From Roman-era Zagreb to the neon hum of Asia, the world’s greatest waterfront party in Sydney, and the emerald drama of New Zealand, this 20-day itinerary threads culture, cuisine, and postcard landscapes into one exhilarating journey. You’ll time your run to catch New Year’s Eve on Sydney Harbour, then drive from North Island fern forests to South Island peaks and fiords.

New Zealand’s Māori heritage anchors this trip—felt in Rotorua’s haka rhythms, seen in carved meeting houses, and tasted in hangi feasts. In the South, glacial valleys give way to alpine lakes and the cathedral-silent fiords of Fiordland. Along the way: skydive views, jet boats, glowworm caves, and Middle‑earth’s Hobbiton.

Practical notes: December–January is peak summer in Australia and New Zealand—book key vantage points for NYE, Milford Sound tours, and popular stays early. Drive on the left in NZ, allow extra time for scenic roads, and pack sun protection. This plan includes estimated travel times and flight cost ranges current through March 2025.

Singapore

Days 1–3: Lion City stopover of food, gardens, and skyline sunsets

Singapore blends Peranakan shophouses with futuristic Supertrees. It’s safe, spotless, and wonderfully edible—hawker centers are UNESCO-listed for a reason.

• Top sights: Gardens by the Bay at dusk (OCBC Skyway), Marina Bay Sands SkyPark, Chinatown and Buddha Tooth Relic Temple, Kampong Glam’s Haji Lane murals, and the National Gallery’s Southeast Asian art.
• Eat & drink: Breakfast kaya toast and kopi at Ya Kun or Tong Ah; hawker hits at Maxwell Food Centre (Tian Tian Hainanese Chicken Rice) and Amoy Street Food Centre (A Noodle Story); dinner at Candlenut (Peranakan, Michelin-star) or Burnt Ends at Dempsey (wood-fired). Cocktails at Atlas (art deco grandeur) or Jigger & Pony.
• Coffee breaks: Tiong Bahru Bakery for kouign-amann; Nylon Coffee Roasters for serious beans.

Where to stay: Browse stays on VRBO Singapore or hotels on Hotels.com Singapore.

Getting there from Zagreb: Morning flight ZAG→SIN via one stop (13–17 hours, typical $550–900 round-trip segments). Search fares on Omio (flights). Alternative search engines: Kiwi.com, Trip.com (flights).

Sydney

Days 4–6: New Year’s Eve on the Harbour and coastal days

Sydney thrills with surf beaches, sandstone headlands, and that iconic Opera House. New Year’s Eve fireworks arc across the Harbour Bridge in a spectacle watched worldwide.

• NYE tips: Reserve ticketed vantage points (e.g., Royal Botanic Garden, Barangaroo Reserve) months ahead; free areas like Mrs Macquaries Point or Blues Point Reserve fill fast—arrive mid-afternoon with snacks and water.
• Essentials: Walk the Opera House and The Rocks; ferry to Manly for sunset; Bondi–Coogee coastal walk for cliff pools and cafes; Barangaroo for waterfront dining.
• Eat & drink: Breakfast at The Grounds of the City (CBD) or Single O (Surry Hills); dim sum lunch at Palace Chinese or Mr. Wong; pre-fireworks bites and bubbles at Opera Bar or Quay’s green apple snow egg successor menu; day-after fish and chips at Watsons Bay Hotel.

Where to stay: See options on VRBO Sydney or Hotels.com Sydney.

Getting there: SIN→SYD nonstop ~8 hours (typical $250–500). Search on Trip.com (flights) or Kiwi.com.

Auckland

Days 7–8: Harbours, volcano cones, and city flavor

Auckland rises over 48 extinct volcanoes and two glittering harbours. Sail culture runs deep, and so does a thriving food scene anchored by local seafood and produce.

• Highlights: Views from Mount Eden and the Sky Tower; ferry to Waiheke for cellar doors; stroll Britomart and the Viaduct; Auckland War Memorial Museum for Māori taonga.
• Eat & coffee: Breakfast at Bestie in St Kevins Arcade or Daily Bread; lunch at Amano (house-made pasta, seafood) or Depot by Al Brown (oysters, tuatua clams); gelato at Giapo; cocktails at Caretaker (speakeasy).

Recommended activities:

• Skydive Auckland — New Zealand’s highest tandem jump at 18,000 ft, with twin-coast views and a 75‑second freefall.

  

• 2025 Award Winning: Auckland City Highlights Half Day Tour — A compact, locally guided look at the city’s best vistas and stories.

