Retreats for remote‑first teams, anywhere in the US

Gather somewhere extraordinary. Leave with a plan.

Wherever your people live, we pick the place that works for everyone: mountain, coast, desert and city retreats with facilitated work sessions built in. One flat fee. Every vendor at cost.

Napa & SonomaHudson ValleyRiviera MayaScottsdaleColoradoLisbonLas Vegas+ Signature collection

The idea

A retreat should change how your team works on Monday. Not just how it feels on Friday.

Remote teams don't need another all-hands on video. They need a few days in the same beautiful place: time to laugh, time to think, and time to decide.

Mornings are facilitated working sessions run with agile methods by a Certified ScrumMaster. Afternoons belong to the place. Then we stay with you for 90 days so the decisions hold.

Why Waypoint

  • 01Coordinated, not just bookedFacilitated working sessions, plus fun that's actually planned: celebrations, boat days, chef's dinners. One point of contact, end to end.
  • 02Built for modern remote teamsFresh, energetic destinations and experiences your team will actually want to fly for.
  • 03Built for every teammateStep-free options, every diet, great non-drinking evenings and opt-in adventures. How we plan it
  • 04Made for remote-first software teamsWe know teams that rarely share a room, and what a few days together needs to fix.

Core destinations

Places that do half the work.

Seven core destinations cover the year for groups of 8–⁠30, wherever your people live: the Hudson Valley near the Northeast hubs, Napa & Sonoma for the West Coast, four fly-in favorites and Las Vegas for sales celebrations. Pick a season to see what's at its best (it filters the Signature and on-request lists too). Per-person ranges are rough estimates for three nights (four for Lisbon, where team retreats run longer), all-in with a typical round-trip fare from a major US hub, before our fee.

Best for

Any season: 7 core picks · 7 Signature

Signature ↓
  • A red barn and silo framed by autumn maples in Hunter, in the Catskills

    01

    New York · Northeast · Poconos overflow

    Hudson Valley & Catskills

    Barn sessions, farm dinners, wood-fired saunas and foliage. Close to the Northeast hubs.

    Best
    Sep–⁠Oct · May–⁠Jun
    Est. all-in
    $1.5k–⁠$4k pp
    Getting there (est.)
    NYC 1.5–⁠3h by road · CHI 2h to ALB · LA 5.5h to NYC
  • Vineyard rows on rolling hills under a clear sky in Napa Valley, California

    02

    California · Wine country · West Coast

    Napa & Sonoma

    Vineyard pavilions, redwood walks, river paddles and harvest dinners. 90 minutes from San Francisco.

    Best
    Apr–⁠Jun · Sep–⁠Oct
    Est. all-in
    $1.5k–⁠$4.8k pp
    Nonstop to SFO / STS (est.)
    NYC 6.5h · CHI 4.5h · LA 1.5h · SF 1.5h by road
  • The Tulum ruins on a cliff above a turquoise sea

    03

    Mexico · Tulum · Playa del Carmen

    Riviera Maya

    Design villas, cenote swims, ruins at sunrise and private-chef dinners. Easy nonstops to Cancún.

    Best
    Nov–⁠Apr
    Est. all-in
    $1.9k–⁠$4.3k pp
    Nonstop to CUN (est.)
    NYC 4h · CHI 3h45 · LA 4h30
  • Red rock spires under a blue sky in Sedona, Arizona

    04

    Arizona · High desert

    Scottsdale & Sedona

    Red-rock hikes, sunrise balloons, stargazing and spa-resort boardrooms in Scottsdale and Sedona.

    Best
    Oct–⁠Apr
    Est. all-in
    $2k–⁠$5.2k pp
    Nonstop to PHX (est.)
    NYC 5h · CHI 4h · LA 1h30
  • The Maroon Bells reflected in a lake, ringed by golden aspens near Aspen, Colorado

    05

    Boulder · Vail · Breckenridge

    Colorado Mountains

    Summit sessions, fly-fishing, aspen trails and fireside evenings. Central for teams coast to coast.

