Official Blog

Category: Travel Trips

Offsite Horror Stories (and How to Avoid Them)

Everyone loves a team retreat.

But let’s be honest, when things go wrong on a company trip, they go really wrong.

The group dinner that turns into a stomach bug epidemic, the “easy hike” that somehow becomes a six-hour survival test, or the Wi-Fi that “totally works” (spoiler: it doesn’t).

Every team has at least one retreat story they tell in hushed tones. And if they don’t… It’s only a matter of time.

Today, we’re serving up a few real-world offsite horror stories and, more importantly, how you can avoid slipping into your own.

The Wi-Fi Was… Decorative

The Horror:
A big planning retreat derailed when “fast internet” turned out to mean barely emailing.

Avoid It:
Get real upload/download speeds in writing. If it’s critical, book a coworking backup.
Pro Tip: Airport hotels often have the best Wi-Fi if you’re stuck. Make sure to install a VPN before accessing, you and your CSO will thank us later.

The Great Ceviche Incident

The Horror:
Team dinner ended with half the group fighting food poisoning instead of team bonding.

Avoid It:
Stick to busy restaurants with lots of locals, and prioritize cooked meals in hot climates.
Pro Tip: Plan at least one “safe” dinner to reset everyone’s stomach.

We’re Stranded. Again.

The Horror:
No rides. No shuttles. Missed dinners and lost team members.

Avoid It:
Pre-book transportation for bigger groups. Even a rented minivan beats 8 frantic Uber calls.
Pro Tip: Confirm all pickups, especially in remote areas.

Oops, No Insurance

The Horror:
An injured cofounder + international hospital bill = $2,300 emergency Venmo.

Avoid It:
Travel insurance is your safety net, build it into the budget early.
Pro Tip: Group coverage is cheap and easy.

Too Much Agenda, Not Enough Fun

The Horror:
Wall-to-wall meetings = an exhausted, resentful team by Day 2.

Avoid It:
Leave space to breathe. Free afternoons = happier humans.
Pro Tip: One half-day of pure free time works wonders.

Final Thought:

Great retreats don’t happen by accident.
Plan ahead. Expect some chaos. Build in flexibility.

And if you want to skip the horror stories altogether?
Vamos is here to help you plan smarter.
→ Join the beta at govamos.io

May 1, 2025
Why Great Team Offsites Start Before You Even Land
Company offsites get hyped as the fix for everything. Culture booster? Of course. Strategy breakthrough? You bet. Burnout cure? Where do I sign? And hey, sometimes they are. But here’s the truth: a truly game changing offsite doesn’t start when you roll into your Airbnb or crack open that first Pellegrino in the welcome circle.

It starts way earlier. Like, weeks before anyone boards a plane.

Let’s talk about the often skipped but totally essential part of any offsite: pre trip planning. And no, we’re not talking about logistics. We’re talking about mindset, alignment, and momentum.

1. Get Clear on the Why

Before you pick a destination, you need to answer one question: What’s the point of this trip?

Is it about connection? Strategy? Celebration? Deep work? Too many teams skip this step and end up with a trip that’s fine, but not focused and definitely not worth the time and money.

2. Involve the Team Early

If you want people to be excited and engaged, make them part of the process.

Ask questions like:
- What would make this trip feel worthwhile to you?
- What do you need (logistically or emotionally) to show up fully?
- What’s one thing you’d love to do or learn as a team?
Even better, get them to vote on a few destinations, themes, or activities. Shared ownership = higher buy-in = better vibes.

3. Define Success

We measure product launches. We measure OKRs. But… retreats?

Before the trip, decide what success looks like. That could mean:
- Our product team aligns on the next 2 quarters of work
- People from different functions leave with stronger bonds
- Everyone gets 3 hours of uninterrupted deep work each day
This gives your trip structure. And helps you make better choices (like skipping that fifth happy hour in favor of a group hike and reflection).

