Italy’s greatest hits — and its best-kept secrets. This 13-day land-and-sea adventure pairs the rolling vineyards of Tuscany with the sparkling drama of the Amalfi Coast. Wander through medieval towns and valley trails, snap that classic Pisa shot, and explore the cliffside villages of Cinque Terre. Then swap cobblestones for open water as you sail to hidden beaches, volcanic islands, and colourful coastal gems. From the elegance of Capri to the pastel perfection of Positano — and maybe even a side trip to Ravello — you’ll experience Italy’s iconic sights and secret corners in one unforgettable trip.
Travel Style
Classic
Service Level
Standard
Physical Grading
3 - Average
What's Included
Your Welcome Moment: Welcome Moment - Meet Your CEO and Group. Guided walking tour of Florence. Visit to Cinque Terre National Park. Lucca Guided Walking Tour. Wine tasting at agriturismo. Free time in Cinque Terre and in the Chianti Region. Sunset in Ischia. Blue Cave Visit. Swimming stops along the sailing route. Cooking class in Sorrento. Free time to explore in Procida, Ischia, Capri, Positano, Amalfi, & Sorrento. All transport between destinations and to/from included activities.
What are the main highlights of this trip?
Take a guided walking tour through the art-filled streets of Florence, Hike the dramatic coastal trails of Cinque Terre, Snap a photo with the iconic leaning tower of Pisa, Spend two nights soaking up the beauty of the Tuscan countryside, Explore the cliffside charm of Capri and Positano, Sail the turquoise waters of the Tyrrhenian Sea past volcanic coastlines
How large will the group be?
Max 16, avg. 10.
What meals are included in this trip?
6 breakfasts, 3 dinners
What are the modes of transportation on my trip?
Private vehicle, train, walking, 16m (54 ft) sailing yacht.
Is there an extra cost for travelling solo?
We believe solo travellers should not have to pay more to travel so our group trips are designed for shared accommodation and do not involve a single supplement. Single travellers joining group trips are paired in twin or multi-share accommodation with someone of the same sex for the duration of the trip. Some of our Independent trips are designed differently and solo travellers on these itineraries must pay the single trip price.
Where will we stay during the trip?
Hotels (6 nts), 2 twin/double bed cabins, 2 cabins with bunks, 2 single cabins, 4 bathrooms (6 nts).
Itinerary
Florence
Arrive in Florence at any time. Meet your CEO and fellow travellers in the evening at a welcome meeting.
Florence to Cinque Terre
Start the day off with a walking tour of Florence seeing all of the famous sites like the Centro Storico, Giotto’s bell tower, the Palazzo Vecchio and The Uffizi. It’s onwards to the Cinque Terre region. On the way the group will stop in Lucca for a guided walk through this medieval town.
Cinque Terre
Enjoy some breakfast before taking a short train to the village Monterosso for the start of today's hike. Walk through scenic trails, then enjoy a free afternoon to continue exploring. You could sign up for a food making class, book a boat trip, or hike any of the other coastal and inland paths that will take you all over one of the most gorgeous stretches of coastline in all of Italy. Spend the morning discovering the five towns within the UNESCO World Heritage Site of Cinque Terre, Corniglia, Manarola, Monterosso al Mare, Riomaggiore, and Vernazza.
Should you opt out of the hike with the group and CEO, the Cinque Terre National Park pass will still be available for you to discover the five towns on your own.
Cinque Terre
A full free day to enjoy the marvels of Cinque Terre. Opt to visit the town of Portovenere or join a pesto-making demonstration in Manarola. You could also spend some time shopping, wine tasting, cafe-hopping, and beach walking if you’re craving more relaxing vibes. Kayaking, boat tours, and hiking are always available.
Cinque Terre to Chianti Region
After breakfast, travel to North Chianti region. En route the group will stop in Pisa briefly to see the Leaning Tower of Pisa. After, continue driving through the stunning Tuscan area and enjoy an included dinner tonight with the group in North Chianti.
Chianti Region
Wake up in the beautiful Tuscan countryside. In the morning, hike the stunning trails around Villa Pitiana and immerse yourself in the beauty of the region. In the afternoon enjoy an included wine tasting and delicious dinner with the group.
Chianti region to Naples via Florence
Travel to Naples by private vehicle passing through Florence along the way. Board the boat in the late afternoon and begin your sailing journey to Procida.
Procida/Ischia
On the beginning of this sea voyage, you will explore Ischia, a volcanic island known for its healing thermal springs and beaches. From lush nature to a historic medieval castle, there’s much to enjoy. The boat will anchor and the group will have time to explore. Sunset will be seen from the castle before dinner at a local restaurant.
Your 16m (54 ft) nimble yacht is the perfect platform to explore the gorgeous Amalfi Coast. Flexibility is key to adapt to local weather conditions, and the skipper will modify the itinerary to our advantage while sailing.
Ischia/Capri
Sail to Capri, famous for its dramatic natural scenery and visit the iconic Blue Grotto. Then, explore Capri on your own and opt to join the group for a sunset drink before dinner at a local restaurant. The boat will moor in the marina for the night.
Capri/Positano
Enjoy a possible swimming stop today at one of the many beautiful options in the area before continuing on to Positano and its postcard-worthy cliffside setting full of colourful buildings appearing to cascade down to the sea. Anchor in the marina and take advantage of free time to explore the town before sunset and dinner at a local restaurant with the group. Choose to experience the nightlife or head back to the boat for a quieter evening.
Positano/Amalfi
Sail to the stunning town of Amalfi, considered the most historic town on the Amalfi Coast itself and home to the impressive 11th-century Cathedral of Saint Andrew. Enjoy time to walk around the town on your own or opt to visit Ravello perched on the hilltop with its villas and gardens. Dinner will be had while in Amalfi and the boat will anchor in the harbour.
Amalfi/Sorrento
Travel to Sorrento with a possible swim stop in a beautiful spot along the way. Take time to explore the town and choose to visit the lemon groves or book a cooking class. Enjoy sunset and limoncello this evening and a delicious dinner together as a group.
Sorrento/Naples
Sail back to Naples from Sorrento and depart after breakfast.
If you would like extra time in Naples after the sailing journey is finished, we recommend booking extra time.
Is travel insurance required for my trip?
Travel insurance is compulsory in order to participate on any of our trips. When travelling on a group trip, you will not be permitted to join the group until evidence of travel insurance has been sighted by your leader, who will take note of your insurance details. When selecting a travel insurance policy we require that at a minimum you are covered for medical expenses including emergency evacuation and repatriation. A minimum coverage of USD200,000 is required. We strongly recommend that the policy also covers personal liability, cancellation, curtailment and loss of luggage and personal effects. Some tours include adventure activities that require extra coverage (e.g. crampon use); please review your itinerary and make sure that you are covered for all included activities. If you have credit card insurance we require proof of purchase of the trip (a receipt of credit card statement) with a credit card in your name. Contact your bank for details of their participating insurer, the level of coverage and emergency contact telephone number.
Terms, conditions and restrictions apply; pricing, availability, and other details subject to change and/ or apply to US or Canadian residents. Please confirm details and booking information with your travel advisor.