    Best
    Jun–early Oct · Jan–⁠Mar ski
    Est. all-in
    $2.3k–⁠$4.5k pp
    Nonstop to DEN (est.)
    NYC 4h30 · CHI 2h45 · LA 2h30
  • Terracotta rooftops of Lisbon under a soft sky

    06

    Portugal · Cascais · Sintra · Ericeira

    Lisbon & the Coast

    Quinta workshops, Ericeira surf, Tagus sunset sails and fado dinners. Team retreats run 4 nights.

    Best
    Apr–⁠Jun · Sep–⁠Oct
    Est. all-in, 4 nights
    $2.1k–⁠$7.2k pp
    Nonstop to LIS, overnight (est.)
    NYC 7h · CHI 8h15 · SF 11h15
  • The Las Vegas Strip lit up at night

    07

    Nevada · Sales Milestone trips only

    Las Vegas

    Off-Strip sessions by day; awards dinners, shows and desert rides by night. Sales trips only.

    Best
    Mar–⁠May · Oct–⁠Nov
    Est. all-in
    $1.5k–⁠$3.3k pp
    Nonstop to LAS (est.)
    NYC 5h30 · CHI 4h · LA 1h15

Flight times are typical scheduled nonstop durations from New York, Chicago and Los Angeles or San Francisco, rounded. They're estimates: some routes are seasonal, and connections add time. We plan arrivals around where your people actually live.

The Signature collection

Seven places worth the extra mile.

Premium trips for leadership offsites, reward trips and once-a-year moments: Great Camps, islands, buyouts and bucket-list landscapes. Ranges are estimated land costs per person per night (lodging, meals, activities, meeting space and ground transport), before flights and our fee. International and island trips add a $2k–⁠$5k planning premium.

Best for

Any season: 7 core picks · 7 Signature

  • Mirror Lake in Lake Placid ringed by autumn trees, with Adirondack peaks behind

    S1

    Signature

    New York · Lake Placid · Saranac · Raquette Lake

    Adirondack Great Camps

    Lakeside Great Camps, guide-boat paddles and High Peaks hikes. A winter edition in Lake Placid.

    Best
    Jul–⁠mid-Oct · Jan–⁠Mar
    Est. land cost
    $400–⁠$700 pp/night
    Via Albany, ALB, + 2h transfer (est.)
    NYC 1h · CHI 2h · LA 1 stop
  • Brant Point Lighthouse and sailboats at sunrise on Nantucket

    S2

    Signature

    Massachusetts · Islands · Best for 12–⁠20

    Nantucket & Martha's Vineyard

    Private sailing regattas, beach clambakes, island bike tours and harbor dinners. Best for 12–⁠20.

    Best
    Jun–⁠mid-Oct
    Est. land cost
    $500–⁠$1.1k pp/night
    To ACK / MVY, summer nonstops (est.)
    NYC 1h15 · CHI 1 stop · LA 1 stop
  • The Château Frontenac above snow-covered Québec City in winter

    S3

    Signature

    Canada · Old Québec · Charlevoix

    Québec City & Charlevoix

    Our winter signature: dog sledding, Nordic spas, ice-hotel cocktails and ski-in sessions.

    Best
    Jan–⁠Mar · Sep–⁠Oct
    Est. land cost
    $320–⁠$600 pp/night
    To Québec City, YQB (est.)
    NYC 1h50 nonstop · CHI 1 stop · LA 1 stop
  • A sailboat anchored in turquoise water off a cay in the Exumas, Bahamas

    S4

    Signature

    Bahamas · Out Islands · Exumas · Eleuthera

    Bahamas Private Island

    The whole island is yours: sandbar picnics, reef snorkels and beach bonfires. Best for 12–⁠24.

    Best
    Nov–⁠May
    Est. land cost
    $700–⁠$2k pp/night
    Nonstop to Nassau, + 15–⁠60 min hop (est.)
    NYC 3h · CHI 3h30 · LA 1 stop
  • Aerial view of the Sete Cidades crater lakes on São Miguel, Azores

    S5

    Signature

    Portugal · São Miguel · Mid-Atlantic

    The Azores

    Crater-lake hikes, whale watching, hot springs and volcanic-earth stews. Team retreats run 4 nights.

