Sailing tours in Italy

Sail the Amalfi Coast or Islands of Sicily in Italy

Ditch the trains, buses, and rental cars and explore Italy the way the ancients did: by sailboat.

If you're an experienced sailor, you can troll the crewing message boards for sailboat owners looking for boathands, cooks, and other sailing gigs and get a free sailing trip (sometimes even get paid for it!). However, realize you will have no choice in the itinerary, and you will be working for your passage.

If you prefer to be a paying passenger with fewer duties and more leisure time (and control over your itinerary), try one of these escorted tour sailings:

Sail the Amalfi Coast and Bay of Naples

Amalfi town
Duration: 4 days
Cost: from $884
Book: Reserve it
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Sail Italy - Procida to Amalfi

Destinations: Amalfi, Pompeii, Torre Annunziata, Naples, Ischia, Procida

Set sail across the sparkling waters of the Mediterranean on an Amalfi Coast Sailing adventure. Cast off from the oldest island in the Bay of Naples, Procida, which has featured in a number of films thanks to its pastel-coloured houses and quaint, atmospheric streets. Explore the medieval fortress Castello Aragonese near the vibrant island of Ischia and bathe in ocean hot springs. View original artefacts from Pompeii at the Archeological Museum in Naples before roaming through the 2,000-year-old city itself, and end the adventure on a high – on a cliff top in Amalfi, gazing out across the azure seas and bright blue skies...

  • Included activities: Sailing!
  • Accommodation: Overnight boat (3 nts)
  • Meals: 3 breakfasts, 2 lunches; budget €90 for other meals
  • Transport: Sailboat
  • Group size: Max 8
Amalfi Coast
Duration: 4 days
Cost: from $884
Book: Reserve it
map

Sail Italy - Amalfi to Procida

Destinations: Amalfi, Capri, Pozzuoli, Procida

Cast adrift along the breathtaking Amalfi Coast and travel to the glittering jewels of the region - Capri, Pozzuoli and Procida. Visit the home of mythical sirens, the ancient holiday homes of great Roman emperors and the spectacular Blue Grotto. Hike along historic trails past olive groves, vineyards, lemon orchards and charming villages; dive into the deep blue waters of the Mediterranean; and sample mouthwatering Italian regional cuisine on this remarkable Amalfi sailing adventure...

  • Included activities: Sailing!
  • Accommodation: Overnight boat (3 nts)
  • Meals: 3 breakfasts, 2 lunches; budget €90 for other meals
  • Transport: Sailboat
  • Group size: Max 8
Sailboat on the Amalfi Coast
Duration: 7 days
Cost: from $1,719
Book: Reserve it
map

Amalfi Coast Sailing Adventure

Destinations: Amalfi, Capri, Pozzuoli, Procida, Pompeii, Torre Annunziata, Naples, Ischia

Imagine carefree days sailing from one stunning island to the next through the glistening Mediterranean. This awesome voyage along the spectacular Amalfi coast gives you the lot - gorgeous beaches, ancient ruins, beautiful landscapes, picturesque villages, sumptuous fresh seafood and chilled out waterfronts. The perfect escape to taste some of the best this region has to offer...

  • Included activities: Sailing!
  • Accommodation: Overnight boat (6 nts)
  • Meals: 6 Breakfasts, 5 Lunches; budget €180 for other meals
  • Transport: Sailboat
  • Group size: Max 8

Sail the Aeolian Islands

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Duration: 7 days
Cost: from $1,917
Book: Reserve it
map

Sail Italy - Aeolian Islands

Destinations: Tropea, Bagnara Calabria, Milazzo, Lipari, Stromboli, Longobardi

Feel like a god on a sailing adventure along Italy’s spectacular Calabrian coast. Wile away the days swimming in inviting azure waters, snorkelling in secluded inlets, lazing about on white-sand beaches and uncovering archaeological treasures. Travel past the dramatic cliffs of Calabria to Bagnara Calabra, visit the historic port of Milazzo in Sicily, explore the stunning, windswept Aeolian islands of Lipari, Stromboli and Panarea, and discover the charming villages of Longobardi. From the ‘Coast of the Gods’, to the heavenly waters of the Tyrrhenian Sea, this divine sea adventure is sure to sweep you off your feet...

  • Included activities: Sailing!
  • Accommodation: Overnight boat (6 nts)
  • Meals: 6 breakfasts, 5 lunches; budget €180 for other meals
  • Transport: Sailboat
  • Group size: Max 8

 

Tips & links

Useful links & resources
Book ahead

While for some activities you can just show up, this is one travel item you really should try to reserve in advance.

Popular activities like cooking classes can sell out.

Many are available only on certain days of the week, so it pays to know that you'll have to set aside, say, Tuesday morning for that guided market walk with a local cookbook author.

Many of the best activities are available by advance booking or appointment only—particularly wineries. Some vineyards welcome walk-ins, true, but many more will give you a cellar tour and wine tasting only if you call ahead a few days (and those tend to be the ones most liberal with the free samples).

If you have your heart set on dining in a particular restaurant, go ahead and call ahead,even if it's just earlier on the same day—though a day ahead is preferable. I have found that a corrollary of Muphy's Law applies to this aspect of travel. Any restaurant I am particularly keen on but blithely assume I can just waltz into will inevitably be filled to the brim: no tables available. However, half the time when I do book a table in advance I'll end up being the only guy in the place (nor near enough for my advance booking to feel like overkill). Still, better safe than sorry. Reserving a table is quick and painless; getting turned away at the door can be crushing.

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