Destination · United States

Hawaii - Maui & the Big Island

Kapalua, Wailea, Mauna Kea & Hualalai (Hawaii)

Plantation at Kapalua, Bay Course Wailea, Mauna Kea, and Hualalai - Pacific cliff golf, lava-flow fairways, and the best winter golf trip in America.

Updated May 2026 · By the Pinseekers Travel team

The short answer

Pinseekers Travel runs 7-9 night Hawaii trips that pair Maui (Kapalua and Wailea) with the Big Island (Mauna Kea and Hualalai), playing the Plantation Course at Kapalua (PGA Tour's Sentry season opener), the Bay and Gold at Wailea, Mauna Kea Golf Course, and Hualalai Golf Course. Best months are December through April. Trips are designed for groups of 4-12 who want bucket-list winter golf with resort hospitality.

Best season

December - April (winter golf escape)

Trip length

7-9 nights / 5-7 rounds

Group size

4 - 12 players

Pricing from

$8,500 - $16,000 per player

Best for

Winter golf escapes, milestone anniversaries, partner-friendly trips

Fly into

OGG (Maui) + KOA (Big Island) - inter-island hop on Hawaiian Airlines

On the Ground

“Hawaii is two different trips depending on the island. Maui is Kapalua Plantation and the spectacle. Big Island is Mauna Lani, Mauna Kea, Hualalai - quieter, more architectural variety. The mistake groups make is trying to do both islands in one trip. Pick one and stay seven nights.”

Billy Belair, PGA Professional · Co-Founder, Pinseekers Travel

The courses we play

CourseDesignerType
Plantation Course at KapaluaBill Coore & Ben Crenshaw (1991, restoration 2019)Cliffside Pacific
Bay Course at WaileaArthur Jack Snyder (1972)Resort coastal
Gold Course at WaileaRobert Trent Jones Jr. (1994)Resort coastal upland
Mauna Kea Golf CourseRobert Trent Jones Sr. (1964, restoration 2008)Lava-flow Pacific links
Hualalai Golf CourseJack Nicklaus (1996)Lava-flow resort

Plantation Course at Kapalua

Bill Coore & Ben Crenshaw (1991, restoration 2019) · Cliffside Pacific · 7,596 yds, par 73

Annual host of the PGA Tour's Sentry (season-opening Tournament of Champions). Massive elevation changes, trade-wind shaping, and a closing 18th that drops 250 feet to the Pacific.

Bay Course at Wailea

Arthur Jack Snyder (1972) · Resort coastal · 6,815 yds, par 72

Walkable, friendly, with three holes along the Pacific. The right opener for Maui - beautiful, playable, and a perfect warm-up before Plantation.

Gold Course at Wailea

Robert Trent Jones Jr. (1994) · Resort coastal upland · 7,078 yds, par 72

The toughest of the three Wailea courses. Lava outcrops, ocean views from every hole, and elevated greens that demand precise distance control.

Mauna Kea Golf Course

Robert Trent Jones Sr. (1964, restoration 2008) · Lava-flow Pacific links · 7,370 yds, par 72

Originally built across raw lava on the Kohala Coast - Trent Jones Sr.'s own favorite of his designs. Hole 3, a 200-yd par 3 over the Pacific to a green carved into the cliff, is one of the great one-shotters in the world.

Hualalai Golf Course

Jack Nicklaus (1996) · Lava-flow resort · 7,117 yds, par 72

Annual host of the PGA Tour Champions' Mitsubishi Electric Championship. Resort-guest-only access at the Four Seasons Hualalai. Pristine conditioning, dramatic black-lava framing, and one of the best clubhouse-to-first-tee experiences in golf.

Sample itinerary

A representative routing - every Pinseekers trip is tuned to the group's travel windows, handicaps, and tee-time preferences.

Day 1

Arrive Maui (OGG)

Land OGG by mid-afternoon. Transfer to The Ritz-Carlton Maui Kapalua. Welcome dinner at Banyan Tree (on-property) with Pacific views.

Day 2

Bay Course at Wailea

Drive to Wailea (40 min). Round at Bay Course. Lunch at the Wailea clubhouse. Afternoon: Wailea beach time or partners' spa appointments. Dinner back at Kapalua.

Day 3

Plantation Course at Kapalua - the marquee round

Morning round on the Plantation Course. Lunch at Plantation House overlooking the 18th. Afternoon: Maui drive (Road to Hana for adventurous half-day, or West Maui scenic loop). Group dinner in Kapalua village.

