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NY By The Glass

7-day small-group wine retreat with Chelsea and Gigi

The Experience

Join Us in the NY Finger Lakes wine region, on a journey shaped by cultural history, regional food, and great company.

To request a place 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):

Interest Form

AT A GLANCE

No money is due until after we meet with you via Zoom. After our meeting, a $500 non-refundable deposit reserves your place. The final balance is due May 1, 2027. Because this journey is limited to six travelers, spaces cannot be held without a deposit. All trip prices are quoted in US dollars.

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.

OUR SECOND BY THE GLASS JOURNEY

Travel with wine expert Chelsea Stephens, PhD and social scientist Gigi Coulson, M.S. for an intimate four-day retreat in one of America’s most historically layered wine regions. The Finger Lakes of upstate New York is home to more than 140 wineries, two of the country’s most significant Underground Railroad corridors, and landscapes shaped by Indigenous nations whose names are still carried by the lakes themselves.

This carefully paced experience moves from Cayuga Lake wine country, where Harriet Tubman made her permanent home after escaping slavery, to the Finger Lakes Wine Train along Seneca Lake, through the historic Keuka Lake wine region, and to the Harriet Tubman National Historical Park in Auburn. Along the way, we will sit with the full story of this landscape: the freedom seekers who traveled these routes, the Haudenosaunee nations whose land this was and is, and the complicated legacy of the women’s suffrage movement born at Seneca Falls. We name what history too often leaves out.

This is not a big-bus wine tour. It is a small, conversational retreat for travelers who want context, connection, beautiful wine, and an honest engagement with the places they are visiting. Space is extremely limited to six travelers. Interested travelers are encouraged to request information early.

Interest Form

Not ready to book, but curious about what’s next?

Join our interest list and you’ll be the first to hear about upcoming By the Glass journeys, along with occasional notes on wine history, regional food culture, and the places we’re researching for future trips. Email at [email protected] and ask to be on our mailing list for future trips.

WHAT IS INCLUDED

Included in the trip price:

Not included:

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.

Learn more about Chelsea

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.

Learn more about Gigi

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.

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: https://gigi.maktechgroups.com/policies/

Travel insurance is strongly recommended. All trip fees are nonrefundable. Find the best fit for your needs here: 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.

FREQUENTLY ASKED QUESTIONS

1. 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 [email protected].

2. 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 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.

3. When is this trip?

September 21–27, 2027.

4. Who is this trip for?

This retreat is designed for wine lovers, history enthusiasts, and curious travelers who want more than a tasting room checklist. You don’t need to be a wine expert, just someone who appreciates good company, beautiful places, and stories that go deeper than the surface. If you want your travel to be both joyful and honest, this trip is for you.

5. What is the price of this trip?

$4,400 per person based on double occupancy (2 guests per room, each with their own queen bed). Solo travelers may request a private room for an additional single supplement of approximately $900.

6. What’s included in the price?

7. What’s NOT included in the price?

8. Can I come solo?

Of course. Pricing is based on two guests per room, each with their own queen bed. Solo travelers may request a private room for a single supplement of approximately $900. Contact us to discuss availability.

9. 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. Get quotes from Faye Travel Insurance here.

10. What will the weather be like in the Finger Lakes in late September?

Late September is one of the most beautiful times to visit the Finger Lakes. Fall color begins to appear around the lakes and vineyards, and harvest season is in full swing at the wineries. Daytime temperatures typically run in the low to mid 60s°F (16–18°C), with cool evenings in the 40s°F (7–9°C). Layers are recommended, and a light rain jacket is worth packing.

11. Where do I fly into?

Frederick Douglass Greater Rochester International Airport (ROC) is approximately 45 minutes to 1.5 hours from Lake Canandaigua. Airport transfers are included in your trip fee.

12. What wines will we taste?

The Finger Lakes is celebrated for Riesling (dry, off-dry, and late harvest) as well as Cabernet Franc, Chardonnay, Pinot Noir, and indigenous American varieties including Cayuga White and Vidal Blanc. Chelsea will guide tastings on Cayuga, Seneca, and Keuka lakes. We will also feature wines from New York’s first Black-owned winery as part of our broader conversation about representation in American wine.

13. Is this trip connected to the Underground Railroad history of the region?

Yes, intentionally. Harriet Tubman lived in Auburn, NY (at the northern tip of Cayuga Lake) for the last 54 years of her life. We will visit the Harriet Tubman National Historical Park as part of our history day. We will also facilitate an honest conversation about the Seneca Falls women’s suffrage movement and its complicated legacy for Black women, and about the Haudenosaunee nations whose territory this wine country occupies.