Start hereStrategy Day
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
Retreats for remote‑first teams, anywhere in the US
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
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
Core destinations
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.
Any season: 7 core picks · 7 Signature

01
New York · Northeast · Poconos overflow
Barn sessions, farm dinners, wood-fired saunas and foliage. Close to the Northeast hubs.

02
California · Wine country · West Coast
Vineyard pavilions, redwood walks, river paddles and harvest dinners. 90 minutes from San Francisco.

03
Mexico · Tulum · Playa del Carmen
Design villas, cenote swims, ruins at sunrise and private-chef dinners. Easy nonstops to Cancún.

04
Arizona · High desert
Red-rock hikes, sunrise balloons, stargazing and spa-resort boardrooms in Scottsdale and Sedona.

05
Boulder · Vail · Breckenridge
Summit sessions, fly-fishing, aspen trails and fireside evenings. Central for teams coast to coast.

06
Portugal · Cascais · Sintra · Ericeira
Quinta workshops, Ericeira surf, Tagus sunset sails and fado dinners. Team retreats run 4 nights.

07
Nevada · Sales Milestone trips only
Off-Strip sessions by day; awards dinners, shows and desert rides by night. Sales trips only.
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
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.
Any season: 7 core picks · 7 Signature

S1
Signature
New York · Lake Placid · Saranac · Raquette Lake
Lakeside Great Camps, guide-boat paddles and High Peaks hikes. A winter edition in Lake Placid.

S2
Signature
Massachusetts · Islands · Best for 12–20
Private sailing regattas, beach clambakes, island bike tours and harbor dinners. Best for 12–20.

S3
Signature
Canada · Old Québec · Charlevoix
Our winter signature: dog sledding, Nordic spas, ice-hotel cocktails and ski-in sessions.

S4
Signature
Bahamas · Out Islands · Exumas · Eleuthera
The whole island is yours: sandbar picnics, reef snorkels and beach bonfires. Best for 12–24.

S5
Signature
Portugal · São Miguel · Mid-Atlantic
Crater-lake hikes, whale watching, hot springs and volcanic-earth stews. Team retreats run 4 nights.

S6
Signature
Iceland · Reykjanes · South Coast
Glacier hikes, geothermal lagoons, the midnight sun or the aurora. Team retreats run 4 nights.

S7
Signature
Canada · Banff · Lake Louise
Turquoise lakes, canoe mornings and gondola summit sessions. An easy hop for West Coast teams.
Quoted individually and delivered with a local partner, contracted by you at cost. Ask through the inquiry form.
None of our on-request trips peak in this season, so here are the closest. Ask anyway: we can still quote one.





Retreat finder
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.
The experience

The offsite your team will still talk about next year, and the plan they'll still be using.
How it works
No markups, no percentage of spend, no surprises when the headcount moves. Here's exactly what you're buying.
A single planning and facilitation fee, fixed for the scope we agree in writing.
You contract venues, activities and transport directly at the rates we negotiate. You see every line.
Pre-retreat interviews shape an agile agenda. You leave with a decision log and named owners.
Check-ins at 30, 60 and 90 days to unblock owners and run a closing retro.
Sample itineraries
Illustrative run-of-show from our packages. Every retreat is designed around your goals, pre-interviews and budget.

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.
09:00 Alignment workshop: where the team stands, plus a health check. Afternoon Cenote swim or reef snorkel. Evening Free; optional beach fire.
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.
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.
Decision log, priorities board and working agreements in writing, then three check-ins.

16:00 Kickoff: what must be true by Friday. 17:00 Walk in the woods. 19:00 Welcome dinner with a personal-stories prompt.
07:00 Optional sunrise movement. 09:00 Working session: the state of the business. 11:00 Three scenarios and a pre-mortem. 14:00 Hike or sauna and cold plunge. 19:30 Chef's dinner.
09:00 Pick the bets, draft OKRs, name owners. 11:00 Operating cadence and working agreements. 12:15 Team retro: what worked, what didn't, what we'll do next. 13:00 Lunch and depart.
Playbook and 12-month roadmap draft delivered, then 30/60/90 check-ins.

Afternoon Pool or spa. 19:00 Welcome dinner in a private dining room.
09:00 Working session: last half's wins and losses, then next-half plays, in an off-Strip boardroom. 14:00 Culinary workshop, go-karts or Red Rock e-bikes. 19:30 Awards dinner and a show.
11:00 Peer deal clinics and commitments. Afternoon Free. Evening Optional group dinner.
09:30 Team retro over breakfast: what worked, what didn't, what we'll do next. Then Fly home with the next-half play sheet and owner list in hand.
Check-ins with sales leadership on the plays you committed to.
The retreats
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.
Start hereFrom $12,000 flat fee
$12k–$14k · + vendors at cost, est. $3k–$15k total
LeadershipFrom $18,000 flat fee
$18k–$25k regional · $22k–$31k fly-in · + vendors at cost, est. $15k–$35k regional · $25k–$60k fly-in
FlagshipFrom $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
CelebrateFrom $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
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.
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.
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.
Striped part: the gap between our low and high estimate.
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
How we compare
Three ways to plan a team retreat, side by side.
| Waypoint | Big event agency | Do 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
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.
Send the short form and we reply within one business day. On a 45-minute call we cover goals, group, budget and dates.
A written proposal with a fixed fee, scope, destination shortlist and an all-in budget estimate. Sign, pay 50%, and your dates are held.
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.
We facilitate every working session and coordinate vendors in real time, so your team can be fully present.
The decision log, priorities and working agreements in writing, then check-ins at 30, 60 and 90 days so the plan holds.
FAQ
Pricing, payment, planning, the retreat itself and what comes after. Can't find your answer? Ask us, or read our booking policy and terms.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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).
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.

Plan a retreat
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.
Book a 20-minute call