TWO WEEK HAWAIIAN HOLIDAY VACATION
(Oahu and Kauai)
We have three teenagers and decided to surprise them with a Christmas trip instead of gifts. Huge success! There were plenty of activities we all liked to do and Hawaii was a warm and relaxing respite from winter weather. We did this on a budget – with just a few luxuries. Pick and choose from this itinerary to plan your own perfect island getaway – 3 days in Waikiki, 7 days on Kuaui and back to Oahu for the final four days.
Day 1
- Arrive in beautiful, tropical Oahu Hawaii late afternoon.
- Honolulu airport is a cinch to navigate and it’s SO easy to find minivan cabs.
- Arrival in Waikiki and check into hotel.
- Long flight, so have an early dinner near the hotel.
- Relax in hotel room for the first night and get ready for a great tropical vacation.
Day 2
- Early start for all – even the teens! – due to the six-hour time difference.
- Take a walk along Kalakaua Avenue and gaze at the ocean in the early morning.
- Scout out a breakfast place and fortify yourself for a great day in paradise.
- Hike Diamond Head. Enjoy the gorgeous views and family photo opps! Takes about two hours.
- Hit the beach! Sunbathe and swim – and then try your hand at surfing. Rentals were easy to secure from several beachside vendors.
- Go window shopping for a while. Waikiki is all decked out for the holidays.
- Enjoy an early dinner.
- Attend the Christmas Eve services at Kawaiahao Church — the “Westminster Abbey” of Oahu.
- To add to the Christmas magic, have the taxi drive by the Honolulu City Lights in the downtown financial district.
Day 3
- Breakfast by the beach – no one gets tired of that! — and then secure a car for the day. Alamo rentals include shuttle service to/from Waikiki hotels.
- Head to the infamous North Shore to check out the surfers, beaches and incredible waves.
- On the way, take in the pineapple fields and prepare for the more laid back side of the island.
- Visit Banzai Pipeline Beach, a great place to watch surfers.
- Drive a few miles to Malaekahana Beach with its family atmosphere and rolling waves for a swim and some napping.
- On the way back to Waikiki, stop for a late lunch at Fumi’s, a roadside shrimp stand. Peel your own shrimp and enjoy a quick feast in Fumi’s covered picnic area.
- To cap off a great day, walk over to House without a Key at the beautiful Halekulani Hotel. No reservations needed when sitting outside to have apps and drinks. Enjoy a local band and authentic hula dancing.
Day 4
- Use Open Table to reserve a table for brunch at Duke’s. Abundant buffet, fabulous views and friendly staff. Finally — enough food to keep two teen boys full!
- Check out of one hotel room – and keep the other at a day rate. Change into swim suits.
- Catch a ride on the Maitai Catamaran (our Groupon deal was $82 for six)
- Laugh for the entire two-hour ride on the Pacific with about 30 other guests – as most are sprayed with cascading waves!
- Shower, change and check out – and head to the airport for the flight to Kauai. Use a service like Hawaii 23 and be sure to have a ride with enough room for people and bags at the time you need it!
- Upon landing in Lihue, have one family member grab a cab and go straight to Costco. Shop for the week.
- Meanwhile have the rest of the group pick up rental car, load bags and drive to Costco to pick up the shopper. Save time and money!
- Use VRBO or another website to find the vacation rental of your dreams!
Day 5
- Enjoy breakfast on your own patio and then explore the area.
- Drive to Hanalei to buy swim shirts and schedule surf lessons for the next day.
- Lunch at the oceanfront condo.
- Relax at condo pool. Walk down to private beach area.
- Play golf on Mini Prince, a walking family course on the grounds of the Princeville Golf Club. So reasonable and beautiful!
- Cook dinner at the condo and play a board game or cards!
Day 6
- Grab a quick breakfast and then head to Hanalei Bay for that early surf lesson!
- Titus Surf Lessons’ two-hour group instruction includes all day use of the board. A great way to reinforce the lesson!
- Pick up sandwiches in Hanalei and picnic at the beach.
- Take an afternoon drive to the Kilauea Lighthouse. This bird sanctuary is just beautiful! Lots of binoculars to borrow, so enjoy whale watching, too!
- Continue on to Kapaa to buy/rent snorkeling equipment for the week.
- Cool off with a gigantic shaved ice from Ono Ono. Delish!
- Relax on the private beach at condo and snorkel – turtles, coral, fish – incredible experience!
- Adults looking for a quiet cocktail hour can walk over to the St. Regis for cocktails on the patio…well deserved!
Day 7
- Breakfast at Kalypso Bar & Grill in Hanalei and watch Sunday NFL football. Be prepared for pitchers of beer with eggs and bacon!
- Walk over to Hanalei Bay and get in a little more surfing – a fun and affordable pastime in Hawaii.
- Drive to Anini Beach for some late afternoon snorkeling.
- Dinner and a movie back at the condo for a quiet evening. Try Hawaii or South Pacific!
Day 8
- Get a bright and early start to tackle the fabulous and breathtaking Kalalua Trail.
- Hike all day – about 7 hours — and experience an unforgettable Kauai experience! (Bring an OLD pair of sneakers of hiking boots for this outing!)