4. Build Pre-Trip Momentum

Now, here’s the fun part: get people excited.

Try this:
- A shared playlist for the flight
- A Slack thread to share “fun facts” or packing tips
- A pre-trip Zoom with mini intros, agenda walk-through, and Q&A
- “Trip bingo” with fun goals like “try a new dish” or “talk to someone new”
It builds anticipation and lowers anxiety. Especially for new hires or introverts, knowing what to expect makes a huge difference.

So, What’s the TL;DR?

Team retreats don’t start with check-in. They start with clarity, collaboration, and a sense of shared purpose all well before you ever leave home.

If you want your next offsite to actually move the needle (instead of just producing pretty photos), start earlier. Ask better questions. Involve your people. Set the tone.

Let’s stop treating offsites like vacation + meetings, and start treating them like strategic tools for culture and connection.

And if you need help figuring all this out?

Vamos is building the platform that helps you plan less and align more.

Join the waitlist here: Govamos.io
April 24, 2025
✈️ “Seriously, Where Should I Take My Team?”
My Top 5 Unique Cities for a Company Retreat That Everyone Will Actually Enjoy

You’re not looking for another list of “Top 10 Conference Cities.” You want something fun, accessible, and actually worth flying the team in for. Somewhere that feels like a break from the usual—and still makes space for real connection.

So, if you’re asking me (your most travel-obsessed friend), here’s exactly where I’d take your 10-person team for a retreat that feels thoughtful, energizing, and yeah, a little unforgettable.

1. Asheville, NC

Why go: It’s like someone blended mountain-town serenity with artsy downtown vibes and sprinkled in 30+ breweries.

Asheville just makes it easy. You can spend your morning hiking in the Blue Ridge Mountains and your afternoon in a cozy coworking space surrounded by murals and music. There’s always something unexpected: a hidden bookstore, a mural that turns into a scavenger hunt, a craft workshop where your team can make ceramics and somehow get philosophical about product strategy. And don’t sleep on the food scene—it punches way above its weight.

What you’d actually do:
You’d stumble into live bluegrass on a Tuesday night, get everyone out on the trails without complaints (yes, even Carl from Finance), and then wind down over a beer flight in a converted auto garage. Asheville somehow gets everyone in sync without trying too hard.

2. Bend, OR

Why go: Think: relaxed mountain town meets adventure playground—minus the crowds and pretension.

Bend is for teams who want to breathe a little deeper, move a little more, and enjoy real conversation in a hot tub or by a fire pit. You can float the river, hike up to an overlook that’ll stop you mid-sentence, or do a team brewery crawl where everyone pretends they understand hops. It’s also full of surprising little gems: lava tube caves, craft coffee spots with stunning views, and outdoor yoga with actual mountain air.

What you’d actually do:
You’ll spend less time in meeting rooms and more time moving together—kayaking, biking, hiking—and come back from dinner realizing no one even looked at their phone. This is where ideas flow as easily as the local IPAs.

3. Santa Fe, NM

Why go: It’s calm, creative, and completely unique. If your team needs inspiration or a reset, this is the move.

Santa Fe is built for reflection—but in the best, least-boring way possible. You’re surrounded by adobe buildings, world-class art, and endless desert skies. There’s this energy that makes people want to create things—paint, plan, rethink how you’re working. You can do team sound baths (seriously), wander through immersive art exhibits at Meow Wolf, or take a group pottery class and talk life over local chile stew.

What you’d actually do:
You’ll trade business casual for cozy shawls and scarves, chat about the future of the company while stargazing, and actually get quiet enough to hear the good ideas. It’s a retreat-retreat.

4. Savannah, GA

Why go: It’s got spooky stories, Spanish moss, and a “sure, take your cocktail to-go” vibe that just puts people at ease.