Day 4

Gold Course Wailea + transit

Morning round at Wailea Gold (or replay Plantation). Pack up, fly OGG → KOA on Hawaiian Airlines (35 min). Check into the Four Seasons Hualalai or Mauna Kea Beach Hotel. Dinner at ULU Ocean Grill (Four Seasons).

Day 5

Mauna Kea Golf Course

Morning round at Mauna Kea - the lava-flow Trent Jones Sr. masterpiece. Lunch at the Mauna Kea clubhouse. Afternoon: snorkel at Hapuna Beach or volcanic crater visit. Dinner at the Mauna Kea Beach Hotel's Manta restaurant.

Day 6

Hualalai Golf Course

Round at Hualalai (resort-guest access required - must stay at Four Seasons Hualalai for guaranteed tee time). Afternoon at the Four Seasons pools, the Spa, or a private snorkel at Kua Bay. Group dinner at 'Ulu.

Day 7

Replay or rest day

Replay Mauna Kea or Hualalai, or take a rest day with snorkeling, helicopter tour over Volcanoes National Park, or the Mauna Kea summit observatory at sunset.

Day 8

Departure

Late morning departure from KOA. Most US groups fly home overnight to mainland east coast.

Lodging & basecamp

Basecamp: Maui: The Ritz-Carlton Maui Kapalua. Big Island: Four Seasons Hualalai or Mauna Kea Beach Hotel

Hualalai Golf Course is reserved for Four Seasons Hualalai resort guests - if you want guaranteed Hualalai access, you must stay there. Mauna Kea Beach Hotel offers preferred-guest tee times at Mauna Kea Golf Course. We split the trip between the two islands so each course gets the right basecamp.

When to go

December through April is the prime window - 78-82°F, the trade winds are reliable, and the rain side of each island stays mostly windward. May-November is summer - hot, humid, and busy with mainland family travel. Avoid the second week of January (Sentry tournament week closes Plantation for play) and Memorial Day / Thanksgiving / Christmas peak weeks unless you book 12+ months out.

Getting there & transfers

Maui (OGG) and the Big Island (KOA) both have direct flights from West Coast US cities (LAX, SFO, SEA, PDX). East Coast players typically connect through LAX or SFO. The inter-island hop on Hawaiian Airlines (OGG → KOA) is 35 minutes and we build it into Day 4. For Black Card trips, private aviation between islands is available.

Pricing tiers

Indicative ranges. Final quotes depend on group size, season, lodging, and tee-time tier - email events@pinseekerstravel.com for a custom build.

Standard

$8,500 - $11,000 per player

  • · 7 nights split between Ritz-Carlton Maui and Mauna Kea Beach Hotel (shared rooms)
  • · 5 rounds: Bay Wailea, Plantation Kapalua, Gold Wailea, Mauna Kea, Hualalai
  • · Inter-island flights OGG → KOA
  • · Welcome dinner + breakfast daily
  • · Airport transfers both islands

Premium

$11,000 - $13,500 per player

  • · 8 nights with Big Island upgrade to Four Seasons Hualalai (single rooms)
  • · 6 rounds (adds a Plantation or Mauna Kea replay)
  • · Three group dinners (Banyan Tree, Manta, ULU)
  • · Half-day Maui or Big Island private adventure (Road to Hana, snorkel charter, or helicopter)
  • · Spa credit at both basecamps

Black Card

$13,500 - $18,000 per player

  • · 9 nights, Four Seasons Hualalai oceanfront suite + Ritz-Carlton Maui suite
  • · 7 rounds with caddies on every round
  • · Private chef dinner with sommelier on the Big Island
  • · Mauna Kea summit sunset experience or volcano helicopter tour
  • · Private aviation inter-island hop (OGG → KOA)

Tipping & budget tips

  • Caddies are not standard at most Hawaii courses - riding carts are the norm. Tip the cart attendant $20 at bag drop.
  • Hawaii state taxes and resort fees can add 15-18% to lodging - factor it into the per-player price.
  • Inter-island Hawaiian Airlines flights are short and cheap on advance purchase. Book 60+ days out for the best fares.
  • Hualalai Golf Course is resort-guest-only - never promise the round unless the Four Seasons stay is confirmed.
  • January through April is trade-wind season - afternoon tee times can blow 20-25 mph; book mornings.

Common questions about Hawaii - Maui & the Big Island golf trips

How much does a Hawaii - Maui & the Big Island golf trip cost per person?

