Saturday 27th August – Saturday 3rd September 2022

It doesn’t get much more glamorous than the Amalfi Coast. The pinnacle of Mediterranean sailing. Make summer 2022 the best summer of your life, sailing alongside the rich and (in)famous in one of the most sought-after destinations in the world. Cruise to the island of Capri, sip on champagne in Sorrento, marvel at the most beautiful town of Positano and explore the oh so many secrets this incredible part of the world has to offer that can only be accessed by joining our Sailing the Med Flotilla this summer.

Full Trip Details


Starts & Ends in Castellammare di Stabia


Premium yacht and skipper


Holiday with a boutique company with 5* reviews


Ideal for both singles and couples, young and old


Some of the best new friends you’ll ever meet

Price: £959

**If you’ve been on a trip with us before, there’s a little discount in your inbox 📧 😉

£380 deposit, remaining balance due 2 months prior to trip.


7 days and night circling the Flegrean Islands and the Amalfi Coast of Italy


The annual Sailing the Med Race


A different harbour and anchorage every night


Unlimited swimming, snorkelling and beach time


Just 29 minutes from Naples airport, we begin our week in idyllic Italy with a little welcome party. Meet your skippers and crewmates, get yourself a glass of rose and let that holiday feeling sink in as we start with a short sail in the early evening to Sorrento.

Sorrento hardly needs an introduction. The Sorrentine Peninsula is arguably one of the most picturesque stretches of coastline in the world, with its sheer cliffs, rustic lemon and olive groves, crystal clear waters and cliffside pastel-coloured houses toppled high on top of each other. Truly mesmerising, the views are those that you’ll never forget.

You can’t think of the Amalfi coast without images of perhaps the most picturesque town in the world coming to mind. Positano is as pretty as it gets! Think picture perfect colourful nestled into dramatic cliffs, overlooking the most striking coastline and sapphire blue waters. There truly is no better way to arrive into Positano than by boat! Dress in your finest as we head into town to explore the luxury boutiques, the winding streets or sit in the sun sipping on limoncello and people watch to your heart’s content. We’ll dine out this evening at a little Italian eatery that we know, you don’t have to pay the earth for the finest Italian cuisine!

Starting today with a short sail to the world-famous island of Capri. We’ll stop for a late morning swim in the azure waters of the med, followed by lunch on deck under the sun in the stunning setting of the Amalfi Coast as our backdrop. Then it’s onwards to sample a little of La Dolce Vita on Capri. The summer home of many Roman emperors including Tiberius who preferred lazy days in the sunshine of Capri vs being in the office back in Rome. Who could blame him?!

Capri is the most pristine of islands, we’ll wander the twisting lanes under a lush canopy of wisteria, ogle at the elegant villas dripping with bougainvillea; even the trees seem to be carefully manicured.

The only way to end a visit to Capri is with a visit to the magical Grotta Azzurra. This extraordinary sea cave illuminated by an otherworldly blue light. Mornings don’t come better than this! 

Then we sail to our Captain’s favourite destination of this Italian adventure, Isola di Ischia. Besides offering exotic sceneries with flowing hills and rocky beaches, this volcanic island is famous for its thermal spas and natural springs. With a history of colonisation on the island dating back to 8th Century BC, it really feels like an honour to be able to explore this enchanted place. After a trek to Ischia’s medieval castle, we’ll toast your newfound sailing skills with the best tipple to come out of Italy, the Aperol Spritz, as we watch the sunset.

Today we take to the seas with our longest sail yet. We’ll cruise from beautiful Ischia to Isola di Ventotene. The dark blue waters of the med will take your breath away as we skim across and arrive in style. Ventotene has an imposing legacy and a history that dates back to the ancient Greeks. This island harbours an environmental richness, it is a Marine Protected Area and Terrestrial Reserve. Explore the historic centre and its colourful houses, before we head back to dine on deck for dinner, under the stars, amidst the impressive backdrop of this low laying island that forms part of the Pontie island chain.

Now you’ll all be absolute pro sailors, it’s time to put your skills to the test with our annual Sailing the Med yacht race. Which boat will make it from Ventotene to Isola di Procida first? Who’ll be crowned the best sailors of the summer? 

Procida Italy is one of the country’s best kept secrets. On this tiny island, you’ll find pastel-coloured fishing villages, black sand beaches, and a maze of narrow winding streets. This tiny spot of land in the Bay of Naples, might be best known as the island between Ischia and Capri. In late January, it was named Italy’s Capital of Culture for 2022, beating nine other candidates—a mix of cities and small towns—and becoming the first island to ever be granted the title. We’ll be gracious guests of this majestic island as we celebrate an almighty week’s sailing, at our fancy-dress awards evening. Forget the Oscar’s, this is the night of the year!

Soak up the sights of the Amalfi Coast as you enjoy your last breakfast under the Italian sunshine. Our final day sees us sailing back across the Bay of Naples. Take your final sunny sailing selfies of the turquoise waters before we disembark back at Castellammare di Stabia. We’ll have our end of summer party back on dry land to mark the end of the best week of the summer!

Getting There/Away

The best option is to fly into Naples (NAP) Airport. This trip will start on Saturday 27th August, at Castellammare di Stabia. There will be a welcome party at 4 pm and we are expected to join the Yachts around 7 pm.

Naples (NAP) Airport to Castellammare di Stabia is a 30 minute car journey and a taxi will cost roughly £30.  

The trip will finish on Saturday 3rd September at Castellammare di Stabia. Departure time off the yachts will be 10 am.

These flights are just our recommendations, please do your own research into the best flight for you.

*Please note the itinerary is subject to weather conditions and may be changed, at any time, by the organisers.*

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