How to Plan the Ultimate Bachelor Party in Portland, Maine

It’s about that time of year – wedding planning season. If any of your friends are getting married in the next year then you know, especially if you’re the best man, that planning a bachelor party is one of the most crucial aspects of the whole event. There’s a lot of pressure to plan something that’s not only cool and fun for everyone, but something more unique than the stereotypical Vegas or Nashville. Enter: Portland, Maine.

We’ve got amazing food, endless bars and breweries, and a ton of activities that will work for everyone in your group. For the most unforgettable bachelor party Portland Maine has to offer, keep reading to find out some must-do’s while you’re here.

Bar-Hop the Old Port

There are seemingly endless bars and restaurants in the Old Port section of the city, with everything from tiny Irish pubs to dance clubs and beyond – there is truly something for everyone. Some of our recommended spots include:

Gritty McDuff’s

Gritty’s has been around forever and is your classic local bar. With plenty of brews on tap and a full bar, sit your crew down at one of the many long family-style tables and get your night started.

Amigos

Definition of a dive bar, complete with strong drinks and an interesting crowd. It’s super casual, complete with billiards, darts and a heated outdoor patio, and one of the spots you’ll want to be for last call.

Pearl Nightclub

Possibly one of the only nightclubs you’re going to find in Maine, Pearl is where you want to be for that ultimate club scene. Go for a few cocktails and check out their massive dance floor, which is always packed.

Bonfire

Looking for a country bar? Bonfire is your spot. Call it a dive bar with a country twist. The drinks come in red solo cups, country music videos play on the TVs, and there are authentic saddle swings throughout.

Oasis

Mixing in a little bit of everything, Oasis has three sections: a bar with giant Jenga, a dance floor upstairs with Mario Kart on a projector, and an outdoor bar that often has live music. You won’t regret this one unless you order their infamous rum bucket.

Mix In a Unique Activity

Every great bachelor party needs one unforgettable experience—and a private boat charter is one your group will be talking about long after the weekend is over.

Instead of hopping from one crowded bar to the next, get out on Casco Bay for a few hours and experience Portland from the water. With Sail Portland Maine, your group gets exclusive use of the boat, giving you the freedom to relax, celebrate, and enjoy the harbor at your own pace.

Bring your favorite drinks and snacks, connect to onboard Starlink WiFi to share photos in real time, turn up your own playlist, and soak in panoramic views of Portland’s working waterfront, historic forts, islands, and lighthouses. Whether you choose a daytime cruise or a sunset charter, it’s the perfect way to kick off the celebration—or recover from the night before.

Our private charters are ideal for bachelor parties because there are no strangers onboard, no fixed sightseeing script, and no crowded decks. It’s just your crew, an experienced local captain, and one of the best views in Maine.

If you’re looking for a bachelor party activity that’s equal parts relaxing, memorable, and uniquely Portland, make a private charter with Sail Portland Maine the centerpiece of your weekend. It just might end up being everyone’s favorite part of the trip.

Hit the Local Breweries

There are so many incredible Maine breweries it can be hard to pick. Some of our favorites include:

• Allagash Brewing Company
• Bissell Brothers Brewing Company
• Rising Tide Brewing Company
• Lone Pine Brewing Company
• Austin Street Brewery
• Foundation Brewing Company
• Goodfire Brewing Company
• Battery Steele Brewing
• Oxbow Bottling & Blending
• Definitive Brewing Company

You can’t go wrong with any of the Portland breweries – each one offers a unique taste and perspective. This is the ideal way to spend a sunny Saturday!

Eat Lobster (In Every Form Possible)

You can’t visit Maine without eating lobster – especially Portland, which is one of the largest fishing hubs in the state. There’s no fresher lobster out there, and there are seemingly endless restaurants that offer this delectable catch.

Highroller Lobster Co. is the easiest way to try lobster in a million different ways – they have lobster grilled cheese, lobster tacos, and “lobby pops” which are fresh lobster tails on a stick. Make sure you stop by the deck of Portland Lobster Co. for their huge lobster rolls and some live music. If you want to treat yourselves, head over to Eventide Oyster Co. for their renowned brown butter lobster roll, which comes in a fluffy bao bun. Our mouths are watering!