    Best
    May–⁠Oct
    Est. land cost
    $350–⁠$550 pp/night
    To Ponta Delgada, PDL, overnight (est.)
    NYC 5h35 nonstop · CHI 1 stop · LA 1 stop
  • Skógafoss waterfall between green cliffs on Iceland's south coast

    S6

    Signature

    Iceland · Reykjanes · South Coast

    Iceland

    Glacier hikes, geothermal lagoons, the midnight sun or the aurora. Team retreats run 4 nights.

    Best
    Jun–⁠Aug · Sep–⁠Mar
    Est. land cost
    $700–⁠$1.3k pp/night
    Nonstop to KEF, overnight (est.)
    NYC 5h45 · CHI 6h · LA 1 stop
  • Moraine Lake reflecting the Valley of the Ten Peaks in Banff National Park

    S7

    Signature

    Canada · Banff · Lake Louise

    Banff & the Rockies

    Turquoise lakes, canoe mornings and gondola summit sessions. An easy hop for West Coast teams.

    Best
    Jun–⁠Sep · Dec–⁠Mar
    Est. land cost
    $500–⁠$850 pp/night
    Nonstop to Calgary, YYC, + 90 min (est.)
    NYC 4h45 · CHI 3h45 · SF 2h45
  • Planning premium, $2k–⁠$5k. Added to the flat fee for Signature trips abroad or to an island (everything except the Adirondacks). It covers vetting a local partner, ferry, charter or border logistics, and contingency plans.
  • Still at cost. Venues, buyouts and local partners are contracted by you at cost; site visits are billed at cost. Ranges are planning estimates, not quotes.
  • Book further ahead. Small islands and buyouts fill early: allow 6–⁠9 months for peak dates. A passport is needed everywhere except the Adirondacks and the islands off Massachusetts.

Custom, on request

Quoted individually and delivered with a local partner, contracted by you at cost. Ask through the inquiry form.

  • Aerial view of a jungle headland above a turquoise Costa Rican bay
    Costa RicaGuanacaste and Arenal, mid-Dec–⁠Apr. Surf lessons, hot springs and rainforest hikes.
  • Palm trees above a blue Puerto Rican coastline
    Puerto RicoOld San Juan, El Yunque and bio bays, Dec–⁠Apr. No passport needed for US citizens.
  • A still Maine lake ringed by autumn trees at sunrise
    MaineLake lodges and coastal inns, Jun–⁠Sep. Unplugged settings for focus-heavy offsites.
  • Limestone islands rising from a turquoise sea in Thailand
    ThailandPremium leadership or reward trips of 5+ nights, Nov–⁠Feb. Planning fee from $30,000.
  • Aerial view of karst peaks rising above the countryside near Guilin, China
    ChinaShanghai & Hangzhou, Guilin or Yunnan; 7+ nights. Visa and connectivity handled for you, from $30,000.

Retreat finder

Four questions. Two places to start.

Answer honestly; there are no wrong picks. We'll suggest a package and two destinations, then refine with you on a call, starting from where your people are based.

1What's the main goal?
2How many people?
3How far will you travel?
4When are you thinking?

The experience

Mornings for the work. Afternoons for the place. Evenings for each other.

A team gathered at a wall of sticky notes during a planning workshop
09:00Work that shipsFacilitated workshops, bets, OKRs and owners, with a closing retro on the last morning. Every session ends in a written output.
14:00Get outsideTrails, surf, kayaks, e-bikes. Shared effort is the fastest way to trust.
17:00BreathePools, saunas, cold plunges and nothing on the calendar.
19:30The long tableChef's dinners and fire-pit stories, where the real conversations happen.
A group stretching together in an open-air studio surrounded by trees
07:00Optional sunriseMovement, a swim or a walk before the first session.
A long candlelit dinner table set outdoors under trees

The offsite your team will still talk about next year, and the plan they'll still be using.

How it works

Transparent by design.

No markups, no percentage of spend, no surprises when the headcount moves. Here's exactly what you're buying.

