Flotilla Sailing
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Your group. Your route. Discover together.
Explore some of the world’s best cruising grounds with the support and reassurance of a Sunsail lead crew, set sailing route, and social events. Captain yourself, or if you aren’t a sailor, or would rather someone take the helm for you, you can hire a skipper for your adventure.
Flotilla vacations offer an offer an informal, relaxed, and unique experience that takes the stress out of chartering. With a set itinerary (weather dependent), organised moorings each night, and even fun group activities. Perfect for families, couples, and groups across 4 stunning sailing grounds in Greece, Croatia (Agana and Dubrovnik) and Italy (Procida, Sardinia, and Sicily).
If you’d rather someone takes the helm for you, you can hire a skipper for the duration of your holiday. We also offer the chance to learn to sail whilst on flotilla, with Flotilla Starter and Flotilla Hero course in Greece and Croatia.
Keep an eye out for our special flotillas too, with our food and wine flotillas available in Croatia and Italy.
Whether you are unqualified, a new skipper or an old hand, there’s a flotilla for you. Great for solo sailors, groups, couples and families, flotillas are the way to go for social sailing.
Flotilla Highlights
- Set sailing route
- Lead crew support
- Guaranteed mooring
- Social evenings
- Beach barbecues
- Punch parties
Flotilla Destinations
Food and Wine Flotilla
If exploring the world of local wines and traditional culinary treats is your passion these flotillas are perfect for you. They combine some of the best sailing in the Mediterranean with tastings of local produce and the chance to meet the artisans who make it.
Book a Croatia Food and Wine flotilla, including vineyards tours and wine tastings.
For more insider knowledge read our Guide for sailing the Mediterranean.
How does it work?
What’s included?
What’s included
What’s Not Included
Lead Crew Support
Your Flotilla Support Team
Every flotilla is led by an experienced Sunsail crew who help ensure a smooth and enjoyable sailing week.
Your flotilla team typically includes:
- Lead Skipper: Plans the route, delivers daily briefings, and provides sailing guidance throughout the week.
- Host / First Mate: Helps coordinate social events, shares local recommendations, and assists with marina arrivals.
- Support Yacht: Provides on-water assistance if needed and helps with mooring in busy harbours. They’re there when you need them, while still giving you the freedom to enjoy sailing your own yacht.
Flotilla Sailing Vacation FAQs
How a Sunsail Flotilla Works
Each yacht sails independently, but the flotilla travels together along a planned route through the week.
Every morning begins with a short daily briefing from the lead crew, covering:
- Weather and sailing conditions
- Recommended route and distances
- Navigation notes and local tips
- Marina and mooring information for the evening stop
- Times to be at each stop by, so you can plan ahead
You’re free to sail the suggested route at your own pace. Some crews leave early to explore swimming spots along the way, while others enjoy a relaxed morning before departing.
In the afternoon, the flotilla gathers in the next harbour or anchorage, where the lead crew helps coordinate mooring and offers local advice on restaurants, beaches, and activities.
Evenings are a mix of optional social gatherings and free time, so you can enjoy the group atmosphere or explore independently. Please note that each morning, during your daily briefing, you will be advised on the days activities as well as any optional gatherings and applicable times.
Itinerary Details: A Typical 7-Day Flotilla Experience
While each route differs, here’s what a one-week flotilla may look like:
- Day 7 – Return to Base: Sail back to base for a final evening celebration with your flotilla companions.
- Disembarkation: takes place the following morning.
- Day 1 – Arrival & Welcome Briefing: Board your yacht in the afternoon, meet the lead crew, and enjoy a welcome briefing followed by dinner ashore.
- Days 2–6 – Island Hopping: Cruise between historic harbours, swim in secluded bays, and explore highlights such as waterfalls, medieval towns, and vibrant waterfront promenades. Evenings might include optional group dinners, wine tastings, or relaxed marina gatherings.
