17 days in Maui, Kauai & San Francisco Itinerary

17 days in Maui, Kauai & San Francisco Itinerary

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Route & dates

17 days in Maui, Kauai & San Francisco Itinerary

Start: Chicago
Fly:  14​h
1
Lahaina
— 5 nights
bus + Fly:  4​h
2
Poipu
— 3 nights
Drive:  1​h 15​min
3
Hanalei
— 3 nights
Fly:  8​h
4
San Francisco
— 4 nights
Fly:  6​h 15​min
End: Chicago


Learn more about your trip

5
nights
Lahaina

Lahaina ©
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.
Give yourself a bit of retail therapy at Olavine Spa & Salon and Maui Prime Fine Foods. You'll get in some beach time at Napili Beach and Wailea Beach. Explore the numerous day-trip ideas around Lahaina: Ali'i Kula Lavender Farm (in Kula), Mele Ukulele (in Wailuku) and Sweet Paradise Chocolatier (in Wailea). There's lots more to do: wander the streets of Lahaina Front Street, look for gifts at Water Works Sports, get all the equipment you need at Maui Mike's Beach House, and view the masterpieces at Kush Fine Art.

To see where to stay, photos, traveler tips, and other tourist information, use the Lahaina trip planner .

Chicago to Lahaina is an approximately 14-hour combination of flight and bus. You can also do a combination of flight, taxi, and ferry. The time zone difference moving from Central Standard Time (CST) to Hawaii Standard Time (HST) is minus 4 hours. When traveling from Chicago in October, plan for a bit warmer days and much warmer nights in Lahaina: temperatures range from 84°F by day to 73°F at night. Finish your sightseeing early on the 5th (Mon) so you can travel to Poipu.

Things to do in Lahaina

Shopping Outdoors Beaches

Side Trips

Wailea, Sherri Reeve, Mele Ukulele, Tutu's Pantry, Karen Lei's Gallery
Highlights from your plan
Wailea Beach ©
Wailea Beach
Ali'i Kula Lavender Farm ©
Ali'i Kula Lavender Farm
Karen Lei's Gallery ©
Karen Lei's Gallery

3
nights
Poipu

Poipu ©
Poipū is a census-designated place in Kauai County on the southern side of the island of Kauai in the U.S. Satisfy your inner culture vulture at Seductions of Kauai Gallery and Aloha 'n Paradise Espresso Bar. Head to Talk Story Bookstore and Aunty Liliko'ifor plenty of shopping. Next up on the itinerary: stroll through Poipu Beach Park, stop by Kapaia Stitchery, and browse the fresh offerings at Kauai Culinary Market.

To find other places to visit, traveler tips, photos, and more tourist information, refer to the Poipu trip itinerary app .

Do a combination of bus, flight, and taxi from Lahaina to Poipu in 4 hours. In November, plan for daily highs up to 81°F, and evening lows to 71°F. Cap off your sightseeing on the 8th (Thu) early enough to go by car to Hanalei.

Things to do in Poipu

Shopping Museums Beaches

Side Trips

Hanapepe, Koloa, Lihue, Waimea, Hawaiian Trading Post
Highlights from your plan
Talk Story Bookstore ©
Talk Story Bookstore
Hawaiian Trading Post ©
Hawaiian Trading Post
Seductions of Kauai Gallery ©
Seductions of Kauai Gallery

3
nights
Hanalei

Hanalei ©
Hanalei is a census-designated place (CDP) in Kauai County, Hawaii, United States. Explore hidden gems such as Anahola Hawaiian Land Farmer's Market and 7 Artists Gallery. Visit Historic Kong Lung Market Center and Wai`oli Hui`ia Church for their historical value. Change things up with these side-trips from Hanalei: Kapaa (Vicky's Fabrics & Garden Isle Bath & Body LLC). And it doesn't end there: stop by Hanalei Farmer’s Market, stroll through Hanalei Beach, buy something for everyone on your list at Princeville Center, and explore and take pictures at Hanalei Valley Lookout.

To see ratings, where to stay, more things to do, and other tourist information, refer to the Hanalei online driving holiday planner .

Traveling by car from Poipu to Hanalei takes 1.5 hours. In November in Hanalei, expect temperatures between 81°F during the day and 71°F at night. Finish your sightseeing early on the 11th (Sun) so you can travel to San Francisco.

Things to do in Hanalei

Shopping Outdoors Beaches

Side Trips

Kapaa, Princeville Center, Anahola Hawaiian Land Farmer's Market, Historic Kong Lung Market Center
Highlights from your plan
Hanalei Beach ©
Hanalei Beach
Wai`oli Hui`ia Church ©
Wai`oli Hui`ia Church
Historic Kong Lung Market Center ©
Historic Kong Lung Market Center

4
nights
San Francisco

San Francisco ©
San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
You'll explore the less-touristy side of things at Castello di Amorosa and Ramini Mozzarella. For shopping fun, head to Ferry Building Marketplace or Sebastopol Center for the Arts. You'll find plenty of places to visit near San Francisco: Nicasio Valley Cheese Company (in Nicasio), V. Sattui Winery (in St. Helena) and Moshin Vineyards (in Healdsburg). Next up on the itinerary: kick back and relax at Bodega Dunes, take in the awesome beauty at Twin Peaks, browse the different shops at Ghirardelli Square, and look for gifts at Fishetarian Fish Market.

For where to stay, other places to visit, photos, and other tourist information, refer to the San Francisco road trip app .

Traveling by combination of taxi, flight, and subway from Hanalei to San Francisco takes 8 hours. Alternatively, you can do a combination of taxi and flight. The time zone difference moving from Hawaii Standard Time to Pacific Standard Time is 2 hours. When traveling from Hanalei in November, plan for slightly colder days in San Francisco, with highs around 64°F, while nights are much colder with lows around 51°F. Wrap up your sightseeing on the 16th (Fri) to allow time to travel back home.

Things to do in San Francisco

Shopping Beaches Outdoors

Side Trips

Pleasanton, Sebastopol Center for the Arts, V. Sattui Winery, Nicasio Valley Cheese Company, Ramini Mozzarella
Highlights from your plan
Ferry Building Marketplace ©
Ferry Building Marketplace
V. Sattui Winery ©
V. Sattui Winery
Bodega Dunes ©
Bodega Dunes

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