8-Day Sicilian Wine & Sea Journey with Chelsea and Gigi
At a Glance
- DATES: May 19 to 26, 2028
- WHERE: Palermo, then a week sailing through the Aeolian Islands off Sicily
- GROUP: Limited to 10 travelers
- YACHT: A private Bali 5.4 sailing catamaran with our own skipper and chef
- PRICE:
- €4,100 per person in a Queen bed cabin, double occupancy
- €700 Queen bed cabin, single occupancy supplement charge
- €4,300 per person in the bunk cabin, double occupancy
- €4,100 per person in a Queen bed cabin, double occupancy
To request a spot on this journey, please fill out this form. No money is due until after we meet with you, and our meeting does not obligate you to travel with us.
After our meeting, a €1,000 non-refundable deposit reserves your place. Deposits are due by September 1, 2027, and the final balance is due January 15, 2028. Because the yacht sails with just ten travelers, spaces cannot be held without a deposit. All trip prices are quoted in Euro (€).
This trip is open to travelers of all races and ethnicities. We ask every participant to help create a respectful, anti-racist, and community-minded travel environment.
Wine on the Water
Our third Italy by the Glass journey trades the villa for a yacht. Travel with wine expert Chelsea Stephens, PhD and social scientist Gigi Coulson, M.S. on an intimate week through Sicily’s volcanic Aeolian Islands, with the whole yacht to ourselves, a skipper who knows these waters, and a chef cooking from the island markets.
Sicily has been pouring wine for travelers since antiquity. Julius Caesar served Mamertino, grown along this same northern coast, at a banquet celebrating his third consulship. On Salina, families still dry Malvasia grapes in the sun for the golden sweet wine the islands have shipped across the Mediterranean for centuries. Between those two glasses sit Greek colonists, Arab farmers, Norman kings, and the island communities who kept the vines going on terraces carved out of volcanic rock.
Mornings ashore, afternoons at sea. We swim from the yacht, walk island villages without cars, taste on deck as the sun goes down, and watch Stromboli spark against the night sky from anchor. Because this journey is limited to ten travelers, space is extremely limited, and we encourage interested travelers to request information early.
- Focus Sicilian and Aeolian wine, island foodways, Mediterranean social history, and volcanic landscapes
- Pace Intimate, sensory, and unhurried, with time every day to swim and rest
- Route Palermo, Vulcano, Lipari, Panarea, Stromboli, Filicudi, and Salina
- Lodging One night at a boutique hotel in historic Palermo, then six nights aboard in cabins that each have their own bathroom
Day by Day
- DAY 1 · FRI MAY 19 Arrive in Palermo – Fly into Palermo and settle into a boutique hotel in the historic center. We gather for a welcome dinner and our first Sicilian glasses together, a crisp Grillo and a Nero d’Avola.
- DAY 2 · SAT MAY 20 Palermo to the sea – A morning in Arab-Norman Palermo, including Santa Maria di Gesù, resting place of San Benedetto il Moro, the African-descended saint who became Palermo’s patron. A private van carries us along the coast past his birthplace of San Fratello to Capo d’Orlando, where we board and sail north to Vulcano.
- DAY 3 · SUN MAY 21 Lipari – The largest and liveliest island. We climb to the old citadel and its archaeological museum, where Lipari obsidian and Greek theater masks tell the story of four thousand years of Mediterranean trade, then spend the evening ashore in town.
- DAY 4 · MON MAY 22 Panarea – The smallest inhabited island, all white and pastel houses and car-free lanes. Lunch ashore, an afternoon swim in clear water, and a quiet night at anchor.
- DAY 5 · TUE MAY 23 Stromboli – North to one of Europe’s most active volcanoes. Chelsea leads a deck tasting of wines from Sicily’s volcanic soils, and we anchor offshore at dusk to watch the crater glow.
- DAY 6 · WED MAY 24 Filicudi – A longer sail west to the wildest and quietest island: terraced hillsides, a single sleepy harbor, and sea caves along the cliffs.
- DAY 7 · THU MAY 25 Salina – The green island, with two volcanic peaks above terraces of capers and vines. We visit a family Malvasia producer for a tasting, then return to the yacht for a farewell dinner by our chef.
- DAY 8 · FRI MAY 26 Back to Sicily – One last long swim and lunch at anchor, then into Capo d’Orlando and a private transfer back to Palermo airport.
