How to Plan & Host a Retreat

A guide to offering your community the group trip of their dreams

There’s an old quote that says, “Easy reading is damn hard writing.” Now, not to go all English 101 here, but that was Nathaniel Hawthorne’s way of recognizing that it takes work to make something feel effortless. Of course, reading The Scarlet Letter isn’t as exciting as traveling, but the same logic applies to retreat planning. The fun you and your Travelers have on a trip is a direct result of planning and prep work you do to ensure everything goes off without a hitch—well mostly. After all it is travel and sometimes sh*t happens. 

Okay, we know that starting to plan your own retreat probably feels scary and overwhelming, but with this guide we hope to show you it can actually be painless and maybe even…enjoyable. With that in mind, here are the key steps when thinking about how to host a retreat.

Key takeaways

• Engage your community to learn their travel preferences, and let that data be your guide when designing or choosing an itinerary.
• Work with local tourism professionals to build a good, realistic flow of activities and trusted accommodations for each day.
• During your trip, consider leading workshops or events in your area of expertise to make your trip truly unique and really connect with your community.
• Get general liability insurance for yourself and encourage those who book to protect their investment by purchasing travel insurance as well.
• Plan out a month-long promotion strategy to engage with potential travelers and invite them on your retreat.
• Stay in touch with your travelers once they sign up! Add folks to a group chat so they can get to know each other, and receive information to help prepare for the upcoming trip.
• You can skip the stress and let Trova handle the logistics of planning a retreat, so you can focus on growing your brand and community.

1. Engage your community

If you’re looking at offering a trip or retreat for your community, chances are you’ve already cultivated a tight-knit and engaged network. These are the loyal people who love you—and your group—enough to pay a high ticket price for traveling the world and sharing experiences together. So, keep them at the forefront of planning and use their preferences to design a retreat they’ll love.

Knowing the details about your community’s travel preferences will give you a big advantage when you open your trip up for bookings. The main things to consider are:

• Top destinations
• Travel budget
• Time of year
• Trip length
• Preferred activities
• Traveler age

One mistake that first-timers often make when figuring out how to organize a retreat is thinking that destination is the be all and end all. The reality is that even your community’s ultimate bucket list destination won’t matter if the rest of the trip doesn’t work. For example, trips to Europe tend to be more expensive than trips to Asia, so don’t be afraid to opt for Bali over France if budget makes the latter impossible. Your community’s 3rd favorite place will actually be the best choice if it’s the one that truly meets their timing and financial needs.

Speaking of those needs, you’re probably wondering how to find out what they are. After all, that information is pretty personal and different for everyone. The answer is simple: Ask. 

Tell your community that you’re planning a retreat and want their input to help create it. Think of this as your trip’s real invitation. Ask folks to DM or otherwise let you know what they want in regards to travel specifics. With so much interaction and information flying back and forth, this part of the process can feel overwhelming. To help, Trova has simplified things with an optional survey that takes about 2 minutes and points you towards the right experience for you and your group.

2. Listen to the data

One person’s dream trip can be another’s travel nightmare. Sound harsh? Think of people in the LGBTQ+ community traveling to a country where the law forbids you from being yourself. Or, less serious, you could be foodies stuck hiking in the wilderness a hundred miles away from the nearest restaurant. The point being, while it’s fun to explore new horizons and break new ground, this is a time to play things a little safer. 

With real data from your audience in hand, you can focus on delivering a trip that’s balanced between their wants and needs. Once travel becomes a larger part of your brand, you’ll have the opportunity to broaden the scope of your trips, but early on it’s a good idea to give your followers exactly what they want. And don’t worry, that doesn’t mean the experience has to be bland and forgettable. With Trova’s massive itinerary library, you can see experiences built for a whole range of interests, from relaxation to exploration. It’s a big world and there’s something for everyone.

💡Trova Tip: When analyzing data, we recommend basing your trip on the median (not average) budget to make the trip accessible to the majority of your community. Oh, and disregard info from responses of those less than 18 years of age due to tricky international travel requirements and budget limitations.