  1. I

    One flat fee

    A single planning and facilitation fee, fixed for the scope we agree in writing.

  2. II

    Vendors at cost

    You contract venues, activities and transport directly at the rates we negotiate. You see every line.

  3. III

    Facilitated outcomes

    Pre-retreat interviews shape an agile agenda. You leave with a decision log and named owners.

  4. IV

    30 / 60 / 90

    Check-ins at 30, 60 and 90 days to unblock owners and run a closing retro.

Built for every teammate.

  • Step-free optionsWe vet venues for step-free routes and accessible rooms, and confirm them with you before you sign.
  • Every tableDietary, allergy and religious meal needs gathered in confidence and briefed to each kitchen.
  • Every eveningA good non-drinking option alongside every bar night or tasting.
  • Always opt-inAdventures are optional, with a relaxed alternative at the same time.

Sample itineraries

What four days actually look like.

Illustrative run-of-show from our packages. Every retreat is designed around your goals, pre-interviews and budget.

The Tulum ruins on a cliff above the Caribbean
3 nights · 20–⁠30 people · Playa del Carmen & Tulum
  1. Day 1

    Arrive & open

    Afternoon Transfer from Cancún, check-in, 16:30 kickoff: why we're here, norms. Evening Welcome dinner, two truths and a lie with a twist.

  2. Day 2

    Take stock & adventure

    09:00 Alignment workshop: where the team stands, plus a health check. Afternoon Cenote swim or reef snorkel. Evening Free; optional beach fire.

  3. Day 3

    Priorities & OKRs

    09:00 Company plan, then team bets. 14:00 Breakouts, then the Tulum ruins or free time. Evening Signature private-chef dinner and team awards.

  4. Day 4

    Commit & review

    09:00 Working agreements and commitments; playbook preview. 11:00 Team retro: what worked, what didn't, what we'll do next. Lunch Depart for CUN.

  5. +72 hrs

    Playbook, then 30/60/90

    Decision log, priorities board and working agreements in writing, then three check-ins.

The retreats

Four ways to gather.

Fixed packages with one flat fee, set by headcount band. Venues, activities and transport are paid directly to vendors at cost, and our travel is billed at cost; pass-through ranges are planning estimates, not quotes. Air is booked by your team.

A planning workshop with sticky notes on the wallStart here

Strategy Day

1 day · 8–⁠15 leaders · near your team's hub city, or a regional anchor

From $12,000 flat fee

$12k–⁠$14k · + vendors at cost, est. $3k–⁠$15k total

  • Pre-interviews and anonymous survey
  • 12-month bets, OKRs, owners, closing retro
  • Or a paid pilot, credited toward a retreat
Red rock formations in SedonaLeadership

Executive Strategy Retreat

2 nights regional · 3 nights fly-in or Signature · 8–⁠15 people · any core destination except Las Vegas, or Signature

From $18,000 flat fee

$18k–⁠$25k regional · $22k–⁠$31k fly-in · + vendors at cost, est. $15k–⁠$35k regional · $25k–⁠$60k fly-in

  • Two facilitated working days (three on fly-in trips)
  • Strategy narrative and 12-month roadmap
  • Curated experiences, chef's dinners
Four colleagues walking a sunny forest trail in ColoradoFlagship

Team Alignment Retreat

3 nights · 4 for Lisbon, the Azores and Iceland · 20–⁠30 people · any core or Signature destination

From $22,000 flat fee

$22k–⁠$30k by headcount ($26k–⁠$36k at 4 nights) · extra night +$4k–⁠$6k · fly-in +$3k–⁠$5k local partner · + vendors at cost, est. $40k–⁠$60k regional · $55k–⁠$125k fly-in

  • Team-wide survey and interviews
  • Three facilitated half-day work blocks
  • 2–⁠3 adventures and a signature dinner
The Las Vegas Strip at nightCelebrate

Sales Milestone Trip

3 nights (2 regional) · 15–⁠30 people · Las Vegas, Scottsdale, Riviera Maya, Napa & Sonoma or the Catskills

From $18,000 flat fee

$18k–⁠$26k by headcount · fly-in +$3k–⁠$5k local partner · 4-night reward option in Riviera Maya, the Bahamas or Iceland +$2.5k–⁠$3.5k · + vendors at cost, est. $30k–⁠$55k total

  • Win-loss review and next-half plays
  • Awards dinner, shows, experiences
  • 30/60/90 pipeline-habit check-ins
Book the year

Yearly Plan

One full retreat plus two Strategy Days in the same 12 months. The retreat sets the plan; the Strategy Days, around months four and eight, check progress and reset priorities.

