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Samantha & Dillon

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    Things To Do

Things To Do

Naval Academy

Annapolis, MD

A beautiful campus, right at the end of downtown Annapolis. Gorgeous for a stroll, and bonus if you see midshipman doing their thing.

Curate Annapolis Cafe & Bakery

141 West Street, Annapolis, MD 21401

A wonderful local coffee shop with incredible drinks, yummy treats, and great tunes conveniently located across the street from where our hotel block is

Great Harvest Bread Company

208 Ridgely Avenue, Annapolis, MD 21401

We love their bread! So fresh and delicious (we recommend the challah and cheddar garlic bread) and it's right next to a dog friendly brewery :)

Light House Bistro

202 West Street, Annapolis, MD 21401

Our #1 brunch spot when guests come into town, also conveniently located right near The Graduate Hotel. They are a mission focused restaurant, where all wait staff are in workforce training for homeless prevention.

Metropolitan Kitchen & Lounge

175 West Street, Annapolis, MD 21401

Another favorite right near The Graduate Hotel! They have a great brunch and dinner menu and, weather depending, a lovely rooftop. The guy who runs Naptown Scoop (our local newsletter), says this is his favorite spot for vegetarian goodies as well

Pennsylvania Dutch Farmer's Market

2472 Solomons Island Road, Annapolis, MD 21401

If you're interested in delicious donuts, pretzel dogs, or incredible baked goods, this is your spot. They're only open Thurs-Sat so if you're joining us for the weekend, make sure to stop here. Their donuts have become our celebration snacks :)

Parley Room

25 State Circle, Annapolis, MD 21401

The best espresso martini you'll ever have in your life. Sami is working very hard on having her and Dillon become regulars here

Forward Brewing

418 Fourth Street, Annapolis, MD 21403

An awesome, dog friendly brewery with vegetarian options! Their menu changes seasonally so check it out before you go.

Chessie’s Wharf

609 Melvin Avenue, Annapolis, MD 21401

A new brewery in town! Indoor and outdoor seating, yummy food, and dog friendly! Also right next to Great Harvest and RIGHT near our favorite ice cream, Always!

Red Red Wine Bar + Bistro

189 B Main Street, Annapolis, MD 21401

A cozy spot for cocktails, apps, and wine flights located on Main St.

Leo Annapolis

212 West Street, Annapolis, MD 21401

This is our absolute favorite spot. We love their drinks, apps, vegetarian options, and vibes. We have loved bringing friends here and coming here for regular date nights. Not to mention, we had our engagement party here :)

Acqua al 2 - Annapolis

236 Main Street, Annapolis, MD 21401

IYKYK. If you don't know, this is a Florence-based restaurant that has stolen Sami and Dillon's hearts. The food, the vibes - you can't wrong. We have taken everyone who comes to visit us to this restaurant. Fun fact: we almost booked this as the wedding venue

The Choptank - Annapolis

110 Compromise Street, Annapolis, MD 21401

The only waterfront rooftop in Annapolis. Their cocktails, fries, and views do NOT disappoint. Come here if you want to see big boats and a water-view

Fox's Den

179B Main Street, Annapolis, MD 21401

Our favorite spot for Neapolitan pizza and a cozy date night.

InGrano Restaurant and Events

17 Annapolis Street, Annapolis, MD 21401

Our new favorite date spot for a cozy, intimate vibe.

Sailor Oyster Bar

196 West Street, Annapolis, MD 21401

A must try for our seafood loving besties. This is an Annpolis staple

Always Ice Cream Company West Annapolis

116 Annapolis Street, Annapolis, MD 21401

THE most yumalicious ice cream (dog and veg friendly)

For all the days along the way
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