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Why Group Travel Is the Ultimate Way to See the World (and Save Money)
- Jessica Seiders
- 4 days ago
- 10 min read
You know that split second when the view is so good it knocks the socks out of you?
When the Eiffel Tower is practically winking at you in golden hour light, or the beach you accidentally found looks like a screensaver? That’s usually when I catch myself thinking, I wish someone else could see this.
It's painted as ultimate freedom, this brave adventure where you discover yourself somewhere between missed connections and hostel bunks. And sure, there's something to that. I can attest to it.
But here's what nobody talks about: solo travel also means paying double for everything.
You’re navigating every problem alone and scrolling through your phone during dinner because eating solo gets old fast.
Group travel gets dismissed as chaotic or full of compromise. But when it's done right, group travel is one of the smartest ways to see the world. You split costs, share the highs and lows, and come home with people who remember the same trip you do.
This isn't just about saving money while traveling, though you absolutely will. It's about making travel more accessible, more manageable, and honestly? A whole lot more fun when you find the right crew.
Why Group Travel Works Better Than You Think
You Have Built-In Support for Everything
Travel highs feel bigger when they're shared.
That perfect sunset, the incredible meal you'll never forget, and finally cracking that complicated metro system in Japan. These become real memories with people who were there with you, not just liked your Instagram post three days later.
The lows get easier, too.
Flight delayed at 2 a.m.? You have someone to commiserate with, someone to watch bags while you grab coffee, someone to split that cramped middle seat misery with.
Language barriers feel less intimidating when one person speaks passable Spanish. Getting lost turns into an adventure instead of panic when you're figuring it out together.
The Logistics Become Simpler
In any group, someone always knows something the rest don't. One person's great with maps, another speaks French, and someone else researched every restaurant within 10 miles.
You're dividing the mental load of travel, which means better decisions about where to eat, what to see, and when to call it a day because everyone's exhausted. Nobody has to be "on" all the time.
And for women travelers, especially, there's real comfort in numbers. Walking back after dinner feels different when you're not alone.
Having people who know where you are, who expect you back, who'll notice if something's wrong. That peace of mind is worth a lot.
Your Money Goes So Much Further
That gorgeous villa with the pool and the killer view in Guatemala? Prohibitively expensive solo. Split four ways or more? Suddenly, it becomes doable.
Rental cars or hired shuttle vans give you freedom to explore, much more reasonable when everyone's chipping in. Activities like cooking classes, private boat tours, and wine tastings all drop dramatically in per-person cost when you're booking for a group.
You can also cook some meals together instead of eating out all the time. One grocery run for breakfast stuff saves everyone money over a week, and honestly? Making breakfast together in a villa kitchen is part of the fun.
Organized Tours vs. DIY — Finding Your Fit
When Organized Tours Make Sense
Companies like Intrepid Travel, G Adventures, and Trafalgar handle literally everything. Accommodation, transportation, activities, and local guides who know exactly where to go. You show up, and it all just happens.
This works beautifully when:
You're visiting a challenging destination for the first time
You don't speak the language
You have limited time and want to see the highlights
You're traveling solo but want company
You simply just want to be around people when you experience the place
You get vetted accommodations and experienced guides who show you things you'd never find on your own. The social piece matters too because you're with people who chose to have the same experience.
For women traveling solo but wanting company, many tour operators offer women-specific groups.
Intrepid Women's Expeditions is excellent; they understand the specific concerns women travelers have about safety and comfort.
The downside? Less flexibility. When the schedule says move on at 3 p.m., you're moving on. You're on someone else's timeline. And yes, organized tours look pricier upfront, though when you calculate what's included, the value often makes sense.
Other Alteratives
There are also smaller group trips that are specifically for women, hosted by fellow travelers like those from Heart of Travel. These are often location-specific (Heart of Travel offers tours specifically in Latin America!) and a more intimate experience compared to large group tours from bigger companies.
Speaking of, Traveling Women Official is one such group, and we’ll be hosting our first women-only group tour to Guatemala in partnership with Heart of Travel soon!
If you’ve been dreaming of exploring Guatemala, check out the itinerary. This could be the one you’re waiting for.
