Company Offsite Planning for Distributed Teams

Your company has 40 people across 12 cities. Leadership says: plan an offsite. Someone in Slack suggests Tulum. Someone else says Nashville. The CEO likes the idea of Lisbon. The office manager opens a Google Sheet, starts checking flights from every city, and realizes this is going to take a while.

Three weeks later, you’ve booked Austin — not because it was the best option, but because it was the first city where nobody could find a reason to say no. Half the team has connections. Two people are routed through airports they’ve never heard of. The flights alone cost more than the venue.

This is how most distributed teams plan offsites. It works, technically. But there’s a better way.

The shift to remote and hybrid work has turned offsite planning from an occasional task into a recurring operational challenge. Most distributed companies now run one to three offsites per year — some for the full company, others for specific teams. The budgets are real. A 30-person offsite in a mid-tier US city runs $40,000-60,000. International? Double that.

With that kind of spend on the line, the destination decision matters more than the icebreaker activities. And the single biggest variable in that decision — the one that affects cost, attendance, and day-one energy more than anything else — is flights.

The flight-first approach to offsite planning

Most offsite planning starts with a destination wishlist. Someone throws out cities they like. The team debates vibes, weather, restaurant scenes. Then — after the excitement — someone checks whether people can actually get there. That’s when it falls apart.

Flip the order. Start with your team’s locations. Find cities where the highest percentage of people can fly nonstop. Then evaluate those cities for everything else.

This isn’t just more efficient. It produces better outcomes:

• Lower flight costs. Nonstop tickets to hubs are almost always cheaper than connections, especially when booked in advance.
• Less travel time. A connection through Dallas adds 3-5 hours to someone’s travel day. Multiply that by 15 people and you’ve burned a collective week of time before anyone arrives.
• Higher attendance. The easier the travel, the fewer people bail. A 6-hour travel day is manageable. A 12-hour one with a layover and a regional jet is the kind of thing people quietly find excuses to skip.

The approach is straightforward. Collect IATA airport codes for your team’s locations. Plug them into a tool that cross-references nonstop route maps. See which destinations have the most direct coverage.

Midway does exactly this. Enter your departure cities and it returns every destination reachable by direct flight from all of them. It supports up to 6 departure cities — enter your whole team’s locations at once.

Here’s what it looks like for a team split between San Francisco and New York:

The map shows every airport with nonstop service from both cities. That’s your starting shortlist — not a wishlist, but a list grounded in actual route data.

For a SFO-JFK pair, you’ll see 40+ overlapping destinations. Denver, Las Vegas, Miami, Cancun, Los Angeles, even London and Paris. Each one is reachable without connections from both coasts.

For teams with people in more than two cities, you can run multiple searches and look for destinations that appear across all of them. Midway will soon support 3+ departure cities in a single search — a feature built specifically for this use case. In the meantime, running a few two-city combinations gets you most of the way there.

If this flight-first approach sounds familiar, it’s the same principle behind finding a meeting point between multiple cities. The difference here is scale — you’re optimizing for a group of 10-50, not two friends picking a weekend trip.

How to evaluate an offsite destination beyond flights

Flight accessibility gets you a shortlist. Now you need to pick one. A weighted scorecard keeps the decision structured and defensible — especially when you’re presenting options to leadership.

Here’s a framework that works:

1. Flight accessibility (40% weight). What percentage of your team can fly nonstop? What’s the average travel time? Are there multiple daily frequencies, or is it one flight at 6 a.m.?
2. Venue availability (20% weight). Does the city have co-working spaces, hotels with conference rooms, or dedicated offsite venues? Can you book a space for your group size without six months of lead time?
3. Cost per person (20% weight). Total cost: flights + accommodation + meals + venue + activities. Some cities are deceptive — cheap flights but expensive hotels. Others are the opposite.
4. Activities and culture (10% weight). What will people do outside of work sessions? Walkability, restaurants, outdoor activities, nightlife. This isn’t frivolous — the informal time is where relationships form.
5. Logistics and accessibility (10% weight). Airport-to-hotel transport. Visa requirements for international team members. Time zone friendliness if you’re planning sessions with people who couldn’t attend in person.

Score each destination 1-5 on each criterion, apply the weights, and you have a ranking. Adjust weights based on what matters to your company. A bootstrapped startup might push cost to 40%. A company with unlimited travel budget might weight activities higher.

The critical insight: flight accessibility should always carry the most weight. A city with a perfect venue means nothing if half the team spends 10 hours getting there.