10% off the whole plan

Strategy Days are $10,500 each inside the plan (instead of $12k–⁠$14k), then 10% comes off the total. For example, a Hudson Valley Team Alignment Retreat at $26,000 plus two Strategy Days: $47,000 $42,300. Each event is invoiced on the usual 50/50 terms; vendors and travel stay at cost.

Add-ons

  • Pre-retreat team surveyA confidential team-health survey, a written report and a 45-minute debrief that shapes the agenda.$1,500
  • Extra leadership dayOne more facilitated day for your leaders, before or after the retreat. Venue and lodging at cost.$4k–⁠$6k
  • Welcome kits from LumenOur sister company makes custom team kits for every room: one point of contact, no planning fee on top. You're always free to use any supplier.No fee from us
  • Photo & video recapWe source and brief a local crew for edited photos and a two-minute recap video. You pay the crew directly.Crew at cost + $500

Ongoing support, if you want it. After the included 30/60/90-day follow-up, an optional retainer keeps us with your leaders each quarter: a check-in, a half-day session and light support in between. $2k–⁠$3k a month.

  • Paid discovery, $1.5k–⁠$2.5k. Destination shortlist and agenda design before you sign, credited in full when you do.
  • Two revision rounds included. Further changes, or a new headcount band, go in a short written change order.
  • ACH or wire at no charge. Cards accepted with a 3% surcharge where allowed. 50% at signing, 50% thirty days before.
  • Site visits and our travel at cost. Billed to you without markup; vendor commissions are credited 100% to you.
  • Fly-in trips. Team Alignment and Sales Milestone trips add $3k–⁠$5k for a local partner on the ground.
  • Signature collection. Trips abroad or to an island add a $2k–⁠$5k planning premium; the Adirondacks don't.
  • Custom destinations. Costa Rica, Puerto Rico and Maine on request; Thailand (5+ nights) and China (7 nights, or 6 for a single city) as premium trips from $30k.

Where your money goes.

You pay hotels and other vendors yourself, at their real price. You pay us one flat fee to plan and run the retreat. We don't add anything on top.

Example: 20-person Team Alignment retreat, Scottsdale & Sedona

Striped part: the gap between our low and high estimate.

  • You pay hotels and vendors$63.2k–⁠$91.2kRooms, food, meeting rooms, activities, buses and your team's flights. They bill you directly. If a hotel offers us a commission, all of it goes to you.
  • You pay us one fee$28kWe plan everything and run the retreat on site. One price, agreed in writing before you sign.
  • You pay our travel, at cost$2.5k–⁠$3.1kOur flights and hotel for the retreat, billed at exactly what we paid.

We credit every venue commission back to you, so you pay vendors exactly what they charge. These numbers are an estimate to show how it works, not a quote. We also suggest setting aside about 5% extra ($3.2k–⁠$4.6k) for surprises; anything you don't use stays with you.

What you can hold us to

Promises, in writing.

  • A fixed fee before you commit. Scope, group size band and sessions agreed up front; the number doesn't drift with your spend.
  • Contracts in your name. Venues and vendors bill you directly. Any commission offered to us is disclosed and credited 100% to you.
  • A written decision log. Same-day owners and next steps; the full playbook within 48–⁠72 hours.
  • A certified facilitator in the room. Sessions are designed and run by a Certified ScrumMaster, on site for the whole retreat.
  • Ninety days of follow-through. Check-ins at 30, 60 and 90 days are included in every package.

How we compare

Why not a big agency, or do it yourself?

Three ways to plan a team retreat, side by side.

