14 Insider Journeys to Book Now

With the end of the year approaching, we’re looking back on where we’ve been and dreaming of where we want to go next. 2019 was filled with some incredible Insider Journeys that ventured all over the globe, from Uzbekistan, Lebanon and Ethiopia to Napa Valley, Lisbon and Rome. With another year of trips now behind us, our team has been hard at work planning exciting new itineraries for 2020. From the peaks of Bhutan, Patagonia and Kilimanjaro to the winding streets of Cartagena, Tokyo and Paris, these small group trips are crafted around your passion points—including art, design, food, adventure and history—and feature truly one-of-a-kind, unforgettable experiences like curator-led tours of private homes and galleries, after-hours access to top museums and monuments, dinner parties with stylish locals and personalized shopping excursions. As you fill out your travel calendar for the year ahead, these are the journeys that you won’t want to miss.

Interested in learning more about our upcoming Insider Journeys? Click here to get in touch with our team.

Cape Town, South Africa

Africa’s most stylish city has been enjoying the spotlight in recent years thanks to exciting openings like The Silo Hotel and the contemporary African art museum Zeitz MOCAA. From the contemporary designers and artists who are reimagining local tradition to the architects modernizing the cityscape, Cape Town’s creatives are some of the world’s best. Now, you can meet them—at special receptions and studio visits offering a behind-the-scenes look at their work—on our new Insider Journey in partnership with Architectural Digest, hosted by Indagare Founder (and Africa expert) Melissa Biggs Bradley and AD Contributing Editor Gay Gassmann. Plus, enjoy time to explore the Winelands, where you can visit epic estates and wander sculpture gardens, and have the chance to make a difference at some of the city’s most impactful community projects.

Chilean Patagonia

Few destinations are as dramatic as Chile: here, salt flats meet snow-capped mountains, and glacial rivers give way to sandy beaches and vast plains. On this journey through the Torres del Paine National Park (which is blissfully undeveloped and known as the eighth natural wonder of the world), you can test your limits on some of the most incredible hiking trails in the world—all against landscapes that must be seen to be believed. In the words of Indagare member Tricia Vanacore, who joined this journey in 2019: “Our trip was meticulously planned—gorgeous, relaxing accommodations, hikes amid spectacular scenery and delicious meals. At the same time, we were able to customize the daily activities to accommodate our own special interests. My daughter and I enjoyed every minute of it.”

Learn more and book now.

Paris, France 

One of our most exciting new Insider Journeys for 2020 is “A Fashion Lover’s Paris,” an exclusive itinerary curated in partnership with the editors at Vogue, featuring behind-the-scenes access to the headquarters of legendary French fashion houses—including Lanvin, Roger Vivier and Schiaparelli—as well as private receptions at the homes of some of Paris’ most stylish residents, accommodations at the indulgent palace hotel Le Bristol and the chance to go shopping with Vogue’s Head of Fashion Initiatives Rickie De Sole. Then, go behind closed doors to see celebrated artisans at work in their studios and privately tour fashion and art collections with their curators. In the words of an Indagare member who joined our inaugural Insider Journey with Vogue to Rome this year: “It was an amazing trip—we got to see the Roman fashion houses at their core, with all of the craftsmen and women creating beautiful pieces right in front of us. All of the hosts at each house were extremely charming and welcoming. It was a beautiful experience my daughter and I will cherish forever.”

Learn more and book now.

Mount Kilimanjaro, Tanzania

The world’s tallest freestanding mountain, Mount Kilimanjaro lures adventurers, thrill-seekers and climbers to Tanzania to summit its peak. Now, you can reach the so-called “Roof of Africa”—and check this amazing achievement off of your bucket list—with our nine-day trip package, which includes all safety equipment and local guides for the spectacular seven-day Machame Route, plus two nights at the lovely Arusha Coffee Lodge to acclimatize before you set off—and a team of experts that have your back (on the way up, and down!). In the words of Indagare Marketing Director Diana Li, who summited Mount Kilimanjaro last year (pictured above): “I discovered more about myself than my surroundings. I had time to listen and be fully present. I focused on achieving a single goal with a community that taught me oneness and perseverance.” A physically and mentally challenging excursion, this trip offers a once-in-a-lifetime experience, where each step can lead to a new discovery, and the journey is as inspiring as the destination.

Learn more and book now.


