Bring your own group

Group Sailing Holidays in Greece & the Caribbean

Looking for group sailing holidays with a relaxed, authentic feel—not the crowded flotilla version? SeaScape creates personalised small group sailing holidays for friends, families, clubs, and social groups who want real sailing, real islands, and real local experiences. Whether you’re dreaming of drifting through the Greek Islands or exploring the turquoise bays of the British Virgin Islands in the Caribbean, our sailing group holidays offer flexible itineraries, private yachts, and skippers who know every secret spot.

Why SeaScape is perfect for small group sailing holidays

A more authentic style of group sailing trips

Our style is calm, friendly, and unhurried. No megayacht crowds. No rigid timetables. Just a small group, a beautiful boat, and a skipper who loves sharing the soul of each island.

Private charters built around your group

Every group is different. Some want quiet anchorages and lazy swims. Others want lively evenings, cultural walks, or lots of sailing. We tailor each trip—whether in Greece or the Caribbean—to your pace and your idea of a perfect week on the water.

Ideal for small groups of friends or families

Our group sailing holidays work beautifully for:

groups of friends
family gatherings
sports clubs
yoga groups
dive, swim, freedive, or activity clubs
corporate teams or retreats
milestone birthdays or small celebrations

Destinations for group sailing holidays

Greece

We’ve been doing sailing holidays in Greece since 1994 and know all the hidden gems of the Dodecanese.

British Virgin Islands

A Caribbean adventure along the beautiful British Virgin Islands on a 50′ catamaran, starting from Tortola.

Group sailing holiday prices

All private charter prices are for the whole boat, per week, and include everything mentioned below.

Greece

1-4 persons

€ 6500

low season

€ 7500

high season

5-6 persons

€ 7000

low season

€ 8000

high season

7-8 persons

€ 7500

low season

€ 8500

high season

Low Season – May and October
High Season – June, July, August and September

*Cabins for private use in Greece are available at a 50% extra fee

British Virgin Islands

10 persons

$ 27500

Due to standard minimal weekly costs of the boat in the British Virgin Islands, the BVI’s price per week is always the same regardless of the amount of people.

What's included with SeaScape Sailing

We don’t do ‘hidden extra fees’. Excluded are transportation to and from the boat, onshore expenses like restaurant dinners, alcoholic drinks after the Happy Hour supply we provide you with (BYO!), and gratuity for the crew.

What to expect on your sailing group holidays

Hands-on sailing (if you want to!)

Help hoist the sails, take the helm, learn navigation basics, or simply enjoy the freedom of life at sea. You set the pace — we guide the adventure.

A typical day at sea

Enjoy breakfast in the cockpit before we set sail to your next island. We usually stop in a remote bay for lunch, where you can swim or snorkel before lifting anchor. Evenings bring local taverna dinners.

Comfortable boats for up to 10 persons

Our adventures take place on well-kept, comfortable boats that are perfect for small groups and real sailing.

Flexible itinerary for groups

You help shape the daily itinerary—whether that means quiet bays or livelier harbours. We always follow the weather, but plan as closely as possible around your preferences.