First time in Hawaii. Which island(s)?

Question

My husband and I are planning a 10 year anniversary trip to Hawaii. We're in our mid-30s. Neither have been before. While we were married in April, we are thinking end of May to have Memorial Day as a bonus day so we don't have to take vacation. (Leaving our 2 kids behind on purpose)

We are really open to where since our wants/needs list is limited based on our lack of knowledge.

Wants/needs:

- See beautiful nature & volcano

- Beach and pool

- Hotel/resort near ocean

- My favorite thing about travel is immersing myself in the culture and vibe of where we are. My husband prefers more touristy vibes

Questions:

1. Is late-May a good time to travel to Hawaii?

2. For a 7-8 night trip, which island(s) do you recommend? (2 island maximum)

3. Should we look into a travel agent?

4. Are there places to avoid?

Thank you for ANY tips!

Answer

Planning your first trip to Hawaii for a 10-year anniversary is exciting, and late May can be an excellent time to visit. The weather is generally warm and pleasant, with less rainfall than the winter months, and the islands are not yet at the peak summer tourist crowds. Ocean temperatures are comfortable for swimming, snorkeling, and other water activities.

Here’s a detailed breakdown to help with your planning:

Weather in Late May: Generally sunny with occasional showers, especially on windward (northeast) sides of islands. Daytime temperatures average in the mid-70s to mid-80s °F (24–29°C). Nights are mild and comfortable. This is also before the higher summer season, making accommodations and flights slightly easier to manage.

For a 7–8 night trip, considering your interests in nature, volcanoes, beaches, and cultural immersion, two islands maximum is ideal to avoid travel fatigue and maximize enjoyment.

Big Island (Hawaiʻi Island): Perfect for volcano exploration, diverse landscapes, and stargazing at Mauna Kea. You can see everything from black sand beaches to lush rainforests. Recommended activities include Hawaii Volcanoes National Park, Akaka Falls, and Kona coffee farms. Resorts in Kona or Waikoloa provide oceanfront comfort and pools.
Maui: Known for luxury resorts, beautiful beaches, and the scenic Road to Hāna. Offers a balance of tourist-friendly areas like Wailea and Lahaina while still providing cultural experiences. You can also take a sunrise trip to Haleakalā Crater for dramatic landscapes.
Alternative options if you want fewer crowds or a more relaxed vibe: Kauai for lush landscapes and hiking, or Oahu for iconic Waikiki beach, cultural sites, and more urban/touristy experiences. Since your husband prefers more touristy vibes, Oahu can satisfy that, but it’s more urban than Big Island or Maui.

Regarding travel planning:

Travel Agent: For a first-time trip, a travel agent can simplify multi-island planning, secure accommodations and inter-island flights, and provide curated recommendations. This can save time and reduce stress, especially if you want a mix of resorts and experiences.
Self-Planning: Possible if you prefer research and flexibility. There are many online resources for booking hotels, rental cars, and activities.

Places and considerations to avoid or be cautious about:

Highly crowded tourist areas during peak hours (e.g., Waikiki beach in Oahu) if you prefer quieter experiences.
Driving in remote areas at night on Big Island or Maui, especially if unfamiliar with winding roads.
Areas impacted by natural events—check for any volcanic activity alerts on the Big Island or flood/fire advisories.

In summary, for your anniversary trip:

Late May is a good time to visit with pleasant weather and moderate crowds.
Consider Big Island + Maui for a mix of nature, volcanoes, beaches, and cultural immersion, or Maui + Oahu if you want more tourist-oriented experiences.
Using a travel agent can be helpful but is not strictly necessary if you enjoy planning.
Focus on safe, scenic, and popular areas, but avoid over-crowded tourist traps or poorly maintained remote roads.

Overall, your trip can combine relaxation, adventure, and cultural experiences while celebrating your anniversary in Hawaii’s unique beauty.