Sailing to Isola Elba and the Tuscan Islands feels like discovering the forgotten corners of Italy, outside the spotlight of Sardinia or Amalfi. These waters are steeped in history, where Napoleon brooded in exile and ancient Etruscans sailed long before Rome was even a thought. The islands are rugged, untamed—each cove a sanctuary of clear waters and hidden beaches. The local fishermen, with faces weathered by the sun and salt, will tell you stories of storms and lost treasures over a plate of freshly caught seafood, the kind that makes you realize how far you are from the glossy, prepackaged Italy of postcards. Here, you sail not just through the sea, but through time.
Starting Location: Marina di San Vincenzo Toscana // closest airport is Pisa International Airport. Florence Airport is an hour drive and we can assist with transportation, both public and private options.
Location
Tuscan Archipelago
Italy
Season
June- September
Day 1: Departure from Tuscany to Capraia
Arrive at Capraia, an unspoiled island with stunning landscapes. Dock at the marina and explore the island's charming village, including the historic fortifications. Enjoy dinner at a local trattoria, sampling fresh seafood and local wines. Overnight on the boat at the marina.
Day 2: Exploring Capraia
Hike to the top of Monte Capraia for breathtaking views of the surrounding archipelago. Alternatively, you can rent a scooter or bicycle to explore the island's scenic paths. Spend some time relaxing on the beaches. Visit Cala del Ceppo or Cala delle Alghe for a swim in crystal-clear waters. Return to the marina for dinner. Experience the local nightlife or take a peaceful stroll along the harbor.
Day 3: Sail from Capraia to Pianosa
Depart from Capraia for Pianosa, which is about 18 nautical miles away (around 3 hours of sailing). Prepare for a leisurely sail across the beautiful Tyrrhenian Sea. Arrive at Pianosa and anchor in one of its protected bays. Spend the afternoon swimming and snorkeling in the vibrant marine reserve. Picnic on the beach or enjoy a barbecue on board. Watch the sunset and relish the serenity of this uninhabited island. Overnight at anchor.
Day 4: Discovering Pianosa
Explore Pianosa by foot. Visit the old prison and learn about the island’s unique history. Take advantage of the trails that wind through its unspoiled landscapes. Go snorkeling or diving at popular spots like the “Cala del Cimitero” to see diverse marine life, Return to the boat for a relaxing evening under the stars, with the sounds of the waves lapping against the hull.
Day 5: Sail from Pianosa to Elba
Depart from Pianosa and head to Elba, approximately 20 nautical miles away (about 4 hours sailing). Enjoy the picturesque views along the way. Arrive at Portoferraio, the main harbor of Elba. Check into a marina and take some time to explore the historic town, including the Medici fortress and charming old streets. Enjoy dinner in Portoferraio at a local restaurant. Sample Elban specialties, such as “Cacciucco” (a Tuscan fish stew). Overnight in the marina.
Day 6: Exploring Elba
Set sail to the southern part of Elba and anchor in the beautiful bay of Fetovaia. Spend the morning swimming and sunbathing on its stunning beaches. Lunch on board, then head ashore to explore the area. Hike or cycle along the coastal paths to discover hidden coves. Return to Portoferraio for dinner. Consider visiting one of the local wine bars to taste Elba's renowned wines.
Day 7: More of Elba and Return to Livorno
Enjoy a leisurely breakfast on board, then sail to the enchanting beaches of Capo Bianco or the colorful village of Marciana Marina. After lunch, start your journey back to Livorno. This leg is about 20 nautical miles and takes roughly 4 hours. Arrive back in Livorno. Celebrate the end of your sailing adventure with a final dinner at a local restaurant, reflecting on your journey through these beautiful islands.
**Example itinerary only - the exact itinerary will change based on the weather conditions and the group's interest. This itinerary will often include up the three days exploring the island of Elba. Depending on the weather and the starting location, we will have time to explore the southern islands in the archipelago.
Provisioning Sailing Collective will provision your journey with local foods and produce. Cooking Aboard: Your Sailing Collective chef/crew is incredibly talented and can handle the group's needs with ease. We are all about participation and learning, so if you'd like to help, just ask and we'll get you involved! Collective groups may choose to dine out more times than scheduled if the group or individuals choose.
