How to Plan a Worry-free Vacation for a Group

bonfire on beach haystack rock

As we move into spring and summer, family and friends will want to reconnect more than ever. That means planning group vacations, which are a joy to experience but can sometimes be a headache to plan. 

The first and most important step is choosing the right person to head up the planning. Since you’re reading this, we assume that’s you! But don’t take it all on yourself! You can be the final decision-maker and communicator, but if you’re planning for a larger group, try to recruit some help. Is your cousin a big foodie? Let him research restaurants! Is your sister the family Cruise Director? She could help plan activities! Once you have some help onboard, you can get started! 

bikes in town

Plan activities that appeal to different types of travelers

Shopping. Beachcombing. Hiking. Gallery-hopping. Lounging. There’s so much to do (and not do!) in Cannon Beach, and each activity will appeal to different members of the group. 

Consider using an online document or spreadsheet to offer people options and let them choose so no one feels they got the short end of the stick. And as we all know, “nothing” is a super fun thing to do on vacation—everyone always has that option and should know there’s no pressure to join in if they prefer a good book on the balcony. 

Elements by the Sea back massage

Plan alone time

Jack Ezon, founder of the luxury travel advisory firm Embark, told The Washington Post, “Space from one another is a must. The key to a successful group trip is to have private time, whether it’s to shop, go to the spa, hit the gym or explore a museum on your own,” he says. “Leaving or joining the group should be fluid, with no judgments.”

A great way to get alone time at Hallmark is to schedule a spa treatment at Elements by the Sea. It’s a full-service spa, so if you’re looking for a massage, hydrotherapy or even a full-body wrap to unwind and give yourself some space, it’s the ideal spot to do it. Check out their services and get your relaxation on.

Get on a group chat prior to the trip

As the organizer, you’ll have lots of questions for the rest of the crew that need to be answered in a timely manner and once you’re at your destination, everyone will be able to reach everyone else. Even better, you’ll be able to send each other great shots from the trip once it’s over, in addition to being able to jump immediately into planning for next year.

restaurant receipt

Create a budget and flexible spending options

Some people like to splurge on high-end restaurants while on vacation. Others like to spend money on experiences instead of rooms or food. And some like to spend as little as possible, always. There’s no moral value to any of those choices, they’re all just preferences, and we should be understanding about choices on either end of that spectrum. 

Additionally, folks in your group might come from different socioeconomic groups, so be mindful of activities or meal prep that would ask everyone to chip in the same amount regardless of their situation. This kind of choice can be worked out ahead of time in a Google sheet or another shared app. Consider offering low- or no-cost activities to make sure no one feels pressured to spend what they may not have. 

If you need ideas for restaurants or activities for groups, please feel free to contact the front desk. They’re happy to make recommendations. 

Pacific Suites interior

Find the perfect accommodations

Choosing the right place to stay is key to ensuring everyone’s happy when you travel with a group. You want there to be plenty of room for the whole crew to enjoy their time together in one space, as well as have somewhere to go for some time alone. 

Thankfully, we’ve recently added an excellent option for groups traveling together: Pacific Suites by Hallmark. 

Pacific Suites, just two blocks from the main resort, offers two king beds (with one in a separate bedroom), a living room, a galley kitchen, a walkout balcony, and beach access across the street. Renovated in 2022, the rooms have beautiful modern details—perfect even for the most discriminating member of the group while still being totally family-friendly. Take a look and book your group or family getaway today! 


With lots of different preferences and personalities, booking group vacations can be a challenge, but it’s always worth it. Creating experiences with people you love is a huge gift, and will provide indelible memories for the rest of all your lives.