3. Design the flow of each day

After locking in the big pieces like destination and budget, it will be time to turn your focus to all the little details that make up the day-to-day of your retreat. Where are you going to stay? What will you take the group to see and do? How will you get there? Is it possible to learn fluent Greek in a couple months?

We recommend starting with a list of activities. Everything the group would like, plus everything you’d be crazy not to do while visiting. Then start cutting (but keep that list handy) and be pragmatic about activities that are actually doable on this particular trip. For example, the best view in the world may not be worth seeing during the off season. Next, organize them by day, paying attention to which activities work best at different times of the morning, afternoon, or night and keeping in mind proximity to each other.

Once you have a rough timeline, you can map out and begin the process of securing the transportation and accommodations, figure out meals, vet guides, and add in “surprise & delight” moments for your travelers. This part is a balance of price hunting, negotiating, and revising your itinerary (good thing you saved that list!) over several weeks or months. Stay flexible here in terms of timing, activities, and even cities as things won’t always come together logistically and you don’t want any uncertainty...especially when trying to work through a language barrier or with foreign currency.

Finally, remember that in the travel industry everything comes down to relationships. The world is an uncertain place where things change quickly, so establishing trust with local tourism professionals is a must. Don’t have the time or energy to do that right now and want to get started anyway? Then consider hosting with Trova where the relationships we’ve built over the past 6 years enable us to offer 100+ itineraries with top activities, perfectly timed transportation, and local Guides.

4. Add value with workshops

Every location has its must-see attractions, the ones that all itineraries include because it would be travel malpractice not to…like Rome without the Colosseum. Who would do such a thing?!

Once you look at enough itineraries, you’ll start noticing that there’s a lot of overlap. So unless your group happens to stumble across a hidden city, your trip won’t end up being all that different on paper from any other. Or will it? When planning a trip, it’s helpful to keep in mind that while Travelers want to experience the destination, they’re also really excited about traveling with you. After all, you’re the one who brought the community together in the first place. 

To capitalize on that, consider holding a workshop in your area of expertise. For example, leading sunrise yoga flows can be a great way to not only start the day, but to bring the group into the same space—physically and spiritually—for the activities ahead. Check on the availability of event spaces where you’ll be staying and book them ahead of time so you can confidently offer your group something they can’t find anywhere else.

💡Trova Tip: Make sure you lock in pricing as early as possible, as rates fluctuate with season and availability. Neglecting to do so can lead to unpleasant surprises for hosts and travelers down the road, which is why Trova builds these add-ons into the price/Traveler so everything is included in a neat bundle.

5. Get insurance

With travel there’s bound to be curveballs. They’re usually harmless like a closed restaurant or bad weather. Sometimes things really do go wrong though, and if that happens *knock on wood* travel insurance is your best friend. Without it you could be on the hook for thousands of dollars and tied up in litigation for years. 

As the host/organizer of the retreat, the buck stops with you. Even if it’s not your fault, the reality is you’ll make a much more inviting scapegoat than, say, a hotel chain in another country with lawyers and resources to fight a legal battle. To avoid the possibility of lifelong financial consequences, we strongly recommend purchasing liability insurance. The specifics will vary by plan and provider—read the fine print!—but in a nutshell you’ll be covered for a certain amount ($7.5 million if you use Trova) in case a traveler or someone else is looking to be compensated for a travel accident.

The folks who sign up for your retreat won’t need to worry about liability, but they may be interested in regular ol’ coverage that protects their investment in case life happens. After all, trips aren’t cheap! Like car or property insurance, travel insurance isn’t standardized, but we’ve found World Nomads to be a reliable provider of plans that cover a trip's many potential pitfalls.

Hopefully you’ll never have to use the insurance, but with all the unknowns involved in planning a retreat this is one area where you can actually enjoy peace of mind.

6. Get the word out

After the planning is done, it’s time to invite people to book! Promotion can feel tricky, as walking the line between posting too much and not enough is one of the great challenges of selling a trip, but you should generally err on the side of doing what feels like too much. There are 2 reasons for this. 1st, the pace of social media and the influence of its algorithms mean that no one sees everything. And 2nd, most people have to be asked multiple times before actually committing to a purchase. The classic sales rule says that people need to see a message 7 times before they’ll take action!

