Traveling with family or a big group can be an incredibly rewarding adventure. It’s the perfect opportunity to build lifelong memories while exploring new places together. But, as anyone who’s planned such a trip can tell you, it has its challenges. Coordinating different personalities, interests, and budgets takes patience—but trust me, it’s worth it. With some planning, clever budgeting, and attention to details, group travel can be a smooth and unforgettable experience.
In this guide, you’ll find everything you need to know to plan and execute the perfect trip with your family or close-knit crew. From destination planning to navigating hiccups along the way, these tips will set you up for success.
Tips for Traveling with Family.
Planning Phase: Choose the Perfect Destination and Stay
The key to a great trip starts here. Choosing a destination that works for everyone. Over the years, I’ve had the joy (and sometimes chaos) of planning trips including two 10-person cruises, a 5-person cruise, and a beach trip for eight people. No two trips are the same, but clear planning always saves the day.
Even a destination wedding needs to be thought about. Not only does it need to suit the bride and groom, but the rest of the family should enjoy this vacation. Making beach resorts or a trip to the mountains a perfect way for everyone attending to lots of activities to choose from before or after the wedding.
1. Pick a Destination That Suits Everyone
When selecting your destination, think about what each person in your group loves doing. For families, national parks, beach resorts, or cruises often work because they offer a mix of activities. Adventure seekers might prefer mountains or cities brimming with history. Large groups need a destination where there’s room to spread out and varied options to cater to everyone’s interests. The goal is to pick different activities for different age groups.
For example, vacations to a theme park can be great for kids, families and young adults, but not the best for those with older adults who will not be riding any of the rides. If a group is planning a trip to Orlando or Universal Studios or Disney World, older adults might like Epcot more than Disney. If you have a large family, age 3 to 83 it will be hard to satisfy everyone every moment of vacation. So, pick an area that has many activities.
Multigenerational trips are very hard to plan for. Family trips with grandparents and grandchildren can be fine because the grandparents like to do whatever makes those grandkids happy usually. But if grandchildren are not involved the age gap can be hard to plan for.
2. Accommodation Matters
The right place to stay can make or break your trip. Large Airbnb or VRBO rentals with shared common spaces are great for bonding but also allow personal downtime. For cruises, family-friendly ships often provide separate activities tailored by age while letting everyone come together later. Hotels with adjacent rooms are a great choice for flexibility without sacrificing proximity.
Cruises can be a great way for large groups to take vacations. You can do what you want. Many activities to choose from, excursions on port days. People can be as active or as lazy as they want on a cruise. But be prepared some people are not fans of large crowds that cruise ships tend to have.
All Inclusive resorts are great for everyone, especially when they are large with many activities for everyone. Many people enjoy relaxing by the beach or pool, and young children love the water activities. Many all-inclusive resorts have access to Spas, golf courses and many other activities. This will make for a great multigenerational vacation. The whole family will have a good time at a resort with many fun activities. Out of the many family trips I have booked as a travel agent, resorts have been the best option for an entire family.
A beach house can be a nice place for an extended family vacation. These large beach houses offer many bedrooms making it cheaper to rent out and break the cost up per person, than booking hotel rooms. Plus, if you are staying on the coast of North Carolina, beach houses are the way to go. A vacation rental on Airbnb and VRBO, but also can be done on Expedia too.
3. Coordinate Transportation Early
For group trips, figuring out how everyone gets to the destination is often the trickiest part—especially if people are flying in from different locations. Enter group airfare discounts, ride-sharing services, and even charter buses for local adventures. Being early helps you score the best deals and avoid last-minute panics.
Booking airport transportation to the hotel or renting a car it is a good idea to book those early. If you are just using Uber, look into prices. It might be cheaper to rent a car if you all will be using Uber a lot.
Budgeting Essentials
Traveling with a large group can get expensive, but a solid plan makes it manageable. The planning process needs to start early and everyone in the group needs to be involved in the discussion.
1. Plan Early to Accommodate Budgets
The earlier you plan, the better. Giving people notice lets them save up for the trip without financial pressure. It also provides time to find good deals on flights, accommodations, and group packages.
Cruises and most All-Inclusive resorts will involve out of the country travel, so make sure everyone has a passport if needed. This can add to additional cost for those that do not have a passport, and planning early is a must because it will take time for a passport to arrive after the application process has started.
2. Organize Cost-Sharing
Whether it's splitting an Airbnb or prepaying group reservations for entertainment, be transparent about the budget early. Apps like Splitwise can streamline contributions and settle balances without awkwardness.
A Credit card makes it easy for everyone to pay separately what they need when a large group is doing a cruise together. Debit cards can be used on a cruise, but credit cards are best and help to make each person on the cruise responsible for their own purchases.
3. Simplify with a Travel Agent
Trust me, this is a game-changer! When planning a large group trip with people from different locations, agents can help secure group discounts, book tickets, and even handle itinerary tweaks.
