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.
Our 4th great sail trip with Sunsail Agana Marina (learning to sail, flotilla and bareboat charters). We really enjoyed our fun trip on the superbly run Hvar Flotilla. Sunsail Agana is a professional, efficient and extremely well run sail base in a beautiful location. We cannot recommend Sunsail Agana more highly and we have already booked to return.
Easy line-of-sight sailing
Short island hops and longer trips
Explore quiet islands and national parks
Discover Croatia's rich and two-millennia old history
Everyone from top to bottom was great and focused on providing us with the best possible charter. Worthy of special note was the chart briefing that was brilliant. The islands were greatly diverse which was a joy
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.
A common misperception of the flotilla is that you have to sail like ‘ducks in a row’. But sailing on a flotilla offers much more independence than that.
Every day your lead crew will brief you on your destination, weather updates and any must-see spots along the way. They’ll help you cast off in the morning and then sail directly to the next destination so they can be there to help everyone moor up at night.
But after that, you’ll be left to explore the high seas yourself. Whether you’re looking for some exciting sailing or searching for the perfect beach, you can sail with confidence knowing that any assistance from your lead crew is only a phone or radio call away.
You’ll mostly stay in village quays and small harbours, and every night you can choose to explore on your own or meet up with the rest of your flotilla for dinner and stories.
The lead crew also organises social events like barbecues on the beach, punch parties and an end of week regatta so you can get to know your flotilla sailing partners.
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 applicabl
What’s Included?
We’ve created a flotilla package just for you, so all you have to worry about is choosing which of our incredible routes to go for and when.
What’s included
Fully equipped cruising yacht for the duration of your vacation
Lead Crew: Skipper, Host and Technician
One tank of yacht fuel*
Full cylinder of cooking gas and full tank of water
Guaranteed mooring at each stopover
Dinghy and outboard
All sailing, navigation and safety equipment onboard
Fully equipped galley/kitchen
All clean linen including bath and tea towels
Activity Coordinator is available on the Meganissi flotilla (select dates in Lefkas only)
Snorkeling Fins
First Morning Breakfast
Flotilla Punch Party
End Cleaning
*Fuel is not included on our specialist flotillas in Italy or BVI flotillas **In place of Flotilla Punch Party, there will be a Gin and Tonic party for some flotillas such as Lefkas.
The lead crew is there to support you. They’ll help you cast off each day before heading to that evening’s stopover to help you moor when you arrive. You can be as independent as you like with the confidence that the lead crew will be there to lend a helping hand when you need it. They can also recommend the best anchorages, harbours, restaurants and places to visit, ensuring that you make the most of your time on vacation.
The lead crew is there to support you. They’ll help you cast off each day before heading to that evening’s stopover to help you moor when you arrive. You can be as independent as you like with the confidence that the lead crew will be there to lend a helping hand when you need it. They can also recommend the best anchorages, harbours, restaurants and places to visit, ensuring that you make the most of your time on vacation.
Onboard your lead boat will be a skipper, host and a technician. On dedicated family flotillas in Greece we add an activities coordinator to help entertain the kids.
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.
Your flotilla skipper is fully RYA qualified and is responsible for the flotilla. They will be on hand at the beginning and end of every day if you need assistance with mooring or casting off. They also hold daily chart briefings to help you make the most of your trip.
Hostess
Your flotilla host will know the best beaches, restaurants and local attractions. They’ll find the perfect place for dinner every evening for you and your flotilla, so you can enjoy delicious local cuisine while sharing tales of the sea with your new friends.
Technician
Your technician will be on hand to make sure that each yacht in the flotilla is running smoothly. Should you have any technical questions, just let your technician know and they’ll be there to help.
Activities coordinator
Available on certain flotillas during the school holidays, our activities coordinator is on hand to give you some time to yourself without having to worry about what the kids are up to. They provide fun beach games and activities to keep kids from five to 17 years old entertained.
Flotilla Sailing Vacation FAQs
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.
Itinerary Details: A Typical 7-Day Flotilla Experience
While each route differs, here’s what a one-week flotilla may look like:
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.
Day 7 – Return to Base: Sail back to base for a final evening celebration with your flotilla companions.
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.
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.
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.
General Flotilla Information
Boarding Time: Typically, late afternoon at 6pm for Mediterranean bases.
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.
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.
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.
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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