From the charming colonial streets of Cartagena and the verdant coffee region to the creative spirit of Bogotá and Medellín, Colombia offers dynamic cultural immersion in a fast-emerging travel hotspot. Our 2020 itinerary balances meaningful discussion of the country’s troubled past with an authentic look at the many ways that it is moving into the future—through the perspectives of locals like ex-soldiers, artists, activists and chefs, who will open doors to unforgettable experiences like a “handcrafted in Colombia” survey of Bogota’s top ateliers and artisan studios, a trip to Comuna 13 to explore the beating heart of political hip-hop and urban modern art, a visit to the Cartagena market with a local chef to learn how to make the perfect ceviche, and a private visit to the finca (estate) of renowned chef and restaurateur Carmen Angel, with the chance to spend time experimenting in the kitchen with Carmen. Plus, enjoy accommodations at the lovely Four Seasons Casa Medina and Casa San Agustín Cartagena, as well as prearranged flights throughout the trip.

Learn more and book now.

Milan, Italy

In partnership with WSJ. Magazine, our Insider Journey to Italy’s most fashionable city is back by popular demand for 2020. Join contributing editor Sarah Medford, who will lead you behind the scenes to meet the city’s most influential tastemakers and explore contemporary art galleries, cutting-edge ateliers and some of the area’s most magnificent and historic villas. Itinerary highlights include receptions at the private homes of iconic designers like Jacopo Etro, the founders of Dimore Studio and the late legendary designer Gabriella Crespi; a private tour and dinner at the historic Palazzo Crespi, which was designed by icon Renzo Mongiardino and contains the largest private collection of old masters in Milan; a private viewing of Leonardo da Vinci’s The Last Supper with an expert curator; VIP access to the Miart 2020 international art fair; and an exclusive invitation to a party hosted by WSJ. Magazine—with the chance to extend your trip by a few days in order to attend the 2020 Salone del Mobile design fair. In the words of an Indagare member who joined the Insider Journey to Milan with WSJ. Magazine in 2019: “It was an unforgettable, ‘Trip Of A Lifetime’ experience. The itinerary was on the absolutely highest level, and the friendships that we all created along the way were priceless!”

Learn more and book now.


Considered the last Buddhist Kingdom, Bhutan sits at the foot of the Himalayas and has remained isolated from the modern world for centuries. It is home to one of the world’s most fascinating cultures (it claims to be the happiest country on earth) and beautiful landscapes that are truly wild (it is the only country that is carbon-negative). You can explore this captivating place with daily hikes through rural towns and lush forests, as you make your way to the legendary Tiger’s Nest and relax at incredible Six Senses lodges. Along the way, discover ancient monasteries and rustic farmhouses, where you will be welcomed for meals and meditations—plus, experience an unforgettable farewell dinner under the stars in the ruins of a 15th-century dzong fortress, complete with live music, folk dancing and a traditional Bhutanese tasting menu.

Learn more and book now.


Often referred to as “the Paris of the Middle East,” Beirut is a modern city layered with paradoxes and cultural complexities that are rarely unpacked by the Western traveler—while the surrounding Lebanese countryside offers ancient towns that are today some of the oldest continuously inhabited places in the world, as well as verdant wineries and citrus groves, crafts centers and opulent mansions. Back by popular demand, our groundbreaking Lebanon journey with Architectural Digest is once again available for the curious traveler to experience. With your hosts, AD‘s Decorative Arts Editor Mitchell Owens and Interiors & Garden Director Alison Levasseur, you can access precious ancient ruins that span civilizations, explore multi-ethnic cuisine and dive into one of the world’s top emerging art and design scenes, with curator- and artist-led visits of top contemporary galleries, ateliers and studios. In the words of Indagare member Eleanor Seaman, who joined the inaugural Insider Journey to Lebanon with AD in 2019: “This trip exceeded all expectations—truly spectacular on every level. Such an exquisite combination of people, places and things to do and view…I could have stayed longer and explored more. I think it is always good leaving a place wanting more, so hopefully this means I will return again.”

Learn more and book now.


Japan is a place where insider access makes the difference between a great trip and a once-in-a-lifetime trip. With the right connections, a lot of closed doors can be opened, especially in Japanese culture, where personal introductions are key. Our 2020 Insider Journey to Tokyo and Kyoto with Architectural Digest, hosted by Indagare Founder Melissa Biggs Bradley and AD editor Gay Gassmann, will provide just that. Emphasizing a special focus on design, contemporary art, textiles and traditional crafts, itinerary highlights include expert-guided tours of top contemporary galleries and museums like the Nezu Museum, 21 21 Design Sight, the Mori Museum and the imaginative flower studio of Makoto Azuma; a day trip to Hakone to visit the Enoura Obervatory, wander the famous open-air sculpture park and get a taste of ryokan life; and immersive cultural experiences like a flower-arranging workshop, a traditional tea ceremony and the opportunity to see a geisha performance—plus plenty of time to taste local delicacies and learn about the art of Japanese cuisine, both past and present, with omakase and kaiseki meals, as well as reservations at top restaurants and stops for noodles and sushi at beloved local spots.

