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Travel Like A Girl Boss: 13 Trips Led By Successful Women Founders

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Photo courtesy of Naya Traveler

Want to experience travel in a more meaningful and authentic way? A number of woman-owned travel companies are running founder-led trips to the world’s most amazing destinations. Some of these trips are led by women who are inviting travelers to the places they grew up. These journeys offer an intimate homecoming experience, providing the opportunity to go beyond the tourist route and discover a country like a local. Other trips are designed by jet-setting travel experts who have gotten to know a place inside out and have tapped into a network of insiders who will give you access to the best a destination has to offer. And other founder-led trips offer everything from business networking to soul searching.

Whatever route you take, a founder-led trip gives a unique opportunity to see the world with like-minded travelers and get an inside look at what it takes for an entrepreneur to launch a successful business.

READ MORE: "Meet The World's First Black Woman Cruise Ship Captain"

Photo courtesy of Naya Traveler

Morocco, Spain and Argentina with Naya Traveler

The Company: Naya Traveler offers highly personalized itineraries and curated experiential journeys to culturally rich destinations.

The Founders: Sofia Mascotena, Sarah Casewit and Marta Tucci believe that the stories and connections that emerge from traveling with “naya” (purpose) are just as important as the tangibles. Naya Traveler works with locals garnered from the founders’ own personal relationships, ranging from traditional artists and literary authors to ethnographers and more.

The Trip: Naya Traveler's first-ever founder-led trip to Morocco is set for June 3-13 with Casewit, who called this country home for over 20 years. She will take a small group of 12 travelers on a 10-day journey through her favorite destinations, including the medieval city of Fez, the Sahara Desert, the Red City of Marrakesh and more. Naya Traveler will offer two additional founder-led trips in 2020 with Tucci leading a small group to Spain and Mascotena leading one to Argentina, their respective home countries.

Photo courtesy of Vaera Journeys

Puerto Vallarta with Vaera Journeys 

The Company: Vaera Journeys runs retreats for entrepreneurial women on the verge of new ideas. The retreats are styled to help women take their personal and professional goals to the next level by helping them explore a project that gives them purpose.

The Founder: Vaera Journeys is the brainchild of New York-based travel writer Meagan Drillinger, who came up with the idea as a way to bring together her passions for uplifting other women and transformational travel.  

The Trip: Each Vaera trip is inspired by a unique destination and includes curated experiences for up to 10 guests that are designed to foster creative discussion, including sessions with a guest speaker and one-on-one coaching. Vaera Journeys’ next retreat to Puerto Vallarta (May 2-7) will include bonding, networking and learning how to grow your personal business and brand. In addition to Drillinger, Elena Ollick — a serial entrepreneur who started her own business at age 16 — will accompany the trip as the featured speaker. A dedicated photographer will provide professional-level pictures to use for business head shots or on social media.

Photo courtesy of Nancy Novogrod

Paris, India, and Japan with Culturati Travel Design

The Company: Culturati Travel Design leads expertly curated intimate group trips focused on art, architecture, design, food and style.

The Founder: After 21 years as Editor in Chief of Travel + Leisure, following five years in the same role at House & Garden, Nancy Novogrod is drawing upon her personal knowledge, insider network and passions to create trips to destinations throughout the world. Working in affiliation with Valerie Wilson Travel, Novogrod personally selects every element of the itinerary, from hotels and restaurants to access-rich experiences of arts and culture.

The Trip: In November of this year, Novogrod will be leading a group of approximately 10 people to India, a country she came to know well — and love deeply — during many past visits for T+L. Created in collaboration with leading specialists on the destination, the itinerary includes Mumbai, Udaipur, Jaipur, Agra and Delhi, with one-of-a-kind experiences of historic sites, such as the Taj Mahal at dawn. There will also be contemporary lifestyle excursions and expert-guided shopping for everything from shawls and fashion to art and decoration. Other Novogrod-led trips: Paris (October 2019) and Japan (March 2020).

Photo courtesy of Deborah Calmeyer

South Africa, Kenya and the Northern Cape Province with Roar Africa

The Company: Roar Africa's travel specialty is in the crafting of highly bespoke, private travel experiences that offer exclusive-access opportunities in Southern and East Africa.

