Italy’s Islands by Private Charter – 14 to 21 Days
Experience the Mediterranean in complete privacy on an Italy islands private charter, sailing between some of the country’s most spectacular islands. Over 14 to 21 days, your fully crewed yacht can explore Capraia, Elba, Giglio, Costa Smeralda and the Maddalena Archipelago, the Pontine and Campanian islands, the Aeolian and Egadi islands, Lampedusa, Linosa and the remote Tremiti.
Every journey is entirely tailor-made: we design the route, select the right yacht or superyacht, and calibrate the onboard services to your group – whether it’s a couple, a family escape or a celebration with friends. Add time along the Cinque Terre, Amalfi Coast or coastal Sicily and Calabria to create your own Italian island grand tour.
Best season: May–September
Duration: 14–21 days (customizable)
Style: Private yacht charter, island hopping, swimming, snorkeling, food & wine
More details
Tailor-Made Configuration: Yacht, Group & Services
This product is bespoke only – no fixed package, no fixed price. In order to best tailor to your needs this Italy islands private charter, at enquiry stage, you’ll define with us:
Yacht Type
-
Motor yacht (approx. 24–40 m) – ideal for guests who want comfort, speed and more stabilization.
-
Sailing yacht or catamaran (approx. 15–25 m) – for a more relaxed, wind-driven experience with wide decks and great stability.
-
Gulet or classic vessel – traditional wooden yachts with generous outdoor spaces, perfect for larger families or multi-generational trips.
-
Superyacht – for guests seeking the highest level of space, privacy and onboard facilities.
Group Size & Cabin Layout
-
Recommended for 2–12 guests, depending on yacht size.
-
Cabin configuration tailored to your group: master suites, doubles, twins, family cabins.
-
Option to add a chase boat or additional support vessels for water sports, luggage or staff.
Crew & Onboard Services
-
Standard fully crewed charter typically includes:
-
Captain
-
Chef
-
Deckhand(s)
-
Steward/ess (interior service and housekeeping)
-
-
On request, we can add:
-
Dedicated butler
-
Private guide or destination concierge
-
Wellness therapist (massage, yoga, Pilates)
-
Dive instructor / water sports guide
-
Nanny or childcare assistant
-
Food & Beverage
-
Menus tailored to your dietary preferences and culinary interests, with an emphasis on:
-
Local seafood
-
Regional Italian dishes
-
Wine pairings from nearby regions (Tuscan, Sardinian, Sicilian, etc.)
-
-
Options for:
-
Fine dining on board
-
Casual beach barbecues
-
Michelin-level restaurant reservations on shore
-
Experience Level
We can design your Italy islands private charter to match your style:
-
Relaxed & family-friendly – more time at anchor, easy swims, shorter legs, simple shore excursions.
-
Adventure & active – hiking, diving, snorkeling, kayaking, paddleboarding, remote coves.
-
Ultra-luxury & lifestyle – beach clubs, fine dining, exclusive events, in-villa or on-deck experiences.
Who This Trip Is For
-
Couples and families seeking total privacy and flexibility at sea.
-
Friends traveling together or celebrating a special occasion (milestone birthdays, anniversaries).
-
Guests who prefer a yacht or superyacht over classic hotel-hopping, without sacrificing comfort.
-
Experienced Mediterranean travelers ready to explore multiple island chains in one extended trip.
Route at a Glance
This is a sample 21-day “Grand Island Circuit”. The 14-day version uses the same logic, but with selected island groups combined or shortened (for example, focusing on Tuscany + Pontine + Campanian + Aeolian).
-
Tuscany & Northern Islands: Livorno, Capraia, Elba, Giglio
-
Sardinia: Costa Smeralda, Maddalena Archipelago
-
Central Tyrrhenian: Pontine Islands (Ponza & Ventotene), Campanian Archipelago (Ischia, Capri)
-
Southern Tyrrhenian & Sicily: Aeolian Islands (Stromboli, Panarea, Lipari, Vulcano), Egadi Islands (Favignana, Levanzo, Marettimo)
-
Southern & Adriatic: Lampedusa, Linosa, Tremiti Islands
Sample 21-Day Itinerary (Private Charter)
Day 1 – Embark in Livorno – Capraia
Welcome aboard your private yacht in Livorno. After a safety briefing and settling into your cabin, cruise to Capraia. Enjoy a sunset aperitivo on deck and an evening stroll through the old fishing village.
Day 2 – Elba Island
Morning sail to Elba. Visit Portoferraio and Napoleon’s former residence, or opt for a panoramic drive. In the afternoon, swim and snorkel in Biodola Bay before dinner on board or ashore.
Day 3 – Giglio Island
Sail to Giglio, with time to explore Giglio Castello and coastal paths. Swim in clear waters or relax on deck. Certified divers may arrange scuba dives in marine-protected areas (as an enhanced or ultra-luxury option).
Day 4 – Costa Smeralda (Sardinia)
Sail overnight or transfer via a short flight and re-embark in northern Sardinia. Dock in or near Porto Cervo for boutique shopping, beach clubs and fine dining, returning to your yacht at anchor or in marina.
Day 5 – Maddalena Archipelago
Spend the day in the Maddalena Archipelago, swimming in the turquoise coves of Spargi and admiring Budelli’s Pink Beach from the water (as regulations permit). Enjoy a leisurely seafood lunch on board, and time for paddleboarding or snorkeling.