When DIY Group Travel Works Better
Planning with friends or family gives you complete control. You decide where you're staying, what you're seeing, and how fast you want to move.
You can accommodate different budgets by mixing splurge experiences with budget-friendly days.
This works best when:
You're traveling with people who communicate well
Someone who genuinely enjoys planning (or you divide the work fairly)
Everyone's aligned on budget and travel style
You want total freedom to pivot plans
The catch? Someone has to do the planning. Coordination can get messy without good systems.
And there's potential for conflict if expectations weren't set clearly from the start of the trip. So planning and communication are definitely key here.
The Verdict
Is it your first time in Morocco (or any challenging location)? Go with an organized tour. Girls' trip to Portugal with friends who love planning? Then DIY all the way. Neither is better; it all depends on what you need.
Where Your Money Goes Further
Accommodation — The Biggest Saver
Here’s a quick example to frame it better:
Four hotel rooms at $150 each = $600 per night total
Four-bedroom villa with kitchen and pool = $400 per night total
That's $100 per person instead of $150. You're saving $50 per person every night, plus you get way more space and amenities.
Vacation rentals through Airbnb or VRBO are game-changers. Everyone gets their own bedroom, but you share living spaces. Having a kitchen means cooking breakfast, packing snacks, and maybe having a big group dinner instead of eating out every night.
Even if you prefer hotels, sharing rooms can save you significantly. Solo travelers face single supplements that tack on anywhere from 50-100% of the room costs.
Transportation Adds Up Fast
Renting a car for five days: $300 total
Split four ways: $75 per person
Compare that to individual Ubers every time you want to go somewhere. Private airport transfers, gas, parking, and tolls. All becomes reasonable when multiple people contribute.
Group Rates Are Real
Many tour operators reduce rates for groups (usually 8+ people, sometimes fewer). Private experiences like cooking classes, wine tastings, and boat rentals often cost the same whether two people or six people go. The per-person difference can be dramatic.
And then there are shared resources: one universal adapter, one first aid kit, one portable charger. Small things that add up to cost savings and lighter suitcases.
Here’s a good perspective:
A week-long trip costing $2000+ solo often comes in around $1200-1500 per person when splitting major costs with three or four others. That's the difference between one trip per year and two.
The Tools That Keep Everything Running Smoothly
Okay, let’s say you’re convinced to try out group trips and you happen to be the one organizing. How do you keep everything running smoothly? Here are a few useful tips and tools to keep everyone’s itinerary and details accessible.
Managing Itineraries
TripIt Pro consolidates everyone's flight info, hotel bookings, and activity confirmations into one shared itinerary. The real magic? Real-time flight alerts. When someone's delayed, the whole group knows immediately.
Free option: A shared Google Sheet with tabs for flights, accommodation, activities, and packing lists. Everyone adds their info and sees updates in real-time.
Handling Money
Splitwise is non-negotiable. This app tracks who paid for what and calculates who owes whom. One person covers the villa, another handles groceries, someone treats everyone to dinner, Splitwise does all the math.
It supports multiple currencies (crucial for international travel) and shows running balances. Pair it with Venmo or PayPal for quick transfers.
Booking Accommodations
Airbnb and VRBO for group properties. Filter by bedrooms and bathrooms, look for "instant book," and read reviews mentioning groups.
Booking.com for hotels with connecting rooms or suites. Their flexible cancellation policies help when coordinating schedules.
If you're going the organized tour route, you can find a host of companies like Intrepid Travel or Heart of Travel to handle everything for you.
Staying Connected
WhatsApp works internationally without extra charges. Group chats for real-time coordination, location sharing for "Where are you?" moments.
Protecting Your Investment
Travel insurance matters more with groups. If one person cancels, it affects everyone's cost splits.
Look for "cancel for any reason" coverage, medical protection, and trip interruption insurance:
World Nomads – great for adventure activities
Allianz – comprehensive coverage, solid service
Travel Guard – covers group bookings well
Wanna learn more about travel insurance? You can find it in this post.
Coordinating Luggage
Before you leave, coordinate shared items. You don't need four hair dryers or four adapters.
Matching luggage sets make spotting your group's bags ridiculously easy. Samsonite, Away, and Travelpro offer durable options with external charging ports and spinner wheels.