  

• Hobbiton Movie Set Small Group Tour from Auckland — Step into the Shire, with time for the Green Dragon Inn.

  

Where to stay: VRBO Auckland | Hotels.com Auckland

Getting there: SYD→AKL ~3 hr (typical $120–250). Search on Trip.com or Kiwi.com. Pick up your rental car at AKL for the road-trip days that follow.

Rotorua & Waitomo

Days 9–11: Geothermal wonders, Māori culture, and glowworm caves

Rotorua breathes—literally. Steam curls from pavements, geysers erupt, and Māori culture is lived and shared with pride. Nearby Waitomo hides a galaxy of glowworms in its limestone caves.

• Rotorua highlights: Te Puia for the Pōhutu Geyser; Redwoods Treewalk at twilight; soak at Polynesian Spa (lake views).
• Waitomo highlights: Silent boat rides under glowworms, or black-water rafting through caverns for the adventurous.
• Eat & coffee (Rotorua): Morning coffee and pastries at Scope or Ciabatta Cafe; lunch bowls at Terrace Kitchen; dinner share plates at Atticus Finch on Eat Streat; Skyline Gondola up to Stratosfare for sunset buffet.

Recommended activities:

• Mitai Maori Village Cultural Experience in Rotorua — Warriors gliding by waka, haka, and a traditional hāngī dinner.

  

• Waitomo Glowworm Caves Guided Tour — Drift under starry bioluminescence, guided by cave experts tied to the land.

  

• Black Water Rafting Experience Waitomo Caves Tour — The original cave tubing adventure, waterfalls and glowworms included.

  

Where to stay: VRBO Rotorua | Hotels.com Rotorua — and if you base near the caves: VRBO Waitomo | Hotels.com Waitomo.

Getting there: AKL→Rotorua drive ~3 hr (car ~$50–80/day). Rotorua→Waitomo ~2 hr, Waitomo→Auckland ~2.5 hr to position for a flight south next morning.

Christchurch & Mackenzie Country

Days 12–13: Rebuild creativity, turquoise lakes, and alpine stars

Christchurch has reinvented itself with laneway eateries, street art, and riverside markets. A few hours inland, the Mackenzie Basin unfurls glacier-fed lakes and some of Earth’s best stargazing.

• Christchurch bites: Coffee at C1 Espresso or Unknown Chapter; lunch-graze at Riverside Market or Little High Eatery; dinner at Twenty Seven Steps (seasonal NZ fare) or Earl (Mediterranean-leaning, local produce).
• Mackenzie highlights: Lake Tekapo’s Church of the Good Shepherd; Dark Sky Reserve stargazing; Aoraki/Mt Cook walks (Hooker Valley Track) and Tasman Glacier view.
• Tekapo eats: Kohan Restaurant (Japanese, lake views); Dark Sky Project’s Astro Café on Mt John (daytime views) and Blue Lake Eatery & Bar for hearty mains.

Where to stay: City or country, your pick: VRBO Christchurch | Hotels.com Christchurch — Mackenzie bases: VRBO Lake Tekapo | Hotels.com Lake Tekapo and VRBO Mount Cook | Hotels.com Mount Cook.

Getting there: Morning flight AKL→CHC ~1 hr 25 min (typical $40–120) via Trip.com or Kiwi.com. Drive CHC→Tekapo ~3 hr; Tekapo→Aoraki/Mt Cook ~1 hr 15; Mt Cook→Queenstown ~3 hr.

Queenstown & Fiordland

Days 14–17: Adventure capital and the grandeur of Milford Sound

Queenstown pairs alpine drama with adrenaline and wine-country ease. Fiordland steals breaths in sunshine or rain—sheer cliffs, ink-dark waters, and waterfalls threaded with mist.

• Queenstown musts: Gondola to Bob’s Peak for sunset; stroll the lakefront; tastings at Amisfield or Gibbston Valley; Arrowtown’s gold-rush streets.
• Eat & coffee: Morning at Bespoke Kitchen or Vudu; lunch line for Fergburger (or the bakery next door); dinner at Rātā by Josh Emett (seasonal NZ) or Botswana Butchery (lakeside). Nightcap at The Bunker or Eichardt’s Bar.

Recommended activities:

• Shotover River Extreme Jet Boat Ride in Queenstown — Skim canyon walls, spin, and grin.

  

• Premium Milford Sound Small Group Tour & Cruise from Queenstown — Boutique coach, scenic stops, and a quiet-boat fiord cruise.