Included in provisioning package*:
6 Breakfasts, 6 Lunches, 3 Dinners (or similar), Light Snacks, Water, Coffee & Tea
* Subjected to change
Dietary Restrictions We can accommodate as long as we know in advance! It is important to notify us of any dietary restrictions ahead of time and include full details in the Guest Form that you will fill out prior to the start of the trip.
Sailing a group journey is a collective experience calling us to ebb and flow with the tides of the group. While alcohol and soft beverages are not included, we find a well curated bar shared across the group works out best. We offer two beverage during group journeys packages during the course of the week*:
• $150 for wine, beer, spirits and soft beverages • $75 for soft beverages and under 5 alcoholic drinks. *Private charters, beverages are billed to the charter
Private Charters: Contact us for details
ADDITIONAL COSTS We recommend planning on having at least $300 – $600 in spending money depending on spending habits. You will be responsible for paying for:
All expenses on shore including meals and drinks
Flights and transportation to and from the marina location
Onboard beverages
Gratuity (a 10% to 20% offering)
GRATUITY Tipping your captain and crew is welcome. If you are satisfied with your service, the industry standard for yacht charters ranges from 15-20% of the cost of the charter. Gratuity is split evenly between the crew and can be paid via cash, check, Venmo, or PayPal. Please contact your Sailing Collective Journey Coordinator if you have any questions.
10% - Standard good time on holiday with good service.
15% - Exceptional service on your holiday with exceptional service!
20% - Extraordinary experience and your crew sent the voyage to the moon and back!!
The Journey Schedule Meeting time is at 9:00am on Day 1 of the charter. Our last night is spent at the starting marina before we disembark by 9:00am on the final morning. All Mediterranean charters return to the home port on Friday evening to spend the final evening at the marina. Disembarkation time is at 9:00am on the final Saturday morning.
Packing Collapsible bags in place of large rigid suitcases are advised for ease of transport on and off the boat. Loading and unloading from the dingy can be a wet activity, a pair of shoes such as flip-flops that you can get wet if we are landing on a beach.
As the vast majority of your time will be spent outside, prepare for elements - bring a light raincoat just in case, a hat to shield yourself from the sun, and a warm layer. Throughout the week we may dine out at a nice restaurant, so bring an outfit looks nice and suits your style. Loading and unloading from the dingy on beaches can be a wet activity, a pair of shoes that you can get wet is recommended.
We also encourage guests bring ecologically appropriate products into ocean environments. You can read more about those recommendations on the Sailing Collective Journal here: Packing for a Healthy Ocean
Terms & Conditions By booking this journey, you agree to comply with the stated Terms & Conditions and Covid Considerations, available on our website. Please contact info@thesailingcollective.com with any questions.
Travel Insurance We recommend purchasing a travel insurance policy that protects you in case of general and covid-related trip interruptions. If you choose not to purchase travel insurance, you forfeit the right to a refund or credit in the event you have to cancel your trip with Sailing Collective.
PASSPORTS AND VISAS Please ensure your passport is valid for the period of travel and for six months after you return. The Sailing Collective cannot be held responsible for refusal of entry or travel due to lack of visas. If you are in any doubt please contact your Embassy for full details.
A culinary program with a focus on locally sourced sustainable foods
The Sailing Collective Travel Co. takes food to a new level. We believe by sourcing local ingredients from local friends we have made throughout our travels pushes us to experience where we are by being engulfed by the regional flavors.
Private chef creating customized menus to your taste and requirements
Each voyage, both group & private, has a private culinary artist aboard preparing some of the most unique, interesting, and thoughtful food you may ever enjoy in your life! From breakfast to dinner each day of the journey, we are blessed by beautiful meals by one of the most talented culinary teams in travel anywhere in the world.
Boarding time is 9:00 am on Day 1 of the charter. There will be a mandatory orientation prior to departing. The exact meet up location will be shared with you by your crew and your crew will be in direct communication to ensure an easy and safe arrival.
All Mediterranean charters return to port on Friday night and the final night is spent at the home port before disembarkation at 9:00am on the final Saturday of the charter. Upon return, your captain must refuel the vessel before docking. Returning to port will take place between 5:00pm - 6:00pm.
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