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Southern Highlights Tour - 3 Days / 2 Nights

From NZD$1650

(3 reviews)

Departs from: Tours from Queenstown

Duration: 72 hours

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Discover the very best of New Zealand’s Deep South on this premium small-group journey from Queenstown. Travel in comfort aboard luxury coaches, stay in handpicked Distinction Hotels, and experience a mix of iconic highlights and lesser-known gems. From heritage rail journeys and wild coastal scenery to the towering cliffs of Milford Sound, every day delivers unforgettable moments. With expert guides, seamless logistics, and breathtaking landscapes, this is southern New Zealand done properly.

Please note

This package combines three separate one-way day tours. Your guide and group will vary each day, giving you the chance to connect with multiple passionate local guides throughout your journey.

Itinerary

Why You’ll Love This

A scenic rail journey through dramatic gorges on the Taieri Gorge Train

Wild and rugged coastal beauty along the Catlins Coast

Historic Central Otago towns full of character and stories

An unforgettable cruise through the fjords of Milford Sound

Premium accommodation perfectly placed for comfort and relaxation

A small-group experience that feels personal, relaxed and immersive

What’s Included

Hotel pick-up and drop-off in Queenstown

All transport in a luxury 15-seat coach

Two nights of premium accommodation at Distinction Hotels

Taieri Gorge Train journey and ticket

Milford Sound cruise with lunch

A small group experience with our famously passionate guides - you'll meet a different expert guide each day

Please note

Exclusions: Meals except lunch on Milford Sound cruise.

Please allow up to 48 hours for us to confirm your booking. Once done we will be in touch with further details for each day of the journey.

The tour itinerary may operate in reverse depending on availability. You will be advised accordingly.

Our preferred accommodation partner is Distinction Hotels. In the rare event a property is fully booked, we'll secure you alternative accommodation of the same standard and location.

Why choose us

Famously passionate tour guides

Our guides share stories, laughs, and Kiwi charm on every journey.

Travel in comfort

Small groups, big comfort. Relax in our modern Mercedes minibuses with style and space.

Award-winning tours

Thousands of five-star reviews and top travel awards - experiences loved worldwide.

Kiwi owned. Kiwi operated

Proudly local and passionate about sharing authentic New Zealand with every traveller.

Stories worth sharing

5/15/2026

Absolutely a must book for your trip to the South Island!

The 3 day/2 night tour was the absolute highlight of our trip to New Zealand! It was so wonderful to know that we just had to show up and everything was booked and arranged for us. This was our first tour with Cheeky Kiwi - it exceeded all expectations and I cannot recommend this tour enough. Day 1 with Robb - this was our trip from Queenstown to Milford Sound and the scenery was fabulous. There was a bit of a miscommunication on our hotel pickup but Cheeky Kiwi handled it quickly and got us picked up without any issues. Robb had some great photo stops for us on our way to Milford Sound. They arranged our boat ride with Cruise Milford and we absolutely loved the boat and the captain/deckhand. There were other boats that were larger and could not get as close to the fiords as we could and there were also some smaller boats that looked a bit questionable but Cruise Milford was the perfect option. Cheeky Kiwi arranged a picnic lunch to bring onboard and that was perfect. (Tip: It is from the same cafe stop that you make at breakfast and included a sandwich, fruit, pastry and juice). After Milford Sound we made it to Te Anau. I will say I was not in love with the Distinction Hotel in Te Anau but being a smaller town with older accommodations it was fine. We enjoyed walking the town in the evening to find dinner. Day 2 with Jase/Jason - We were promptly picked up in Te Anau and made our way through Invercargill and the Caitlins to Dunedin. I wasn't sure what to expect with Day 2 based on the itinerary but it was absolutely magnificent. Jase is truly a gem and you can tell this is not just a job for him. He was so kind and an expert at what he does. The sights at the Southern Ocean were gorgeous and we enjoyed every minute of this day. Cheeky Kiwi - you truly have a rock star with this guide. We ended in Dunedin and the Distinction Hotel there was absolutely beautiful. The bed was so comfortable, a renovated room that included a washer and dryer in the bathroom. We walked a few blocks and found a great Mexican restaurant to enjoy dinner. We appreciated that pickup wasn't quite as early for Day 3 (: We did not eat at the restaurant on site but others on our tour did and said it was great. Day 3 - we started day 3 with a taxi ride (arranged by Cheeky Kiwi) to the train station. The Taieri Gorge Train ride was spectacular and the views were breathtaking. It's a lovely 2 hour ride to Pukerangi where a Cheeky Kiwi guide (Colin) was waiting for us. The train does have a catering company that had the best caramel slice and some amazing pastries and toasties. Colin brought us back to Queenstown with a few stops. I appreciated that the rest of day 3 was more relaxing after 2 days of busier travel. There is water and snacks provided in the vans and plenty of rest stops. There are also USB charging ports and wifi (when it's available). For some of the more remote areas of Fiordland and the Southern Ocean, there will not be wifi but you should be enjoying the views and not your phone anyway (: I absolutely cannot recommend this tour (and Cheeky Kiwi) enough. This was our first trip to NZ and it took all of the stress out of finding transportation, tour bookings and accommodations. Tip: This is actually 3 of their one way trips stacked together so you will have a new driver (and possibly new passengers) each day. Also, be sure to bring clothes for all seasons. We visited at the end of April and did find rain 2 of the 3 days but it made Milford Sound that much more amazing. We were able to leave our larger suitcases back at our accommodation before we started our tour so we only had to manage with a small suitcase each for the 3 days.

ndmom11

3/26/2026

Laughter & Beauty: Queenstown & beyond

We spent 3 days with Cheeky Kiwi. They were so much fun. Three unique, knowledgeable, fascinating, humorous drivers. Day 1 Jonathan (Queenstown to Dunedin) - had great stories & wonderful riddles. The train journey was great, especially because our conductor Craig gave our car a great history lesson. Day 2 Jason (Dunedin to Te Anau) - good sense of humor, lots of information about so many things, stories, & so much wildlife viewing. Day 3 Andy (Te Anau to Milford Sound to Queenstown) is also very informative, knowledgeable, and friendly. All-in-all, a great tour. We plan to continue to use Cheeky Kiwi, and highly recommend.

Rudi

2/20/2026

Endless highlights on this tour

If you are looking for the absolute best way to get around and see the southern half of the island, look no further! We had the most passionate guides (Joseph, Jason, and Jonathan) and every detail of the trip/itinerary was well planned out with excellent communication. We gained so much knowledge about the history, terrain, flora/fauna, and of course memories to last a lifetime. We never wanted it to end. We cannot wait until we can come back and see more of NZ with Cheeky Kiwi :)

Mikhaila S

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