Cafe Ole

You cannot beat this local gem. The owners wonderful personality and the consistent service and quality make this a sure win every time.

Great cozy spot on West St. Awesome Chicken salad wrap. Great Grab and Go lunch specials.

cute but wicked cramped. woman behind the counter was very nice. Looks like a great local joint.

I got a chai latte and it was pretty good! The woman working there was friendly and it was definitely one of those places that sees a lot of regulars. My only complaint would be that it was really small and they didn’t have any merchandise for my coffee-​adventure collection. :P

LOVE Café Olé. Small but filled with good food, smiles, and familiarity. Fresh coffee, cakes, and sandwiches, and amazing service from Claudia. Laid back, relaxed, and comfortable.

EASILY my favorite place in Annapolis to get my morning cup of coffee.
It’s easy to miss this gem of a coffee shop, due to it being smaller than most shops, but I highly recommend you give it a try. You really can’t beat Café Olé’s relaxed environment in the morning and Claudia is one of those people that’ll put a smile on your face before you head on to work.

Hidden Treasure

Love this place for a latte to go. It’s a cozy little hole in the wall run by a lovely local. Espresso made with love. The place is tiny, so you’ll want to get it to go, but who wouldn’t want to stroll around Annapolis with a cuppa. Support your local coffee shop!

One of my favorite local haunts in downtown Annapolis! This is a great place to stop in for a quick cup of coffee and pastry or sandwich to go, or a cozy rendezvous point if you like to sit and sip your morning cup over a newspaper. The café, which used to be called Pony Espresso, changed owners last year and is now Café Olé, owned by Claudia (long-​time barista under the former owner), whose bubbly personality perks you up almost as much as the Seattle’s Best coffee! There is a warm and comfortable feel here, the staff knows almost every customer’s name, as most of the clientele are regulars, or quickly become regulars once they’ve discovered it.
It’s directly next door to Ram’s Head Tavern on West Street, but is so little (I prefer «cozy») that sometimes even long-​time Annapolitans have taken years to happen upon it, myself included.
Delicious sandwiches and wraps are usually available for lunch, and muffins, coffee cake, bagels, yogurt bread, cookies, biscotti, yogurt, soft drinks, coffee, tea, and espresso drinks are plentiful. Also, ask for a «kiss card», a card that is stamped by a kiss-​shaped stamper with each beverage. Once your card has been filled up with all 12 stamps, your 13^th drink is free.
A well-​kept secret by locals and professionals who work downtown.