Wine Tasting at Cellardoor Winery

Embark on a romantic evening of wine tasting at Cellardoor Winery in Portland. Sample a variety of local wines while taking in the beautiful scenery of the vineyard. Learn about the winemaking process and discover new favorite blends to enjoy with your partner.

Alternative options: Maine Mead Works, Urban Farm Fermentory

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Sunset Cruise on Casco Bay

Experience the beauty of Casco Bay aboard a sunset cruise with your loved one. Enjoy breathtaking views of the coastline as the sun dips below the horizon. Sip champagne and savor the moment as you relax on the water.

Alternative options: Lucky Catch Cruises, Portland Schooner Company

Dinner and a Show at Portland Stage

Plan a night out on the town with dinner and a show at Portland Stage. Enjoy a delicious meal at a nearby restaurant before heading to the theater to catch a live performance. Immerse yourself in the arts and create lasting memories with your partner.

Alternative options: Merrill Auditorium, State Theatre

Walk around Old Port

Take a leisurely stroll through the historic Old Port district of Portland. Explore charming cobblestone streets lined with shops, restaurants, and galleries. Stop for a drink at a local bar or cafe and soak in the atmosphere of this bustling neighborhood.

Alternative options: East End Promenade, Eastern Prom Trail

Cooking Class at Stonewall Kitchen

Unleash your inner chef with a cooking class at Stonewall Kitchen. Learn new culinary skills and techniques while preparing a delicious meal with your partner. Enjoy the fruits of your labor together and take home new recipes to recreate at home.

Alternative options: Salt & Honey Cooking School, Fork Food Lab

Relaxing Spa Day at Inn by the Sea

Indulge in a day of pampering and relaxation at the spa at Inn by the Sea. Treat yourselves to a couples massage, facial, or body treatment. Unwind in the serene atmosphere and rejuvenate your minds and bodies.

Alternative options: Soakology, Rejuvenation Day Spa

Brewery Tour at Allagash Brewing Company

Beer lovers will delight in a brewery tour at Allagash Brewing Company. Learn about the brewing process and sample a variety of craft beers. Take a behind-the-scenes look at how your favorite brews are made and enjoy a fun outing with your partner.

Alternative options: Bissell Brothers, Shipyard Brewing Company

Bowling at Bayside Bowl

Get competitive with a night of bowling at Bayside Bowl. Enjoy a friendly game or two while sipping on cocktails and snacking on delicious food. Strike up some fun conversation and let loose with your partner at this lively bowling alley.

Alternative options: Saco Sport & Fitness, Colonial Bowling Center

Ice Skating at Thompson’s Point

Embrace the winter season with a romantic ice skating outing at Thompson’s Point. Glide hand in hand with your partner on the ice under the twinkling lights. Warm up with hot cocoa afterwards and enjoy the magical ambiance of the winter wonderland.

Alternative options: Troubh Ice Arena, Biddeford Ice Arena

Paint Night at Muse Paintbar

Get creative with your partner at a paint night at Muse Paintbar. Unleash your artistic side as you follow a step-by-step painting tutorial with expert guidance. Sip on wine or cocktails as you create a masterpiece together to cherish as a memento of your date night.

Alternative options: Pinot’s Palette, Wine & Design

Are you ready to treat yourselves to a much-deserved night out in Portland, ME? Hire a trusted and reliable babysitter through Wyndy to ensure that your kids are in good hands while you enjoy your date night. Create lasting memories with your partner and rekindle the romance in your relationship with a fun and exciting outing in this charming city by the sea.