How to Plan a Trip With Your BEST Friends! | 7+ Tips from an LGBT Travel Blogger!

November 10, 2021

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Today on my blog, I want to share tips on how to plan a vacation with your friends. I’ve traveled all over Western Europe and the USA with my friends, and I have a whole LIST of tips on how to plan a vacation with friends!

Below, I’ve shared my process on how to plan a vacation with friends, as well as a few extra tips and things to note!

How to Plan a Trip With Your BEST Friends

Before we get started, I want to be sure to share a little information about me. When I read travel blog posts from bloggers, I always appreciate it when they share info on who they are + their background, so I know which tips will apply to me!

A few things to know about me:

I’m 30 (at the time of writing this post)
I own my own business and I’m fully self-employed
I don’t have kids or pets
I’ve done a lot of work on learning how to be a better communicator (woo therapy and coaching!)
When I travel, I focus on experiences. I love luxurious and impactful experiences.

Tip #1 How to Plan a Trip With Your BEST Friends: Start Small & Get Answers

The first tip on how to plan a trip with your best friends is to start SMALL and be sure that you understand how your friends approach travel.

More than one super stellar friendship has been ruined due to traveling together.

Because of this, I recommend that you build up slowly to longer trips. If you’ve never gone on a day trip with your friend(s), then it’s not a good idea to start out with a 2 week safari in Kenya!

Below are some questions to answer for each friend you’re thinking of traveling with!

Questionnaire:

How does (Friend Name) react when a flight is delayed or when running late?
Does (Friend Name) communicate when they need alone time to recharge?
Will (Friend Name) need to do business or work tasks while we’re traveling?
How many hours of sleep a night does (Friend Name) need?
If traveling across timezones, how does (Friend Name) adjust to time zone changes?
How does (Friend Name) feel about plane travel? Do they get stressed or nervous?
Do I believe that (Friend Name) will bring up issues or problems they’re having to me in a helpful way? (ie Will this friend blow up at you without warning?)
How many activities does (Friend Name) like to do each day when traveling? Do they like to be super busy or more chill?

If you’re not sure on some of the above questions, then I recommend sitting down and discussing each of these.

For example, my friends know when traveling with me I’m going to work remotely while traveling (blog post guide on that here). My friends also know that I usually take an afternoon nap from 2-3, aaaand they know that I don’t like to jam pack my schedule with activities while traveling – like to do 2 a day (one morning and one afternoon/evening).

Tip #2 How to Plan a Trip With Your BEST Friends: Plan an Explicit Budget

The second tip on how to plan a trip with your best friends is to communicate super clearly and explicitly about money.

Whew! This item has gotten me in trouble more than once. Figuring out how to pay for things done as a group and who is doing what is a whole thing, and it can be stressful – especially if friends make different incomes.

So, for this tip, I recommend having everyone share a total budget for a potential BFF trip or friend vacation. The number can vary a LOT!

Then, plan a trip based on the lowest budget.

Plan a trip where friends who make more pay for more of the trip.

It is idiotic and dangerous to a friendship to put one friend under financial stress, because other friends have a larger budget.

If you don’t feel comfortable communicating with your friends about money, then I wouldn’t plan a trip together!

For my own friendships, we’ve either planned a trip based on the smallest budget or I have covered a larger portion of the trip costs. I’ve looked at my own budget and we whip out an Excel spreadsheet to plan this. It can be uncomfortable to talk about money, but this has made it so I can take really fun trips with my best friends.

Note: If you can’t have a transparent conversation like this with friends, then plan on going with the lowest budget.

Tip #3 How to Plan a Trip With Your BEST Friends: Plan Payments on Trip

The third tip on how to plan a trip with your best friends is to plan who is swiping their card on the trip – and for what!

This tip is related to the above, wherein you figure out how you’re going to pay for activities, meals, and accommodations on the trip.

I don’t mean whether you’re paying cash or card, I mean who is covering what!

Examples:

Dining: When you and your besties go out to dinner on vacation, how are you splitting the check? Are you going to ask for separate checks when being seated? Is one person going to pay and then charge folks later?
Gas or Lyfts: When you get a rental car or a rideshare, who is going to pay for it? Will they venmo request other folks?

These situations can get sticky, as folks who make a lower income than their friends may feel self-conscious about doing exact accounting or asking for folks to pay them.

Here are some options to make this less stressful:

Do an exact budget, complete with specific rideshare and dining estimates. Total that up, and then split it between each person. (Ex: A total of $1,000 expenses could be divided equally between the friends.) Then, each friend keeps track of their own budget and pays accordingly.
Assign expense categories to a specific friend (Ex: “Sam is getting Lyfts and Shayla is getting morning lattes”

Ask yourself: Who is paying for what?

