Tell me more, I’ll get better.
Sign up and I'll remember your taste, your people & your saves.
© 2026 Go Playfully Inc
Tell me more, I’ll get better.
Sign up and I'll remember your taste, your people & your saves.
© 2026 Go Playfully Inc
⛵"a highlight of our trip!"
🙌You can help raise the sails if you want
🧣Blankets provided for when it gets chilly
Sail a classic schooner through Boothbay Harbor while the crew works the sails and brings cocktails to your seat. The perfect blend of old-school sailing and sunset views without lifting a finger.
Classic schooner sailing
Sunset harbor views
Kid-friendly crew
Hands-on sail raising
⛵"a highlight of our trip!"
🙌You can help raise the sails if you want
🧣Blankets provided for when it gets chilly
Sail a classic schooner through Boothbay Harbor while the crew works the sails and brings cocktails to your seat. The perfect blend of old-school sailing and sunset views without lifting a finger.
Classic schooner sailing
Sunset harbor views
Kid-friendly crew
Hands-on sail raising