15 Tips To Help You Plan An Ultimate Trip With Friends

Plan the ultimate trip with friends. 

We just got back from the ultimate trip to Puerto Vallarta, Mexico. We asked 8 friends to join us on the trip of a lifetime spending a week at a fully staffed (with chef) beachfront villa. We’ve had a ton of people ask us how we did it so we are going to lay it out, step by step, so you can have a trip with friends too!

When planning a trip like this you must always keep one thing in mind: Cost vs Quantity. The 2 major costs associated with a trip like this are flight costs and lodging costs. The lodging costs can vary greatly based on the quantity of people going. You’ll want to do a little research before you mention the trip to any of your friends. 

 1. Plan ahead, a whole year in advance if possible. On my girlfriend’s (Nadja) 29th birthday she told me she wanted to take an epic trip with friends for her 30th. We started planning for the trip a year out, and we are glad we did. When planning dates, we highly recommend traveling during the off-season of your ideal destination. Usually it will be much cheaper and you will have more lodging options! Plus you'll have a whole year to get excited for your upcoming trip! 

Puerto Vallarta

2. Choose the right destination. Consider flight costs, currency exchange rate, and lodging costs. This gets somewhat complicated depending on your budget level. We wanted to make the trip as affordable as possible for our friends so we looked at countries in the Caribbean and Latin America that offer a great exchange rate for the US Dollar. In the end it came down to a few countries – Mexico, Belize, and the Dominican Republic. In these places, the dollar goes fairly far and all have major airports for easy accessibility.

3. Accessibility is very important. Consider air, ground, and water transportation costs. We eventually narrowed our search to several destinations in Mexico but had to cross out a bunch because there were no international airports nearby. You’ll want something close to an airport so you don’t have to pay huge fees for ground transportation to and from your final destination.

Check out the table below to see what months are cheaper to travel!



Mexico Villa

4. Choose your lodging strategically when you have your destinations narrowed down. I highly, highly recommend looking into homes/villas on VRBO.com or Airbnb.com because you can split costs with your friends for the entire property. This is how you can make your trip affordable for everyone while getting an incredible value.

The villa we stayed at was $1000/night x7 nights =$7000 for the week. That seems like a lot, but when you split the costs with 10 friends, it comes down to only $100/night per person. That's less than what you would pay for a budget hotel! But instead of being in a boring hotel, you can be traveling in complete luxury.

5. Talk it up with your friends once you have an idea on various costs. If you can, invite twice as many people as you want to come because a lot of people will back out. We invited 22 people and most of those people obviously couldn't come for various reasons. Ideally you want 12 or less people in the end, because beyond that transportation becomes a major hassle.

When you invite friends, be sure to give them an idea of how much the flight will cost and let them know roughly what lodging will cost based on the amount of people you are inviting. GIVE THEM A TIMELINE! Let them know you need a firm yes or no by a certain date. Make sure it's in writing! Find out if any of your friends are okay sharing a room with someone else as this can also drastically bring down cost for everyone. Besides, you shouldn't be spending too much time in your room anyway!


6. Dont invite party poopers or people who you think won't mesh well with the group. If you wouldn’t let these people spend a week with you at your house, don't invite them on your trip. Have a good mix of people, don't have a bunch of extroverts and one introvert. Don't take someone who hates the outdoors on an outdoors trip. Invite friends that are okay being flexible if something happens or changes are made.

7. Start collecting funds ASAP. For those who give you a definite yes on your trip, start collecting funds from them. We created a separate bank account for everyone’s trip money and kept a detailed log of who gave how much and when they gave it to us. Don't play around with people’s money. Keep it separate and keep track of everything. People who give you money are showing you they are serious about going. Now you have a better idea of how many can actually go!


8. Figure out the exact price. Look at your lodging again with the quantity of people that have given you money. Use that information to narrow down your lodging search. Now you can figure out more accurate pricing for your guests who are serious about going. Reach out to them again with a more accurate price and setup a payment plan to pay the balance due on the lodging.

You will want to book your lodging 4-6 months in advance so set a “ALL IN” date where no refunds will be given after a specific time. This will alo encourage these people to be locked in on going on your trip. If your villa doesn't come with a chef or complimentary meals, try choosing a place to stay where there are restaurants or stores within walking distance so you are not paying for a taxi for every meal.

9. Passports, passports, passports. Make sure everyone that is going on your trip gets a passport far in advance of your trip. US passports can take up to 3 months to come in, and you cannot travel to a different country without them. Make sure everyone does this ASAP.


10. Book flights AFTER you secure the lodging. You will want to book your flights about 2-3 months out for best price and ease of mind. Set price alerts on your phone to get updated with daily prices of the flight you are wanting. I recommend collecting funds from everyone for the flight as well and book them all together. Obviously this is not an option if some of your friends are flying from different airports so you will need to coordinate the arrival time with them. Plus if you book all together, you generally get to sit with all of your friends on the plane!


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11. Find and book ground transportation after you book the flights. Remember you will want to take a bus or large taxi to take your group from the airport to your final destination. Make sure you collect funds from everyone for this as well.

12. Keep everyone updated on all aspects. We created a facebook group/event plus sent out email reminders. You will need to remind everyone of dates, amounts owed, passports, taking time off, etc. Create a packing list for everyone. Let everyone know how much currency to bring for food, drinks, misc expenses. I highly recommend exchanging currency at your bank if possible so you can get a good exchange rate! Exchanging currency at the airport or at your final destination can be very expensive! It's your job to keep everyone accountable and informed! If some of your group will be sharing a room, try to pair them up based on personality. Let them know who they will be sharing a room with beforehand.


13. Purchase trip insurance. If you booked everyone’s flights and lodging I would recommend looking into trip insurance just in case something goes wrong such as an unexpected hurricane, bad weather, or natural disaster. They happen! 

14. Plan a very early check-in time at the airport to meet up with your group if you are flying together.

15. Relax and have fun! Don't try to be over controlling on the trip, let people do their own thing. It is their vacation too. If you have planned any activities in advance, don't force people to do activities they don't want to do. Enjoy the reward of a sweet vacation with all of your friends in paradise!! 


Taking a trip with friends is an unforgettable experience, especially if you have the right mix of people. Hopefully this guide gave you some things to consider before taking your trip. Let us know if you have any questions or comments, we love to hear from you!

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