One more thing about this scorecard. Don’t skip it. The temptation is to eyeball the shortlist and go with gut feel. The problem is that gut feel is biased toward cities you’ve personally been to and enjoyed. A structured score forces you to evaluate cities you might not have considered — and it gives you something concrete to show leadership when they ask why you picked Nashville over their preferred option of, say, Park City.

The best offsite cities for distributed teams

These cities consistently rank highest when you combine flight connectivity, offsite infrastructure, and value for money. Some are obvious. A few might surprise you.

Denver. The default choice for US-based distributed teams, and for good reason. United hub with nonstop service from essentially every US city. Hotels are 30-40% cheaper than coastal cities. The outdoor activities — hiking, skiing, brewery tours — give you built-in team bonding that doesn’t feel forced. Four to five hours from either coast. One catch: winter weather can delay flights.

Nashville. Exploded as a corporate offsite city in the past five years. Over 140 nonstop routes, compact walkable downtown, and a food scene that’s become genuinely excellent. Hotel rates are reasonable. The live music thing is real but doesn’t have to define your trip. Good for teams of any size.

Austin. Tech-friendly, warm most of the year, strong direct flight coverage from major cities. The Rainey Street and East Austin neighborhoods work well for group dinners. Venue options range from boutique hotels to dedicated retreat spaces outside the city. Gets hot in summer — plan for spring or fall.

Chicago. Two airports, 270+ combined nonstop routes. June through September, it’s one of the best cities in America — the lakefront, rooftop bars, architecture tours, deep-dish debates. October through April, you’re gambling on weather. But if your offsite falls in summer, Chicago is hard to beat for a group that wants city energy.

San Diego. Reliable weather, walkable Gaslamp Quarter, beaches for downtime. Fewer nonstop routes than the mega-hubs, but strong coverage from major US cities. Good value compared to LA or San Francisco. Works particularly well for West Coast-heavy teams.

Miami. Beach plus Latin American culture plus nightlife. Strong connectivity on the East Coast; workable from the West Coast via several nonstops. Wynwood and Brickell have transformed the city beyond South Beach. November through April is the sweet spot.

Lisbon. The standout international option for teams split between the US and Europe. Direct flights from New York, Newark, Boston, Miami, San Francisco, and most European capitals. Affordable by Western European standards. Excellent food. Walkable. The weather is good eight months of the year. Lisbon has quietly become the default offsite city for transatlantic teams.

Cancun. Not just a resort town. The Hotel Zone works surprisingly well for offsites — all-inclusive resorts handle logistics, and the airport has direct flights from 30+ US cities plus several European ones. Cost per person is low. Visa-free for most nationalities. The trade-off: the resort bubble can feel disconnected from an actual city.

San Juan, Puerto Rico. No passport needed for US travelers. Direct flights from 20+ US cities. Colonial architecture, beaches, excellent food, and a walkable old town. Group-friendly hotels and event spaces. An underrated choice that feels international without the international logistics.

Charleston. Smaller than the cities above, but punching above its weight for offsite appeal. Beautiful historic downtown, outstanding restaurants, and enough nonstop routes to work for East Coast and Midwest teams. Less ideal if a significant portion of your team is on the West Coast.

For a deeper look at which US cities have the strongest overall flight connectivity — and why that matters for any kind of group travel — see our guide to the most connected cities in America.

International offsite destinations

At some point, a domestic offsite stops making sense. Maybe your engineering team is half in Europe. Maybe you’ve done Denver three times and the team wants something different. Maybe leadership wants the offsite to feel like a reward, not just a meeting in a different city.

International offsites cost more. They also create stronger memories, build deeper team bonds, and signal that the company invests in its people. The key is picking a city where the flight logistics don’t eat the budget.

A common mistake: assuming “international” means “expensive.” Lisbon is cheaper than San Francisco. Mexico City is cheaper than Austin. Marrakech is cheaper than basically anywhere in the US. The flight is the expensive part — and if your team already spans continents, the flight cost is baked in regardless of where you go. At that point, the cheaper ground costs of many international cities actually make them more economical than domestic alternatives.

Cities with the strongest direct flight coverage from both US and European tech hubs:

London. The most connected city in Europe. Direct flights from nearly every major US city and every European capital. Expensive, but you know what you’re getting — excellent meeting spaces, restaurants for any taste, and enough to do that no one’s bored. Works for purely European teams or US-Europe hybrids.

Barcelona. Strong connectivity from European cities, plus direct flights from New York, Newark, Miami, and a few others. Weather is reliable from April through October. The city itself — architecture, beaches, food, nightlife — is probably the single best offsite destination in Europe for teams that want a mix of work and experience.

Lisbon. Already mentioned above, but worth repeating for international context. It’s the most cost-effective Western European city with strong transatlantic flight coverage. Teams that have done a Lisbon offsite tend to go back.

