Hawaii 2027 — Whales, Volcanoes & Aloha
A 12-night island-hopping adventure for two
January 6–18, 2027 • Big Island → Ka'anapali → Wailea
🗺️ Route Overview
Three destinations, two islands, one unforgettable trip. Start with volcanoes and stargazing on the Big Island, then cross to Maui for whale watching, coastal hikes, and the Road to Hana.
🌋 Big Island
4 nights · Jan 6–10
Kohala Coast base. Volcanoes National Park, Mauna Kea stargazing, helicopter tour, Kona coffee farms, and a splurge dinner at CanoeHouse.
🐋 Ka'anapali
5 nights · Jan 10–15
West Maui's whale watching capital. Two whale watches, sunset sail, Kapalua Coastal Trail, Waihee Ridge hike, and the Old Lahaina Luau.
🌺 Wailea / Kihei
3 nights · Jan 15–18
South Maui serenity. Road to Hana full day, 'Iao Valley, Kula Botanical Garden, and a splurge finale at Mama's Fish House.
📋 At a Glance — 13 Days
| Day | Date | Location | Highlights |
|---|---|---|---|
| 1 | Jan 6 (Wed) | Big Island | Arrive KOA, A-Bay sunset, Lava Lava Beach Club dinner |
| 2 | Jan 7 (Thu) | Big Island | Greenwell Farms coffee tour, Pu'uhonua o Honaunau, CanoeHouse splurge |
| 3 | Jan 8 (Fri) | Big Island | Volcanoes NP full day — crater overlooks, lava tube, Chain of Craters Rd |
| 4 | Jan 9 (Sat) | Big Island | Helicopter tour AM, Botanical Garden PM, Mauna Kea stargazing PM |
| 5 | Jan 10 (Sun) | Big Island → Ka'anapali | Fly KOA→OGG, drive to Ka'anapali, Hula Grill dinner |
| 6 | Jan 11 (Mon) | Ka'anapali | Whale watch AM, Ka'anapali Beach, Black Rock sunset, Japengo dinner |
| 7 | Jan 12 (Tue) | Ka'anapali | Kapalua Coastal Trail, Merriman's lunch, sunset sail, Monkeypod dinner |
| 8 | Jan 13 (Wed) | Ka'anapali | Second whale watch, Waihee Ridge Trail hike, Fleetwood's dinner |
| 9 | Jan 14 (Thu) | Ka'anapali | Beach/pool recovery, Whaler's Village shopping, Old Lahaina Luau |
| 10 | Jan 15 (Fri) | Ka'anapali → Wailea | Check out, 'Iao Valley, Maui Tropical Plantation, arrive Wailea, Nalu's |
| 11 | Jan 16 (Sat) | Wailea | Road to Hana full day — Twin Falls, black sand beach, Pipiwai Trail |
| 12 | Jan 17 (Sun) | Wailea | Kula Botanical Garden, Lavender Farm, Mama's Fish House splurge |
| 13 | Jan 18 (Mon) | Departure | Optional Kihei Caffe breakfast, OGG departure (MLK Day) |
🌤️ January Weather
January is peak whale season and the "cooler" time in Hawaii — perfect for active exploring without oppressive heat. Expect occasional brief rain showers, especially on windward sides.
💰 Budget Estimate (2 people, 12 nights)
| Category | Low Estimate | High Estimate | Notes |
|---|---|---|---|
| Flights (TPA→KOA, OGG→TPA) | $1,200 | $1,800 | Economy, connecting, per couple |
| Inter-island flight (KOA→OGG) | $150 | $250 | Hawaiian/Southwest, ~45 min |
| Hotels (12 nights) | $3,360 | $4,560 | $280–380 avg/night |
| Rental Cars (2 rentals, 12 days) | $840 | $1,200 | $70–100/day incl. insurance |
| Dining (all meals) | $2,000 | $3,000 | Incl. 2 splurge dinners ($550–750) |
| Activities & Tours | $1,400 | $2,100 | Helicopter, stargazing, whale watches, luau, sail |
| Park Fees & Misc | $200 | $350 | NP entry, Hana reservations, tips, parking |
| Gas | $150 | $200 | ~$5/gal Hawaii; ~50 mi/day avg |
| Shopping & Souvenirs | $200 | $400 | Coffee, macadamia nuts, aloha shirts |
| TOTAL | $9,500 | $13,860 |
💡 Savings Tips
Book Big Island hotel with Hilton Honors points (80,000–95,000/night) to save $1,200–$1,600. Use Capital One Venture X for 10x on hotels booked through portal. Pair with Rakuten 3-5% cashback on Hilton.com.
Booking Tools & Strategy
Flight search links, cashback portals, Points Yeah for award flights, and TripIt integration are on the Booking & Tips page.
