How to Plan a Pod Beach Vacation Like a Pro

Make the most of quality time — and skip drama and logistical headaches — with travel experts’ group travel planning tips.

April 23, 2021
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Coordinating getaway plans with an assortment of your favorite people is a special kind of balancing act. An idyllic vacation spot, complete with friends and family: what a lovely-sounding proposition! Juggling assorted calendars, budgets, expectations and more: ah, there's the sand in your eyes.

Women on Beach

Take a deep breath. This is all going to work out just fine.

Photo by: Shutterstock/Versta

Shutterstock/Versta

Take a deep breath. This is all going to work out just fine.

"When doing anything as a group, it's important to remember that each person is coming in with their own boundaries and expectations around everything from spending to space to time," says Stefanie O'Connell Rodriguez, a personal finance author and founder of Statement Cards. "The trouble is, we rarely talk about those expectations and boundaries, especially when it comes to something as taboo as money – leading to stress, resentment and conflict. But chances are, your friends are feeling a lot of the same stresses around group travel as you are, so talking about it, and getting everyone's expectations and boundaries out on the table can help you come to a shared understanding that works for everyone involved."

While a certain amount of fancy footwork is, alas, unavoidable, clever choreography behind the scenes can minimize missteps and maximize the time and energy you and your crew should be spending on the shore (and enjoying each other's company — remember that?). We turned to professional planners for their tried-and-true moves; read on to learn how they put together the vacations of their dreams, and set your sights on paradise.

Pick one! We’ll give you 30 seconds.

Photo by: Lauren Oster

Lauren Oster

Pick one! We’ll give you 30 seconds.

1: Keep Questions Simple

While diving into initial research and offering fellow travelers a dizzying array of travel options might seem like a helpful move, too much information is, well, too much. Paula Pant, founder of Afford Anything and host of the Afford Anything podcast, learned that firsthand as she planned a trip with a group of friends: "one woman was going out of her way to be accommodating and sent a super-long email with lots of options, detailing the advantages and disadvantages of each, and asked for feedback. That seems like a great way to minimize strife, but she didn't get much of a response from the group — maybe two or three people out of 10 wrote back!" Pant advises avoiding open-ended questions about budget, as well. "Suggest narrow sample price ranges for expenses like accommodations, food budget and a rental car."

Rodriguez, in turn, suggests reaching one crucial figure up front. "I find it's much easier to start with an agreed-upon, all-in budget, then plan from there," she says. "That number tells you so much on its own – for example, whether there's enough financial flexibility for destination travel or whether you should limit your search to staycations and drivable distances."

At some point, you’re going to have to take a leap of faith.

Photo by: Lauren Oster

Lauren Oster

At some point, you’re going to have to take a leap of faith.

2: Be Prepared to Pull the Trigger

"If your group has one organizer, at a certain point they have to be decisive and just say, 'unless there are any objections, I'm going to go ahead and book this option by this time on this day,'" Pant says. "Give everyone a specific deadline to respond."

Speaking of organizers, are you ready to be the one? "One of the best ways to make sure the group plans fit into your financial situation is to take on the responsibility of that project manager role yourself, or to communicate your financial boundaries and expectations to the person filling that role as close to the start of the planning process as possible," Rodriguez says.

Are you sure that room has a cot? What time are you arriving, again?

Photo by: Lauren Oster

Lauren Oster

Are you sure that room has a cot? What time are you arriving, again?

"It's much harder to back out once plans and commitments have already been made. So start communicating your financial boundaries and expectations from the outset of the planning process. For example, 'I'm willing to spend no more than $350 on this weekend away. I expect that to include all meals in addition to travel and accommodation costs. I'm happy to cook and will share a room, but do not want to sleep on a couch or air mattress.'"

3: Coordinate With Your Host

Are you looking at this the same way?

Photo by: Lauren Oster

Lauren Oster

Are you looking at this the same way?

Pant learned this one the hard way as an Airbnb host: she mentioned that her guests could use an air mattress and linens to supplement her apartment's one bedroom, but those guests didn't contact her to ask for them until she herself was out of town (and on her own vacation). Don't wait until you've arrived at your destination to inquire about amenities: "If you're booking a rental and the host says they have X number of bedrooms but a capacity to accommodate more guests, let them know how many people you need to house up front! You're assuming that things like air mattresses and extra linens will already be there, but your host might assume you'll request them if you need them. You don't want a mismatch between guest and host expectations."

