by Jeroslyn JoVonn
June 12, 2024
SquadTrip wants you to make this summer the last summer you and your friends keep vacation plans stuck inside the group chat.
Make this summer the last summer you and your friends keep vacation plans in the group chat. Poor planning and inconvenient timing often leave travelers exhausted before they even begin.
Situations like these inspired SquadTrip to launch its all-in-one group travel platform. Designed to provide both first-time travelers and seasoned explorers with tools for stress-free trips, the free, user-friendly platform has simplified domestic and international travel for groups and solo travelers.
“Being from Brooklyn, the entrepreneurial spirit was ingrained in me, and I always saw creatives crafting solutions to everyday problems,” SquadTrip founder Darrien Watson tells BLACK ENTERPRISE.
“SquadTrip responded to problems I saw after being added to a birthday trip group chat. It started with good intentions, but getting everyone on the same page to plan was a nightmare!”
Through resourceful features like chat messaging, questionnaires, pre-planned itineraries, booking, and the often dreaded payment collection, SquadTrip offers a complete trip planning execution. The features reveal Watson’s professional background working with software vendors and natural passion for travel.
Darrien Watson/Courtesy of SquadTrip
“My co-founder and I knew we wanted to equip Black travelers with a marketplace tailored to their needs,” Watson says. “SquadTrip offers experiences curated by Black-owned tour operators and travel companies, from luxury and cultural excursions abroad to turn-up trips.”
“We aimed to eliminate setbacks that can take the fun out of group travel to ensure a seamless and enjoyable experience.”
Launched in Brooklyn, New York, in 2022, SquadTrip is the premier travel marketplace tailored specifically for Black travelers that serves as a platform to discover trips curated by Black tour operators and travel companies. Through its comprehensive software solution, travelers can streamline group trips with features such as the TripBuilder tool, pre-planned itineraries, and automatic monthly payment plans, all accessible via a user-friendly centralized dashboard.
“Our software is the first online platform to create booking pages, accept payments, and manage communications and finances all in one place,” Watson shares.
Additionally, while the company was launched in Brooklyn, it has since relocated its headquarters to Tulsa, Oklahoma, to participate in Build In Tulsa’s Techstar Accelerator program for POC founders.
“Now, we’re a part of the rising Black tech sector reviving Black Wall Street in Tulsa,” Watson says.
Courtesy of SquadTrip
Over the last two years, SquadTrip has facilitated hundreds of trips in over 50 countries, enhancing the travel experience and meeting the unique needs of Black travelers worldwide. To help other Black travelers embark on a group trip this summer or even later in the year, SquadTrip put together an eight-step guide to orchestrate a successful group trip and create unforgettable memories with your squad.
Gauge The Group – Know who you’re traveling with and their interests, budgets, and travel styles to guide the planning process effectively.
“Understanding the intention is crucial for trips outside of specific celebrations like weddings or graduation,” Watson says. “To start on the right foot, ensure participants share interests, whether it’s history for a city tour or music taste for a festival.”
Democratize Decision Making – Involve your group from the start to ensure everyone feels heard. Use SquadTrip to brainstorm destinations, travel dates, and budgets.
“SquadTrip empowers users with decision-making by allowing them to create questionnaires tailored to trips,” Watson explains. “To ensure everyone’s preferences are heard and accounted for in the planning process.”
Pick Suitable Accommodations—Research to find accommodations and transportation that are convenient for the group overall. Consider flights, trains, or car rentals for cost and travel time.
“Consider using room types to accommodate preferences while seeing accurate pricing and floor layouts,” Watson adds. “It’s helpful to see bed arrangements, occupancy limits, and more ahead of time to make sure everyone is comfortable.”
Courtesy of SquadTrip
Create Your Itinerary & Embrace “Maybe” – Group planning can get tricky and involve compromise, as preferences vary. SquadTrip helps by creating flexible itineraries with group activities and free time, ensuring everyone enjoys the trip.
“It’s a good idea to head into a trip with a plan, even if it’s not super detailed,” Watson notes. “Having an idea of what each day might look like helps provide structure so you can get the most out of your adventures.”
Avoid Chasing Down Payments — Avoid awkward conversations by collecting and scheduling payments through SquadTrip and eliminating the need for group texts, spreadsheets, or apps like Venmo and PayPal.
“Usually, trips hit a snag when it comes to collecting money,” Watson admits. “We added automatic payments through SquadTrip to avoid dealing with uneven amounts and ensure everything is fair.”
“With transparency on individual contributions, total cost, and payment progress, there’s no need for reconciliation or awkward “can you send me” conversations when everyone returns home,” he adds.
Update Your Squad – Prioritize clear communication during planning. Keep everyone updated on decisions and changes. With SquadTrip, send emails, trip updates, and automated payment reminders to your group.
“There’s no such thing as too much communication when planning group trips. But it’s best to keep all the critical updates and foundational
planning in a central location,” Watson says. “By keeping things simple, everyone will be on the same page without hassle.”
Courtesy of SquadTrip
Celebrate Differences & Acknowledge the Inevitable – Group trips blend diverse personalities. Embrace differences to uncover hidden interests. Expect the unexpected: flights are delayed, luggage gets lost, and personalities clash. Handle hiccups with flexibility and humor.
“Compromise will occur in any endeavor involving multiple people, especially without focusing on a celebrant in group trips,” Watson explains. “Also, embracing flexibility in itineraries allows for exposure to new passions, so keeping an open mind is essential.”
Consider a Travel Agent – For hands-off group leaders, SquadTrip offers a curated selection of travel agencies specializing in group trips here.
“If your group prefers a hands-off approach to planning, don’t hesitate to ask for extra help,” Watson suggests. “SquadTrip’s travel marketplace offers curated Black tour operators and travel companies for seamless management.”
