When the hubs was turning 40, we knew that we had to celebrate the greatness that is Chris!

Seriously… Chris is one of the best and USUALLY let’s me make decisions and be in the spotlight, while he supports in ALL the ways. He needed to be fully celebrated. I also may or may not have missed planning something for his 30th birthday, SO I couldn’t miss this one. (A story for another time.) 😬 🤦🏻‍♀️

When I asked him what he wanted to do for his birthday, he said that he wanted to stay in one place, on a beach, with his people, (parents included) and not have to make any decisions!

SO… this is the process I used to plan a multi-generational group trip, with multiple couples, and a birthday to celebrate! 🎉
I hope you get a little insight into **my planning thought process** and know what to consider when planning a trip like this in the future!

When to start planning?

I’m always a fan of ‘the earlier the better’ to begin general planning ESPECIALLY with a group trip. (BUT, unless you’re booking cruises, most accommodations and flights won’t even give you booking quotes until you’re within 11-12 months of travel.) 🗓️

For a one-stop-shop all-inclusive / flights group trip, I would suggest to start planning 6-9 months out. If you’re coordinating multiple people, commitments, etc. give everyone time to finalize budget plans, childcare (as needed) etc. so then you know what the group will be before finalizing any big decisions and bookings.

We actually started planning in August for a January trip, but I would have started a LITTLE earlier, if I had a redo. 🫠

Where to begin? What to consider first?

FIRST… Choose your TRIP LEADER. Who is in charge of coordinating, communicating, following up and keeping information organized? There are TWO ways to approach this, depending on the purpose of your trip.

IF you are celebrating a special occasion (i.e. a birthday, promotion, graduation, etc.) the person or people being celebrated get to make the decisions! This means that they may or may not want to be the one in charge of the planning and coordinating. I was in charge of planning this trip for my husband and I still would have been in charge if it was for my birthday. #controlfreak #travelplanner 👀

IF you and your friends / family decide you want to go on trip for fun… you will need to choose a point person and make it CLEAR. Others can help, but, ultimately, one person MUST be in charge. It will make all the rest of the coordination so much easier for everyone involved. 🫡

What are your priorities? Finalize the ‘Big Three’

(anyone get that reference? 😉) What is most important to the person making the decisions or that the group with have to decide on? The Big Three: - Budget - Dates - Location - These can be prioritized in any order, but all three need to be finalized before a group can move forward with final price quotes, bookings, and potential group rates.

📆 For our trip, my husband was the decision maker. This was his thought process and how he finalized the ‘big three.’ Chris wanted to make sure a majority of his people would have the option to come, so he narrowed in on the dates first. He chose a 4 Day Trip over a holiday weekend, so that most people would only have to miss a day or two of work, if they wanted to join.

💰 Then, he thought through budget. My husband cares much less about luxury and will always prioritize quality time with his people… wherever that may be! SO… I reached out to Chris’s closest friends that might have a tighter budget than others. I let them know the dates and the purpose of the trip and if it was something they were interested in, I asked them what their max budget would be, so that they could join. (We also planned this trip in January, immediately following the holidays!)

⍰ This isn’t always thought about when planning group trips (and that’s OK) but if you REALLY want to make sure certain people are included, ask the question. “Hey, we would love for you to join if you think you can make it and take time away. If you want to join, what do you think your max budget would be?” It’s NOT offensive. It’s actually quite kind and inclusive, and clarity is KEY.

💸 We finalized on a $3,500 budget per couple; including flights, accommodations & transfers. If people wanted to upgrade flight seats or accommodation levels, and they had the budget to do so - they had that option. We also said that excursions would be an extra cost and people could decide, based on their budget!

🗺️ Since we decided on dates and budgets, before location, we narrowed down the location using the dates and the budget that were already decided on. Chris wanted an all-inclusive, on a beach, outside of the U.S. So I ran searches on flight/hotel packages with that budget in mind and looked at several places in the Caribbean. We ended up choosing our location AND our hotel at the same time because Chris was the sole decision-maker and I knew his priorities.