  

• Walter Peak Gourmet BBQ Lunch & Queenstown Lake Cruise — Steam across Wakatipu to a lakeside farm for a notably good grill.

  

• NZONE Skydive Queenstown — Lakes and peaks from freefall—Queenstown’s classic adrenaline fix.

  

Where to stay: Base in town for dining and lake views: VRBO Queenstown | Hotels.com Queenstown. For Fiordland overnights: VRBO Te Anau | Hotels.com Te Anau.

Getting there: Drive Aoraki/Mt Cook→Queenstown ~3 hr. Milford Sound is a full day by coach and cruise (12–13 hr round trip) or self-drive to Te Anau first (2 hr) then to Milford (2 hr).

Dunedin & the Otago Peninsula

Day 18: Wildlife, Victorian streets, and great coastal curves

Dunedin wears its Scottish roots proudly—gold-rush architecture, steep streets, and a university-town creative pulse. The Otago Peninsula shelters penguins, sea lions, and albatross.

• Wildlife: Join a small-group farm-based eco-experience to see yellow-eyed penguins and other species in their natural habitats.
• Eat & coffee: Coffee at The Perc or The Good Oil; wood-fired brunch at Vogel St Kitchen; fresh fish at Best Café (classic NZ) or dinner at No.7 Balmac in Roslyn; local pints at Emerson’s Brewery.

Recommended activity: Clearwater Wildlife Tours (small group 10max) Otago Peninsula — Fewer people, more wildlife, on a family farm with rich biodiversity.

Where to stay: VRBO Dunedin | Hotels.com Dunedin.

Getting there: Drive Queenstown→Dunedin ~3.5 hr via fruit stalls and rolling hills. Position for a next-morning flight north to connect to Tokyo.

Tokyo

Days 19–20: Neon nights and temple calm before flying home

Tokyo is a city of a thousand micro-moments: incense curling at Sensō-ji, neon melting over Shibuya, knives flashing at Tsukiji’s outer market. Two days is a tasting menu—enough to know you’ll return.

• Essentials: Meiji Jingu’s forested hush; Omotesandō architecture; Shibuya Sky for citywide views; Asakusa’s Nakamise shopping street; teamLabs’ digital art if time allows.
• Eat & coffee: Breakfast kissaten-style at Café de L’Ambre (for coffee purists) or Blue Bottle (Aoyama); ramen at Afuri (yuzu shio) or Ichiran for a solo booth experience; tempura at Tsunahachi; sushi splurge at Kyubey Ginza; cocktails at Bar Orchard or SG Club.

Where to stay: VRBO Tokyo | Hotels.com Tokyo.

Getting there: Dunedin→Tokyo via Auckland or Christchurch (16–22 hr total, typical $700–1100). Search on Trip.com or Kiwi.com. Tokyo→Zagreb homebound 15–18 hr via one stop (typical $650–950); compare on Omio (flights).

Putting it all together: Travel legs at a glance

• Zagreb → Singapore: 13–17 hr, 1 stop, ~$550–900. Search flights.
• Singapore → Sydney: ~8 hr, ~$250–500. Trip.com | Kiwi.com.
• Sydney → Auckland: ~3 hr, ~$120–250. Trip.com | Kiwi.com.
• Auckland → Christchurch: 1 hr 25 min, ~$40–120. Trip.com.
• South Island drives: CHC→Tekapo 3 hr; Tekapo→Aoraki 1 hr 15; Aoraki→Queenstown 3 hr; Queenstown→Dunedin 3.5 hr. Car hire ~$50–80/day.
• Dunedin → Tokyo: 16–22 hr via AKL/CHC, ~$700–1100. Trip.com | Kiwi.com.
• Tokyo → Zagreb: 15–18 hr, 1 stop, ~$650–950. Omio (flights).

Optional add-ons and swaps

• If you want more Middle‑earth: From Auckland, consider a combined Hobbiton + Waitomo day from the city instead of splitting days between Rotorua and Waitomo.
• Weather wildcard: In heavy rain, consider a Doubtful Sound cruise day from Te Anau as an alternative to Milford—equally moody and majestic. Bookings via local providers or the Milford tours listed above.
• Queenstown boats: The TSS Earnslaw steamship undergoes maintenance from May 19 to Oct 1, 2025; the Walter Peak experience operates with alternative vessels in that window.

In 20 days you’ll taste hawker classics in Singapore, toast New Year’s under Sydney’s sky, and traverse New Zealand from glowworm caves to glacier valleys. It’s a route that balances city energy with nature’s hush—epic drives, great plates, and a few daring leaps along the way.