The Founder: Deborah Calmeyer has lived between New York and Cape Town for the past 20 years, giving the Zimbabwe-born entrepreneur an understanding of the needs and desires of sophisticated American travelers. Her pioneering family’s 329-year history in South Africa forms the core of her ultra-luxe bi-cultural travel company run by women and supported by native-born guides and a curated network of experts, all committed to the preservation and support of the people, animals and environment of their fragile and extraordinary homeland. (You can read more about Calmeyer in "It's A Jungle Out There: 10 Wild Career Tips.")

The Trips: Calmeyer will lead Roar Africa's "Rewilding: Roar & Restore Retreat" (May 31 to June 5), a learning journey of reconnecting, self-discovery and self-realization in the wilds of Kenya at Segera Retreat. The lineup of speakers includes visionaries, game-changers and eco-pioneers who will encourage and stimulate thinking about rewilding and how our instinctual relationship with the wild is the best prescription of all. One week later, Calmeyer is joined by media legend Pat Mitchell for Roar Africa’s first-ever "Women’s Empowerment Journey" at Tswalu. Together, they have created a highly specialized experience hosted by an all-female team of pilots, guides, trackers, conservationists, chefs and hospitality staff who have overcome the industry "norm” in the male-dominated safari business. 

Photo courtesy of Kristin Karst

European Rivers with AmaWaterways

The Company: AmaWaterways offers unforgettable river cruise vacations with 23 ships sailing Europe’s Danube, Rhine, Moselle, Main, Rhone, Seine, Garonne, Dordogne, Dutch and Belgian Waterways and Douro Rivers, Southeast Asia’s Mekong and Africa’s Chobe River.

The Founder: Co-owner and Executive Vice President Kristin Karst believes that travel is imperative to opening up your understanding of diverse cultures. For Karst, there is no better way to learn and grow than exploring the world. In 2002 along with Rudi Schreiner (her husband) and the late Jimmy Murphy, Karst set out to create a river cruise company that she herself would want to travel with – and AmaWaterways was born.  The name, “Ama,” comes from the Latin word for "love," and it's a concept that is woven into every aspect of their river cruises, from the design of the ships to the carefully-crafted itineraries

The Trip: AmaWaterways’ special Founder’s Cruises debuted in 2018. The 2019 dates will be announced soon on Karst’s blog on the company's website. Guests who choose these cruises will have the unique opportunity to get to know Karst personally, experiencing firsthand her passion for river cruising while learning what’s on the horizon for this innovative company. In addition to enjoying the variety of daily excursions, active hiking and biking tours, wonderful meals and wine and beer that are offered complimentary by AmaWaterways, guests on board these Founder’s Cruises will have the option to also participate in the company’s popular wellness activities, led by a dedicated Wellness Host and championed by Karst herself.

Photo courtesy of Melissa Biggs Bradley

Italian Dolomites with Indagare

The Company: Indagare is a members-only, boutique travel-planning company that offers curated content, customized trip-planning and group trips around passion points. Indagare partners with its members to design a personalized roadmap for their lifetime of journeys and unlocks behind-the-scenes access they won’t find anywhere else.

The Founder: After a successful career as an editor at Town & Country and Town & Country Travel, Melissa Biggs Bradley founded Indagare in 2007 because she believed that creating a platform for exchange between passionate travelers would allow for more transformative journeys and meaningful global connections. Bradley has visited over 100 countries in her travels, and, most recently, she has been scouting in Lebanon, Saudi Arabia, Madagascar, Egypt and Colombia.

The Trips: Indagare's Insider Journeys offer one-of-a-kind itineraries crafted around passion points, including contemporary design and architecture, outdoor adventure and wellness. One of the longest-running and most popular journeys is a wellness- and fitness-focused trip hosted by Bradley that explores the Italian Dolomites on daily guided hikes and a stay at Rosa Alpina lodge (September 15-20). This year, there will be more than 40 Insider Journeys all over the globe, from Marrakech and Rwanda to Milan and Beirut. Some of this year’s other in-demand itineraries include a spring trip to Havana, Cuba for the Biennial art fair and a fall trip to Egypt to see the pyramids and cruise down the Nile.