The cruise industry offers group booking that travel agents can get you set up into, which will drop the prices of cabins if you book enough of them. Each cruise line is different on how many cabins are considered a group, but NCL is the best right now with the lowest number of cabins to be considered a group booking.
4. Don’t Forget Travel Insurance
It may feel like an optional extra, but travel insurance is a must for large group trips. Flights are delayed, accommodations get canceled, or someone might get sick—better safe than sorry when covering all your bases.
I prefer Allianz for Travel insurance, it offers the best prices and covers more than the travel insurance purchased with the cruise line, airline or any other supplier you are using for vacation. It will add to the cost but will be worth it if something unforeseen happens. It's the best purchase you hope to never use.
Packing Smart
Packing is an art for group travelers—strike a balance between being prepared and overloading your suitcase.
1. Start with a Checklist
Create a group packing checklist covering essentials like travel documents, toiletries, chargers, weather-appropriate clothing, and medications. Encourage members to label or lightly coordinate items (like reusable water bottles) to avoid confusion.
2. Keep It Light and Organized
Remind everyone to pack light. Trust me, juggling oversized luggage with a big group is no picnic. Packing cubes and roll-up bags are your best friends for staying organized.
Building a Balanced Itinerary
A successful group trip strikes the perfect balance between togetherness and alone time.
1. Tailor Activities by Age
Be mindful of the group dynamic. Young kids might love ziplining, but it might not be ideal for older adults in the group. Find a mix of relaxed activities like sightseeing and high-energy adventures to keep everyone happy.
2. Include Something for Everyone
During one of our cruises, we planned snorkeling for the adventurers, on-board spa time for relaxation seekers, and trivia nights for bonding over laughs. The secret? Giving each member their moment to shine.
Also plan for free time. Don't keep a strict schedule all the time. I love to go with the flow and meet up for dinner to discuss the fun of the day with everyone. This can be the hardest thing for some people to do. Some will want to relax and enjoy, and some will enjoy staying busy. Meeting up for dinner is a great meet in the middle for open communication, to catch up with friends or family or the events of the day.
3. Factor in Alone Time
Vacations aren’t only about group bonding. Allow space for members to enjoy solo moments—a quick café visit, a quiet hike, or even reading poolside. It’s a small addition to the itinerary that makes a world of difference.
Navigating Challenges
Every trip has its share of surprises, so a go-with-the-flow mentality is key.
1. Have a Contingency Plan
Plan for the unexpected by keeping a rainy-day activity list, extra snacks, and emergency contacts up to date. While things rarely go 100% smoothly, staying adaptable makes them easier to handle.
Have a contingency plan. For example, if it is a rainy day at the beach and you are near some great shopping spots or a casino. Ask and see if anyone would like to check out those places. Some may not, and that is fine too. Everyone is on vacation and should do what they want to do.
2. Keep Communication Open
Group chats (WhatsApp or Facebook Messenger) are essential for seamless communication. Updates about changes, reminders, and meeting points make wrangling larger groups much less stressful.
Making Memories Together
Travel isn’t just about the destination—it’s about the moments you create along the way.
1. Prioritize Connection
Spend dinners catching up on the day’s highlights. Whether it’s sharing funny moments or exciting discoveries, mealtime is the perfect bonding opportunity. Extended family members who you do not see very often will appreciate the bonding time with each other over good food and yummy desserts.
2. Organize Mini Experiences
On one trip, we organized a beach scavenger hunt that thrilled the kids while keeping the adults entertained. Small, intentional activities like these go a long way. One one family girls trip we all read a small book discussing, the funny thing about it is we all hated it, and good a good laugh out of it. One time on a week trip to Fort Lauderdale on a large family vacation, we took a boat to Freeport Bahamas for the day. This trip ended up being an interesting adventure but made for some memorable moments.
3. Capture It All
Take photos and videos to cherish later! If your group loves creative projects, consider creating a shared online album or even turning those lasting memories into a printed photo book post-trip. Some of my favorite memories are from looking back at the pictures taken on my large group cruises. As you can tell I have shared a few on this blog.
Personal Highlights from My Group Trips
One of the most memorable experiences from our friends and family cruise was an impromptu karaoke night. We had everything from Broadway-worthy performances to hilarious off-tune singalongs—which became the trip’s running joke. Another was our beach trip scavenger hunt, where even the most reluctant participants got competitive. Joining in on Poker Runs on a cruise ship where you visit each bar can be one of the fun things to do on a cruise.
These shared moments are the kind that strengthens relationships and makes group travel uniquely rewarding.
Take the Leap and Start Planning
There’s something magical about traveling with family or a close-knit group. Yes, it takes work, but the laughter, connections, and countless memories more than make up for it. I hope you have enjoyed reading the tips for traveling with family or a large group. Whether you’re planning your first big group adventure, a destination wedding, or adding another notch to your travel belt, these tips will ensure a smoother, more enjoyable experience.
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