What is Included
Included in the trip price
- 1 night at a boutique hotel in Palermo’s historic center
- 6 nights aboard a private Bali 5.4 catamaran, in a shared cabin with its own bathroom
- Private skipper and chef for the week
- Daily breakfast, and lunches aboard with wine
- Welcome dinner in Palermo, five dinners ashore in the island harbor towns, and a farewell dinner aboard
- Malvasia winery visit and tasting on Salina
- A cellar of Sicilian and Aeolian wines hand-picked by Chelsea and brought aboard for our tastings
- Palermo walking visit, Lipari citadel and museum, and the Vulcano sulphur pools
- Private transfers from Palermo to the yacht and back to Palermo airport
- Fuel, marina and port fees, paddleboards and snorkel gear
- Crew gratuity
- Educational leadership by Gigi Coulson, M.S., and Chelsea Stephens, PhD
- Planning, coordination, and reservation management for the group itinerary
Not included
- Airfare
- Travel insurance
- Drinks outside included meals and tastings
- Optional activities, such as a guided evening climb on Stromboli
- Extra hotel nights before or after the journey
- Personal purchases and wine shipping
- Passport, visa, baggage, medical, or other personal travel costs
To request a spot on this journey, please fill out this form. No money is due until after we meet with you, and our meeting does not obligate you to travel with us.
Policies
Costumers of Color trips are open to travelers of all races and backgrounds. We ask every participant to help create a respectful, anti-racist, and community-minded travel environment. This includes following our community policies and being open to correction if harm occurs. Please review the policies at costumersofcolor.org/policies.
Travel insurance is strongly recommended. All trip fees are nonrefundable. You can compare plans here at Faye Travel Insurance.
Travel Terms & Conditions
By submitting a non-refundable per person trip deposit or balance payment, Guest is acknowledging, agreeing and accepting our Terms & Conditions Agreement, Policies, and Liability Waiver on behalf of himself, herself, themself and all persons for whom Guest is making payment. Guest understands that this is a legally binding and enforceable contract.
About the Hosts
Chelsea Stephens, PhD is a sommelier and wine educator whose technical knowledge is matched by a genuine love for the cultural life of wine. With WSET Level 2 training and years of teaching experience, Chelsea helps travelers move past intimidation and into curiosity, learning to read a glass, understand what they’re tasting, and ask better questions at every stop along the way.
Gigi Coulson is a social scientist, public historian, and historical costumer who has spent fifteen years studying Italy through the lens of culture, community, and identity. She brings that depth to every itinerary, connecting the wine in your glass to the landscape that shaped it, the people who made it, and the long history of place that surrounds it.
Together, they offer something most wine tours don’t: the pairing of technical wine knowledge with serious cultural and historical context. One tells you what’s in the glass. The other tells you everything behind it.
Frequently Asked Questions
Do you offer refunds?
All tickets, trip deposits, and trip payments are non-refundable. If you would like to transfer your deposit or payment to someone else, please email Gigi at gigi@costumersofcolor.org
How do I book my spot?
Click the Wine Journey Interest Form button to send us your information. Shortly after, you’ll receive an email from us with instructions to schedule a videoconference, make your deposit, and confirm your reservation. Spots are reserved on a first come, first served basis.When is this trip?
May 19 to 26, 2028. Plan to arrive in Palermo by the afternoon of May 19. We return to Palermo airport in the late afternoon of May 26, so an evening flight or an extra night in Palermo works best.
Who is this trip for?
Wine lovers, food lovers, and curious travelers who want a deeper taste of Sicily and are happy to trade a hotel lobby for a deck at sunset. You don’t need to be a wine expert or a sailor, just someone who enjoys good company, warm water, and beautiful places.
I’ve never sailed. Is that okay?
Absolutely. Our skipper handles the sailing, and our chef handles the galley. You are welcome to help with the lines if you’re curious, or to read in the shade all week. Catamarans sit wide and level on the water, which makes them steadier and roomier than a single-hull sailboat. If you are prone to motion sickness, bring whatever remedy works for you.
What is the yacht like?
The Bali 5.4 is a spacious 54-foot catamaran with six cabins, each with its own bathroom. Our ten travelers share four double cabins and one bunk cabin, and the trip leads share the twin cabin. The skipper and chef sleep in their own crew cabins. Up top is a flybridge with a jacuzzi, and below it a shaded lounge for meals, a sunny foredeck, and swim steps down to the water.
What is the price of this trip?
€4,100 per person in one of the four Queen bed cabins (double occupancy), or €4,300 per person in the bunk cabin, which has two stacked beds and suits friends traveling together.
Can I come solo?
Of course. A private cabin is possible by paying the single occupancy supplement.
Do I need travel insurance?
Yes. We strongly recommend comprehensive travel insurance that covers trip cancellation, medical emergencies, and medical evacuation. Given the non-refundable deposit and final payment, it’s an important safeguard.
What should I pack?
Pack light and soft. A duffel or soft bag stows easily aboard, while hard suitcases do not. Bring swimwear, a sun hat, reef-safe sunscreen, a light layer for evenings on deck, and shoes with good grip for wet decks and island lanes. We will send a full packing list after you book.
What will the weather be like in late May?
Late May is one of the loveliest times in the Aeolian Islands. Expect daytime highs around 72 to 77°F (22 to 25°C), evenings around 61 to 64°F (16 to 18°C), and sea temperatures near 68°F (20°C), warm enough for a daily swim.
Costumers of Color, Inc. is a Washington State 501(c)(3) nonprofit. Questions? Email Gigi at costumersofcolor@gmail.com.