Learn more and book now.

St. Petersburg, Russia

St. Petersburg is an architectural laboratory, built by the greatest architects from Europe over a 300-year period,” says AD Contributing Editor and the host of our 2020 Insider Journey to St. Petersburg, Howard Christian. “Every major building is by a noted architect, and every building was bigger and grander than what came before. That’s why everything we’re going to see is special.” You can experience the magic of the “window to Europe” for yourself on our trip next spring, with the opportunity to visit the famed Hermitage Museum, after it has closed to the public, and go behind-the- ropes to explore its storage chambers (a treasure trove of Imperial items, from gilded carriages and Fabergé eggs to world-class works of art); enjoy VIP entrance to Catherine Palace, with a behind-the-scenes tour of the Amber Workshops and the Agate Pavilion; and see St. Petersburg’s most ornate architectural monuments and view rarely- seen collections of Repin, Kandinsky and other masters with expert guides. In the words of an attendee on the fall 2019 Insider Journey to St. Petersburg with AD: “St. Petersburg was a trip of a lifetime. You gave us all the biggest gift in opening the most amazing palaces and museums and most delicious restaurants in the city. The entire trip was so incredibly special, and we all loved meeting each other. As you said, this happens on all your Indagare trips—but it was perfect…so thank you!”

Learn more and book now.


Although Ethiopia is known as “the Geneva of Africa” and is home to one of the oldest Christian civilizations in the world and UNESCO-protected monuments, it is often overlooked by travelers who choose instead to head to its southern, safari-focused neighbors. On our trailblazing 10-day itinerary, which crosses from the capital of Addis Ababa through the rock-hewn churches of the Gheralta Mountains to the wild Omo River Valley, you can experience a rich combination of ancient history and urban life, untouched natural landscapes and astounding native cultures, adventure and deep unplugging from the minutiae of daily life in a remote oasis. Says Indagare Founder Melissa Biggs Bradley, who just returned from hosting our inaugural Insider Journey to Ethiopia in November: “From our hike to the ‘world’s most dangerous church’ (barefoot above a sheer 650-foot drop) to our immersion among the Omo River Valley tribes, this journey was awe-inspiring and eye-opening—one of the most physically and intellectually challenging trips I’ve ever made.”

Learn more and book now.

Related: Melissa’s Travels: Ethiopia


Related: Going Behind-the-Scenes in Egypt

Mexico City

From its colorful buildings and breathtaking Modernist murals to the cuisine served at its most innovative restaurants, many elements of Mexico City are works of art—so it’s no surprise that it was named 2018’s World Design Capital (and it continues to be one of the hottest travel destinations of this year). On our upcoming spring and fall Insider Journeys, hosted in partnership with Architectural Digest, you will venture out on studio visits with top designers and expert-guided tours of contemporary art museums and galleries, as well as the private houses of the Pritzker Prize-winning architect Luis Barragán and the homes and studios of Diego Rivera and Frida Kahlo. Other itinerary highlights include a an after-hours tour of the incredible National Museum of Anthropology and reservations at leading restaurants—plus, add on time in the charming colonial town (and artisan studio paradise) San Miguel de Allende

Learn more and book now.

Italian Dolomites

“I have never found a place where I love hiking more than the Dolomites,” says Indagare founder Melissa Biggs Bradley, who has joined Indagare members on hiking trips to the region in four of the last five years. “The combination of spectacular mountain scenery, expert local guides and amazing food and accommodations makes it a knock-out experience for anyone who loves the outdoors and being active.” The majestic Italian Dolomites, a UNESCO Natural World Heritage Site, offer untouched landscapes where you can truly unplug and get back in touch with nature and your own thoughts. With breathtaking views of the picturesque countryside, emerald-green meadows, waterfalls and jagged mountain peaks, you can test your limits on this beloved annual September Insider Journey, while exploring natural sites on daily hikes led by expert local guides. Your home base, the lovely Rosa Alpina resort in San Cassiano, offers access to hundreds of miles of trails, and active mornings will be followed by delicious, well-deserved meals at the best restaurants in the area—including the three-Michelin-starred Restaurant St. Hubertus—and free time to enjoy the lodge’s luxuries (like massages, spa treatments and the opportunity to participate in cooking and yoga classes).

Learn more and book now.

Coming Soon

Our team is working on exciting new itineraries to your most-requested places as well as up-and-coming destinations—including Senegal, India, Rwanda, Napa Valley, Uzbekistan, Botswana, France and more. Be the first to know when they are released by emailing our team at to join our preview access mailing list.

Interested in learning more about our upcoming Insider Journeys? Click here to get in touch with our team.

– Indagare on December 17, 2019

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