Sailing Greece with Friends: How to Plan the Ultimate Group Trip

Sailing with friends is a blast — until it isn't. We've seen groups have the time of their lives and groups that fall apart by day three. The difference? Planning. Here's how to organize the ultimate group trip without the drama.

How to Organize 6–12 Friends

First: pick a "captain" — someone who organizes the trip, collects money, makes decisions. It can't be everyone. One person. They don't need to sail; they need to coordinate. Second: set a deadline. "We need deposits by March 1." People who don't commit by then don't come. Third: create a WhatsApp group. Share the itinerary, the packing list, the rules. Everyone knows what to expect.

Choosing the Right Size Boat (or Two)

6 people: one 45–50 foot yacht or catamaran. 8 people: one large catamaran (50–55 ft) or two 40-footers. 10–12 people: two boats. Sailing in company (flotilla style) is fun — you race, you meet for dinner, you have options. Two smaller boats often cost less than one huge one and give everyone more space.

Splitting Costs Fairly

Charter cost: divide by number of people. Simple. Provisioning: everyone chips in. Create a kitty — €50–100 per person for the week. One person buys, keeps receipts. Fuel: split at the end. Marina fees: split. The key is to agree upfront. No surprises. We've seen groups argue over €20. It's not worth it. Agree on the rules before you leave.

Managing Different Expectations

Some want to sail all day. Some want to beach. Some want to party. Some want to sleep. Talk about it. "We're thinking: up early, sail 3–4 hours, anchor for lunch, maybe one more hop, then evening in port." Get buy-in. Compromise. Maybe one day is a "party day" (Mykonos) and one is a "chill day" (quiet bay).

Best Routes for Groups

Partiers: Cyclades — Mykonos, Paros, Ios. Nightlife, bars, beaches.

Mixed group: Ionian — something for everyone. Gentle sailing, good tavernas, some nightlife in Fiskardo.

Adventure group: Cyclades — longer passages, stronger winds, more challenge.

Handling the Friend Who Gets Seasick

Stugeron (cinnarizine) or Dramamine. Take it before you sail. Stay on deck. Look at the horizon. Avoid the cabin when it's rough. If someone is really seasick, plan shorter passages. The Ionian is gentler. And remember: most people get used to it after a day or two.

Vasile's Guide to Group Decisions

Vote on big things: where to go, when to leave. For small things, someone just decides. "We're eating at that taverna." "We're anchoring here." Don't debate every detail. And rotate: one person picks dinner one night, another the next. Everyone gets a turn. No one feels left out.

Conflict-avoidance: no alcohol before noon. Seriously. Hungover people make bad decisions. And if someone is upset, talk about it. Don't let it fester. A week on a boat is long. Clear the air.