Pinseekers Travel Hawaii - Maui & the Big Island trips run $8,500 - $16,000 per player. Final pricing depends on group size, season, lodging tier, the caddie program, and whether you add premium rounds or off-property activities. We publish standard, premium, and black-card tiers on this page; email events@pinseekerstravel.com with your dates and roster size and we'll come back with a custom quote within one business day.

What is the best time of year for a Hawaii - Maui & the Big Island golf trip?

The prime window for Hawaii - Maui & the Big Island is December - April (winter golf escape). Conditioning, weather, and tee-time access all peak in that range. Shoulder months can drop pricing 20-30% with most days still playable. We don't book outside the prime window unless the group prefers off-season value over guaranteed weather - the "When to go" section above breaks down each month in detail.

How many days should a Hawaii - Maui & the Big Island golf trip be?

Most Hawaii - Maui & the Big Island groups travel for 7-9 nights / 5-7 rounds. Shorter than that and the marquee rounds feel rushed; longer and fatigue cuts into scoring on the closing days. We size every trip to the group's travel windows, handicaps, and how many courses they want to play - the sample itinerary on this page is one representative routing, not the only shape the trip can take.

What are the must-play courses at Hawaii - Maui & the Big Island?

The marquee rounds we sequence on a Hawaii - Maui & the Big Island trip are Plantation Course at Kapalua, Bay Course at Wailea, Gold Course at Wailea, Mauna Kea Golf Course. Each is profiled in "The courses we play" section above with designer, course type, and the strategic reason it earns a tee time on the schedule. Additional add-on rounds and replay options are available for groups that want to extend the trip or get a second crack at a favorite layout.

What's the closest airport to Hawaii - Maui & the Big Island?

Most groups fly into OGG (Maui) + KOA (Big Island) - inter-island hop on Hawaiian Airlines. Pinseekers arranges group transfers from the airport to the basecamp and between courses for groups of four or more, with larger groups split across multiple vans. Private aviation arrivals are coordinated separately when the group has access. The "Getting there & transfers" section above lists the alternates worth considering.

Can I ship my golf clubs to Hawaii - Maui & the Big Island?

Yes. Pinseekers handles club shipping on every trip via Ship Sticks or Luggage Forward, with door-to-door pickup from your home or club and delivery to the resort bag room before arrival. Most groups ship one direction and fly back with their sticks; we coordinate the pickup window, the labels, and the resort hand-off so you land and play.

What's a typical group size for a Hawaii - Maui & the Big Island golf trip?

Hawaii - Maui & the Big Island trips typically run 4 - 12 players. The format suits winter golf escapes, milestone anniversaries, partner-friendly trips. Smaller groups (under the listed minimum) are workable but lose tee-time flexibility; larger groups need a custom build and a longer lead time for lodging blocks. Tell us your roster size in the brief and we'll size the routing - and the sample itinerary - around it.

How early should I book a Hawaii - Maui & the Big Island golf trip?

Book Hawaii - Maui & the Big Island trips six to twelve months ahead for prime-season dates. Marquee rounds and on-property lodging fill earliest, especially over weekends in the December - April (winter golf escape) window. Off-season and weekday trips can sometimes be confirmed inside 90 days. Send the brief as soon as the group's dates are firm; we hold tee times the same week the contract is signed.

Are caddies available at Hawaii - Maui & the Big Island?

Caddies are available at most Hawaii - Maui & the Big Island courses and required at a few. Pinseekers books the caddie program with the round - including forecaddies, pro-line caddies, and walking-only setups where the property requires it. We brief every caddie on the group's preferences before the round goes off, and tipping guidance is included in the trip packet so nobody is guessing on the first tee.

Does Pinseekers handle non-golfer activities at Hawaii - Maui & the Big Island?

Yes. Pinseekers coordinates non-golfer activities on every Hawaii - Maui & the Big Island trip - spa, dining, off-property tours, cultural experiences, fishing, and whatever else the group's spouses or non-golfing partners want to fit in. Tell us in the brief who's traveling and what they want to do, and we'll build the parallel schedule into the trip without making it feel like a separate booking.

Further Reading

Plan your Hawaii - Maui & the Big Island trip

Pinseekers Travel runs Hawaii - Maui & the Big Island trips end-to-end - tee times, lodging, transfers, dining, and the on-trip schedule. Send a brief and we'll come back with two routings within one business day.

Inquire about Hawaii - Maui & the Big Island

Last updated: 2026-05-05