Tuscany to the Amalfi Coast: Italy by Land & Sea - 13 Days
Who is this trip for
Age range
16 - 100Physical rating
Group size
1 - 16Meals included
9Highlights
- 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
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Summary
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.
Itinerary
Day 1
Florence
Arrive in Florence at any time. Meet your CEO and fellow travellers in the evening at a welcome meeting.
Day 2
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.
Day 3
Cinque Terre
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.
Day 4
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.
Day 5
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.
Day 6
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.
Day 7
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.
Day 8
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.
Day 9
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 the boat will moor in the marina for the night.
Day 10
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.
Day 11
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.
Day 12
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.
Day 13
Sorrento
Depart after breakfast.
If you would like extra time in Sorrento after the sailing journey is finished, we recommend booking extra time.
What's Included
Accommodation
Hotels (6 nts), 2 twin/double bed cabins, 2 cabins with bunks, 2 single cabins, 4 bathrooms (6 nts).
Meals
Breakfasts: 6, Lunches: 0, Dinners: 3
Vegetarian options are available on all meals throughout the adventure.
Vegetarian options availableLocal Guide
GuidedThis adventure is led by a local guide throughout. The main language of this adventure is English. Please contact us for other languages available.
Wifi
Wifi is available during the adventure. In some areas and / or accommodation / transport Wifi may be free.
Dates & Prices
May 26
from £3,296Jun 26
from £3,405Jul 26
from £3,296Aug 26
from £3,147Sep 26
from £3,405
- Save 1%Sun 16 Aug 2026 > Fri 28 Aug 2026Guaranteed Departure6+ spaces of 16 leftPay Monthly£3,179Best offer£3,147Book for£250 today, pay the rest later
- Save 1%Sun 23 Aug 2026 > Fri 4 Sep 2026Guaranteed Departure6+ spaces of 16 leftPay Monthly£3,179Best offer£3,147Book for£250 today, pay the rest later
- Save 1%Sun 30 Aug 2026 > Fri 11 Sep 2026Guaranteed Departure6+ spaces of 16 leftPay Monthly£3,179Best offer£3,147Book for£250 today, pay the rest later
Essential trip information
Our Important Notes and Packing List cover all essentials, from necessary equipment to inclusions, ensuring you're fully equipped and informed for this extraordinary adventure and more.
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