To make sure those multiple messages land with maximum impact, come up with a promotional calendar ahead of time that covers at least the 1st month.

Spend week 1 dropping teasers (fun clues, trivia, and polls) to hype your community up for launch. Don’t forget to mention any perks that might be available for those who join early, anything from a discount to a special gift from you. This will help eventize the launch itself.

Then over the next 3 weeks—with a day off every other day or two—keep your audience interested by breaking down the itinerary, doing a live Q&A, setting aside time to respond to DMs, answering FAQs for the community, and giving weekly updates on remaining spots. At the end of the month, if you still have spots left, we recommend asking directly what might be holding folks back and tailoring your content to address their concerns.

7. Make it easy for your travelers to pay

As your promotion campaign gets underway and people are interested in booking, you’ll want to make sure it’s as easy as possible for them to give you money. Popular options include taking payment through your website (if you have one that’s set up for commerce), or using apps like Venmo or Zelle. The pros of these are security and ubiquity, but both also have drawbacks that can throw a wrench into retreat planning.

Websites rely on services like Stripe or PayPal which take a percentage of the transaction as a fee. It’s not a huge amount but it can add up to hundreds of dollars for a large enough group. Let’s say you’re taking 10 people on a trip that costs $2,000/person. Assuming there are no additional fees, Stripe (for example) will take close to $600 and if you have travelers based in other countries that could be even higher. As a result you’ll need to increase your margins to make up for the fee which, as you can imagine, won’t make your trip any easier to sell. 

Using payment apps like Venmo (again, for example) you can avoid fees by sending money from a linked bank account or an existing Venmo balance. However, you’ll also be at the mercy of the app itself and can find your account frozen unexpectedly if they deem activity “suspicious.” Once that happens, the process of getting unsuspended is…not easy.

Payments don’t have to be a hassle though. One of the benefits of partnering with an established platform like Trova is that you don’t have to cosplay as an accountant (or worse a bill collector when travelers are slow to pay up). Instead you’ll be able to enjoy payment processing that’s built into the booking experience. With that also come options for making the financial aspect of travel even easier, like pay-over-time plans with Affirm which offers 6, 12, or 18 month terms* or with Trova itself (25% down and the rest due 90 days before the trip begins).

*Example: A $2,000 trip might cost $180.68/mo over 12 months at 15% APR. A down payment may be required.

8. Make your travelers feel included

Once Travelers are booked (yay!) you’ll want to keep them engaged to build chemistry and avoid last minute cancellations. Adding folks who book to a group chat will make them feel welcome immediately and allow them to start connecting with you and each other. There is no “right” place to start the chat, we’ve seen this done over Instagram DMs, private Facebook groups, Slack, Zoom…you name it! Just pick somewhere that feels right for you and your group and #sendit.

In addition to making introductions and keeping the conversation going, you can also help the group prepare with info about the destination (similar to Trova’s Trip Prep Guides). A few local phrases, info about tipping, and a packing list go a long way towards putting people’s minds at ease about what to expect.

How to plan a retreat the easy way

When setting up a group trip, these steps can serve as a retreat planning checklist. That’s still a lot to do on your own though, so you may want to consider working with a partner to make the process more manageable. (It’s us, hi. We’re the partner, it’s us.) 

From making a trip to seeing it through, Trova helps Hosts by handling all the logistics along with processing payments, vetting guides/activities, and providing customer service. There’s also no upfront cost (this is so rare, you can consider it a group travel 🦄) and you’ll have access to tools like automated marketing emails, early bird discounts, and pay-over-time options.

We also provide step-by-step resources for promoting, launching, and confirming trips on different social channels, as well as techniques for talking about money or building your personal mailing list. Selling a group trip—especially your 1st one—can feel like a heavy lift at times, so we do our best to keep things organized and easy. That way, you can focus on what truly matters: growing your brand, connecting with your community, and seeing the world.

Interested in becoming a Trova Host and getting paid to travel? Get started here!

Want to learn more first? Head to TrustPilot and see what people are saying about our trips!