Marrakech. A bold choice, but increasingly popular for European teams. Direct flights from most European capitals. Dramatically affordable once you’re there — riads, restaurants, activities. The sensory overload of the medina creates shared experiences that are hard to replicate elsewhere. Less accessible from US cities without a connection, so best for European or EMEA teams.

Dubai. Connects Europe, Asia, India, and Africa. If your team spans the Eastern Hemisphere, Dubai is the logistics answer even if it’s nobody’s first choice on vibes. Modern infrastructure, reliable weather November through March, and high-end venues for corporate events. Expensive, but predictable.

Mexico City. Direct flights from most major US cities, plus growing connectivity from Europe. One of the best food cities on the planet. Affordable. Altitude-adjusted weather means it’s pleasant year-round. The Roma and Condesa neighborhoods are walkable, full of cafes and restaurants, and have co-working infrastructure built for remote teams.

Here’s what the flight overlap looks like for a team split between San Francisco and London — a common setup for companies with US and European offices:

The overlap is smaller than a domestic search, but you’ll still see viable options — New York, Boston, Dublin, Lisbon, and others depending on the season. For teams with members in both the US and UK, these results narrow the field fast.

Budgeting: how flight accessibility impacts total offsite cost

The difference between a flight-optimized offsite and a “pick a cool city” offsite is measurable. Here’s where the money goes.

Flight costs. A nonstop round-trip ticket from a team member’s city typically runs $200-500 domestic, depending on distance and how far ahead you book. Add a connection and that ticket jumps 30-80% — plus you’re paying for the time cost. For a 20-person team where half need connections, that’s an extra $3,000-8,000 in flights alone.

Travel time costs. This one’s invisible on the budget spreadsheet but real. A connection adds 3-5 hours each way. For a team of 20 with 10 people connecting, that’s 60-100 hours of collective travel time per offsite. If your team’s average cost is $75/hour, that’s $4,500-7,500 in implicit cost — time people could have spent working or, more importantly, arriving fresh enough to make day one productive.

Accommodation and ground costs. These vary by city, not by flight routing. But flight-accessible cities tend to be well-connected hubs, which usually means competitive hotel pricing. Nashville and Denver are both flight-friendly AND cheaper per night than, say, Aspen or Napa — cities that look great on a mood board but require connections from most origins.

A rough model for a 20-person, 4-day domestic offsite:

Category	Flight-optimized city	Non-optimized city
Flights (avg per person)	$350	$520
Hotel (3 nights, avg)	$600	$750
Venue + meals	$400	$400
Activities	$150	$150
Total per person	$1,500	$1,820
Total for 20 people	$30,000	$36,400

That’s a $6,400 difference. Enough to fund a second, smaller offsite — or extend the first one by a day.

The pattern holds internationally. Choosing Lisbon over Zurich for a transatlantic offsite can save $800-1,200 per person while offering comparable (arguably better) offsite infrastructure.

One number that often gets ignored: the cost of a wasted first day. If 10 people arrive exhausted from connections and the first afternoon’s sessions are unproductive, that’s 40+ person-hours of offsite time lost. At $75/hour loaded cost, that’s $3,000 — not on any line item, but very real. Flight-optimized destinations don’t just save on tickets. They save the offsite itself from starting in a hole.

For companies running two or three offsites per year, these savings compound. A $6,000 per-offsite saving across three events is $18,000 annually — enough to add another team dinner, extend by a day, or simply return budget to the bottom line.

Logistics playbook

Once you’ve picked the city, execution matters. Distributed teams face booking challenges that single-office companies don’t.

Booking flights from multiple origins. Don’t try to book everyone’s flights centrally unless you have a dedicated travel manager. Instead, set a budget cap per person, share the destination and preferred arrival/departure dates, and let people book their own flights. Reimburse actuals up to the cap. This avoids the nightmare of coordinating 15 different itineraries through a single booking tool.

For teams over 25, a corporate travel platform like Navan, TripActions, or TravelPerk can automate policy enforcement and centralize booking. Below 25, it’s usually more hassle than it’s worth.

Managing different budgets across departure cities. A flight from New York to Nashville is $180. From Seattle, it’s $350. Some companies set a flat reimbursement regardless of origin. Others reimburse actual cost. Both approaches create friction — the first penalizes people in expensive-to-fly-from cities, the second rewards them. The cleanest solution: set the per-person budget at the average flight cost across all origins, then let people adjust within it.

Arrival and departure coordination. Not everyone will arrive at the same time. Stagger your agenda so that the first half-day is optional — check-in, settling in, informal drinks. Put the critical sessions on the full days when everyone’s present. Same principle for the last day: make it light so early departures don’t miss anything important.

