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Italy by the Glass

8-Day Italian Wine & Food Journey with Chelsea and Gigi

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):

At a Glance

  • March 31 to April 7, 2027
  • Tuscany, Emilia-Romagna, and the Veneto
  • Limited to 6 travelers, plus trip leads
  • €3,900 per person double occupancy
  • €4,500 per person single occupancy
No money is due until after we meet with you via Zoom. After our meeting, a €500 non-refundable deposit reserves your place. Deposits are due by September 1, 2026. The final balance is due October 31, 2026. Because this journey is limited to eight travelers, spaces cannot be held without a deposit. Please note that all trip prices are quoted in Euro (€).
This trip is open to travelers of all races/ethnicities. We ask every participant to help create a respectful, anti-racist, and community-minded travel environment.
Wine Journey Interest Form

Our Inaugural Inclusive Wine Journey

Travel with wine expert Chelsea Stephens, PhD and social scientist Gigi Coulson, M.S. for an intimate Italian journey designed for curious travelers who want more than a tasting room checklist. This carefully paced experience explores Italy through wine, food, social history, landscape, and community.
From the Medici legacy of Florence to the fortress culture of Montalcino and Romagna, from Chianti Classico and Brunello di Montalcino to dry Lambrusco and Veneto sparkling whites, each day is built as a chapter in a larger story: how Italian wine reflects land, labor, class, trade, family, memory, and place.

This is not a big-bus tour. It is a small, conversational journey for travelers who want context, connection, good food, and wines that open the door to history. Because this trip is intentionally limited to six travelers, space is extremely limited. Interested travelers are encouraged to request information early.

  • Focus: Italian wine, foodways, social history, cultural landscapes, and regional identity
  • Pace: intimate, educational, sensory, and thoughtfully paced
  • Regions: Tuscany, Emilia-Romagna, and the Veneto
  • Lodging : 4 or 5 star boutique inns near San Casciano in Val di Pesa and near Castel San Pietro Terme

What is Included

Included in the trip price:

  • 7 nights lodging in carefully selected 4 or 5 star accommodations
  • Arrival transfer from Florence airport to Tuscan villa lodging
  • Return transfer from Bologna-region lodging to Florence airport
  • Group transportation for scheduled itinerary activities
  • Winery, enoteca, and tasting appointments listed in the final itinerary Daily breakfast
  • 6 selected group meals, including welcome and farewell dinners
  • Educational leadership by Gigi Coulson, M.S., and Chelsea Stephens, PhD
  • Curated discussions on wine, foodways, social history, and regional identity
  • Planning, coordination, and reservation management for the group itinerary

Not included:

  • Airfare
  • Travel insurance
  • Personal purchases and wine shipping
  • Meals or drinks outside the group itinerary
  • Optional activities during free time
  • Passport, visa, baggage, medical, or other personal travel costs
  • Tips and gratuities unless included in final trip materials

Led by Chelsea and Gigi

Chelsea Stephens, PhD, is a sommelier and wine educator (WSET L2) who brings technical knowledge, tasting guidance, and a deep appreciation for the cultural life of wine. Chelsea will help travelers understand grape varieties, regional styles, winemaking choices, and how to taste with confidence and curiosity. Learn more about Chelsea here.

Gigi Coulson is a scientist, historical costumer, historian, and longtime scholar whose research and interests center cultural heritage, community, identity, and the stories told through dress and place. Gigi brings 15 years of study of Italian history to this journey, with special attention to social context, historical memory, and the lived experience behind monuments, meals, and landscapes.Learn more about Gigi here.

Together, Chelsea and Gigi create a journey that blends scholarship and pleasure: serious enough to be meaningful, relaxed enough to be joyful.
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):
Wine Journey Interest Form
Chelsea Stephens, PhD
Gigi Coulson, M.S.

Journey Gallery

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 here:

Travel insurance is strongly recommended. All trip fees are nonrefundable. Find the best fit for your needs here https://www.forbes.com/advisor/l/best-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.
Terms & Conditions PDF

Frequently Asked Questions

Do you offer refunds?
All tickets, trip deposits, and trip payments are non-refundable. If you would like to transfer your ticket, deposit, or payment to someone else please email Gigi at costumersofcolor@gmail.com
Click the “Wine Journey Interest Form” button to send us your information. Shortly after, you’ll receive an email from us with further instructions on how to schedule a videoconference, make your deposit, and confirm your reservation. Spots are reserved on a first come, first served basis.
March 31 to April 7, 2027
This retreat is perfect for wine lovers, food enthusiasts, and curious travelers who want a deeper taste of Italy, culturally and literally. You don’t need to be a wine expert, just someone who enjoys good company and beautiful places. If you appreciate quality over quantity and authentic experiences over tourist traps, you’ll love this trip.
€3,900 per person for double occupancy. Single supplement is +€600 (€4,500 total for solo travelers).
  • 7 nights in a 4 or 5-star historical accommodations
  • Daily breakfast + 4 dinners + 2 lunches (all with wine)
  • 5 boutique winery visits & tastings
  • Olive grove visit & olive oil tasting
  • Wine pairing guidance
  • Private minivan shuttle + Florence airport transfers
    • Arrival transfer from Florence airport to Tuscan villa lodging
    • Return transfer from Bologna-region lodging to Florence airport
    • Group transportation for scheduled itinerary activities
  • Winery, enoteca, and tasting appointments listed in the final itinerary
  • Educational leadership by Gigi Coulson, M.S., and Chelsea Stephens, PhD
  • Curated discussions on wine, foodways, social history, and regional identity
  • Planning, coordination, and reservation management for the group itinerary
  • All entrance fees, activities, and taxes
  • Airfare to/from Italy
  • Travel insurance (highly recommended)
  • Meals not listed in the itinerary
  • Alcoholic beverages, meals, or drinks outside of included meals & tastings
  • Optional activities during free time
  • Passport, visa, baggage, medical, or other personal travel costs
  • Personal purchases & wine shipping
  • Tips and gratuities unless included in final trip materials
Of course! Pricing is based on double occupancy, so solo travelers pay a single supplement of +€600. You’ll have your own private room and bathroom.
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.
  • Spring is a beautiful time to visit Italy!
    • Tuscany, usually has mild and pleasant temperatures. You can expect daytime highs around 63-70°F (17-21°C) with cooler evenings of around 46-50°F (8-10°C).
    • In Emilia-Romagna, April brings mild, pleasant spring weather, with average daily highs in the mid-to-high 60s°F (18–20°C) and chilly nighttime lows in the mid-40s°F (7–9°C). Light rainfall is possible, so bring a rain jacket or umbrella.

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