All in all, I find it easiest to try to be equitable throughout the day, and then each night do a quick accounting to make sure everyone is at a similar spending amount (if splitting equally).

It does NOT work to wait until the end of the trip. Folks will be tired and just “let stuff go” which can harbor resentment.

Tip #4 How to Plan a Trip With Your BEST Friends: All Inclusive Resorts

The fourth tip on how to plan a trip with your best friends focuses on simplification.

Because discussion around money can be SUPER stressful, an all-inclusive resort may be the way to go.

Going on a besties vacation to an all-inclusive resort makes planning costs easier to predict, and you can plan add-ons (or excursions for an extra fee) before the trip!

All-inclusive resorts can make planning a trip with your best friends far less stressful!

My BFF group is currently looking at resort vacations from Olivia Travel, a travel company for LGBTQ+ folks. Finding an all-inclusive resort that is super welcoming of LGBTQ+ folks has been basicallyyy impossible! So, now we’re looking at LGBT tour companies that plan trips for LGBTQ+ folks and basically take over a resort.

Tip #5 How to Plan a Trip With Your BEST Friends: Itinerary Planning

The fifth tip on how to plan a trip with your best friends is about being free spirited – and doing a bit of planning.

When it comes to planning a trip a trip with friends, I recommend getting super clear on expectations around activities.

When I travel with friends, we don’t always have the same exact interests.

I could spend a whole vacation in museums nerding out over art, and some of my best friends can last max 2 hours in a museum before they need a change of scenery.

Use time blocking to plan activities and excursions!

For this reason, I usually plan on doing 1 activity a day with all the besties on the trip, and breaking out solo or into smaller groups for other activities.

It’s easiest if you have a time of day for this. When planning a trip with my friends, we usually have the morning for whatever folks want to do and plan an afternoon or evening jaunt for everyone!

Also, depending on how you’re splitting costs, I would set a time every night to share spending + check bank statements. Then charge each other on Venmo or Zelle as needed!

Tip #6 How to Plan a Trip With Your BEST Friends: Separate Spaces

The sixth tip on how to plan a trip with your best friends focuses on creating a plan to recharge.

So, this isn’t doable for everyone – but it’s a requirement for me.

When sitting down to plan a trip with your best friends, I really recommend making sure everyone has their own space.

Make sure every friend has their own space to recharge!

This could be making sure the AirBnB has multiple bedrooms or getting multiple hotel rooms next to each other.

In my early 20’s, I shared a hotel room with my besties and it was all good! Fast forward a few years, and it makes such a difference when people have their own space to sleep and recharge. We’ll hang out in eachother’s rooms (I love getting a hotel room with a connecting door that can be unlocked), but having separate spaces is critical for trips over 4 days!

Tip #7 How to Plan a Trip With Your BEST Friends: Hire a photographer

The seventh tip on how to plan a trip with your best friends focuses on capturing memories!

Ok, so I’m a blogger/content creator, so you know I make it a point to do a photoshoot whenever I travel!

But, hiring a photographer isn’t just for influencers!

Hire a photographer to get great photos!

On your trip, you can hire a photographer for an hour or two to get photos in a downtown area or key landmark. Then you’ll have high quality photos from your trip – which will be cherished memories!

I find my photographers through recommendations, and sometimes I’ll look up photographers using hashtags on Instagram (ex: #WashingtonDCPhotographer). I’ve heard from other travel lovers that they book a photographer through AirBnB experiences, but I’ve never tried that!

Tip #8 Tip How to Plan a Trip With Your BEST Friends: 3-4 planning sessions

Ok, so this blog post covered a lot – and in my time planning numerous trips with friends, I’ve learned that you can’t plan the whole trip in one go.

Here’s how I plan the planning sessions:

Pre-Work: Share budgets in Google Doc or in text chat. Agree on budget. Answer questionnaire from Tip #1, and make sure everyone has info on how other folks like to travel.
Meeting #1: Brainstorm destinations, and assign research to each friend (ex: activities, accommodations, flights, etc)
Homework: Share costs in shared Google Spreadsheet
Meeting #2: Decide on hotels & flights. Decide on methodology to pay for costs on trip. (Tip #2 and Tip #3)
Homework #2: Each friend share what activities or things they want to do on the trip (Tip #5)
Meeting #3: Create a rough itinerary based on this (Tip #5)
Meeting #4: Book!

If a separate conversation about covering costs/travel needs to happen, I recommend doing that first – before anything else!

Also, if folks don’t want to have this number of meetings and just “play it by ear,” then I usually don’t travel with them. “Playing it by ear” can cause so many issues, blurgh!

After travel a bunch with specific group of friends, a lot of the above meetings can happen over text, but I usually always demand at least 2 planning sessions or meetings to plan the friend trip!