The South Island Circumnavigation is an anti-clockwise voyage around New Zealand’s remote and spectacular South Island. This Category 1 offshore expedition follows in the wake of Captain James Cook’s explorations, taking you through some of the wildest and most beautiful waters in the Southern Hemisphere.
Departing from Picton, we sail south along the rugged east coast, round the Otago Peninsula, and enter the deep south, where Southern Ocean swells and exposed headlands demand skill and respect. The voyage then ventures into the heart of Fiordland, where glacier-carved valleys plunge into sheltered waters. Weather permitting, we will visit several fiords, each offering untouched wilderness rich in birdlife, waterfalls, and towering cliffs.
From Fiordland, we round the southwest capes and head north along the challenging West Coast. This leg brings long offshore stretches, dramatic mountain backdrops, and the chance to spot rare seabirds, seals, and dolphins. Finally, we re-enter Cook Strait and return to Picton, having experienced every face of the South Island — dramatic, isolated, and unforgettable.
With a flexible itinerary shaped by weather, this voyage requires preparation, offshore experience, and a spirit of adventure. For those ready to take on the challenge, it is an extraordinary way to experience the power, history, and majesty of Aotearoa’s southern shores.
Sail the full circumference of New Zealand’s South Island
Complete an extraordinary anti-clockwise circumnavigation, retracing the legendary route of Captain Cook and experiencing the diverse, dramatic coastline of one of the world’s most remote islands.
Master offshore sailing across some of the wildest waters in the Southern Hemisphere
Navigate powerful Southern Ocean swells, cross open straits, and round rugged capes as you build advanced offshore miles and seamanship in real blue-water conditions.
Explore Fiordland’s glacier-carved sanctuaries
Drop anchor in iconic fiords like Doubtful and Dusky Sound. Go ashore to hike mossy trails, kayak among sheer cliffs and waterfalls, and immerse yourself in the pristine wilderness of this UNESCO World Heritage Area.
Hike and kayak in some of the island’s most remote corners
Weather permitting, access hidden beaches, hike into wild headlands, and paddle quiet waterways surrounded by alpine landscapes, temperate rainforest, and endemic wildlife.
Witness rare wildlife and raw nature
Spot albatross, fur seals, penguins, and dolphins in their natural habitat. Scan the sea for whales, and marvel at the towering cliffs, deep valleys, and untouched coastline that define the South Island.
Conquer the temperamental West Coast and cross Cook Strait
Sail along the isolated, brooding West Coast before making the dynamic crossing of Cook Strait—one of the most challenging stretches of water in New Zealand.
Experience true expedition sailing
This flexible Category 1 itinerary responds to weather and sea conditions, offering an authentic and adventurous journey for experienced sailors ready to take on a once-in-a-lifetime challenge.
Picton Marina
Gateway to the Marlborough Sounds with full marina services
Surrounded by cafés, shops, and scenic waterfront walks
Queen Charlotte Sound / Tōtaranui
Sheltered waterways lined with forested hills and quiet bays
Popular for sailing, kayaking, and spotting dolphins
Rangitoto ki te Tonga / D’Urville Island
Remote island with rugged coastline and strong tidal currents
Known for fishing, diving, and wildlife-rich waters
Kaiteriteri
Golden sandy beach and sheltered anchorage at the edge of Abel Tasman National Park
Access to coastal walking tracks and turquoise bays
Milford Sound / Piopiotahi
World-famous fiord with sheer cliffs, waterfalls, and towering Mitre Peak
Rich marine life including seals, dolphins, and penguins
Bligh Sound
Remote, narrow fiord surrounded by steep forested slopes
Offers sheltered anchorages and pristine wilderness
Te Houhou / George Sound
Deep, unspoiled fiord accessible only by sea or on foot
Known for dramatic scenery and rich marine biodiversity
Te Awa-o-Tū / Thompson Sound
Scenic fiord branching inland between steep mountains
Connects with Doubtful Sound for sheltered cruising
Doubtful Sound / Patea
Vast and remote fiord three times longer than Milford
Noted for its silence, abundant wildlife, and serene anchorages
Oban
Only township on Stewart Island/Rakiura
Base for exploring native bush, birdlife, and island walking tracks
Akaroa
Picturesque harbour town set in the crater of an ancient volcano
Known for French heritage, dolphin encounters, and scenic coastal walks
Tory Channel / Kura Te Au
Major shipping route between Cook Strait and Queen Charlotte Sound
Steep-sided channel with strong tidal flows and rich marine life
Marlborough Sounds
Network of drowned river valleys with sheltered bays and forested hills
Popular for sailing, kayaking, fishing, and spotting dolphins
Acting as watch captain (day and night), helming, navigating, checking weather and monitoring AIS and radar and for both traffic and rain squalls. View gallery
Downloading and analysing the latest weather forecasts and calculating best route to destination. View gallery
Navigating, hazard identification, entering waypoints and calculating updated ETA’s. View gallery
Watch roster planning, matching responsibility to experience, crew management and communication. View gallery
Familiarisation of all safety procedures, sail planning, storm preparation planning and abandon ship procedures. View gallery
Advice on how to take responsibility for managing clothing, hydration, sleep and nutrition to maintain your health and well being aboard. View gallery
Planning our arrival and route to safe harbour including timing with daylight (if required), weather factors, navigational hazards, communications / customs and sail/motor arrival plan. View gallery
Hoisting, trimming and reefing both upwind (main, genoas, and jibs) and downwind sails (poled out headsails, spinnakers, gennakers and code 0’s (subject to weather). View gallery
