Annapolis in 1 Day for Friends - Private-group format (corporate, bachelor/bachelorette, friends & family)
In Collaboration with Tipsy Bay Co.. Updated on February 13, 2026.
Private-group version of the Tipsy History tour: a guided historical pub crawl through downtown Annapolis that pairs short history talks with recommended period drinks. Timed with happy hour, the tour meets at Galway Bay on Maryland Avenue and moves through downtown's walkable historic core. Guests choose and pay for their own drinks; the guide provides stories, pacing, and directions. The tour is
This itinerary was created in collaboration with Tipsy Bay Co., inspired by the tour Tipsy History: The Private Group Historical Pub Crawl. Please check the tour information during your booking process.
Highlights
- Private-group format (corporate, bachelor/bachelorette, friends & family)
- Guided historical stories tied to colonial rum, Maryland whiskey, and Prohibition
- Timed to happy hour in downtown Annapolis
Itinerary
Day 1
Two-hour private pub crawl through downtown Annapolis. Meet at Galway Bay (Maryland Avenue) at 16:00 for check-in and introduction; the guide will lead three short stops with local history tied to recommended period drinks.
Meet & check-in — Galway Bay
Gather at Galway Bay on Maryland Avenue for group check-in, ID check (21+), safety briefing, and short introduction to the Tipsy History format and route.
Tips from local experts:
- Arrive 10 minutes early to allow time for check-in and ID verification.
- Bring government-issued photo ID for all guests aged 21+ — the guide will check IDs before entering pubs.
- Wear comfortable shoes for walking on brick sidewalks; rain or shine the tour runs as scheduled.
First pub stop — Galway Bay (history & recommended drink)
Short guided talk linking early Annapolis drinking culture to colonial rum followed by time to order the guide's recommended period-style drink or a beverage of your choice.
Tips from local experts:
- If you prefer to keep the group moving, choose beer, wine, or a single serving spirit rather than a large-format cocktail.
- Ask staff about happy-hour menus — many downtown pubs offer reduced-price drink options during this time.
- If anyone in the group prefers non-alcoholic options, request them early to avoid slowing the group.
Walk down Main Street toward City Dock (stroll & quick historical notes)
A short guided walk along Main Street from Maryland Avenue toward City Dock. The guide will share stories about waterfront trade, distilling, and Prohibition-era Annapolis while the group moves between stops.
Tips from local experts:
- Keep to the right on narrow brick sidewalks and watch for occasional delivery vehicles on Main Street.
- Use this short walk to stretch and hydrate; public restrooms are limited on the route so plan ahead.
- If someone needs step-free access, let the guide know — alternate, level routes are available on request.
Second stop — City Dock area (history tied to maritime spirits)
Stop near City Dock for a guided story about Annapolis’ maritime spirit trade and the local distilling tradition; time to order a drink at a nearby pub or tavern chosen by the guide.
Tips from local experts:
- City Dock can be busy during happy hour; follow the guide's instructions to keep the group together.
- If you plan to sit on the dock or nearby benches, keep an eye on personal items — waterfront areas are open to the public.
- Split tabs within your group if ordering separately to speed up service between stops.
Short walk to Church Circle
A brief walk uphill toward Church Circle where the final stop and the tour wrap-up will take place. The guide will note historic buildings along the way.
Tips from local experts:
- The walk to Church Circle includes short stair sections in places; guests who need a gentler route should notify the guide.
- Watch for traffic at intersections; the guide will cross with the group for safety.
- This is a good moment to use restrooms if needed — plan to do so before the final pub stop.
Final pub stop & tour wrap-up — Church Circle area
Final guided segment focusing on local figures who flouted Prohibition and how modern Annapolis remembers that era. Time to order a closing drink, ask questions, and conclude the tour.
Tips from local experts:
- Conclude responsibly: pace drinks during the final stop and use rideshare or taxis if needed after the tour.
- If your group is large, request separate checks early to keep service efficient during the busy evening period.
- If anyone requires step-free seating or quieter space, notify staff on arrival — many Church Circle venues can accommodate with advance notice.
Itinerary Attributes
| Days | 1 |
| Highlights | 3 |
| Season | - |
| Month | - |
| Persona | Friends |
| Transfers | - |
| Restaurants | 1 |
| Total Activities | 6 |
| Total Places | 6 |
| Activities Types | Restaurant, Nightlife, Neighborhood |