🚗 Rental Cars
A rental car is essential on both islands — there's no public transit, rail, or rideshare in rural areas. You'll need two separate rentals.
Rental Breakdown
| Island | Pickup | Drop-off | Duration | Est. Cost |
|---|---|---|---|---|
| Big Island | KOA Airport, Jan 6 | KOA Airport, Jan 10 | 4 days | $280–400 |
| Maui | OGG Airport, Jan 10 | OGG Airport, Jan 18 | 8 days | $560–800 |
Booking Tips
- Book early — January is peak season, and Hawaii rental inventory is limited
- Mid-size SUV recommended — handles Volcanoes NP roads and Road to Hana comfortably
- No 4WD needed — Mauna Kea tour provides transport; Hana Hwy is paved
- Skip GPS — use Google Maps or Apple Maps on your phone (works fine offline with downloaded maps)
- Prepay fuel — gas stations near OGG/KOA charge more; prepay if mileage is predictable
- Check credit card coverage — many premium cards cover rental insurance (Capital One Venture X, Chase Sapphire)
Comparison Sites
Google Cars • Kayak • Costco Travel • AutoSlash (price tracking) • Discover Cars
Parking Costs
| Location | Parking | Notes |
|---|---|---|
| Hilton Waikoloa Village | $40–55/day | Self-park or valet; in-and-out privileges |
| Ka'anapali Beach Hotels | $25–40/day | Self-park; free at some condo properties |
| Wailea Hotels | $20–35/day | HGV Maui Bay Villas may include free parking |
| Volcanoes National Park | Free | Included with $30/vehicle entry |
| Wai'anapanapa (Hana) | $10/vehicle | Reservation required |
Driving Tips
- Hawaii drives on the right (same as mainland US)
- Speed limits are strictly enforced — 25-45 mph in most areas
- Road to Hana: start by 7 AM, allow 10-12 hours round trip, one-lane bridges yield to oncoming
- Big Island distances are deceptive — Volcanoes NP is 2+ hours from Kohala Coast
- No driving on beaches. Sand + salt = expensive rental damage
- Return with a full tank or face $8-10/gal refueling charges
📅 Booking Timeline
| When | Action | Why |
|---|---|---|
| 9–12 months out (Jan–Apr 2026) | Book flights TPA→KOA, OGG→TPA | Best prices; connecting routes sell out |
| 9–12 months out | Book hotels (Hilton direct for points) | Peak season; free cancellation policies |
| 6–9 months out (Apr–Jul 2026) | Book rental cars | Hawaii inventory is limited; rebook if price drops |
| 6 months out | Book inter-island flight KOA→OGG | Hawaiian Airlines or Southwest; flexible |
| 3–6 months out (Jul–Oct 2026) | Book Mauna Kea stargazing tour | Popular; limited spots per night |
| 3–6 months out | Book helicopter tour (Big Island) | Weather cancellations common; flexible date helps |
| 3–6 months out | Book Old Lahaina Luau | Most popular on Maui; sells out weeks ahead |
| 2–3 months out (Oct–Nov 2026) | Book whale watching (×2) | Can wait; frequent departures in peak season |
| 2–3 months out | Book sunset sail (Ka'anapali) | Moderate demand; flexible |
| 2–3 months out | Reserve Wai'anapanapa (Hana black sand) | State requires advance reservation ($5pp + $10/vehicle) |
| 1–2 months out (Nov–Dec 2026) | Book splurge restaurants (CanoeHouse, Mama's) | Small venues; peak season reservations essential |
| 1 week out | Download offline maps, confirm all reservations | Cell coverage is spotty on Hana Hwy and Volcanoes NP |
🧳 Packing Recommendations
Essentials
- Reef-safe sunscreen (SPF 50+, mineral-based — Hawaii law requires it)
- Light rain jacket or windbreaker (tropical showers, Mauna Kea evening)
- Warm layer for Mauna Kea (drops to 40°F/4°C at 9,000 ft)
- Comfortable hiking shoes (Waihee Ridge, Pipiwai Trail)
- Water shoes or Tevas (black sand beach, tide pools)
- Polarized sunglasses (whale spotting + glare reduction)
- Binoculars (whale watching from shore)
- Wide-brim hat
- Waterproof phone pouch (boat tours, Hana waterfalls)
Photography Gear
- Camera with zoom lens (200mm+ for whales)
- Tripod for Mauna Kea stargazing and long exposures
- Extra batteries (cold temps at altitude drain fast)
- Lens cloth (salt spray on boat tours)
⚠️ Holiday Notice
Martin Luther King Jr. Day — January 18, 2027 (Monday)
Your departure day falls on MLK Day. Expect heavier traffic to OGG airport and potentially busier flights. Some shops and restaurants may have modified hours. Allow extra time — depart hotel 3 hours before your flight.