Waypoint compared with a big event agency and planning it yourself
WaypointBig event agencyDo it yourself
Who plans it?Raheem and Abdul, the two founders, from the first call to the last night.A team of staff, who often hand you from one person to the next.Someone on your team, on top of their job.
What does it cost you?One flat fee. Hotels and vendors at their real price, with no hidden markup.A fee, plus markups on hotels and vendors that you often can't see.No fee, but weeks of your team's time.
Who is it for?Remote teams of 8–⁠30 people.Mostly big conferences and events.Anyone with time to spare.
Who runs the meetings?We do. We're both Certified ScrumMasters, trained to run them.Usually someone extra, at extra cost.Your team does.
How much of your time does it take?A few short check-ins.Some meetings and reviews.A lot.

Bottom line: agency-level planning, without the markup or the hand-offs.

About & how we work

Small by design. Hands-on from start to finish.

Waypoint Retreats was founded by brothers Raheem and Abdul Chaudhry, both Certified ScrumMasters. That facilitation background shapes everything we do: each retreat is built around the decisions your team needs to make, and the logistics are designed to serve them.

We're an independent studio based in New Jersey, working with remote-first teams across the US. You work with the founders directly, from the first call to the 90-day retro.

  1. 01

    Inquiry & discovery

    Week 0

    Send the short form and we reply within one business day. On a 45-minute call we cover goals, group, budget and dates.

  2. 02

    Proposal & agreement

    Within a week of the call

    A written proposal with a fixed fee, scope, destination shortlist and an all-in budget estimate. Sign, pay 50%, and your dates are held.

  3. 03

    Design & sourcing

    Typically 2–⁠4 months out

    Pre-interviews and survey, venue and vendor sourcing, and contract review. You sign vendors directly at cost. Agenda, run-of-show and traveler guide follow. The balance is due 30 days before.

  4. 04

    The retreat

    On site, start to finish

    We facilitate every working session and coordinate vendors in real time, so your team can be fully present.

  5. 05

    Playbook & 30/60/90

    48–⁠72 hours, then 90 days

    The decision log, priorities and working agreements in writing, then check-ins at 30, 60 and 90 days so the plan holds.

FAQ

Good questions.

Pricing, payment, planning, the retreat itself and what comes after. Can't find your answer? Ask us, or read our booking policy and terms.

Pricing & payment

How much does a retreat cost?

Our flat fee is $12,000–⁠$14,000 for a standalone Strategy Day, $18,000–⁠$25,000 for a two-night regional Executive Strategy Retreat ($22,000–⁠$31,000 for three nights fly-in or Signature), $18,000–⁠$26,000 for a three-night Sales Milestone Trip and $22,000–⁠$30,000 for a three-night Team Alignment Retreat ($26,000–⁠$36,000 at four nights, the default for Lisbon, the Azores and Iceland). Sales Milestone and Team Alignment fees are set by headcount band, and their fly-in trips add $3,000–⁠$5,000 for a local partner on the ground. An extra Team Alignment night is $4,000–⁠$6,000; a fourth reward night on a Sales Milestone Trip to Riviera Maya, the Bahamas or Iceland is $2,500–⁠$3,500 ($4,000–⁠$6,000 with a second working session). Signature trips abroad or to an island add a $2,000–⁠$5,000 planning premium. Book a full retreat and two Strategy Days within 12 months as a Yearly Plan and the Strategy Days drop to $10,500 each, with 10% off the total. Optional add-ons are priced separately. Custom destinations are quoted individually; Thailand (5+ nights) and China (7 nights, or 6 for a single-city leadership trip) start at $30,000. Venues, food, activities and transport are separate and paid by you at cost, and our own travel and any site visits are billed to you at cost. The per-person and package ranges on this site are planning estimates, not quotes.

Do you charge for a proposal?

A first call and a written proposal are free. For retreats, we offer paid discovery for $1,500–⁠$2,500: a researched destination shortlist with all-in budgets and a draft agenda. It's credited in full against our fee when you sign. A Strategy Day can also run as a paid pilot that's credited toward a retreat with us, as set out in your proposal.