A Typical Day on Flotilla
- 08:30 – Morning briefing with weather and route guidance
- 10:00–11:00 – Depart at your leisure
- 3–4 hours sailing between destinations on average
- Afternoon arrival at the next harbour or anchorage
- Evening free time or optional social gathering
Distances are typically 10–20 nautical miles per day, allowing plenty of time for swimming stops and exploring ashore.
Why Choose a Sunsail Flotilla?
What sets a flotilla apart is the balance of freedom and guidance. You skipper your own yacht, choosing how you sail each leg, while our professional lead crew charts the route, provides daily briefings, and organizes social gatherings ashore.
- Carefully Crafted Routes: Each itinerary is thoughtfully planned to showcase the best of the region, iconic highlights and hidden gems alike. Duration of 1-2 weeks.
- Ideal for All Experience Levels: Flotillas are perfect for first-time charterers in the Mediterranean, building confidence or seasoned sailors who enjoy the social side of sailing. (A sailing resume & licence is required; alternatively, hire a skipper.)
- Guided Independence: Sail confidently with expert support. Our lead and support yachts are there to assist with mooring, local tips, and technical help if needed.
- Ready-Made Community: Meet fellow sailors at beach BBQs, waterfront dinners, and relaxed evening socials. Perfect for families, couples, and groups of friends.
General Flotilla Information
- Boarding Time: Typically, late afternoon at 6pm for Mediterranean bases.
- Disembarkation: Morning of the final day.
- Experience Required: A completed sailing resume & licence, is required for bareboat charters. Skippers can be hired if needed.
- Provisioning: Pre-order supplies or shop locally before departure, available at select bases.
Good to Know
- *Mooring fees and tourist taxes are typically paid locally.
- Routes may occasionally change due to weather or marina availability.
- Social events are always optional.
- Exact yacht models are confirmed before departure when possible.
*Speak to your lead crew for alternatives to recommended mooring options. There may be an option to anchor for free nearby in select areas.
Optional Extras
- Hire a Skipper: Find more time to enjoy your charter when you hire a Sunsail Skipper.
- Add Provisioning: Make the most of your time on vacation by letting Sunsail take the hassle out of provisioning your yacht, available at select bases.
- Optional extras: We know your vacation is as unique as you are, so we offer a choice of optional extras to add to your personalized charter experience. From renting a paddle-board to hiring a skipper, we can provide the extra details that help your sailing vacation exceed your expectations. Water toys are subject to availability.
Before You Arrive
To help your flotilla holiday start smoothly, here are a few helpful things to know before arrival.
- Resume/CV & Licence requirements: Certain regions require formal certifications to charter a yacht. Please find your desired destination here to learn more about the certifications required.
- Check-In & Boarding: Most flotillas board in the late afternoon on Day 1. After check-in, you’ll meet the lead crew for a welcome briefing and safety overview.
- Provisioning: You can pre-order groceries in advance or shop locally before departure. Many crews choose to provision for breakfasts and lunches onboard while enjoying dinners ashore.
- Experience Required: To charter a yacht without a skipper, a sailing resume is required to confirm your experience. If you prefer to relax or build confidence, you can hire a professional skipper.
- Local Sailing Conditions: Mediterranean flotilla routes typically involve short sailing distances and line-of-sight navigation, making them ideal for relaxed cruising.
- Your Yacht: While yachts are maintained to high standards, they are working vessels. Layouts and equipment may vary slightly depending on the specific model assigned.
- Sailing difficulty: Each of our destinations is grouped by experience level so you can find the right sailing ground for your skills and qualifications.
The Sunsail Flotilla Difference
A Sunsail flotilla is about more than sailing, it’s about shared sunsets, spontaneous swims, and friendships formed over dockside dinners. You’ll explore spectacular coastlines with expert guidance, yet still enjoy the thrill of skippering your own yacht.
Independent when you want it. Social when you choose it. Supported every step of the way.
That’s the magic of a Sunsail Flotilla Yacht Charter. Don’t just sail. Sunsail.
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