Savannah is one of those cities that instantly disarms people. It’s charming without being cheesy, with old-world architecture and quirky energy around every corner. You’ll spend afternoons meandering through town squares, then duck into a speakeasy for a team toast. Or bond with your team over ghost tours, cooking classes, or just sitting under an oak tree talking about everything but work (until you’re suddenly solving a problem you hadn’t even brought up).

What you’d actually do:
You’ll eat well, laugh more than expected, and leave feeling like you really know your coworkers—because you spent three days getting a little weird together in the most delightful way.

5. Boise, ID

Why go: This one’s a sleeper hit. Affordable, outdoorsy, and surprisingly vibrant—with mountains in view and no drama in sight.

Boise gives big “pleasant surprise” energy. Downtown is super walkable, there’s a gorgeous river trail running right through the city, and you’ve got hot springs, hikes, and breweries all within 30 minutes. The city’s vibe is relaxed but active, which makes it super easy to plan everything from whitewater rafting to a pop-up meeting on a rooftop patio with mountain views.

What you’d actually do:
You’ll bike along the river with iced coffees in hand, have the best group meal you didn’t expect, and maybe even get the team to do something adventurous—like rock climbing or rafting—and actually enjoy it. It’s the kind of trip people talk about long after the Slack thread goes quiet.

TL;DR – My Pick?
- Outdoorsy & collaborative? → Bend
- Peaceful & creative? → Santa Fe
- Memorable & offbeat? → Savannah
- Cool culture + conversation? → Asheville
- Unexpectedly awesome? → Boise
Want help figuring out which one fits your team vibe? I’ve got ideas for where to stay, what to do, and how to make it seamless. Just say the word.

Go Vamos!
April 17, 2025
The Most Overlooked Costs When Planning a Company Trip
Spoiler: It’s never just flights and hotels.

Planning a team offsite? Company retreat? Founder getaway with a few Airbnb and Hotel spreadsheets already open?

Great!

But before you hit “book,” let’s talk about the sneaky, under the radar costs that tend to surprise even the most seasoned trip planners. Because the truth is: the real cost of a company trip is way more than just flights and a place to sleep.

Here’s your unofficial guide to the overlooked stuff and how to stop getting blindsided by it.

Transportation (aka “We’ll Just Uber”)

You’ve booked the flights. Everyone’s landing around the same time. What could go wrong?

More than you think actually.
- Airport transfers for a 10-person team? That’s $300+ before you’ve left the terminal.
- Daily rides to venues or restaurants add up fast, especially in spread-out cities like L.A. or Miami.
- No group transportation plan = 17 Uber receipts and a headache for whoever’s handling reimbursements.
Pro Tip: Price out a private shuttle or even a minivan rental if your group is mid-sized. It’s often cheaper and more fun than coordinating 4 Ubers at 6:45am.

Taxes, Fees & “Oh Wait, That’s Not Included?”

You found a great AirbnB.

Wonderful!

Until the cleaning fee and local occupancy tax hit.

Or that beautiful hotel conference room? $300 extra for A/V setup and $200 for water bottles.

These little add-ons can stack up fast:
- Tourism taxes
- Cleaning/service fees
- Resort fees
- Tip-included meals
- Gratuities for group experiences
Pro Tip: Always click through to the final checkout screen and read the fine print.

The Admin Time Sink (aka “Your Time Is a Cost Too”)

One of the most overlooked costs? Your time. Or your ops lead’s time. Or your EA’s sanity.

All the hours spent:
- Comparing 12 cities and 8 Airbnb tabs
- Chasing down RSVPs and calendars
- Coordinating airport pickups
- Managing 37 Slack messages about food allergies
It’s time that could be spent, well… doing the job you were actually hired for.

Pro Tip: Use tools that reduce that admin drag. (We’re biased, but Vamos exists for exactly this reason.)

Final Word: Plan Like a CFO, Travel Like a CEO

Group travel is one of the best things you can do for your team. It strengthens relationships, creates memories, and gets everyone aligned on what’s next.

But that doesn’t mean you have to blow the budget or get hit with surprise costs every step of the way.

