What does AI say about planning a bachelor or bachelorette party in the Chesapeake Bay region?

Story by Eli Wohlenhaus (and some AI programs)

According to several AI programs, fishing or being out on the water is the popular thing to do for bachelor parties in this region.

Outside of Chesapeake Bay Wedding Magazine, I juggle a lot here. One of the more interesting aspects of what I do, however, is research and test ways our company can integrate artificial intelligence into our newsrooms in an ethical way. I won’t go too deep explaining how complex it can be, but I thought it would be fun to see what different programs would answer when given a prompt about bachelor and bachelorette parties. I wonder if you will notice the same thing I did.

Prompt: In fewer than 150 words, could you please plan a bachelor party for a group of 4-8 in the Chesapeake Bay region of Maryland?

Response by Gemini

Plan a weekend getaway in Annapolis, Maryland. Book a waterfront house or a few hotel rooms. Start Friday evening with dinner and drinks at a local pub. On Saturday, charter a fishing boat for a half-day of fishing on the Chesapeake Bay. Afterward, head to a brewery for a tasting and lunch. Later, explore historic downtown Annapolis, grab dinner, and enjoy the nightlife. Sunday can be a relaxed brunch before everyone departs. This plan balances outdoor activities, good food and drink and a fun nightlife, making it suitable for a range of interests.

Response by ChatGPT

Kick off with a morning fishing charter out of Kent Island for rockfish and blue crabs, followed by a dockside lunch with fresh seafood and local craft beer. In the afternoon, rent kayaks or a pontoon to explore secluded coves, or hit a nearby golf course for nine holes. Check into a waterfront Airbnb or inn in St. Michaels or Annapolis. Enjoy a private oyster-shucking and bourbon tasting before a dinner of Chesapeake classics like crab cakes and oysters Rockefeller. End the night with live music at a waterfront bar or a fire pit by the bay.

Response by Claude

Here's a solid bachelor party plan for the Chesapeake Bay area:

Day 1: Start with a chartered fishing trip or crab boat excursion from Annapolis — book a half-day charter that includes beer and lunch. Afternoon at Historic Inns of Annapolis for drinks and exploring the Naval Academy area. Evening dinner at The Boatyard Bar & Grill with waterfront views.

Day 2: Morning kayaking or paddleboarding in the bay, followed by a brewery tour — Union Craft Brewing or Heavy Seas Beer are great options. Afternoon activities could include axe throwing at Bad Axe Throwing in Baltimore or topgolf.

Evening/Night: Hit Federal Hill or Fells Point in Baltimore for bar hopping — start at The Wharf Rat, then Pickles Pub for a more casual vibe.

Accommodation: Consider renting a waterfront house on VRBO or staying at Graduate Annapolis for easy access to nightlife.

Budget: Expect $200-400 per person depending on charter boat choice and accommodation level.

Response by Perplexity

Plan a Chesapeake Bay bachelor party packed with fun and local flavor.

Start with adventure: Charter a private tiki boat or sailing cruise from Annapolis for BYOB fun on the water, or book a group fishing trip. For more action, try axe throwing or jet ski rentals near the waterfront.

Explore classic Maryland: Feast on steamed crabs at a renowned crab shack like Cantler’s or Dock Street, or chill at a waterfront dock bar such as Libbey’s Coastal Kitchen or The Point Crab House for drinks and bay views.

Nightlife: Bar-hop along Annapolis’s Main Street, especially Dock Street, for live DJs and late-night fun. Alternatively, visit Ocean City for high-energy clubs and boardwalk vibes.

Customize: Add golf, a brewery tour, or history at the Naval Academy to round out the trip. Whatever you choose, book in advance for popular summer weekends.

Prompt: In fewer than 150 words, could you please plan a bachelorette party for a group of 4-8 in the Chesapeake Bay region of Maryland?

Response from Gemini

Plan a relaxing and celebratory weekend in Annapolis or St. Michaels. Book a waterfront house for a home base.

Friday evening: Arrive and settle in with a casual dinner at a waterfront restaurant with outdoor seating.

Saturday: Enjoy a morning of pampering at a local spa. In the afternoon, head to a nearby winery or brewery for a tasting, or consider a sunset cruise on the Chesapeake Bay for stunning views. In the evening, have a nice dinner out and then explore the town's nightlife.

Sunday: Sleep in, enjoy a leisurely brunch, and then head home, refreshed and ready for the wedding. This plan offers a mix of relaxation, scenic beauty, and celebratory fun for the whole group.

Response from ChatGPT

Start with a private brunch cruise from Annapolis, mimosas in hand while taking in bay views. Spend the afternoon at a local spa or winery such as Great Frogs for tastings and charcuterie. Check into a chic waterfront Airbnb in St. Michaels or Kent Island, where you can relax by the water. Enjoy a sunset sail, then head to a farm-to-table restaurant for fresh seafood and seasonal dishes. End the night with dancing at a lively Annapolis bar or a cozy bonfire with champagne back at your stay.

Response from Claude

Here's a fun bachelorette party plan for the Chesapeake Bay area:

Day 1: Start with a wine cruise or sunset sail from Annapolis — many charters offer champagne packages. Afternoon spa session at Westin Annapolis or a group massage at a local spa. Evening at The Graduate Annapolis rooftop for cocktails with harbor views.

Day 2: Morning yoga on the water or a scenic bay cruise. Afternoon wine tasting in nearby countryside — Boordy Vineyards or Black Ankle Vineyards offer group experiences. 

Evening: Dinner at Iron Rooster for upscale comfort food, then bar hopping in downtown Annapolis — start at Pusser's Caribbean Grille, then hit West Street for dancing at Stan & Joe's Saloon.

Alternative: Rent a waterfront Airbnb on the Eastern Shore for a more intimate weekend with private chef dinner.

Activities: Consider paddleboard yoga, pottery painting, or a cooking class.

Budget: $250-450 per person including accommodation and activities.

Response from Perplexity

Celebrate a Chesapeake Bay bachelorette party with a perfect blend of relaxation, fun, and local flair.

Day on the Bay: Start with a private chartered boat cruise (tiki or sailboat) for your group out of Annapolis or Kent Island — bring snacks, bubbly and music.

Pampering: Book a group spa session or yoga class at a resort spa like The Inn at Chesapeake Bay Beach Club.

Eat & Sip: Savor steamed crabs at Cantler’s or enjoy brunch and bay views at Libbey’s Coastal Kitchen. Add a wine tasting at a nearby vineyard or a casual waterfront brewery stop, like Cult Classic Brewing.

Nightlife: Head to Annapolis’s Main Street for chic cocktail bars, rooftop lounges or live music. For extra fun, organize a pedal party bike tour through the historic district.

Customize: Plan sunset photos on the beach or a keepsake craft session at an art studio. Book early for weekend dates.

Conclusion

I found it fascinating while doing this how alike a lot of these programs’ responses were. It’s also hard to argue with the reality that life and activities in this area rely on the Chesapeake Bay. I did find these answers to be too narrow of a focus, however. That could have been fixed with further prompting.

If you find yourself needing some brainstorming help, any of these programs would work great, especially because you can tailor your prompt for your group better. For example, your group may want to go to a sporting event, or you may want to go golfing, shopping or try out a new hobby. Adding to the prompt “the bride enjoys reading, singing, basketball and pasta” would help.