Photo courtesy of Andeana Hats

Peru with Andeana Hats and Glossy Paradise

The Company: Andeana Hats works with Quechua artisans in the Sacred Valley of Peru to create pieces that capture the energy of the Andean people. Each of the hats has a woven intention band with its own meaning. Glossy Paradise is a natural beauty company that creates face oils that come directly from the depths of the Amazon rainforest, where nutrient-rich superfoods have been healing the indigenous population for centuries.

The Founders: For founders Laura Grier and Pats Krysiak, their mission behind the creation of Andeana Hats is to empower women, help support global artisans to continue their vanishing crafts and enable them to lead their communities out of poverty.

The Trip: Grier and Krysiak invite travelers to join them on one of their inspirational eight-night journeys through the Sacred Valley and the Amazon in Peru, visiting the origin of both of their businesses: Andeana Hats and Glossy Paradise. They've partnered with the non-profit organization, Awamaki, to create sustainable tours that not only are fun and educational, but provide a positive impact in the Quechua communities. On the tour, you'll get to meet the communities behind the products, see how they create them from scratch and get in a bit of relaxation and exploration while taking in the incredible beauty of the Sacred Valley and the Amazon, two completely different worlds that exist within Peru.

Photo courtesy of Stacy Readal

Tanzania with Duma Explorer

The Company: Duma Explorer, a safari and trekking company based in Arusha, Tanzania, provides a unique window into the landscape, wildlife and culture of this extraordinary region.

The Founder: Originally from the U.S., Stacy Readal first visited Tanzania in 1998 while studying at the university there. After volunteering in education and HIV/AIDS prevention for two years in a small town on the slopes of Mount Kilimanjaro, she joined with a local partner and started Duma Explorer. In 2012, Readal and a business partner launched a second company, Chaka Camps, and now operate three tented camps in Tanzania's national parks.

The Trip: In the summer of 2020, travelers can explore Tanzania with Readal on an eight-day founder-led safari that starts in Arusha and includes locations like Tarangire National Park, Ngoronoro Crater and Serengeti National Park. You’ll visit the village and house where Readal spent her first several years in Tanzania, see the school that Duma Explorer built and have an amazing safari experience staying in Chaka Camps' luxury tents.

Photo courtesy of Kelly Lewis

Hawaii with Damesly

The Company: Damesly is a boutique women's tour company that runs trips that combine travel with creative and professional development workshops.

The Founder: Kelly Lewis — a women's travel industry maven — has founded several companies in the space. Her projects include Go! Girl Guides (travel guidebooks for women) and the annual Women's Travel Fest. She started Damesly as a way to help women see the world, while also learning new skills that can help them grow creatively and professionally.

The Trip: Travel to Hawaii with Damesly and Lewis herself, who grew up on Oahu, where this tour takes place. The "Islands + Identity" tour (May 17-23) includes surf lessons, hula lessons, snorkeling and paddle boarding, as well as spa time and some deep soul work with a licensed professional to help you get clear on your strengths and purpose. Other signature trips include "Cameras + Canyons" (September 6-9), a photo workshop led by a pro through the Grand Canyon, Antelope Canyon and Horseshoe Bend and "Writing + Riding" (June 7-10), a Denver-based creative writing workshop combined with horseback riding in the Rocky Mountains.

Photo courtesy of Jordan Ashley

Tibet, Rwanda and South Africa with Souljourn Yoga

The Company: Souljourn Yoga is a nonprofit that raises awareness and funds in developing countries through yoga retreats as a way to promote female empowerment and girls' education to communities where equal opportunities aren't always readily available.

The Founder: An international journalist-turned-yoga teacher, Jordan Ashley recognized a need for service-based yoga and a need for experiences that give perspective to the self through selflessness. Feeling extremely blessed to not only be given the opportunity for education, but to have a voice in society, she felt it was imperative to raise both awareness and funds for girls all over the planet who are denied such essential human rights.

The Trip: Ashley is leading three upcoming retreats, starting with “A Tribe Called Tibet” (May 25 to June 1), a week of yin and yang, movement and meditation, luxury and social change on the Tibetan Plateau. The trip will include a transformative day with Educating Girls of Rural China, a nonprofit dedicated to providing higher education to impoverished young women. On Souljourn’s “Yoga Adventure Rwanda” (June 25 to July 5), you'll experience a full cultural immersion, go chimpanzee trekking and visit a women's collective in Kigali. In January 2020, Ashley will lead a journey to Cape Town, South Africa (January 17-26) that includes volunteering for the Female Empowerment Program with Lalela Project, which uses an arts curriculum to ignite imagination and teach children how to map and manifest their dreams and goals.