Plan smarter. Build in buffers. Ask the annoying “what’s NOT included?” questions.

And maybe, jusssttttt maybe let Vamos handle the heavy lifting.

→ Want to start planning smarter right now? Join the waitlist at Govamos.io
April 14, 2025
Ready for Takeoff: Your Guide to Smarter, Smoother Group Travel
Planning a trip is already a lot. Planning one for a 50+ person team? That’s a whooleeeeee different game.

From Chief of staff to executive assistant, If you’ve ever tried to book travel for your team, coordinate a leadership offsite, or pull together an entire company retreat, you already know the drill… endless spreadsheets, fragmented emails, and decision fatigue from multiple leaders. Welp, that’s why we decided to build Vamos. A smarter way to make group travel not just logistically easier, but actually enjoyable for the entire team.

With that being said, welcome to our first blog on travel advice & guidance! In the coming weeks and months and until the internet ceases to exist, we will be sharing some travel trends, real-world tips, and a sneak peek at how Vamos is changing the way teams move. Enough of the intro, let’s dive in.

The Group Travel Glow-Up Is Here

Over the last few years, team travel has gone from a “nice to have” to “I’m not joining unless there’s a trip planned for sales & marketing”. Whether you’re remote first or just looking to shake up the usual office routine, getting the team together IRL builds momentum, clarity, and genuine connection. Unfortunately, it’s the year 2025 and most tools still treat it like it’s Y2K.

Concur Navan, Expedia? Built for individuals.

Retreat planning agencies? Built for large companies with large budgets.

Google docs and calendar polls? Built for… pain.

Modern teams need a modern tool that makes planning any size offsite feel less like a logistical headache and more like what it should be: exciting.

Trends Worth Paying Attention To

If you’re already gearing up to plan your next team trip, here are a few 2025 trends shaping how smart companies are traveling:

1. Small but Mighty Retreats

Smaller teams of 5-15 people are skipping massive all-hands and going hyper-focused. From strategy sessions in Lisbon, to wellness retreats in Tulum. They’re cheaper, easier to organize, and more impactful for real decision making.

2. Cost-Conscious Travel, Not Budget Travel

The economy’s at a weird spot. Teams want to be smart with spend, but not at the cost of immaculate vibes. Instead of cutting trips, they’re just making them more intentional and looking for tools (hello 👋) that help weight total costs of destinations quickly, from airfare to food to fun.

3. Sleep, Space, & Schedule

A good team trip now includes time to rest, play, and not be around people 24/7. The best planners are building in unscheduled time, offering activity opt-ins, and booking locations with chill zones (think: rooftop hammocks, not dry boardrooms)

Pro Tips for Smarter Planning

1. Choose your “Why” before your Where.”

Is this trip for vision setting? Bonding? Deep work? Your reason drives your destination.

2. Ditch the back-and-forth.

Polls, calendars, and email chains make planning painful. Collaborative tools (yup, we’re building those) let everyone weigh in without chaos.

3. Don’t overbook the agenda.

Leave room for unstructured moments. The best ideas usually come between meetings, not during them.

What Vamos is Building (And Why It Matters)

At Vamos, we’re not just building another dull tool. We’re reimagining what team travel could look like if it was designed with actual humans (and their calendars, group chats, and budgets) in mind.

Imagine this:
- Picking the perfect destination for your team based not just on vibes, but on total cost, travel time, and availability
- You could spin up a full offsite or retreat in a few clicks, with trusted recommendations for where to stay, what to do, and how to keep your team engaged.
- Planning a trip didn’t require 27 back-and-fourth email threads and spreadsheets named “Team Retreat Final v3”
That’s the future we’re building towards.

And we’re starting with one belief: team travel should be easier, faster, and way more fun

Whether you’re a startup planning your first offsite or a global team syncing across time zones, Vamos is here to help you get there. Literally and figuratively.

Let’s make team travel something people actually look forward to.
April 6, 2025