Baltimore
October 30-November 1, 2026

Come to Baltimore for a Halloween weekend with Debauchery Travel Crew, where the city’s historic charm meets after-dark energy. We’ll kick things off with an indulgent dinner in an intimate, sultry setting, featuring delicious food, cocktails, and plenty of time to get dressed up and settle into the weekend’s mischievous mood.

From there, we’ll continue the party for a spirited neighborhood crawl filled with elaborately decorated bars, creative Halloween costumes, festive drinks, music, and Baltimore nightlife, with plenty of opportunities to mingle, dance, and make questionable decisions in the best possible way.

We’ll keep the energy going with a night of karaoke, cocktails, laughter, and unapologetic performances, so start thinking about the song you’ve been waiting for your moment to sing. Expect a weekend filled with costumes, great food, cocktails, dancing, music, late nights, and good people, all wrapped in that unmistakable Baltimore energy.

Dress up. Go out. Get into a little trouble. 🎃🥂

Book

Trip Overview

What's Included

For the weekend, we’ll be staying in a spacious Baltimore retreat designed for fun and relaxation...after the fun. There’s plenty of room to get comfortable and recharge between adventures.

Located just a short distance from downtown Baltimore, the house puts us close to dining, entertainment and nightlife, with the Inner Harbor just minutes away. It’s the perfect home base for a Halloween weekend in Charm City—spacious enough for the crew to spread out, comfortable enough to relax between activities, and close enough to the action that the fun doesn't have to stop when we leave the house.

Queen Room (up to 2 people) - $575
Solo Spot (in shared room) - $275
All room bookings include daily breakfast and a ticket for the Halloween Bar Crawl

For this trip, we are also offering a Weekend Party Pass option for $150 per person, which includes:

Access to the property on Friday and Saturday (exit by 4 AM)
Refreshments for Play Parties at the property on Friday and Saturday
Attendance for Karoake at a Karoake Bar
Ticket for Halloween Bar Crawl with one free drink included
VIP section at Tabu (You must pay for your Tabu door entry)
Bottomless Brunch at a restaurant (food and mimosas included)
To book, visit the booking page.

Amenities

5 Bedrooms | 2 Full Bathrooms
Fully Equipped Kitchens
Smart TVs Throughout
Spacious Living Area
Wi-Fi
Hot Tub

Itinerary

Friday, October 30

Welcome drinks
Group BDSM themed Dinner at a restaurant
Speakeasy
Strip Club
Afterhours Play Party at the property

Saturday, October 31

Halloween Bar Crawl with an organized group
Karoake at a Karoake Bar
VIP Sections @ Tabu
Afterhours Play Party at the property

Sunday, November 1

Bottomless Brunch at a restaurant

Note: Itinerary is subject to change. Activities are an additional cost and will be booked closer to the trip date.

What to bring