Private Tour
Available languages
1 hour 30 minutes
Mobile ticket
Toast to Ptown’s past on a Commercial Street stroll blending craft cocktails and bohemian history. Perfect for drink lovers and history buffs, this tour celebrates our maritime, artistic, and LGBTQ+ legacy.
Kick off at local establisment with a Cape Cod Blueberry Martini. Enter the Old Colony Tap Room, one of America's oldest, most weathered dives made completely from old shipwrecks. Pass the iconic Lobster Pot and Governor Bradford to stop at Lopes Square to see its 1801 anchor, and learn about the old colony railroad. Look up at the UU Meeting House’s 1847 Greek Revival steeple, then head into the Ptown Library to glimpse the grand schooner inside.
Pay homage to literary history at the Atlantic House (A-House), a 1798 tavern loved by Tennessee Williams. Next, keep the energy high with a shaken Espresso Martini at a local favorite. Finally, wrap up at the famous Boatslip Resort for the legendary Tea Dance—a disco-fueled, open-air tradition pulsing since the 1970s.
Service animals allowed
Public transportation options are available nearby
Suitable for all physical fitness levels
All Tours End at Bubalas Restaurant @5pm
For a full refund, cancel at least 24 hours before the scheduled departure time.
Sip a Blueberry Martini surrounded by views of Ptown Harbor. Stroll past the Lobster Pot to the Old Colony Tap, a gritty 1937 dive built with shipwreck wood where fishermen swap tales. Pause at Lopes Square, where an 1801 anchor marks the 1873 Old Colony Railroad path—the line that brought artists like Eugene O’Neill to town. Mingle at Cannery Wharf Park for stunning waterfront views, then spot the UU Meeting House’s 1847 Greek Revival steeple, a beacon of inclusion since 1829. Next, head inside the Ptown Library, a former 1860 church, to marvel at the Rose Dorothea, an incredible half-scale schooner right inside the reading room! Pass the Atlantic House, a 1798 tavern where Tennessee Williams wrote plays, Billie Holiday sang in 1955, and the LGBTQ+ community found refuge since the 1920s, making it one of America’s oldest gay bars. Then, elevate the energy with a shaken Espresso Martini at an iconic waterfront landmark as nightlife begins to glow. Finally, conclude at the famous Boatslip Resort (est. 1965). Join the legendary, open-air Tea Dance, a disco-fueled LGBTQ+ tradition pulsing since the 1970s. It's the ultimate mix of history, drinks, and fabulous company!
starter
Cocktail-Cape Cod Blueberry vodka Lemonade
Made with Fresh Blueberries Served at an Iconic Spot with Fabulous Harbor Views! Great Spot for photos!
dessert
Espresso Martini
The best in Provincetown and will get you amped for Provincetown's famous Tea Dance.
Espresso Martini - Cape Cod Blueberry Martini
2 Hours of Rich Provincetown History
one Slice of piping hot fresh Pizza pp Choice of Cheese or Pepperoni
Gratuities
Martinis & Mingle-no pizza
choosing this option provides cover to enter the famous tea dance held everyday in the Summer from 4:00pm to 7:00 pm.
Spiritus Pizza Slice: enjoy a delicious pizza slice from famous Spiritus pizza! Enjoy your choice of Cheese, Greek or pepperoni
21 reviews
Total reviews and rating from Viator & Tripadvisor
jeanmarie s,Sep 27, 2025
- Review from Tripadvisor
What’s better than martinis & friends? Add Cathy as your host/tour guide! She’s accommodating, entertaining and full of fun facts about Ptown. So happy we booked!
Linda C,Sep 5, 2025
- Review from Viator
Lots of history and local lore will be provided on the tour. You will receive tons of restaurant and experiential suggestions. Cathy was a lot of fun. I would suggest this tour for groups and couples.
Sophy B,Sep 2, 2025
- Review from Viator
Cathy was an amazing guide. She was very knowledgeable about the history of Provincetown and all the people who made it what it is today. The pizza at Spiritu is perfectly toasty and cheesy. The Espresso Martini at Babalu divine.
debbyp593,Aug 30, 2025
- Review from Tripadvisor
Cathy was amazing!! We enjoyed every minute of the tour!! She is the hest!😂 we started out in the rain and ended in the rain but she made it so much fun hoping in and out of places! Learned so much about Provincetown! Recommend the tour!!
Sara R,Aug 26, 2025
- Review from Viator
Well worth it! Cathy is fun and really knows her stuff. I want to do another of her tours next visit.
choogirl39,Aug 23, 2025
- Review from Tripadvisor
Wonderful tour with a great guide. We did this tour at the end of our first day exploring the Cape, and it was perfect. Cathy is so personable and makes the tour fun and informative. The drinks are great, the scenery is beautiful and her knowledge of Ptown and its history makes for a fabulous tour! We highly recommend this!
Mona P,Aug 8, 2025
- Review from Viator
We had a wonderful time on the tour. The tour- and the jokes- were personalized as we were the only ones on the tour that day. And the choice of restaurants for drinks and pizza were fabulous. We also learned a lot about the history and art of the town.
Brendan L,Jul 31, 2025
- Review from Viator
Our guide Cathy was great, great local knowledge, high energy, clearly a local. She was very informative and had a lot of inside information. Pacing was good, she had good conversational skills and was willing to be flexible. Highly recommend.
derekdasilva24,Jul 30, 2025
- Review from Tripadvisor
Great Tour!! Very informative and very interesting! Cathy is great and very fun!!! Beautiful time in P Town!!!
Kathie W,Jul 24, 2025
- Review from Viator
Cathy was exceptionally knowledgeable in Provincetown history from when it was settled to the present time. She had a great personality which made the day a fun experience. Both cocktails were very good and the pizza was great. Would definitely recommend to others
Operated by Cathy