- Pack a lunch and picnic along the way.
- Upon returning home, wash or throw away all the muddy sneakers/boots!
- If you have the energy, go out to dinner! Otherwise, prepare a snack meal and play a competitive board game like “Apples to Apples”.
Day 9
- Have a lazy morning! Sleep in, go for a walk, drink coffee while whale watching from the lanai.
- Snorkel at the private beach.
- Head to the pool to read and relax in the warm sun.
- For lunch or dinner, try one of the many good restaurants in Hanalei and/or Princeville. Tiki Iniki owned by rocker Todd Rundgren’s wife, is fun and offers an island atmosphere with delicious food and drinks!
- In the evening, watch The Descendents filmed just around the corner. Pick out landmarks you recognize.
Day 10
- Wake up early and drive 1.5 hours to Waimea Canyon, the Grand Canyon of the Pacific. Morning is best as clouds tend to settle later in the day. Truly gorgeous!
- Drive to Kalalau Lookout at mile marker 18. It’s the wettest place on earth (so the signs say) and offers a spectacular view of Na’Pali Coast.
- On the way back, stop at Kauai Coffee Co. Sample different brews, check out the small museum and enjoy a walk around in the sunshine.
- A must do for teens is ziplining through Kauai Back Country Adventures. At one point participants are 250’ off the ground!
- For non-zipliners, Poipu Beach is a short drive away. Have lunch surfside and enjoy the view!
- Drive to Wailea Falls – filmed for the opening of the old TV show Fantasy Island! A beautiful and quick side trip!
- Head into Hanalei to walk around, have an ice cream and shop a bit!
Day 11
- Last day on Kauai! Pack, clean and check out of condo.
- On the way to the airport, carefully hike down the path to Queen’s Bath. Beautiful spot, but not a place to snorkel or swim. Handmade sign listed about 25 people have been killed there.
- Stop at a roadside Juice bar for whole coconuts or fruit smoothies. Fresh and delicious!
- Head straight to the airport for the return flight to Oahu.
- Once in Honolulu, pick up the rental car – why not try a convertible?! — and head to the final hotel stay: Disney Aulani Resort.
- Lei greeting upon entering – our teens loved it!
- Beautiful resort, but very pricey. Disney Vacation Club suites with kitchenette sleep five and are a bit less expensive Two downsides to the Vacation Club: only one bathroom per suite and maid service every four days. Be prepared to empty the garbage and grab clean towels from the pool. Bummer, but doable!
- Buy the $20 insulated cup for unlimited drinks. Well worth it!
- Wandered around pool area in the evening. Quick relaxing swim and a dip in the hot tub – ahhh!
Day 12
- Breakfast in the suite. Have some bread, cereal, snacks on hand. Hot coffee in the Disney mug!
- Early morning swim for those who want to wake up quickly.
- Drive to Pearl Harbor. Be sure to make your reservations well in advance. The holidays are very busy! Arrival is one hour prior to the ticket time, so enjoy the time to walk around.
- Visit the museum on site. All three teens had studied World War II, so the museum with its photos and artifacts was a riveting prelude to the boat trip out to the USS Arizona Memorial.
- Drive around Oahu with top down if weather cooperates!
- Back to the resort for a light dinner and a dip in the hot tub overlooking the ocean and watching the sunset. Beautiful!
Day 13
- Hot coffee in the Disney mug! But poolside this morning to secure our chairs for the day.
- Lazy morning watching some of the Disney characters walk around. Teens are not so into the Disney scene – especially in naturally beautiful Hawaii. (After casual snorkeling in Kauai, it was hard to contemplate paying to snorkel in a swimming pool with a life jacket on!)
- Watch NFL playoff games at the pool bar – complete with pineapple drinks. Yum!
- Dinner across from the resort in a small center – lots of choices.
- Late night swim and a family water slide competition. Lots of laughs!
Day 14
- Try for late check out and enjoy the better part of the day at the resort. Not an option on our trip, so we packed up and headed out to see more of Oahu before heading to the airport.
- Drive up the winding Mount Tantalus Road to Puu Ualakaa State Park. At the look out enjoy gorgeous sweeping views of downtown Honolulu.
- Have lunch at Hank’s Haute Dogs in downtown Honolulu before your flight. Featured on Diners, Drive Ins and Dives, there are plenty of choices for the whole family.
- Return the rental car and head to the airport. It’s hard to leave such a beautiful place. But with more islands to see, start planning your return trip to Hawaii. Try Maui or Lanai or The Big Island – or a return trip to Oahu and Kauai!
- Sign your children up for frequent flier programs…even if they don’t fly enough to earn a ticket, you can use their balances to add to yours. It can really help if you’re shy a few miles.
- Send yourselves a daily postcard. Your hotel will likely sell stamps and mail them for you! When you arrive home, enjoy reliving the experiences all over again.
- Be flexible. If your daily itinerary is weather-dependent, don’t hesitate to switch activities and make the most of a sunny day.
- If you’re traveling over a weekend in Europe, do a little research and make sure activities/places on your itinerary are open on Sundays.
SCRAPBOOK
SHARE YOUR THOUGHTS
LEAVE SOME FEEDBACK