Corporate travel policies. If your company has a travel policy that requires booking through a specific platform or using preferred airlines, communicate this early. Nothing derails offsite momentum faster than someone booking a great fare on their personal card only to find out it won’t be reimbursed because they didn’t use the approved tool.

Expensing from different countries. For international teams, expense policies can vary by entity. A team member in Germany may have different per diem rules than one in the US. Surface this early and set clear expectations. A shared FAQ document covering “how to expense your offsite travel” saves a dozen confused Slack messages.

Visa and entry requirements. Don’t assume. A US destination seems simple until you remember your contractor in Brazil needs an ESTA or visa. An EU destination is easy for Europeans but may require advance paperwork for team members from other countries. Check entry requirements for every team member’s passport the moment you shortlist destinations.

Timing the booking. For domestic offsites, 8-12 weeks of lead time is usually sufficient. International offsites need 12-16 weeks minimum — more if visa processing is involved. Flight prices for popular offsite cities tend to climb sharply inside the 6-week window, especially on routes with limited daily frequencies. Book early. The ops manager who locks in flights at 10 weeks saves more money than the one who spends those 4 extra weeks debating between two equally good cities.

Ground transportation. In walkable cities (Nashville, Lisbon, Barcelona), you can skip car rentals entirely. In spread-out cities (Austin, Miami, San Diego), budget for rideshare credits or a shuttle service. A shared Uber account or prepaid rideshare credits distributed to the team simplify expensing and keep people from waiting for reimbursement.

Accommodation strategy. For teams under 15, a single hotel keeps things simple — everyone’s in one place, breakfast is handled, and the lobby becomes an informal gathering space. For larger teams, negotiate a room block for a group rate. Some hotels offer complimentary meeting space when you book enough rooms, which can eliminate a separate venue cost entirely. Airbnbs and vacation rentals work for small teams but create logistical headaches at scale — different check-in times, split locations, no front desk.

Offsite city profiles

Quick reference for the most popular offsite destinations. Each city is evaluated on flight connectivity, offsite infrastructure, and cost. Detailed profiles with venue recommendations, neighborhood guides, and seasonal planning tips are coming soon.

US cities:

• Nashville, TN — 140+ nonstop routes. Walkable downtown. Strong restaurant and bar scene. Budget-friendly. Good for teams of any size.
• Austin, TX — Tech-friendly. Warm climate. Dedicated retreat venues. Best in spring and fall.
• Denver, CO — 200+ nonstop routes. Outdoor activities. Mountain backdrop. Affordable hotels. Year-round but watch winter delays.
• Charleston, SC — Historic charm. Excellent food. Smaller airport but growing connectivity. Best for East Coast and Midwest teams.
• San Diego, CA — Reliable weather. Walkable Gaslamp Quarter. Beaches. Good West Coast hub.
• Chicago, IL — 270+ nonstop routes across two airports. World-class food and culture. Best June through September.
• Miami, FL — Beach plus city. Latin American culture. Strong East Coast connectivity. November through April.
• San Juan, PR — No passport for US travelers. 20+ nonstop US routes. Colonial charm. Affordable.

International cities:

• Lisbon, Portugal — Direct flights from 6+ US cities and most European capitals. Affordable. Walkable. Great weather.
• Barcelona, Spain — Top-tier offsite city. Food, architecture, weather. Strong European connectivity plus select US routes.
• London, UK — Most connected city in Europe. Expensive but predictable. Works for any team composition.
• Cancun, Mexico — 30+ US nonstop routes. All-inclusive logistics. Visa-free. Budget-friendly.
• Mexico City, Mexico — Excellent food. Affordable. Growing flight connectivity. Walkable neighborhoods.
• Marrakech, Morocco — Great for European teams. Affordable. Unforgettable atmosphere.
• Dubai, UAE — Eastern Hemisphere connector. Modern infrastructure. November through March.

Start with the flights

The offsite city decision doesn’t have to be a three-week debate in Slack. Collect your team’s locations. Run the flight search. Score the shortlist. Book it.

The city that’s easiest to reach is almost always the one where the offsite goes best. People arrive on time, in good spirits, ready to be present. Nobody’s complaining about their 5 a.m. connection through Charlotte. Nobody’s jet-lagged from a routing that added six hours to a three-hour flight.

Try Midway with two of your team’s biggest locations and see what comes back. You’ll have a shortlist in under a minute. The rest — venue, agenda, team dinner reservations — is the easy part.

For a deeper dive into the retreat planning timeline and logistics, check out our remote team retreat planning guide.