Packing cubes from Eagle Creek to keep everyone organized. Color-code them so you know whose stuff is whose.
Making Different Budgets Work
Have the budget conversation before booking anything. Create a rough range everyone's comfortable with for major expenses: flights, accommodation, and daily costs.
Be direct about what you can spend. Zero shame in saying "My budget is $1500 total" or "I can do $100 daily."
Build in flexibility:
Core shared costs (villa, rental car) split evenly
Optional activities? Everyone pays their own way
Some want the expensive wine tasting, others explore the town? Both work
Strategies that help:
Set daily budgets for shared meals and track spending
Rotate who plans and pays for dinners
Mix splurge experiences with budget-friendly days
Use free activities (hiking, beaches, walking tours) as equalizers
Check in regularly during the trip. Pull up Splitwise, see where things stand, and make sure everyone's comfortable.
Picking the Right Travel Group
Traveling with Friends or Family
Traveling with people you love doesn’t automatically mean you’ll travel well together. You can be best friends and still drive each other crazy on the road, and that’s okay. The key isn’t how close you are, but how well your travel styles align.
Some of us are up at sunrise, coffee in hand, ready to explore by 8 a.m. Others prefer slow mornings and don’t hit their stride until after lunch.
Some thrive on structured itineraries, checking off every landmark in one day. Others would rather linger at a café, savoring one neighborhood at a time.
Neither is wrong, but when styles clash, tensions build fast.
Money is another make-or-break factor. Budget travelers are usually happy to trade a little comfort for a good deal, while comfort seekers will spend more to keep things easy.
If you don’t talk about this early, small differences can become big resentments later. For many women over 40, comfort often matters more than it used to, and that’s nothing to apologize for.
Before committing to a big trip:
Take a shorter weekend getaway first. You’ll quickly see how decision-making and spending really work together.
Have the budget talk upfront. Get clear on priorities like accommodations, meals, and experiences.
Pay attention to early red flags: one person taking over all the planning, vague answers about money, constant indecision, or mismatched expectations no one wants to address.
You don’t need perfect alignment on everything, but shared rhythms and mutual respect make a world of difference.
Traveling with a Group of Strangers
Organized group trips can be a wonderful option, especially if you love travel but don’t want to handle every detail yourself. You get a ready-made itinerary, built-in travel buddies, and the comfort of knowing logistics are handled. But just like with friends, the right fit matters.
Every group trip has its own personality. Some are fast-paced and structured, ideal if you love seeing it all.
Others lean toward slower travel, with free time built in. Pay close attention to the itinerary, pace, and group size. It’ll give you a good feel for whether the trip suits your travel style.
Also, think about the kind of travelers you’ll be with. There are adventure-focused groups, cultural deep-dives, foodie tours in New York, luxury escapes in Europe, and women-only journeys.
Choosing the right niche makes it much easier to connect with like-minded people.
A few tips to make it smoother:
Know your deal-breakers. If waking up at dawn for every activity isn’t your thing, pick a trip that allows breathing room.
Manage your expectations. You won’t click with everyone, and you don’t have to. Enjoy the moments of connection that do happen, and permit yourself to step back when you need space.
Keep your independence. Just because it’s a group trip doesn’t mean you have to be “on” 24/7. A quiet coffee alone or a solo walk can be just as memorable as the group excursions.
For many women, joining a group of strangers isn’t about being alone, but about finding freedom, flexibility, and community on your own terms.
Start Planning Your Group Adventure
Group travel makes incredible experiences more accessible, more affordable, and a whole lot more memorable.
Whether you’re joining an organized tour or pulling together your own small group, the magic is the same: shared laughter, inside jokes, and stories you’ll tell for years.
The biggest hurdle is often just picking the dates. Once that’s set, everything else starts to fall into place.
And here’s something exciting: Traveling Women Official is getting ready to offer unforgettable group trips to Guatemala in 2026.
Think breathtaking landscapes, vibrant culture, and the joy of experiencing it all with like-minded women who love to explore. Early birders get a huge discount, so make sure to check it out!
What's your biggest question about planning a group trip? Drop a comment, I'd love to help!
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