Gelato Fiasco Old Port is a great spot for a first date. They serve Italian-style gelato and sorbet made with local ingredients at very reasonable prices. Located in the heart of the Old Port, it’s easy to extend the date with a walk along the waterfront or by popping into nearby shops. For parking, the most convenient option is the Old Port Square Garage right next door at 427 Fore Street, Portland, ME 04101. You can sample as many flavors as you wish before deciding, and there are abundant dairy-free and gluten-free options.
EVO Rock + Fitness Portland is a fun, adventurous choice for a first date with a strong sense of community. This indoor climbing gym offers bouldering and auto-belay routes, making it easy for beginners to jump right in with rental gear available. If you’ve never climbed before, bouldering is a great place to start—no training required, and you can climb only as high as you’re comfortable. Beyond climbing, EVO offers yoga classes and fitness equipment, and they intentionally foster a welcoming, inclusive environment for climbers of all levels. With friendly, supportive staff and affiliation nights that create accessible spaces for women and folks in the BIPOC and LGBTQ+ communities, it’s easy to feel comfortable and at ease from the moment you walk in.