Accommodations

This can be overwhelming! So start with your priorities and create a space for comparison. (I created a planning spreadsheet that I use to line up accommodation options, side-by-side.)

For large groups, some think that Short Term Rentals are more cost-effective than multiple, separate hotel rooms. But, it’s not always the case when you take into account all the food, transportation, amenities, drinks, and other things included. All-inclusive resorts are a stress-free option, ESPECIALLY with managing groups. Also, even though we are both extroverts, Chris and I do love our own space - especially late night and morning times - separate from the big group. I love my people, but even extroverts need to recharge!

Things to consider and possibly prioritize in your research: (This is with a Caribbean all-inclusive as the target.)

Beach: 🏖️ Hotel proximity / access to the beach. What kind of sand? Shade / tree coverage on the beach?
Ocean: Is the water clear? Calm water or is it known for undercurrents and waves? (Super important for people that want to be in the ocean and if you are traveling with children.)
Amenities: Nightly entertainment? Fitness Center? Free activities? Group classes? Spa? Night Club?
Are there additional attractions / excursions in the area?
Number of rooms / guests at the resort 🏨
Adults Only or Family Friendly?
Number of pools (this matters with the number of guests allowed at the resort!)
Restaurants: 🍽️ How many? What kind of food? Do they allow reservations or first come, first serve?

Pro Tip: READ REVIEWS! Read the most recent reviews. Read reviews on Google and third party sites (NOT the reviews from their website!)

After doing some research, I found some places that could accommodate our big group while still offering the amenities that we were looking for (pools, beach, different restaurants, coffee bars, night life, etc).

If the accommodation decision is a group choice / group vote - the google sheet can be a great way to put the options in one place and let people comment and vote! In Chris’s case, he chose the one he liked the most. We landed on the RIU Palace in the Dominican Republic. 🏝️

RIU is a large, all-inclusive chain, located in several countries. They are mid-budget option with different levels of hotels all on the same property. They also have SO many amenities. If you like a small, luxury vibe - they aren’t for you. BUT, for our fun group that likes dancing, eating, entertainment, sports… ALL the things. My favorite thing at this RIU resort was the midday pool party. 🥳

Transportation

Because we decided on an all-inclusive + flight package, transportation with this trip was EASY. (Also a bonus to booking group trips in packages / bundles.) Several all-inclusive hotels have flight package options when booking rooms. This is also a good time to use a travel agent. 👀 JUST SAYING. Luckily, I am a certified travel agent and actually found our package options in one of my back-office suppliers. 😉 Feel free to email me for vacation packages - and all other travel planning needs!

Other transportation items to consider:

Airport Transfers: Normally included in vacation packages, BUT we splurged and got a party bus. #birthday TOTALLY worth it! Make sure to book private or group transfers at least 30 days in advance.
Excursion Transportation: I ALWAYS book excursions that include transfer to and from the hotel. (Excursion notes below!)

Pro Tip: If a hotel offers a airport transfer ‘voucher,’ DON’T DO IT! That usually means they use a third party transfer vendor, shared with other hotels in the area, not a tight schedule and super unreliable, with no one to hold them accountable.

🚐 I think booking a private car ahead of time or using local transport from the airport is worth every penny. It’s always aligned with your schedule and you can hold them accountable if something goes wrong.

Excursions & Tours

Planning activities for a large group can be tough! What’s nice about all-inclusive hotels, is that they usually have several free activities, group classes, free basic water sports, and nightly entertainment. 🪩 As I mentioned above, that weekly themed pool party at the RIU was one of my favorite things! And that was a part of our all-inclusive experience.

