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2026-01-22

The group trip itinerary template (with 3 worked examples)

A copy-paste itinerary template for group trips, plus three filled-in examples for Lisbon, Mexico City, and Cape Town. Built for squads, not solo travelers.

Most itinerary templates online are built for solo travelers. They list a single person’s preferences, a single budget, a single pace.

Group trips need something different. The squad has multiple people with different sleep schedules, different food preferences, different “must-do” lists. A good group itinerary doesn’t try to over-coordinate (that’s how the host burns out). It pre-decides the few things that need pre-deciding and leaves the rest open.

This guide is the template, plus three worked examples you can adapt.

What you’ll find

The principles before the template

Before the template itself, three principles that make group itineraries work:

  1. Pre-decide group time. Leave personal time open. Plan group dinners and group activities. Don’t over-schedule mornings — let people walk, run, or sleep in.
  2. Three meals a day is a lot. Most squads can coordinate one shared meal per day reliably. Two is hard. Three is impossible. Plan one shared dinner per day and leave breakfast/lunch loose.
  3. One signature activity per day. Not three. The squad doesn’t have the energy for three.

The template below builds in all three principles.

The group trip itinerary template

Copy this into your squad’s shared trip space (or TripSquad’s trip space, or anywhere you can pin it). Fill in the bracketed sections.

[DESTINATION] — [DATES]
squad: [NAMES]
home base: [ACCOMMODATION + NEIGHBORHOOD]

────────────────────────────
day 1 (arrival): [DATE]
────────────────────────────
arrivals:
  [NAME] lands [TIME] at [AIRPORT]
  [NAME] lands [TIME] at [AIRPORT]
  ...
  anchor flight: [NAME / TIME]

evening:
  [TIME] — group dinner at [PLACE]
  [TIME] — drinks back at the place / explore neighborhood

what nobody has to do today: anything ambitious. let people land.

────────────────────────────
day 2 — [THEME]
────────────────────────────
morning: open. coffee on your own.
afternoon: [GROUP ACTIVITY] (2-3 hours, not all day)
  meet at [PLACE] at [TIME]
evening:
  [TIME] — group dinner at [PLACE]
  optional after: [LOCAL THING]

────────────────────────────
day 3 — [THEME]
────────────────────────────
morning: open
midday:
  [GROUP ACTIVITY OR DAY TRIP]
  who's in: [NAMES]
  who's optional out: [NAMES]
evening:
  [TIME] — group dinner at [PLACE]

────────────────────────────
day 4 — [THEME]
────────────────────────────
morning: open
afternoon: [GROUP ACTIVITY]
evening:
  [TIME] — group dinner at [PLACE]
  [LATE THING IF SQUAD WANTS IT]

────────────────────────────
day 5 (departure): [DATE]
────────────────────────────
morning:
  final group breakfast / coffee at [PLACE] [TIME]
  pack up
  [DEPARTURE LOGISTICS]
afternoon: airport runs
  [NAME] departs [TIME]
  ...
  last out: [NAME] handles final clean + key

────────────────────────────
group expenses tracker:
[NAME] is owning the running tally. log spends in the squad chat.

logistics agreed:
- room assignments: [SUMMARY]
- groceries day 1: [NAME] buys, splits equal
- bailer policy: [SUMMARY]

Worked example 1: 5-night Lisbon for 5 people

LISBON — Tue Oct 13 → Sun Oct 18, 2026
squad: Tasha, Marcus, Lebogang, Casey, Jen
home base: 4BR Airbnb in Alfama (Rua das Escolas Gerais)

────────────────────────────
day 1 (Tue Oct 13): arrivals
────────────────────────────
arrivals:
  Marcus lands 10:15am at LIS (anchor)
  Tasha + Casey land 11:40am at LIS
  Lebogang lands 4:25pm at LIS
  Jen lands 7:55pm at LIS

evening:
  9:00pm — group dinner at Cervejaria Ramiro
    (Marcus + Tasha + Casey arrived early; rest meet there)
  Late: drinks at Topo Chiado for the rooftop view

────────────────────────────
day 2 (Wed Oct 14): the city
────────────────────────────
morning: open. solo coffee at Fábrica Coffee Roasters.
afternoon: walking tour through Alfama → Mouraria → Graça
  meet at Miradouro de Santa Luzia at 2pm
  end at Miradouro Senhora do Monte for sunset
evening:
  8:30pm — group dinner at Taberna do Calhau
  optional: fado at Mesa de Frades (book in advance)

────────────────────────────
day 3 (Thu Oct 15): Sintra day trip
────────────────────────────
morning: 9:30am train from Rossio to Sintra
midday:
  Pena Palace + Quinta da Regaleira (skip Castle of the Moors unless time)
  who's in: all 5
evening:
  back to Lisbon by 6pm
  9:00pm — group dinner at A Cevicheria

────────────────────────────
day 4 (Fri Oct 16): beach day
────────────────────────────
morning: open
afternoon: train to Cascais (35min)
  beach + lunch
  optional: walk to Boca do Inferno
evening:
  back to Lisbon
  9:00pm — group dinner at Belcanto (book 6 weeks ahead)

────────────────────────────
day 5 (Sat Oct 17): the soft day
────────────────────────────
morning: open. brunch at Dear Breakfast.
afternoon: LX Factory + Belém (custard tarts)
  optional: Berardo Museum
evening:
  9:00pm — group dinner at Solar dos Presuntos
  late: bairro alto for drinks

────────────────────────────
day 6 (Sun Oct 18): departure
────────────────────────────
morning: final breakfast at Comoba
  pack up
  cleaning fee covered by the deposit, but tidy up before leaving
afternoon:
  Tasha departs 12:15pm
  Marcus + Casey depart 2:50pm
  Jen departs 4:30pm
  Lebogang last out, handles final clean + keys

────────────────────────────
expenses: Tasha owns the running tally.
groceries day 1: Marcus, $80, split 5 ways.
bailer policy: agreed on Sept 5 — full share covered.