4: Know Your Group's Spending Styles

Make sure you’re seeing the forest and the trees.

Photo by: Lauren Oster

Lauren Oster

Make sure you’re seeing the forest and the trees.

"Cost sharing can get messy if you're dealing with a lot of people, and there are a couple of approaches to it," Pant says. "One person can just pay for everything on a single credit or debit card; that way, at the end of the trip, there's just one statement that's easy to add up and divide. You can also agree that different people will pay for different portions of the trip: When I went on a trip with three friends, I paid for the accommodation, someone else paid for the rental car, and the last two members of our group paid for all of our restaurant meals. That works if the group is relaxed and no one's a stickler about breaking things down to the last penny, but it all depends on the personalities of the people you're traveling with." On that note…

5: Track Expenses With Tech

Rodriguez notes that while establishing an all-in budget and sending funds to a group leader who can then manage all payments is a solid starting point, "it can be hard to predict total costs and there are almost always incidentals." Consider one of these tools to corral unexpected cash flow (and avoid angering a side-salad enthusiast who doesn't want to foot the bill for someone else's multiple fancy umbrella drinks). She recommends these three free apps:

Splitwise "lets you easily split costs with multiple people," Rodriguez explains. "You can create different groups within the app to see all of your shared expenses organized in one place, so each person in each group can see how much they owe, which can be great if you're splitting costs with some people and not others. The best thing about Splitwise is that it tracks borrowing and lending over time, which can be helpful when you're planning an event, like a group trip where you have shared costs to keep track of over the course of several months of planning. Splitwise can help you keep tabs on it all from month to month, itemizing what each person owes until everything is ultimately settled up."

Tab "is a great option for a group dining scenario," Rodriguez says. "It allows each person in the group to easily pay for just the items they ordered without having to ask the server for separate checks. With Tab, you just take a picture of your bill and the app automatically reads each item. Then each person in the group taps the items they ordered to claim them. Tax and tip are divided proportionally among each person. It's a great tool for sharing the cost of a group meal while traveling together."

There’s no shame in writing a hotel address on your arm.

Photo by: Lauren Oster

Lauren Oster

There’s no shame in writing a hotel address on your arm.

Venmo, Rodriguez says, is your friend when it comes time to actually make payments (and it happens to integrate with Tab). Venmo "lets you easily pay or get paid back through your phone. You can just connect your bank account to the app, then send or request payment from your friends through it."

6: Nail Down Your Meetup

If you’ve got your heart set on morning yoga, give your pals some notice.

Photo by: Lauren Oster

Lauren Oster

If you’ve got your heart set on morning yoga, give your pals some notice.

"If you're all traveling separately to your destination, make sure you have a really good meeting point," Pant advises. "If it's a foreign country and you're all flying there, does everyone understand how to get to the hotel or the rental? Do they know how to get cash at airport ATMs or somewhere else, and will they be able to arrange transportation if there aren't options like Ubers or Lyfts?"

7: Define ‘Group Fun’

Solo time: Totally OK.

Photo by: Lauren Oster

Lauren Oster

Solo time: Totally OK.

"Be very clear about what your group activities will be in advance," Pant says. "Some beach vacations consist of spending time at the shore during the day and drinking at night, and others require a certain pace of travel; everyone has to be up for that. If you're hiking, for example, is that a leisurely stroll over three scenic miles with a lot of stops, or is that ascending 5,000 vertical feet? Having an understanding of that ahead of time is key."

8: Break Up (and Get Back Together)

"For a group that's traveling together for the first time, the most crucial skill to practice is communication. Not everyone is going to want to do the same things all the time," says Rachel Staggs, a touring musician, artist and photographer who curates group travel for women through her customized Vamos Chicas trips to Mexico. "Even on my retreats, once guests have their footing, know how to get around and understand our location, I'm happy to see them become curious and explore on their own or ask about experiences they are drawn to."

That said, getting into new habits is part of the fun: "When traveling with a friend group, I think it's a great idea for everyone, individually, to come up with a list of their top stops, experiences, and/or places to eat — their absolute must-do list," Staggs says. "At some point down the lists, there may be a split in group activities where some share must-dos that others don't. This is totally okay. As you go through the process, it's exciting to see what others wish to do and you may even discover something that becomes a must-do for you in that moment." You can trust Staggs on this; as a longtime tour manager, she's quite literally spent decades balancing group priorities on the road.

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