Tripsha Takes Group Travel To A New And Personal Level

By Michael Alpiner, Contributor

Most travelers return home after a vacation with souvenirs and some great memories. Tripsha, the brainchild of Cassie Shih, founder and CEO, specializes in community-focused travel where adventurers return from their journeys with meaningful experiences and a new group of friends.

Cassie Shih, Founder and CEO of Tripsha. Courtesy of Tripsha

Unlike most group travel, which is often filled with uncertainty. Tripsha’s unique formula reduces the chance that one’s travel companions might be strange ingredients in an otherwise tasty soup. It starts with the themed trips, clear expectations, personalized member profiles, and the expertise of the host(s).

Tripsha encourages travel with personal connections. Courtesy of Clifford Pickett

Using an example from a recent trip, Upstate NY Getaway, which ran from August 14-16, 2021, host Kerry Botensten created a trip based on her interests and knowledge. Kerry, who is also Head of Trips for Tripsha.com, appreciates the beauty of Upstate New York, the benefits of exercise, the essential elements found in good wine and new friends, and the importance of capturing all those experiences for posterity.

Thus, she curated an itinerary that included accommodations, transport, meals, activities and down time. She invited experts to assist her with the themed activities, working with the rest of the Tripsha team to manage and advise with the organization, budget, marketing and miscellaneous details.

Kerry Botensten, Head of Trips for Tripsha. Courtesy of Clifford Pickett

Once a date and cost was established, Tripsha posted the trip on their website and assisted with invites and social media messaging. Interested guests then set up a Tripsha profile so that they can communicate with the team as well as other guests that they will meet. Often, they already know other guests as word of mouth serves to be one of the best modes of marketing. 

Kerry invited photographers, Susan Magnano and Clifford Pickett, to accompany the guests, who instructed them on how to best utilize the features on their mobile devices for the purpose of enhancing vacation photos and adding creativity to those Instagrammable moments. 

Photographers Susan Magnano and Clifford Pickett Courtesy of Susan Magnano

“We are not only giving them tips on how to take pictures,” said Susan, “but on how to see the world differently. We share with them how to see beautiful light and interesting compositions, as well as anticipate special moments.” 

Cliff agreed, “We hope our students walk away with a deeper appreciation of the beauty that surrounds them. Any camera, even your phone, is the perfect tool to explore your curiosity and experience the world around you.”

Skytop Tower at Mohonk Mountain, within the Alfred K. Smiley Monument, New Paltz, NY. Courtesy of Michael Alpiner

Some of the other activities Kerry planned was a biking tour and wine sipping in association with Outerthere (because an uphill bike ride under a summer sun deserves the gift of wine) and care of Robibero Winery.

The team of Outerthere. Courtesy of Clifford Pickett

The group also strolled to the Water Street Market to refresh with coffee and light bites. At the residence selected for the group, a comfortable Airbnb central to all the activities, the group was treated to a wine and cheese pairing by Francesca Defranchis, founder of iloveitalianfoodnyc.com. Her stories of personal passion for food and destinations were punctuated by the camaraderie of the group gathered around a fire pit, the selection of cheeses, wines, breads, and topped by shavings of black truffle. With an Old World charm and contemporary flare, Francesca helped make the group of travelers feel as if they had known each other for years.

Francesca Defranchis, Founder of iloveitalianfoodnyc.com Courtesy of Clifford Pickett

The same comfort and warmth was felt during the final dinner at Garvan’s Gastropub, which occupies a building built in 1759 on historic Huguenot Street, and where the group sat outside among locust trees, and acted like this was not the last formal gathering of the trip. The Guinness was thick and rich, the food expertly prepared, and the service friendly and joyful. 

What sets Tripsha apart from so many of its competitors is the focus on building relationships among a travel-friendly community through a membership platform, social media connections, opportunities for discussions and face-to-face gatherings.

The Upstate New York Getaway group, August 14-16, 2021. Courtesy of Susan Magnano

The travelers share common interests, know ahead of time whether the adventures are within their range of possibility, and end up learning something applicable to future travel. 

Personal connections are priceless, and essentially the deepest purpose of travel.


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