Help to get us started: late 50s, active, 9 nights, 2 island

Question

I try not to post "open ended" questions - but I'm at loss of where to start.

My husband and I (late 50s, love hiking, photography, not foodies) will arrive Sept 25, depart Oct 4. We have previously explored Oahu and Big Island (with kids in tow). This time considering Maui and perhaps Kauai. We prefer a condo (kitchen) to a hotel, plan to have a rental car. We like to wander & explore. We like the beach and snorkeling, and pool is nice, too.

Wondering if we should spend all 9 nights in Maui - in 2 locations, or if we should include Kauai in this trip.

Appreciate any and all suggestions on where to focus on looking for lodgings. We don't need high end. Would prefer to avoid large resorts - but that might not be possible? I've read the comments about using airbnb or vrbo as a resource - but book directly or via rental agency.

I realize that I didn't give you a lot of information - but I appreciate some ideas for our research. Thanks!

Answer

For a 9-night trip to Maui (and possibly Kauai) in late September to early October, focusing on flexibility, hiking, photography, snorkeling, and a relaxed pace, there are several approaches to consider. Since you prefer condos with kitchens and a rental car, you have the freedom to explore different regions at your own pace without relying on resort amenities.

One question is whether to stay entirely in Maui or split time with Kauai. Given your timeframe of 9 nights, it is feasible to spend most of your trip in Maui, potentially dividing it between two locations to reduce driving time and maximize exploration. Including Kauai would add flight logistics and reduce time in each location, so it may feel rushed unless you specifically want to experience Kauai’s lush landscapes in addition to Maui’s diversity.

Here are some lodging area suggestions in Maui:

West Maui (Lahaina/Kaanapali/Kapalua): Great for beaches, snorkeling, and easy access to shops and restaurants. Lahaina has historic charm, Kaanapali has snorkeling spots like Black Rock, and Kapalua is scenic with hiking nearby. Condos are abundant, ranging from mid-range to luxury, with pool access.
South Maui (Wailea/Makena): Quieter than West Maui, upscale condos, excellent beaches, and good snorkeling at Wailea Beach or Makena Beach. Also close to short hikes like the La Perouse Bay trail. This area is ideal if you want a mix of beach, pool, and scenic coastal walks.
Upcountry Maui (Kula/Hali‘imaile): Perfect for photography and hiking enthusiasts, cooler temperatures, panoramic views, and proximity to Haleakalā National Park. Condos here are more private and less resort-focused, giving a different perspective from the coast.

For a 9-night Maui trip, a practical approach is to split your stay between two areas, such as 4–5 nights in West or South Maui for beach and snorkeling, and 4–5 nights in Upcountry or near Hana for hiking, waterfalls, and scenic drives. This allows variety without feeling rushed.

If you consider adding Kauai, the logistics might look like:

5–6 nights in Maui (covering both West/South Maui and Upcountry/Haleakalā)
3–4 nights in Kauai (Princeville or Poipu) for hiking, photography, and lush landscapes

This option requires inter-island flights and careful planning to avoid feeling rushed. If your priority is relaxation and exploration without time pressure, focusing solely on Maui is likely more satisfying.

Regarding booking, VRBO and Airbnb are excellent for condos, especially if you want kitchens and privacy. Booking directly through the host or property management company can sometimes yield better rates and clearer communication. Look for places with good reviews, free parking, and convenient access to beaches or trails you plan to explore.

In summary, for a late 50s, active couple who loves hiking and photography:

Consider splitting Maui stay between two regions to experience beaches, snorkeling, and scenic hikes.
Focus on condos with kitchens in West or South Maui for beach days and Upcountry or Hana for hiking and photography.
Only add Kauai if you are comfortable with inter-island travel and shorter stays in each location.
Use VRBO or Airbnb for condo rentals, and contact hosts directly for the best experience.

This approach balances exploration, comfort, and flexibility while allowing you to enjoy Maui’s diverse landscapes without rushing.