The Ultimate Bachelorette Weekend in Portland, Maine

Looking to plan a memorable bachelorette party or girls weekend in the charming coastal city of Portland, Maine? We’ve got you covered! As locals, we’ve been able to test out so many options, and we curated the ideal itinerary to ensure an unforgettable and (…mostly) elevated experience with the girls! This itinerary is for a summer trip, the most popular time to visit our hometown.

Friday:

• Lunch with Live Music at Portland Lobster Company. Kick off the weekend at Portland Lobster Company, with live music, lobster rolls, and drinks right on the water.
• Get on the Water with a Wine or BYOB Sail or BayCycle Cruise. One of our favorite ways to enjoy Portland is to get on a boat, and there are many options! Pick an afternoon Wine Wise Sail for a classy option, or a BayCycle Cruise, which requires peddling but is also BYOB and a great time! Or, book a BYOB (beer and wine) sail through Portland Schooner Co.!
• Dinner at Via Vecchia. The stunning decor at Via Vecchia, together with its Italian food/cocktails, make it the perfect place for dinner with the girls. Be sure to book a reservation far in advance.
• Pre- or Post-Dinner Drinks at Luna Rooftop or Room for Improvement. These are two of our favorite cocktail spots in Portland. Luna Rooftop is a posh spot and closes a little earlier, and it would probably be worth getting a reservation if you decide to go here. Room for Improvement, is a small spot on the lively Wharf Street, with semi-dive bar vibes but top notch cocktails.

Saturday:

• Brunch at The Friendly Toast. Start your day at this fun brunch spot, with a large menu of breakfast items, including breakfast cocktail flights. Be sure to join the waitlist online before heading over.
• Hit up the Beach or Go Shopping in the Old Port. Hit up a nearby beach (find our suggestions here), or just spend time exploring and shopping throughout the charming Old Port. Our favorite Old Port stores are Fore & Wharf, Bobbles & Lace, and Bella Funk.
• Enjoy a wine tasting or split a bottle(s) at Grippy Tannins. We cannot get enough of Grippy Tannins. Maine is not exactly a wine destination, but this female-owned wine store and tasting lounge curates amazing wines from across the world. Be sure to make a reservation in advance. If you prefer to pour your own glasses for a unique tasting experience, be sure to visit Angoor Wine Bar.
• Dinner at Scales. Time for upscale seafood at Scales, one of our favorites in town. This open-aired restaurant has divine seafood. Be sure to make a reservation far in advance, and get the rolls!
• Stop by the Porthole before and/or dinner for live music. You’ll be able to see the Porthole from Scales, and it’s a fun option in the summer (including in the afternoon) for live music right on the water.
• Dance the night away at Bubba’s. The full name is apparently “Bubba’s Sulky Lounge,” but everyone knows it as “Bubba’s.” Bubba’s is a wild establishment with the most eclectic decor (think, a life-size fake horse, lunch boxes, a canoe, weird dolls, … it’s one of a kind), and the best (and light-up) dance floor in town. Tips: Do NOT walk there – take an uber/cab both ways, and be sure to protect your drink there. Other than that, it’s a blast and hilarious. If you choose to do Bubba’s on Friday night, just know it’s 80s night.

Sunday:

• Brunch at Front Room. If you have some time before you have to depart on Sunday, check out Front Room, a locals’ favorite for brunch, and maybe get a mimosa or bloody mary to cure a hang over?!

Stay Recs:

Here are some options for staying downtown! Note we may make commission off affiliate links (at no further cost to you) if you book through a link below, but we would never recommend a place we don’t genuinely want to recommend.

• Canopy by Hilton: Located on Commercial Street on the edge of Portland’s historic Old Port district. The Canopy hotel has multiple restaurants, including one of the only rooftop bars in Portland, Luna Rooftop Bar. 
• Longfellow Hotel: Located in Portland’s West End. As you step into the beautifully decorated lobby, you’ll find the Twinflower Café in the morning, which transforms into the Five of Clubs bar in the evening. For an even more relaxing experience, visit the on-site Astraea Wellness Spa.
• The Weldon: Located in Portland’s West End, The Weldon offers beautifully designed apartment-style suites with full kitchens, record players, and luxury touches throughout. Guests enjoy access to a modern fitness center, cozy lounge, and easy walkability to the Old Port, arts district, and waterfront.
• The Westin Portland Harborview: A modern hotel located in a historic building with stunning views of the harbor. The Westin features comfortable rooms, an enclosed rooftop bar, and a fitness center.
• Portland Harbor Hotel: Located near the waterfront, this hotel offers the ideal location for exploring all that Portland’s historic Old Port District has to offer.
• Other: There are lots of hotels in Portland. Prices tend to be higher during the summer and early fall, so if these aren’t available to you, we just recommend staying in the Old Port. 

Enjoy your trip to Portland!

– Kasey & Karen