Group Trip to Cabo: How We Plan One, From Headcount to the Last Dinner

The group trip is the one people get wrong. Not because Cabo is hard, but because eight adults with eight opinions and one group chat is hard. We have planned enough of these for friends to know where they break. The headcount changes, nobody books the big dinner, and the last night ends in a taxi argument. This is the order we plan in, and it works.

1. Lock the dates before the people

Pick the dates first and let the headcount settle around them. November to April has the best weather, dry and warm, and December to April adds whale watching season. It is also when everything fills, so a group has to book well in advance. Summer is hotter and more humid, and June to September is storm season, but there is far more availability. Whatever you choose, collect deposits from everyone early. A group with money down is a group that shows up.

2. Decide how you sleep

Groups split into two camps. One house for everyone keeps the trip together and makes breakfast easy. A resort gives each couple a door that closes. Our guide to group weddings makes the case for a block of villas for the core group: more space and privacy than a row of hotel rooms, and a private chef can handle the first night so nobody has to decide anything. A resort works better when the group spans ages and bedtimes. Decide this second, because where you stay decides everything after it.

3. Book the big dinner first

One reservation matters more than the rest: the night everyone eats together. Our guide to restaurants for large groups gives the advice we use. Ask for a family-style or tasting menu so nobody negotiates a twelve-person order, and confirm the gratuity policy for large tables in advance. These are the rooms we book.

Mango Deck

On Playa El Medano, open 8am to 10pm. $$, a 4.4 from over 6,000 reviews, with bar games, live music and dancing. The festive choice, and the easy one for a group that wants to stay on the beach all day.

Jazmin's Restaurant

On José María Morelos in San José del Cabo, open 8am to 11pm. $$, a 4.5 from around 1,900 reviews, with a private dining room and live music. The room where everyone fits at one table.

Salvatore G's

Italian on Vicente Guerrero downtown, open 11am to 10:30pm and from 4pm on Sunday. $$$, a 4.8 from close to 2,000 reviews. This is the dinner the group talks about later.

Flora Farms

The farm at Las Ánimas Bajas, $$$, a 4.7 from about 3,400 reviews. Dinner is 5:30pm to 9pm Tuesday to Saturday, and it is closed Monday. There is a cooking school too, if the group wants an activity that ends in a meal.

Sunset Monalisa

The splurge night. Km 6 on the Corridor, open 4pm to 10:30pm, $$$$, a 4.5 from over 2,100 reviews. Reserve as soon as you have dates.

Cabo Wabo Cantina

On Vicente Guerrero, open 9am to 11pm, $$, with live music and dancing. A 4.3 from more than 6,200 reviews. The last-night bar, not the dinner.

4. Plan one shared day, not five

A big group does not need a packed schedule. It needs one day everyone does together, and free time around it. Our guide to ATV rentals for groups makes a useful point: private bookings work best for groups, and the cost per person is often close to an individual booking. So take the private version and set your own pace. Mornings are cooler. In peak season, book a few days ahead.

5. Solve transport on day one

• Pre-arrange the airport ride. One booked pickup from SJD for the whole group beats a line of taxis, and everyone arrives together.
• Agree the taxi price before you get in, especially late at night.
• Keep each night in one town. Cabo San Lucas and San José del Cabo are a drive apart. Do not cross the Corridor twice in one evening.
• Carry pesos for tips and small bills.

6. Money without the group-chat fight

One person books. Everyone pays that person before the trip. Shared costs, like the stay, the big dinner and the shared day, come out of one pot. Personal spending stays personal. At dinner, split the bill evenly and move on.

Before you go

• Dates, deposits, stay, big dinner, shared day, airport ride. In that order.
• Give one person the reservations and another person the money.
• Leave one full day with nothing on it. It will be the day everyone remembers.

Lock the dates, book the dinner, arrange the ride. The rest takes care of itself. If the group wants one roof, start with our villas in Cabo.