What's included in the flat fee, and what isn't?

Included: discovery, pre-retreat interviews and survey, destination and venue sourcing, vendor negotiation and contract review, agenda design, on-site facilitation and coordination, the written playbook, and 30/60/90-day follow-up.

Not included: lodging, venues, food and drink, activities, ground transport, flights, insurance and optional extras like a photographer. You pay those directly to each vendor. Our own travel for on-site days and any site visits are billed to you at cost, never marked up. Two rounds of revisions to the plan are included; further changes are agreed in a short change order.

Who pays the venues and vendors?

You do, directly. You contract with each venue, caterer, activity provider and transport company at the rates we negotiate, and you pay them on their terms. We never mark anything up, and we don't handle vendor money. If a vendor offers us a commission, we tell you in writing before you sign and credit 100% of it to you. Before you commit, we walk you through each vendor's deposit and cancellation terms.

Why is there a planning fee, and who pays the markup?

There's no markup. The flat fee is how we're paid for planning, sourcing, facilitation and running things on site, so we don't need to earn anything on your spend. Venues and vendors bill you directly at the rates we negotiate, any commission they offer is disclosed in writing and credited 100% to you, and our own travel is billed at cost. Planners are often paid partly through hotel commissions or vendor markups that never show up as a line on your invoice; a flat fee keeps our advice independent of how much you spend.

What are the payment terms?

50% of the flat fee at signing, and the balance 30 days before the retreat, by bank transfer (ACH or wire) at no extra charge. Cards are accepted with a 3% surcharge where the law allows it. If you book 30 days or less ahead, the full fee is due at signing. Our travel and any site visits are invoiced at cost. Vendor deposits follow each vendor's own schedule. Details are in our booking policy.

What if we need to cancel or reschedule?

Cancel more than 30 days before the retreat and you owe only the signing payment. The balance is never charged. Cancel within 5 business days of signing (when the retreat is more than 60 days away) and we refund the signing payment in full. You can move your dates once for free with more than 30 days' notice. Vendor refunds follow your contracts with them. The full rules are in our booking & cancellation policy.

What if our headcount changes?

The fee is fixed for your group-size band (for Team Alignment, 20–⁠25 or 26–⁠30 people), so a few people more or less doesn't change it. Moving to a different band, or adding days or sessions, is agreed in a short written change order. Hotels may charge for unused rooms under your contract with them, so we negotiate for flexible terms.

Planning

What group sizes do you work with?

We specialize in 8–⁠30 people: leadership teams, departments and whole remote-first startups. For bigger groups, tell us your numbers and we'll tell you honestly whether we're the right fit, and whether you'd need a second facilitator, quoted up front.

How long should our retreat be?

Three nights is the industry norm for a team that travels, and it’s our default for Team Alignment and Sales Milestone trips (cross-country groups can add a fourth). Leadership groups meeting regionally do well with two nights; fly-in leadership retreats get three. Transatlantic trips to Lisbon, the Azores or Iceland run four or five nights, so people recover from the flight and still get full working days. Reward trips can stretch to four nights in Riviera Maya, the Bahamas or Iceland. Thailand runs 5+ nights and China 7 (6 for a single-city leadership trip).

How far ahead should we book?

For small domestic groups, 3–⁠6 months is typical, with the venue signed 2–⁠4 months out. International trips and peak seasons are better at 4–⁠6+ months, and Signature islands and buyouts at 6–⁠9 months. A Strategy Day can come together in a few weeks, if a venue is free.

Our team is spread across the US. Where should we meet?

We start from where your people actually live. A short pre-survey maps everyone's nearest airport, and we compare total travel time, nonstop options and time zones across two or three destinations before you choose. Teams split between coasts often land on central picks like Colorado, Scottsdale or Las Vegas; teams clustered in one region can stay regional with the Hudson Valley or Napa & Sonoma. Flight times on this site are rounded estimates; we check live schedules for your dates.

Do you book flights?

No. We're not a travel agency, and your team books its own air, through your own travel tools if you have them. We recommend routes and arrival windows and build the airport-transfer plan, so everyone lands at the right time.

