Group travel

A group trip without a leader is guaranteed chaos. Everyone can pitch in and have a role, but one person needs to be the point of contact, keep the shared document up to date, and make the calls.

Before booking anything, get the group aligned on four things: the budget per person, the kind of trip (5 stars vs hostel, active vs relaxing), the length, and the dates. Surprise equals resentment.

The most manageable group size. Any fewer and it's just an outing. Any more and it gets logistically complicated, and sub-groups inevitably form.

One person for lodging, another for transportation, another for restaurants and excursions. Assign roles by strengths and interests. Someone who hates shopping around isn't the right person for the flights.

One place for everything: Google Doc, Notion, Trello. Itinerary, bookings, emergency contacts, cost sharing. Open to everyone, kept up to date by the leader.

The most widely used expense-sharing app. Everyone enters their expenses as they go, and the app works out who owes how much to whom. Settle up at the end of the trip. No late-night math, and no tension over money.

Don't plan every minute. Pick 1 or 2 anchor activities a day (a dinner, an excursion) where everyone gets together. The rest of the time, everyone does what they like.

If someone wants to skip an excursion to stay at the spa, or skip a dinner to sleep, encourage it. Guilt or social pressure kills group trips.

Lodging big enough for groups (villas, suites, blocks of adjoining rooms) goes fast. Book 7 to 11 months ahead for popular destinations.

Many hotels, cruise lines and tour operators offer special rates from 10 rooms (sometimes 8). Possible perks: a free room for the organizer, upgrades, a private evening. A travel agent can negotiate these terms.