. You can also drive; or take a bus. Due to the time zone difference, you'll gain 3 hours traveling from Washington DC to San Diego. Plan for somewhat warmer temperatures traveling from Washington DC in October, with highs in San Diego at 78°F and lows at 64°F. You'll set off for Kailua-Kona on the 26th (Tue).

Things to do in San Diego

Outdoors · Parks · Tours · Nightlife

Kailua-Kona, Island of Hawaii

— 2 nights

Heart of the Kona Coast

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.
Your day by day itinerary now includes Kīlauea as well as Rainbow Falls. Start off your visit on the 26th (Tue): explore the wealth of natural beauty at Puukohola National Historic Park, kick back and relax at Hapuna Beach State Recreation Area, then stroll through Mauna Kea Beach, and finally steep yourself in history at Puako Petroglyph Archaeological Preserve. Keep things going the next day: take a memorable drive along Saddle Road, take in the dramatic scenery at Rainbow Falls, and then get impressive views of Kīlauea.

To see ratings, reviews, where to stay, and tourist information, go to the Kailua-Kona holiday builder.

You can fly from San Diego to Kailua-Kona in 8 hours. Traveling from San Diego to Kailua-Kona, you'll gain 2 hours due to the time zone difference. In October, Kailua-Kona is a bit warmer than San Diego - with highs of 86°F and lows of 75°F. Wrap up your sightseeing by early afternoon on the 28th (Thu) to allow time for the flight to Lahaina.

Things to do in Kailua-Kona

Parks · Outdoors · Nature · Beaches

Side Trips

Lahaina

— 4 nights

Crown Jewel of Maui

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.
You've now added Haleakala Crater to your itinerary. When in Lahaina, make a side trip to see Zipline in Kula, approximately Kula away. Next up on the itinerary: see some colorful creatures with a scuba or snorkeling tour, get engrossed in the history at Baldwin Home Museum, see the interesting displays at Whalers Village Museum, and pause for some photo ops at Lahaina Jodo Mission.

Plan my trip to Lahaina with suggested itineraries provided by Inspirock.

Traveling by flight from Kailua-Kona to Lahaina takes 2.5 hours. In October, daytime highs in Lahaina are 84°F, while nighttime lows are 73°F. Finish up your sightseeing early on the 1st (Mon) so you can catch the flight to Honolulu.

Things to do in Lahaina

Outdoors · Parks · Beaches · Tours

Side Trips

Honolulu, Oahu

— 3 nights

Big Pineapple

In many ways much more Asian than American, Honolulu is Hawaii's largest city and its center of government, transportation, commerce, and tourism.
You've now added Kuliouou Ridge Hike to your itinerary. Next up on the itinerary: explore the galleries of USS Arizona Memorial, see the vivid underwater world at Pele's Chair, appreciate the history behind King Kamehameha Statue, and explore the activities along Hanauma Bay Nature Preserve.

To find more things to do, where to stay, maps, and other tourist information, use the Honolulu trip builder website.

Getting from Lahaina to Honolulu by flight takes about 2.5 hours. In November, daytime highs in Honolulu are 84°F, while nighttime lows are 72°F. Wrap up your sightseeing on the 4th (Thu) early enough to fly to San Diego.

Things to do in Honolulu

Parks · Outdoors · Beaches · Trails

Side Trip

San Diego

— 2 nights

America's Finest City

Start off your visit on the 4th (Thu): stroll around Sunset Cliffs Natural Park. On the 5th (Fri), you'll have a packed day of sightseeing: meet the residents at San Diego Zoo and then kick back and relax at La Jolla Cove.

To find maps, other places to visit, traveler tips, and other tourist information, you can read our San Diego day trip planner.

Traveling by flight from Honolulu to San Diego takes 7 hours. The time zone difference moving from Hawaii-Aleutian Standard Time (HST) to Pacific Standard Time (PST) is 2 hours. In November, San Diego is slightly colder than Honolulu - with highs of 73°F and lows of 57°F. Wrap up your sightseeing by early afternoon on the 6th (Sat) to allow enough time to fly back home.

Things to do in San Diego

Parks · Zoos & Aquariums · Museums · Outdoors

Hawaii travel guide

4.4
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.

Maui travel guide

4.4
Scuba & Snorkeling · Beaches · Zipline
The Valley Isle
The second largest of the eight major Hawaiian Islands, Maui features a rugged landscape ranging from high mountain peaks to deep valleys. Half of Maui lies within 8 km (5 mi) of the coastline, and most tourists come for the sandy beaches, many of them backed by fashionable resorts offering every modern convenience. Diversity of tourist attractions is Maui's major allure, with each of the island's shores offering a different set of vacation ideas. You can swim with dolphins, snorkel with sea turtles, or hike over the otherworldly landscapes of the world's biggest dormant volcano. A foodie paradise, the island also features dozens of small farms and gourmet restaurants.