Worked example 2: 4-night Mexico City for 6 people

MEXICO CITY — Thu Mar 12 → Mon Mar 16, 2026
squad: 6 friends, mix of couples + singles
home base: 4BR + 3BA Airbnb in Roma Norte (Av Álvaro Obregón)

day 1 (Thu): arrivals
- 4 fly in via mid-day, 2 via evening
- 8pm dinner at Contramar (book 4 wks ahead)
- after: drinks at Limantour

day 2 (Fri): Roma + Condesa walk
- morning: open / Café Negro
- 1pm: tacos at El Pescadito
- 4pm: walk Parque México + Parque España
- 8pm: dinner at Máximo Bistrot

day 3 (Sat): Teotihuacán day trip
- 7am: pickup with private driver (~$150 for the day, split 6 ways)
- pyramids + tlacoyos lunch on-site
- back by 5pm
- 8pm: dinner at Pujol (or skip and do Mercado Roma street food)

day 4 (Sun): the chill day
- morning: open
- 11am: brunch at Lardo
- 2pm: Anthropology Museum (3 hours minimum)
- 7pm: dinner at Maximo or El Hidalguense

day 5 (Mon): departure
- final breakfast at Buna
- airport runs throughout the day

logistics:
- groceries day 1: $80 (split 6)
- room assignments: 2 couples get the master + 2nd-largest; 2 singles share the third room with twin beds
- bailer policy: confirmed at deposit (Jan 15)
- daily expense tracker: the couples handle the running tally

Worked example 3: 7-night Cape Town for 7 people

CAPE TOWN — Sat Dec 5 → Sat Dec 12, 2026
squad: 7 friends — 30th birthday milestone trip
home base: 4BR villa with pool in Sea Point ($600/night)

day 1 (Sat): arrivals + pool day
- arrivals throughout the day
- evening: pizza + drinks at the villa, low-key

day 2 (Sun): Table Mountain + V&A
- morning: cable car up Table Mountain (early to beat the wind)
- afternoon: lunch at Test Kitchen Light
- 4pm: V&A Waterfront wander
- 8pm: dinner at Kloof Street House

day 3 (Mon): Cape Peninsula drive
- 8am pickup with 2 SUVs (split costs)
- Chapman's Peak Drive → Boulders Beach (penguins) → Cape Point
- lunch at Buffelsfontein
- 8pm: dinner at La Tête

day 4 (Tue): wine country (Stellenbosch)
- 9am: drive to Stellenbosch (1 hour)
- 3 wineries: Babylonstoren (lunch), Tokara, Boschendal
- back by 7pm
- dinner at the villa (private chef arranged ahead, $700 for 7 people)

day 5 (Wed): the rest day
- morning: pool / beach
- afternoon: Bo-Kaap photo walk
- 7pm: birthday dinner at Salsify at the Roundhouse
- after: Lion's Head sunset (or hike if the squad's up for it)

day 6 (Thu): safari day trip (optional, ~$300/person)
- pre-dawn pickup
- private game reserve, full day
- back by 9pm

day 7 (Fri): the lazy last day
- pool morning
- lunch at Mondiall
- afternoon: Camps Bay sunset
- final dinner at Mzansi (try Cape Malay)

day 8 (Sat): departure
- airport runs, last out cleans up

logistics:
- 4BR villa: master gets birthday person, partners pair up, 2 doubles for the rest
- private chef night 4 + safari day are the big splurges
- bailer policy: confirmed Sep 1 (3 months out — bigger deposit means earlier conversation)

How to actually use this template

  1. Copy the template into wherever your squad coordinates (TripSquad’s trip space, a shared note, a Notion page).
  2. Fill in arrivals first. The anchor flight (first arrival) sets the day-1 dinner timing.
  3. Pick one signature activity per day. Write it in. Dinner times follow.
  4. Leave mornings open. Don’t try to plan breakfast for 7 people — let it happen.
  5. Pin the document where the squad can find it. Update if anything shifts.

The template is meant to be a living document. The first version takes 30 minutes. After that it gets edited two or three times before the trip.

FAQs

How much detail should the itinerary have? Less than you think. Over-planning makes the squad feel managed. The template above gives you the dinner times and one signature activity per day; the rest stays open. That’s enough scaffolding for a great trip.

Who should write the itinerary? Whoever volunteered for the “Day 1 dinner planner” + “signature activity” jobs from the host’s-jobs checklist. It doesn’t have to be one person.

Should we share the itinerary in advance? Yes. Send a draft to the squad 2 weeks before the trip. Get reactions. Adjust. Pin the final.

What if the squad doesn’t want a structured itinerary? Fine. The minimum viable group itinerary is: arrival times, accommodation address, and one shared dinner per night. Below that, the trip starts to fray.

Should we book restaurants in advance? For trips with 5+ people, yes — most good restaurants in good cities can’t take walk-in 5-tops at 8pm on a Saturday. Book the headline dinners 2-4 weeks ahead. Leave 2-3 dinners unbooked for spontaneity.

Where does this template fit in TripSquad? TripSquad has its own day-by-day plan that Scout pre-fills based on the squad’s vibes and dates. The template above works alongside it (or independently if you’re not using TripSquad). The main difference: in TripSquad, the squad sees changes in real time and can react inside the trip space chat.

Written by the team at TripSquad. Try the app →