Stroll historic MacMillan Pier while learning about Provincetown’s fishing fleet, maritime history, whale watching industry, and the arrival point of many visitors to the Outer Cape. Guests will enjoy harbor views, working waterfront activity, and some of the best photo opportunities in Provincetown.

Walk through one of Provincetown’s most colorful hidden spaces while learning about the town’s rebellious art culture, outsider artists, and free-spirited creative history. Guests will explore the famous mural-covered alleyway, hear the story of artist Bob Gasoi, and enjoy one of Provincetown’s most unique photo opportunities.

Pilgrim Monument & Mayflower Bas Relief Walk to the base of Provincetown’s iconic Pilgrim Monument while learning about the Mayflower Pilgrims’ first landing in Provincetown Harbor in 1620 and the signing of the Mayflower Compact before the group later continued on to Plymouth. Guests will view the famous Mayflower bas relief sculpture and hear how Provincetown became the Pilgrims’ first stop in the New World.

Walk along the heart of Provincetown while exploring Commercial Street’s colorful mix of local shops, art galleries, historic architecture, restaurants, theaters, and street life. Guests will experience the town’s unique artistic and free-spirited culture while hearing stories about Provincetown’s history as one of America’s oldest art colonies and one of the country’s most iconic LGBTQ+ destinations.

Enjoy tastings at one of Provincetown’s longtime waterfront favorites during its final season after decades on Commercial Street. Guests will experience the lively energy of Provincetown harbor while enjoying food tastings and hearing stories about the restaurant’s long history as a gathering spot for locals, tourists, artists, and nightlife crowds. This stop highlights Provincetown’s mix of seafood, hospitality, and vibrant waterfront culture.