Use of PDF’s (Personal Flotation Devices), PLB’s (Personal Locator Beacons), safety tethers, dan buoy’s, storm drogue, liferaft and any other equipment required to ensure you remain safe in all conditions. View gallery
Onshore activities include hiking and bushwalking to scenic lookouts, exploring local towns, and discovering the unique charm of each destination. Enjoy cultural immersion through local traditions, relax with games, or uncover hidden gems as you explore islands. View gallery
Coastal exploring offers the thrill of venturing to remote places using a RIB, uncovering hidden gems like pristine reefs, secluded beaches, and winding rivers. Discover shipwrecks teeming with history, indulge in beach combing for unique treasures, and experience the untouched beauty of coastal landscapes. View gallery
Dining out offers the chance to enjoy local flavours, explore regional specialties, and experience unique culinary traditions. From seaside cafes to hidden gems, each meal is an opportunity to savour the culture and cuisine of the destination. View gallery
Fishing provides an opportunity to connect with nature, whether casting a line from the shore or exploring deeper waters. Enjoy the thrill of the catch, the serenity of the surroundings, and the chance to bring home a fresh, rewarding meal. View gallery
Exploring historic places offers a glimpse into the past through ancient sites, architectural landmarks, and local stories. These visits bring history to life, connecting you with the culture, traditions, and events that shaped each destination. View gallery
Kayaking allows you to glide through serene waterways, explore hidden coves, and get up close to nature. It’s a peaceful yet adventurous way to discover rivers, coastlines, and marine life from a unique perspective. View gallery
Snorkelling offers an up-close view of vibrant underwater ecosystems, from colourful coral reefs to fascinating marine life. It's a relaxing and immersive way to explore the wonders beneath the surface of the water. View gallery
Swimming offers refreshing escapes in stunning settings, from crystal-clear bays and tranquil rivers to diving off the back of the boat into azure waters. It's a perfect way to relax and be rejuvenated by nature. View gallery
Wildlife watching offers unforgettable encounters with nature, from observing birds and dolphins to spotting whales, turtles, and sharks. Discover diverse marine life, from playful fish to delicate starfish, in their natural habitats. View gallery
Step aboard Silverfern, a sleek and spacious sailing yacht crafted for comfort, camaraderie, and coastal exploration. Whether you're navigating hidden bays, sharing stories over dinner on deck, or trimming sails on an offshore leg, Silverfern offers the ideal balance of relaxation and hands-on adventure. With warm hospitality, inviting living spaces, and a spirit of discovery at its core, every journey on Silverfern feels like coming home—only at sea.
You can fly directly into Blenheim or Picton or arrive in Picton by Cook Strait Ferry.
26 Jan 2027
Arrive at the vessel in Picton Marina by 3:00pm
Crew training and safety familiarisation
Yacht systems orientation and route briefing
Crew welcome dinner and stay onboard
Depart for first overnight anchorage
27 Jan - 15 Feb 2027
Complete 1,500nm anti-clockwise circumnavigation of the South Island
15 Feb 2027
Arrive back into Picton Marina by mid-afternoon
Farewell crew dinner
16 Feb 2027
Depart from Blenheim or Picton Airport or catch the Picton Ferry to Wellington
Inclusions
Your crew package includes; all meals onboard, accommodation onboard, your Ocean Sailing Expeditions crew shirt, marina fees, the use of a PFD (personal floatation device), PLB (personal locator beacon), and a safety tether. Your bedding, a pillow and towel are also included along with suncream.
Exclusions
Your crew package excludes; meals and accommodation ashore, flights and transport to and from departure and arrival ports, alcohol, toiletries, clothing and wet weather gear.
Its always recommended that you book flights with date flexibility incase of unforeseen changes due to weather or schedules.
Eligibility
You will need to complete a 5-hour online or 2-day Sea Safety and Survival Training Course or equivalent at least 1 month prior.
Accommodation
If you plan to fly in a day earlier, or stay onboard the night after we return to port, an extra night's accommodation is available onboard, prior to departure and/or after arrival as an add-on, for $100 per person, per night. This can be purchased through your We Travel account during the booking process or prior to departure.
Accommodation options if you want to stay ashore either side of trip: AirBNB, Booking.com, Wotif & HomeAway.
Book and pay
Click Book Now button above to secure your place. Choose from Pay in Full or deposit options. Direct debit from bank account, debit card or credit card options available. Pay in the currency of your choice.
Personalise your payment plan
If you want to set up a payment plan, contact us here and let us know your desired deposit (minimum 10% required) and your preferred payment. You can make up to 18 payments, for the balance. You can choose the frequency and customise each payment amount.
Not ready to pay, but want to secure your place?
Reserve your place onboard today, with no obligation. We’ll send the confirmation details, itinerary, deposit invoice and be sure to answer all your questions, while you finalise your plans before confirming. Reserve here.
100% cancellation guarantee
If you book and then cancel prior to an event, for any reason, 100% of your payment will be issued as a credit, that you can apply to any future event/s. For a full refund of sailing trip, flights and hotel costs, we recommend travel insurance. View Terms & Conditions.
Members
Check for Member's availability here before booking this event, using Members Benefits. When you book Reserve your place here.