What your quote can include
- Round-trip flightsFrom your home airport in the US
- 4 nights of lodgingWailea or Kīhei
- Airport transfersArranged to match your flight times
- Tours & reservationsFor the activities in this plan
- Your day-by-day planPlus a book-ahead checklist
Pick only what you need. Each part is quoted with current prices before anything is booked.
Trip overview
The essential Maui highlights in five days, arranged so jet lag works in your favor (early mornings for sunrise and snorkeling). When to go: April–May and September–November usually bring good weather, lower rates and fewer crowds. For seasonal details, see our best time to visit Maui guide.
- Suggested base
- Wailea or Kīhei
- Fly into
- Kahului Airport (OGG)
- Trip style
- Nature & beaches
Day-by-day itinerary
A sample plan. We adjust the days, pace and activities to fit your trip.
Arrive and beach
Pick up your car, check in, and catch the sunset from the south shore.
- Wailea beach day. Wailea and Makena beaches have soft sand and generally calm morning water. Walk the coastal path that links the resorts.
- Sunset dinner by the ocean. Fresh fish, poke and island produce with a sunset view. Reserve early for popular spots in Wailea, Pāʻia and Kāʻanapali.
Haleakalā sunrise and Upcountry
Jet lag makes the early start easier. Warm layers essential; reservation required.
- Haleakalā sunrise. Watch the sun rise above a sea of clouds from the 10,000-foot summit. Sunrise entry requires an advance reservation from the National Park Service via Recreation.gov, and it's cold at the top, so bring warm layers.
- Upcountry farms and Makawao. Visit lavender and goat-cheese farms in Kula, sample local produce and wander the paniolo (cowboy) town of Makawao.
Molokini snorkel
Morning boat to the crater, afternoon at Big Beach.
- Molokini Crater snorkel. A morning boat trip to a partly submerged crater with famously clear water, often paired with a turtle snorkeling stop. Seas are calmest early.
- Mākena (Big Beach). A long, wide, undeveloped golden beach in a state park. The shorebreak can be powerful, so swim with caution.
Road to Hana
Leave very early, stop often, and drive respectfully. Consider staying the night in Hāna.
- Road to Hana. A winding coastal drive past waterfalls, black-sand Waiʻānapanapa State Park (reservations required) and bamboo forest. Start early, pull fully off the road at stops, and consider staying overnight in Hāna.
- Pīpīwai Trail and ʻOheʻo Gulch. In the Kīpahulu District of Haleakalā National Park past Hāna: a 4-mile round trip through a bamboo forest to 400-foot Waimoku Falls.
Pāʻia and departure
Coffee in Pāʻia and turtles at Hoʻokipa on your way to the airport.
- Pāʻia and Hoʻokipa turtles. Browse Pāʻia's surf shops and cafés, then watch windsurfers and basking green sea turtles at Hoʻokipa Beach Park. Give turtles plenty of space.
Choose your comfort level
The same itinerary works at different budgets. Pick the level that fits, and we'll quote it for your dates.
Essential
- A comfortable, well-reviewed 3-star hotel
- Economy flights at sensible times
- Shared airport transfers
- The plan's must-do tours, the rest at your own pace
Area to consider: Wailea and Kīhei (South Maui)
Choose EssentialSignature
- A 4-star hotel in a well-located area
- Economy or premium economy, best-timed flights
- Private airport transfers
- Guided tours and reservations for the key days
Area to consider: Hāna
Choose SignatureLuxury
- A 5-star hotel, with room upgrades where available
- Premium cabins where available
- Private transfers and guides
- Spa, dining and special-occasion reservations
Area to consider: Wailea and Kīhei (South Maui)
Choose LuxuryPrices depend on your dates, departure city and hotel, so we quote each comfort level on request. You can mix and match, for example a Signature hotel with Essential transfers.
Where to stay
Wailea and Kīhei (South Maui)
The sunniest, driest side of the island. Wailea has polished resorts and beach paths; Kīhei next door has condos and casual restaurants. Close to Molokini boat departures and good snorkeling.
Book these ahead
These parts of the trip need reservations or timed tickets that can sell out:
- Sunset dinner by the ocean
- Haleakalā sunrise
- Road to Hana
Pricing and policies, up front
Your quote shows the total trip price, per person and for your group, with taxes and the mandatory fees we can see included. Anything paid separately, such as some resort fees collected at check-in, local tourist taxes or checked bags on some fares, is listed clearly.
Many hotels, resorts, cruise lines and tour operators offer a deposit with the balance due before departure. Options vary by supplier, and we confirm them before you book.
Policies depend on the supplier and fare. We tell you the exact cancellation deadlines and any fees in writing before you commit.
Fares and rates change until they're booked. Some suppliers let us hold a rate briefly and many airfares can't be held, so we'll tell you what's possible for your trip.
You pay the travel provider directly, and RoamPlanned never takes payment for travel. How booking works.
Similar trips
Prefer a different pace? Try the 7-Day Maui Family Vacation Itinerary, read the full Maui travel guide, or build your own Maui plan.
