How to plan a vacation with friends

Jul 30, 2024

Friends vacation on beach

Planning a trip with your friends is super exciting! But, it can also get a bit tricky sometimes. Don't worry, though! I've got some really cool tips to help you & your crew have an awesome vacation together. Let's dive in & make your next adventure unforgettable!

Pick your crew

First things first, figure out who's coming along for the fun. It's super important to choose friends who:

  • Have similar travel styles

  • Get along like peanut butter & jelly

  • Are reliable & will stick to the trip

Remember, the friends you invite can make or break your vacation! So, choose smartly!

Set a budget

Talking about money is not always fun, right? But it's super important when planning a group trip. Here's how:

  • Chat openly about what everyone can spend

  • Agree on a price range for places to stay & activities

  • Consider using a shared calendar app like Outside to track costs & share expenses

Being clear about money from the get-go saves you from awkward talks later!

Choose your destination

Now comes the exciting part—where are you going?! Here's how to choose:

  • Brainstorm ideas together as a group

  • Research options that work within your budget & interest

  • Vote on your top choice

  • Ask your AI planner in Outside for travel ideas

Pro tip: Use that group chat in Outside to share fun ideas & vote on your favorites!

Decide on dates

Picking dates that work for everyone can be tough. Make it easier by:

  • Planning way ahead of time

  • Using a shared calendar to see when folks are free

  • Being flexible & open to compromises

The Outside app has a great shared calendar—it makes this part so easy!

Book your accommodations

Once you've picked those dates, it's time to book where you'll stay! Think about:

  • Hotels or vacation rentals

  • Location & what things you need

  • Fairly splitting rooms among yourselves

Pro tip: Have one person in charge of bookings so it stays organized.

Plan your activities

Now comes the best part—what are you going to do? Here are some ideas:

  • Research the coolest attractions & must-see spots

  • Include some downtime for relaxing or spontaneous fun

  • Use the Outside app to create a shared schedule

If people want to do different things sometimes, that's totally normal!

Sort out transportation

Getting around is key for any trip. Consider:

  • Flights or whatever way you're getting there

  • How you'll travel once you're at the destination (like rental cars or buses)

  • Who's taking care of booking what

The Outside app can keep those travel details all in one place including any important notes with important info.

Communicate clearly

Good communication is super important on any group trip! Make sure you:

  • Create a group chat for planning

  • Share key info like flight details & where you'll stay

  • Use Outside to keep everything organized

Clear chat helps avoid mix-ups and makes planning much smoother!

Be prepared for hiccups

No matter how well you plan, things might not always go as expected. That's totally okay! Just remember to:

  • Stay flexible and go with the flow

  • Have backup plans for key activities

  • Keep a positive attitude

Unexpected moments often turn into great memories!

Get excited!

Finally, get pumped for your trip! You can:

  • Start counting down in the Outside app with your countdown widget

  • Share fun photos or info about where you're going in the group chat

  • Plan a pre-trip meet-up to wrap up all details

Getting excited makes planning just as fun as the actual trip!

Stay organized with Outside

Planning vacations with friends is fantastic, but keeping track of everything can be tough. That's why Outside is super useful! This cool app allows you to:

  • Use a shared calendar for sorting out dates

  • Split costs easily

  • Keep all info in one handy spot

  • Set up countdowns leading up to your trip

Plus, Outside isn't just for trips! It helps you stay connected with friends & organize events too. Why not try Outside for your next group getaway? You might find vacation planning goes smooth as a gentle breeze at the beach! If three friends sign up with you, you get Outside Premium for free!

Friends on the beach at night