For travellers who enjoy learning as much as exploring, the presence of the right guide can change everything. Captain’s Choice’s expert-led journeys are built around this idea. This curated collection for 2026 features itineraries with experts in their fields, offering guests the opportunity to travel well, understand more, and delve deeper into the local culture.
Whether following a historic flight route, driving Italy’s most scenic roads in a supercar, or exploring the wines and cuisine of Southern Italy, these journeys are tailored for those who value depth as well as ease. Each offers the reassurance of carefully planned logistics from private transfers and accommodations to meals, tipping and valet luggage service, leaving guests free to immerse themselves fully in the experience.
Sydney to London: The Modern Kangaroo Route
In February 2026, Captain’s Choice will recreate the historic Kangaroo Route from Sydney to London, the pioneering Qantas journey first flown in 1947. This 14-day itinerary operates aboard a privately chartered Qantas Airbus A330, allowing travellers to experience the route itself as part of the journey rather than as a long-haul transfer.
Guests travel with retired Qantas Captain Greg Fitzgerald, whose aviation expertise offers insight into the history, mechanics, and culture of long-haul flight, and cultural historian Kenneth Park, formerly Curator of Collections at Wesley College Melbourne. Park’s knowledge brings each stop to life, connecting cities and sites to wider cultural and historical narratives.
Stops include Singapore, with its blend of colonial and modern architecture, vibrant street food culture, and waterfront precincts and Italy, where guests may explore the canals of Venice, the piazzas of Florence, or the quieter corners of Tuscan villages. Along the way, there is time for guided walks, private tours, and personal discovery, all framed by the expertise of the accompanying hosts.
The journey is deliberately unhurried, with evenings in well-chosen hotels and thoughtfully selected dining. Departing 3 February 2026, prices start at £26,650 per person, fully inclusive, with support from both a Tour Manager and Tour Doctor.
Italy by Supercar: From Lake Como to the Amalfi Coast
For those who enjoy being behind the wheel, Captain’s Choice’s Italian supercar journey in April offers an 11-day self-drive experience that balances enjoyment with insight. The route runs from Lake Como to the Amalfi Coast, following roads selected not just for their scenery, but for the way they reveal Italy’s landscapes.
Guests drive a rotating selection of Ferraris, Lamborghinis, Maseratis and other high-performance cars, supported each day by rally champion Lorenzo Granai and professional racetrack driver Fabio Mancini. Their guidance focuses on technique, confidence and control, complemented by stories drawn from years spent in competitive motorsport.
Away from the road, the journey allows time to explore. Lake Como offers quiet lakeside towns, private time on the water and visits to historic villas set among formal gardens. Further south, the route winds through Tuscany’s vineyard-lined hills and open countryside before reaching the Amalfi Coast, where narrow cliffside roads, citrus groves and pastel-coloured towns bring the journey to a striking close.
Accommodations are luxury hotels, chosen for their character and comfort, and meals include a combination of Michelin-starred restaurants and more informal regional dining experiences, giving a full picture of Italian culinary life. The Milan-to-Naples journey departs on 30 April 2026, priced from £27,500 per person, fully inclusive.
Southern Italy: A Culinary and Wine Immersion
For travellers who prefer a more measured pace, Captain’s Choice’s May 2026 journey through Southern Italy focuses on food, wine, and culture. Over 15 days, guests travel from Bari to Naples, guided by wine expert Michael Trembath. With over 25 years of experience importing Italian wines, Trembath introduces guests to winemakers, producers, and chefs, offering insight into both local viticulture and culinary traditions.
The route moves through some of Southern Italy’s most distinctive settings, from the cave dwellings of Matera to the trulli-lined streets of Alberobello, before continuing along the Amalfi Coast, where villages cling to the cliffs above the sea. Along the way, guests visit working vineyards for tastings and gentle walks among the vines, spend time with local chefs in their kitchens, then share meals that celebrate the flavours, traditions and rhythms of each region.
Accommodation is in elegant Masserias and small boutique hotels, each reflecting the character of its surroundings. The pace is relaxed, allowing time for private exploration, conversations with locals, or quiet moments to take in the scenery. Departing 23 May 2026, prices start from £23,450 per person, fully inclusive.
Exploring with Expertise
Across all three journeys, Captain’s Choice places the emphasis on thoughtful planning, expert guidance, and careful attention to detail. Expert hosts provide context and insight, ensuring that each experience has depth, while logistical arrangements are managed discreetly, leaving travellers free to enjoy the journey itself.
Whether it is the sense of history on the Kangaroo Route, the thrill of Italy’s roads, or the flavours and landscapes of Southern Italy, these itineraries allow guests to travel with confidence, curiosity, and ease. For those seeking experiences that are well-informed, seamless, and genuinely engaging, Captain’s Choice’s 2026 programme offers a compelling invitation to explore the world.