Photo courtesy of Judi Wineland

Tanzania with AdventureWomen

The Company: AdventureWomen invites women traveling solo and/or with their friends or family on active explorations full of empowering discoveries across over 30 destinations. AdventureWomen is co-owned by Judi Wineland, who is also cofounder of Thomson Safaris and founder of Thomson Family Adventures. (You can read more about Wineland in "9 Lessons From The Wild That Will Help You Get Ahead In Business.")

The Co-Owner: Along with her daughters Erica and Nicole, Judi Wineland is co-owner of AdventureWomen, which she believes is much more than a travel company. AdventureWomen is a "relationship" company, encouraging women to build new connections with the world, with themselves and with other like-minded women around the globe. Wineland is also cofounder of Thomson Safaris, a safari tour operator in Tanzania that she created in 1981 with her husband Rick Thomson. In 1998, Wineland also founded the U.S.-based Thomson Family Adventures, which is dedicated to providing families with exciting trips around the world.

The TripWineland is leading three "insiders" trips to Tanzania with AdventureWomen in May and October 2019, where she has migrated annually since 1979 (and where she and her husband launched Thomson Safaris in 1981). This unique itinerary includes an opportunity to watch the annual Great Migration in the Serengeti, go on day and night game drives in Ngorongoro Crater and enjoy gourmet, farm-to-table cuisine and luxurious accommodations at Gibbs Farm. This trip also offers unparalleled experiences for women to fully embrace the culture of Tanzania as they get to know entrepreneurial Maasai women and meet the self-empowered leaders of the Enjipai Women’s Group in a remote region of Northern Tanzania.

Photo courtesy of WHOA Travel

Bavaria and Oktoberfest with WHOA Travel

The Company: WHOA Travel is an adventure travel company for women by women that’s all about stepping out of your comfort zone, connecting with women from around the world and having a crazy fun time in the process. (The WHOA in the name stands for Women High on Adventure.)

The Founders: Cofounders/chief adventurers Allison Fleece and Danielle Thornton believe that the WHOA style of adventuring is about more than just travel. It’s about taking risks, not taking yourself or life too seriously and taking every opportunity to be outside and activeFleece and Thornton (aka "Dallison," short for Allison and Danielle) also believe in going out of your way to make choices that align with what you believe in, like supporting woman’s interests and locally owned businesses, especially when you’re traveling.

The Trip: Fleece is leading one of WHOA’s annual flagship adventures: a trip to Bavaria and Oktoberfest (September 19-24). It’s one of WHOA’s only journeys that’s not at a high altitude, but it’s still high on adventure, with hiking, biking and paragliding around Bavaria, a place where all trails lead to a beer garden. The grand finale is a coveted reservation at Oktoberfest in Munich. Fleece called Munich home for three years, so you can count on lots of insider local experiences and tips, and you’ll quickly discover that there is much more to Munich than beer.

Photo courtesy of Phyllis Stoller

Global Trips with the Women's Travel Group

The Company: For 27 years, the Women’s Travel Group has created affordable yet luxurious small group tours that appeal to adventurous travelers. The company's goal is to tap into up-and-coming destinations and bring women deep into a country, its culture and food.

The Founder: After living overseas for 10 years, Phyllis Stoller moved back to the U.S. and found American women were reluctant to travel solo. She left an executive banking position to create the Women’s Travel Group, which provides a safe and fun way for solo women to see the world. 

The TripsStoller regularly hosts founder-led trips. This year, she'll be leading journeys to Albania and Corfu (April 15-22), a destination that's newly popular with Europeans, as well as another trip to Croatia, Montenegro, Bosnia and Herzegovina (September 27 to October 6) that begins in Zagreb and ends in Dubrovnik. In 2020, Stoller will be leading a trip to Dubai, Oman, Abu Dhabi and Sharjah (March 14-24).

READ MORE:

"Meet The World's First Black Woman Cruise Ship Captain"

• "Quit Your Job And Live Abroad in 2019: 10 Places So Cheap You Might Not Need to Work."

• "The 38 Cheapest Places To Travel In 2019."

• "Airport And Airline Hacks: 9 Ways To Travel Like A Pro"

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