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Tuscan Archipelago | SALE ✨
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: Castiglioncello / Marina Cala de' Medici is the starting marina // closest airport is Pisa International Airport. Florence Airport is an hour drive and we can assist with transportation, both public and private options.
5% EARLY BOOKING DISCOUNT: earlybooking at checkout
Sailing to Elba and the Tuscan Islands is a joyous escape, where the gentle sway of the boat harmonizes with the azure waves and sun-drenched landscapes, inviting you to explore hidden coves, taste exquisite local wines, and bask in the serenity of this enchanting Mediterranean paradise.
Hidden Italy
Itinerary
Marina Cala de' Medici to Gorgona (approx. 18 NM) Your journey begins at Marina Cala de' Medici, a bustling port with historical depth and provisioning convenience. After a relaxed morning departure, head west to the mysterious island of Gorgona, the northernmost and least accessible of the Tuscan Archipelago. Though landing is restricted due to its status as a prison island, anchoring off its rugged coastline offers a wild and contemplative first night at sea, with views of dramatic cliffs and seabirds wheeling above.
Gorgona to Capraia (approx. 25 NM) Hoist anchor early for the crossing to Capraia, an island with volcanic origins and a rich, off-the-beaten-path charm. Enter the sheltered harbor on the eastern side or drop anchor in Cala del Ceppo for a more secluded experience. The tiny village of Capraia Porto, with its pastel houses and slow rhythm, offers simple trattorias and paths up to a crumbling Genoese fortress. The swimming and snorkeling in Capraia’s marine reserve are some of the best in the region.
Capraia to Marciana Marina, Elba (approx. 27 NM) Today’s sail brings you southeast to Elba, the crown jewel of the Tuscan islands. Aim for Marciana Marina, a picturesque and well-equipped port on Elba’s northern coast. Along the way, keep an eye out for dolphins and basking tuna in the channel. Once docked, explore the quaint town or hike into the hills for sweeping views over the Tyrrhenian Sea. Dinner ashore promises fresh seafood and local wine.
Marciana Marina to Biodola Bay, Elba (approx. 10 NM) A short sail around Elba’s northwestern point brings you to Biodola Bay, one of the island’s most inviting anchorages. With its clear waters, sandy bottom, and backdrop of pine forests, this is a perfect place to relax. Swim, paddleboard, or dinghy ashore to a beachfront trattoria. In the evening, the bay glows under the soft light of Elba’s western sunsets.
Biodola Bay to Porto Azzurro (approx. 18 NM) Cruise leisurely around the cape and down Elba’s rugged northern coast toward Porto Azzurro. Nestled in a deep, well-protected inlet, this harbor town offers lively piazzas and a surprisingly cosmopolitan vibe. After tying up, wander the narrow lanes, enjoy an aperitivo under the shade of palm trees, or take a short hike to Fort San Giacomo for panoramic views.
Porto Azzurro to Piombino or Punta Ala (approx. 25–30 NM) On your final day, cross back to the mainland, choosing either Piombino or Punta Ala depending on wind and your onward travel plans. With a full heart and salt on your skin, you’ll return to shore having tasted the wild and varied beauty of Tuscany’s sea-bound gems—an archipelago that rewards sailors who savor the journey as much as the destination.
**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.
Crew
Dayyan Armstrong
Founder, Captain
Captain Armstrong founded the Sailing Collective with a passion for connecting people with the world through adventures and sailing. Having been raised with values based on multi-cultural awareness and the importance of global culture, Armstrong combined his enthusiasm for sailing and exploration to create an intergrated sailing vacation organization open to adventuers, explorers, and sailors alike. In addition to founding the Sailing Collective Travel Co, Armstrong is the co-autor of Sailing the Seas. He is also a trained musician having graduated from music conservitory in New York City and holds a graduate degree in Economics. Captain Armstrong is also wildly passionate about food and wine, which is very evident to anyone joining him on a Sailing Collective voyage.
Amy Yi
Chef
Amy Yi believes that food is community. For her, the power of food is most deeply demonstrated in the bonds it can forge; the social, environmental and economic implications it can illuminate; and the experiences it can bring to life for those who come together to break bread. Born and raised in Los Angeles, Amy was initially drawn to the competitive pace of New York City as an advertising associate for magazines such as Glamour and Fortune but soon realized that what she craved was a much more visceral connection to her work and an opportunity to nourish and delight others through food. Amy’s culinary inspiration and worldview draws from family traditions infused with a passion for cultural diversity. Amy strives to bring an everyday rapture to what you crave, how you care for your community, and why a collective impact matters.
About the Food
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.
General Information
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.
Start & End Schedule Overview
Arrival Schedule
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.
End of Week Schedule
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 - 7:00pm.
Boats
Dufour 48 Catamaran
The Dufour Catamarans 48 has been designed to satisfy the requirements of charter guests wishing to live on board throughout an adventurous week. Offering a large living room was essential and the result is perfectly achieved. The kitchen connected to the cockpit, is fully equipped and ergonomic with its many storage spaces. At the front, there is the office space – chart table, equipped with a repeater screen and an autopilot control with joystick, to control the boat from the inside.
Bed size: Mattress is between a double and queen size bed
For more informatoin about the Dufour 48
Galleries
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