Day 6 – Pontine Islands – Ponza
Navigate towards the Pontine Islands, arriving in Ponza with its pastel harbor. Choose between a hike to natural rock pools, a coastal tour by tender, or simply relaxing on the yacht’s sundeck.
Day 7 – Ventotene (Pontine Islands)
Short hop to Ventotene, known for Roman ruins and serene beaches. Explore the island at your pace, then enjoy a private dinner on deck under the stars, with a menu tailored to your tastes.
Day 8 – Campanian Archipelago – Ischia
Morning sail to Ischia. Options include:
-
Thermal gardens and spa
-
A vineyard tour on volcanic slopes
-
Panoramic drives and village visits
Return to the yacht for a relaxed evening, or dine in one of Ischia’s traditional restaurants.
Day 9 – Capri
Cruise to Capri and dock in Marina Grande. Visit the Blue Grotto (sea conditions permitting), walk through Capri town or Anacapri, and enjoy an aperitivo in the Piazzetta before returning aboard for dinner.
Day 10 – Amalfi Coast (Optional Add-On)
If you choose to add the Amalfi Coast, cruise past Positano and Amalfi, stopping for swims and photos. Optionally, arrange a private cooking class in a cliffside villa or a special lunch on shore. Otherwise, you can use this day as a flexible buffer elsewhere on your route.
Day 11 – Aeolian Islands – Stromboli
Sail south to the Aeolian Islands, anchoring off Stromboli in the evening. With the right conditions, watch the volcanic lava flows from the sea – a dramatic natural “fireworks” display.
Day 12 – Panarea
Continue to Panarea, with its whitewashed houses and chic yet laid-back vibe. Spend the day exploring hidden coves by tender, shopping in small boutiques, or relaxing on beaches. A beach barbecue with fresh fish can be arranged as a special ultra-luxury moment.
Day 13 – Lipari
Head to Lipari, the largest Aeolian island. Visit the archaeological museum, explore pumice stone areas and enjoy time in the historic center. Afternoon at leisure for swimming and snorkeling.
Day 14 – Vulcano
Sail to Vulcano, known for mud baths and hot springs. For the active, a hike to the crater rim rewards you with panoramic views. Return to the yacht for a relaxed evening under the stars.
Day 15 – Egadi Islands – Favignana
Cross to Favignana in the Egadi Islands. Explore by bike, discover hidden beaches and swim in aquamarine coves. Taste local tuna specialities inspired by the island’s maritime traditions.
Day 16 – Levanzo
Short sail to Levanzo. Visit prehistoric cave paintings (Grotta del Genovese) with a local guide, then anchor in Cala Minnola for swimming, snorkeling and lunch on board.
Day 17 – Marettimo
Continue to Marettimo, the most remote of the Egadi. Spend the day hiking, exploring sea caves by tender and snorkeling in crystal-clear waters, far from the crowds.
Day 18 – Lampedusa
Sail (or reposition) to Lampedusa, where you can relax at Rabbit Beach, often cited among the world’s most beautiful. Enjoy a laid-back day of swimming and sun, with a refined dinner on deck.
Day 19 – Linosa
Visit Linosa, with its black volcanic beaches and wild character. Nature lovers can join a seabird-spotting outing with a marine biologist (as a high-end enhancement), before returning to the yacht.
Day 20 – Tremiti Islands
Make your way towards the Tremiti Islands, exploring sea caves and visiting medieval abbeys that overlook the sea. Enjoy a final full evening on board with a farewell dinner.
Day 21 – Return & Disembark
Sail or reposition towards your chosen disembarkation port (for example, the Apulian coast or another convenient harbor). After a final breakfast on deck, disembark and transfer privately to your onward destination.
Typical Inclusions (Tailor-Made, No Prices)
Exact inclusions depend on the yacht, charter contract and season, but a typical Italy islands private charter package arranged through your DMC can include:
Yacht & Crew
-
Fully crewed private yacht, sailing yacht, catamaran, gulet or superyacht
-
Professional captain, chef, deck crew and steward/ess
-
Daily cabin and common-area housekeeping
-
Use of tenders and standard onboard water toys (kayaks, SUP, snorkeling gear – depending on yacht)
Onboard Services
-
Custom menu planning and onboard meals as per agreed provisioning plan
-
Soft drinks and standard bar selection (upgraded wine or spirits lists on request)
-
Fuel for the agreed itinerary (within defined navigation limits)
-
Standard mooring arrangements as specified in the charter agreement
Shore & Concierge Services
-
Personalized itinerary design and route planning
-
Advance restaurant, beach club and experience reservations
-
Selected on-shore experiences (e.g., vineyard visits, cooking classes, spa visits) as pre-confirmed in your program
-
24/7 emergency support and in-trip assistance during the charter
Typical Exclusions
To be confirmed at quote stage, but often not included in Italy islands private charter itinerary:
-
Fuel beyond standard cruising or itinerary changes requested during the trip
-
Port, marina and anchoring fees outside the agreed plan
-
Premium wines, Champagne and top-shelf spirits (unless pre-negotiated)
-
Specialized activities (diving, private guides, external drivers, helicopter transfers)
-
Gratuities for crew (optional but customary)
-
Travel insurance, flights and pre/post-charter hotels
Per person – Vat included
Maybe can interest also...
White Truffle & Fine Wines of Italy – 8 Days (Montepulciano + Langhe)
Per person – Vat included