Do you plan international retreats?

Yes. Riviera Maya (Tulum and Playa del Carmen) and Lisbon and the coast are core destinations. The Signature collection adds Québec City & Charlevoix, a Bahamas private island, the Azores, Iceland and Banff. Costa Rica, Puerto Rico (no passport needed for US citizens), Thailand and China are available on request. Each traveler is responsible for passports, visas and any health entry requirements. We flag them early and point to official sources. For China, US citizens need a visa: we walk each traveler through the application and timing, and plan connectivity (VPN, approved devices) around your IT policy before anyone flies. On fly-in trips we work with a local on-the-ground partner, covered by our fly-in fee; for custom destinations a local partner is contracted by you at cost. Allow extra lead time.

Can everyone on our team take part?

That’s the goal. Every retreat is planned so the whole team can join. We vet venues for step-free routes and accessible rooms and confirm the details with you before you sign. Dietary, allergy and religious meal needs are gathered in confidence and briefed to each kitchen. Every bar night or tasting has a good non-drinking alternative, and adventure activities are always opt-in, with a relaxed option running at the same time. Venues and activity providers set their own facilities, so we confirm what each can offer in writing rather than promise it ourselves.

Can you accommodate dietary needs and accessibility requirements?

Yes. We collect dietary needs, allergies and access needs in confidence and brief venues and caterers directly. We can shortlist venues with step-free access and accessible rooms, and every activity has a lower-intensity alternative. Kitchens are run by vendors, so we get allergen handling confirmed in writing rather than promising it ourselves. See our accessibility statement.

Do we need insurance?

We strongly recommend event cancellation insurance for your company, which can protect vendor deposits if the retreat is cancelled for a covered reason. We also recommend that attendees have travel and medical coverage, especially abroad. We don't sell insurance, but we'll help you ask the right questions and check that vendors carry their own liability cover.

Can we keep the retreat lower-impact?

Yes. If most of your team lives in one region, a regional pick (the Hudson Valley and Catskills in the Northeast, or Napa and Sonoma on the West Coast) keeps travel short for most of the group. For distributed teams, we favor destinations with nonstops from where your people live and fewer connections. We can also prioritize local vendors and seasonal menus, and keep ground transport shared.

On the retreat

Who facilitates, and what happens in the sessions?

Raheem and Abdul Chaudhry, our founders and both Certified ScrumMasters, design and run every session using agile-style facilitation: priorities and OKRs, decisions with named owners and working agreements, then a closing retrospective on the final morning. Every session ends in a written output, not just a good conversation.

Do you come with us?

Yes. We're on site for the whole retreat, running the sessions and coordinating vendors in real time so your team doesn't have to. Our own travel is billed to you at cost, never marked up.

Is it all work?

No. A typical day is a facilitated morning, an afternoon outdoors or free, and a long dinner together. Every activity is optional, and there's always a lower-key choice.

After the retreat

What happens after the retreat?

You get the decision log and owner list the same day, and the full playbook within 48–⁠72 hours. Then come check-ins at 30, 60 and 90 days: a session with your leads, a short pulse check, and a closing retro on what stuck. These are included in every package.

Can you keep helping after 90 days?

Yes, if it's useful. After the included 30/60/90-day follow-up, an optional retainer keeps us with your leaders: a quarterly check-in and half-day session, with light support in between, for $2,000–⁠$3,000 a month. You can also add Strategy Days (or book them up front in a Yearly Plan) or an extra leadership day.

Who owns the playbook and session notes?

You do, once the fee is paid. We keep everything from your sessions confidential, report interview and survey input without names, and never list you as a client without written permission. See our terms.

How do we get started?

Send the short inquiry form. We'll reply within one business day with a recommended package, destination ideas and a budget range, and suggest a time for a call.

The Tulum ruins above a turquoise sea

Plan a retreat

Tell us about your team.

Share a few details and we'll reply with a recommended package, two or three destination ideas and an all-in budget range.

The quickest way to reach us is the short inquiry form. We reply within one business day.

We reply within one business day.

Plan a retreat