Mykonos waterfront
Mykonos waterfront
Under sail
Under sail
The Acropolis
The Acropolis
Island harbour town
Island harbour town
Sailing & Beaches

Greek Islands Sailing

Cyclades, Greece10 days (or 9 days – 2 weeks)

A week on a skippered yacht hopping the Cyclades.

Two nights in Athens, then book a cabin on a skippered sailing yacht for a week around the Cyclades — swimming stops in turquoise coves, harbour tavernas every evening, and a big night out on Mykonos or Ios.

Best time to go

Best Good✕ Not ideal$ Peak pricesTap a month to leave then

July–August is hottest, windiest (the meltemi) and most expensive. Late May–June and September are warm with calmer seas and lower prices.

Peak prices: Jul, Aug

Your trip

Season

Peak: Jul, Aug

Travellers

Rooms, cars and boats are split per person

1

Trip length

10 days
9 days2 weeks

Build your trip

Switch blocks off to make it cheaper, add extras, or tap a block for options and booking links.

Livepulled from a live price feedResearchedbased on published ratesEstimaterough budget figure
  • $1,150
  • $300
  • $1,400
  • $350
  • $60
  • $35
  • $400
  • $50

Day by day

Plan for the standard 10 days trip.

  1. Days 1–2

    Athens

    Acropolis, Plaka and rooftop bars with Parthenon views.

  2. Days 3–9

    Sail the Cyclades

    Skippered yacht week — swim stops, island harbours, Mykonos night.

  3. Day 10

    Fly home

    Back via Athens.

Getting there from BDA

Typical routings from L.F. Wade International. Live fares coming soon.

  • BDAJFKATH
    Best bet

    JetBlue/Delta + Delta/Aegean

    ~14h · 1 stop

  • BDALONATH

    British Airways

    ~13h · 1 stop

Passport & entry

Visa
Visa-free (Schengen)
Max stay
90 days in 180

BOTC holders are generally visa-exempt for short Schengen stays (90 days in any 180), with the same Entry/Exit System registration and upcoming ETIAS requirement. Confirm with the embassy if unsure.

In transit: Bermudian-status BOTC passport holders can usually transit the US without a visa or ESTA, and can visit or transit the UK visa-free.

Entry rules change. Always confirm with the embassy or your airline before you book.

Official source

Off Island Agent

Let an Off Island agent plan it

You've built the trip. We'll confirm every price, book it all, and stay on WhatsApp while you're away.

  • A personal plannerOne person who knows your trip from first chat to flight home.
  • A full itinerary with confirmed pricesEvery block checked and priced for your dates, no estimates.
  • Booking handled for youFlights, stays, camps and tours booked, so you don't juggle ten sites.
  • Your trip packConfirmations, entry rules for your passport, and local contacts in one place.
  • WhatsApp support while you're awayA real person to message if plans change or something goes wrong.
$150 per trip$150 + $50 per extra traveller

Nothing to pay now. The fee is paid after your first chat with your agent.

Reply within a few hours On WhatsAppNew service · founding clients

Per person · 1 person · peak · 10 days

$3,745