Personally, even if I’m staying at an all-inclusive resort, I try to get offsite with some local excursions, so that I can explore a little more of the area. 🔎

These are two companies that I use regularly to book local tours for my clients and myself! 💻 (These are my personal referral links below - let me know if you need help navigating them.)

Pro Tip(s): Don’t wait to book excursions! Book them early (with free cancellation) and then, if you make a last minute switch, you can cancel. If you wait, certain excursions may not be available AND the vendors that hang out in hotel lobbies, try to convince you to join their tours and up-charge you. 👎 And, same pro tip for accommodations… read reviews!

Birthday Boy wanted a Catamaran Tour! (**This is the one we booked!**)

It was SO MUCH fun. We had the Catamaran to ourselves for a couple hours. We spent time on the water, did a little snorkeling and had a birthday dance party on the boat with cake and beverages! 🎂They did a GREAT job.
This is our crew loving our time on the remote island we visited during our time on the boat. ⛵️

Group Norms & Expectations

Last, but CERTAINLY not least, setting group norms and expectations about the trip is a MUST. Group trips can make or break friendships, or at least leave people a little frustrated or awkard. Many times, that happens because there were gaps in communication and/or people were on different pages about what was expected of them during the trip. (If you think I’m exaggerating, ask me to share some of my personal experiences with this. 🫠 My recommendation is to get ahead of this!

Here are some things to create, think through and communicate clearly:

Group Communication: Create a group thread before you travel with EVERYONE in it. (Not just one spouse, or the wives, or the planners, etc.) Even if one person in a family unit is the normal communicator, just make sure everyone is in the know about all group events, changes, last-minute updates, optional opportunities that arise! If your “planner wife” is napping on a lounger and you miss an invite to a round of golf - that’s on you, boo. Make sure you’re in the group thread and you LOOK AT IT. 🫵
Packing List: The point person should communicate what needs to be packed, based on resort dress code, themed parties, excursion attire, etc. 🧳
Schedule: If there is a group schedule (and you should have a basic schedule, at least) make sure everyone has it! Build in A LOT of flex time. But also make sure you have any times for group excursions, meals and even optional activities that some people will definitely want to do!
Group Time: To maintain a sense of togetherness, designate a few must-attend moments, like a special group dinner or an excursion. Let everyone know that these are the priority gatherings, but outside of them, they have the freedom to explore as they wish. This is especially important for celebratory trips!
Norm that the big group does not stay together the entire time. (Unless you’re that obsessed with each other 🤷🏻‍♀️) Not everyone in the group will have the same interests, so encourage people to split into smaller groups or do things by themselves! Some may want to stay by the pool, while others might want to book a spa session or try water sports. Give people options and encourage it! We want everyone to have an awesome vacation!
Norm a “no guilt rule.” If someone needs to take a break from the group, let’s make sure they are comfortable saying that without feeling obligated to ‘tough it out.’ Peer pressure can still be a very real problem in adult friend groups.
Norm that everyone will assume the best. Remember it’s not personal, and people need to try not to be offended if they missed out on something!

This section may feel elementary and unnecessary, but I PROMISE, it’s necessary. Adults are often the worst because they make up their own expectations in their head and then get frustrated when other people don’t meet them. Over-communicate 💪🏼

For our trip we had a THRIVING group thread, that we still drop texts in from time to time. 📲 For our Group Times, we make it a point to have dinner every night together and had that one boat excursion together as well! The rest of the time our group did whatever they wanted to! We definitely took advantage of the activities included in the resort-yoga, live music, magic show, pool parties, etc.

I take at least 1-2 large group trips a year and have learned a lot. I hope this was helpful for you to think through, or maybe encourage you to say your first ‘yes’ to a group trip - as long as it’s planned the right way! 😬

And even though this was birthday celebration for my hubby, I’m truly grateful for him every day. AND grateful for the people in our life who say YES to all our travel proposals!! 🤍

Ciao Ciao,

Chelsea

How To Plan a Group Trip: (All-Inclusive)