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Annapolis Bachelorette Party

Last weekend, I was in Annapolis, MD for the bachelorette party of one of my closest childhood friends. She’s getting married next month and her twin and I planned the weekend together. If you reside on the Eastern Seaboard, definitely add Annapolis to your list–it’s such a wonderful little city! (If you’ve been reading awhile, you may remember this post.) While it’s probably not the most intuitive destination for a bachelor or bachelorette party, it’s actually a great spot (especially for the latter), thanks to the walkable downtown, location right on the water, and robust food and bar scene. I barely snapped any photos and neglected my phone to enjoy the moment, but wanted to share what we did in case you’re looking to plan a (or have your own) Annapolis bachelorette party.

Most of us arrived on Friday and checked into our Airbnb, which was a lovely house a short drive away from the center of town. It was perfect for the occasion despite sometimes having to sometimes wait about 10 minutes for an Uber/Lyft, but not terrible if you budget for time. We got takeout from Lemongrass and had drinks at the house as people trickled in…it was a low key, fun way to start the weekend.

Annapolis bachelorette party featured by popular Washington DC blogger, Monica Dutia

Three of us drove from DC, two flew into BWI (about a 20-30 minute drive from Annapolis), and one took the Amtrak to New Carrollton and hopped in an Uber to get into town. We didn’t use the one car once after we arrived, so if you can get yourself there and are keeping your activities central–which I recommend you do if you’re there with a group just for the weekend–you really don’t need one.

After a late Friday night, we had a slow Saturday morning and made breakfast at home–this may seem obvious, definitely stock up on tons of groceries beforehand! We made eggs + Crescent rolls + mimosas before heading into town for a two hour sailboat ride. The sail was through Schooner Woodwind and was really nice…two hours is kind of long so be prepared to snag a bottle of wine or prosecco or a beer (unfortunately you can’t BYOB, but prices were reasonable). The expected rain luckily held off and the overcast skies ended up being perfect, so we stuck with our plan to head to Pusser’s for a late lunch + drinks. If the weather is nice, it’s worth trying to snag a table outside because you’re right on the water and there’s a casual, upbeat vibe.

A note on the sailboat: We actually wanted to do a private sail, but I discovered that most affordable options cap out at six people–we had seven–and after that, you’re essentially chartering a large boat the way you would for a big group, office party, etc. One guy I spoke with said that the six person limit has something to do with a Coast Guard restriction and that any more people entail having a certain license, which means needing to go with a larger (and more expensive) operation. That’s what prompted us to do a group sail rather than a private one!

Annapolis bachelorette party featured by popular Washington DC blogger, Monica Dutia

We headed back to the house after lunch for a nap and freshen up before enjoying homemade margaritas on the fenced in porch. This is when we did a couple of traditional bachelorette party games before heading to a 8:15 dinner reservation at Carpaccio. If you’re looking for something nicer and want to make reservations–many restaurants in Annapolis are walk-in only, which makes planning a meal for a group pretty difficult–I highly recommend it even though it’s a little bit of a walk (20 minutes) from the docks and main bar area in town.

After dinner, we ventured down to the bars. I highly recommend taking full advantage of how close everything is downtown and planning accordingly…we went to Federal House, Dock Street Tavern, and Middleton’s as they’re all practically next door to one another. Middleton’s had a fun piano bar that was definitely the most low key; the crowd leaned older and it wasn’t jam packed, which was really nice. We stayed there for a handful of songs and decided to migrate somewhere more lively–Federal House. This place is the other extreme…it literally felt like the basement of a frat house. Fun for a little bit, but just sort of a lot in the the way of college-aged or early 20-somethings and spilled drinks, so we went to Dock Street next. I think I can safely say this was our group’s favorite in the way of music, dancing, and a more manageable crowd. Katie and I had gone there earlier in the night on this trip and just like last time, the bartenders were so incredibly nice.

Things seem to shut down around 1:30-2am and we made our way home around 1. Annapolis isn’t going to deliver if you’re looking for a Vegas-like or all-night scene, but it certainly fits the bill when it comes to a bustling, lively bar scene and good food and drinks. I have a couple of friends from the area and they’ve always raved about many nights out…now, I totally get why!


Our plans on Sunday were really just brunch at Iron Rooster and practicing a group dance for the wedding (it’s an Indian one, so the bridesmaids are doing a choreographed number!), which was necessary after Saturday night. Iron Rooster is phenomenal and is well-regarded for good reason. They typically don’t take reservations for weekend brunch, but I called about a month out and they were able to set aside a table for us. It’s worth a try and if not, at least snagging a table as a walk-in or if you’re in town mid-week.

Again, I highly recommend an Annapolis bachelorette party…I’m really not sure why it’s not more highly regarded in this respect! The prices are reasonable, there are so many good bars, and you really can’t beat the waterfront views–there’s a reason it’s a favorite destination for those of us in the area!

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