Retriever's live-ish TR BI/Kauai 2/14-3/6 (continued)

Question

Aloha!

Hubby and I are very excited to be returning to two of our favorite places on earth- Big Island and Kauai- for the next 3 weeks! Our party of 2 turned into a party of 4 when we found out my SIL was celebrating her 70th B’day in February, and was considering Hawaii as their destination. That was a no brainer for us to invite them along- we adore them, and I LOVELOVELOVE celebrating birthdays!

Hubby is a young and fit 70 y/o, whereas I’m 59 and actively battling stage 4 rectal cancer, with both good and less-than-good days, but still very much enjoy two of my greatest passions- travel planning and vacationing. BIL and SIL are both active and fit as well (like hubby), and land in-between us in age. We have never traveled together, but the guys play golf regularly and we always enjoy each others company during our family get togethers. In the course of planning, we discovered that we have many different interests, so we all agreed separate cars were needed for the duration of the trip.

We are splitting our time between islands evenly (10 nights each), and also splitting our time between sides of the islands, weighing more heavily where we’re using our timeshare (and trade), in Waikoloa on BI and Princeville on Kauai. The other nights will be spent at AirB&Bs in Volcano Village and Poipu respectively.

I’m using this intro for both islands, and will link the other Island’s TR when we move, but start fresh in a new thread when we get to Kauai. I’m also going to start below with the activity part of the report so there is not a long scroll to get to the heart of things.

I’m also not a “short and sweet” kind of “trip reporter”. I like to include details and impressions for my memory and family/friends following our travels, as well as for those who like that in TRs, so if that’s not your thing, please disregard this one. BUT If you like that kind of read, please feel free to join us on our travels! Between the 4 of us, I believe we’re setting off for an excellent adventure!

Answer

Aloha and welcome to your live-ish trip report! It sounds like you’ve got an incredible adventure planned across two of Hawaii’s most stunning islands, with a mix of family bonding, scenic exploration, and personal milestones to celebrate. Splitting your time evenly between the Big Island and Kauai will give you a wonderful contrast of landscapes, from volcanic terrain to lush green cliffs, while also allowing you to enjoy a combination of resorts and local AirBnB experiences.

Here are some considerations and tips to make the most of your trip, especially with your group dynamics and diverse interests:

Car Rentals: Since each couple has different interests, having separate cars is ideal. Make sure to book early to get vehicles that are comfortable for both long drives and short island excursions. For Kauai and Big Island, SUVs or mid-size cars work well for both comfort and navigating winding roads.
Activity Planning: With a mix of ages and fitness levels, consider categorizing activities into “must-do” and “optional.” This helps balance days so everyone has something enjoyable without overexerting anyone.
Health Considerations: For those with medical needs or lower stamina, plan for rest periods and easy-access activities. Volcano Village on Big Island is a great base for lighter exploration and scenic drives, while Princeville provides easy access to Kauai’s north shore beaches and gentle hikes.
Celebratory Events: Since your SIL is celebrating her 70th, look into special dining experiences or sunset cruises for memorable moments. Both islands offer excellent options from casual luau-style experiences to upscale oceanfront dining.

Accommodation Strategy:

Using timeshares in Waikoloa and Princeville allows you to enjoy comfortable, well-equipped bases while saving on some nightly costs.
AirBnBs in Volcano Village and Poipu provide local charm and flexibility, plus the opportunity to enjoy kitchens and outdoor space for relaxing evenings.
Consider proximity to grocery stores, beaches, and popular attractions when selecting specific AirBnB units, as travel time can vary greatly between towns.

Island-Specific Tips:

Big Island: Waikoloa is perfect for golf, shopping, and beach days. Volcano Village is great for exploring Hawaii Volcanoes National Park, local hikes, and charming small-town experiences.
Kauai: Princeville offers gorgeous north shore vistas, easy access to Hanalei Bay, and shorter drives to Na Pali Coast lookouts. Poipu has sunny beaches and convenient amenities.
Plan activities around sunrise or sunset to avoid crowds, especially at popular scenic spots like Waipi’o Valley (Big Island) or Hanalei Bay (Kauai).

General Travel Notes:

Keep a flexible itinerary to accommodate weather changes or energy levels.
Bring layers and comfortable shoes, especially if you plan on hiking or walking in varied terrain.
Document your experiences with photos and notes for your personal record and for sharing with family—sounds like you enjoy detailed trip journaling!

Overall, your trip promises a balanced mix of adventure, relaxation, and family celebration. Planning for flexibility, multiple transportation options, and a range of activities will allow each of you to enjoy your passions while creating memorable shared experiences. Enjoy your journey across Big Island and Kauai!

Retriever's live-ish TR BI/Kauai 2/14-3/6 (continued)

More Kauai Travel Questions

The attractions mentioned in this question

Popular Destinations

Popular Travel Questions