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Sailboats, Seafood & Small-Town Charm: A Weekend in St. Michaels
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items We just got back from the most relaxing getaway in St. Michaels, Maryland — a little waterfront town that feels worlds away. Think cobblestone sidewalks, sailboats drifting by, amazing seafood, cozy inns, and boutique shopping. This list pulls togeth...
Sections
4
Places to Stay
Places to Eat
Places to Shop
What to Pack
Places to Stay
From iconic waterfront luxury to hidden-gem B&Bs, St. Michaels has the perfect spot for every style of getaway.
Could not recommend this place more! We absolutely adored it. Perfect size, very attentive staff and beautiful rooms and grounds. 10 out of 10!
The Wildset Hotel
We did not stay here but we did walk the grounds and my oh my is it beautiful. Pricey yes but the grounds are killer and you feel like you are in a movie!
Inn at Perry Cabin
A quiet, historic bed & breakfast surrounded by water on three sides. Perfect if you’re craving peace, sunsets, and a slower pace.
Wades Point Inn
Places to Eat
Whether you’re craving steamed crabs by the water or a modern spin on Chesapeake seafood, the town’s dining scene delivers flavor with charm.
Our favorite meal by far (and our Anniversary dinner!) Staff was amazing, drinks were top notch and the food was incredible. We got the dumplings, corn, chicken, oysters and pasta…all 10 out of 10. Do not skip this place!
Ruse
Fun laid back place with fantastic drinks and appetizers. We had a spot right on the water by the live music and it was a great time. I had the watermelon crush and it was so good!
Foxy's Harbor Grille
We had lunch here and it was so good! LOVE the pizza and the fresh ingredients.
Ava's Pizzeria & Wine Bar - St. Michaels
You really can't go to St. Michael's and not have crabs or go to Maryland for that matter. A great crab joint right on the water
The Crab Claw
A local coffee place that won't disappoint. We had the iced vanilla latte and it was just what we wanted. Not much atmosphere but that's kind of we like our local places, right?
Blue Heron Coffee
Coffee was great. Wish we had time to eat here, the food looked sooo yummy! Particularly the sandwiches.
The Blue Crab
Places to Shop
Boutiques, antiques, and coastal treasures — St. Michaels’ shops are full of finds you’ll actually want to take home.
My husband was like a kid in a candy store here with vintage antiques and a rotating selection of vinyl records (new items every week), it’s a great spot for anyone seeking something timeless or musically unique
Oyster House Antiques & Vinyl Records
So many gift ideas in this store. We found a unique set of salt and pepper shakers for my in-laws that they will love.
The Preppy Redneck
Offers inspired coastal décor and gifts. Think thoughtfully curated housewares that evoke the relaxed Eastern Shore lifestyle.
Come By Chance
Brings authentic Italian charm to St. Michaels. Explore ceramics, linens, jewelry, and enjoy free tastings of Limoncello, Prosecco, and local bites.
Simpatico LLC
A delightfully sensory experience. Taste your way through infused olive oils, high-quality vinegars, and tempting coffee and chocolates.
Olivins Tasting Room - Aged Infused Fine Olive Oil & Vinegars
A haven for vintage lovers. Browse antiques and collectibles, with multiple dealers offering a broad variety of charming pieces with history.
Antiques On Talbot LLC
A really charming shop celebrated for its nautical flair and curated coastal aesthetic—especially those custom flag patches that make for standout souvenirs or personalized gear. There are so many way to personalize items in this store!
The Bench Goods
This store was going out of business so I'm not sure how much longer it will be open but the sale prices were incredible and the quality of clothes was amazing!
FatFace US
Wish our budget was bigger a lot bigger. A beloved institution since 1942, this upscale furniture and interior-design destination has earned the title of “Best Furniture Store & Interior Design Services on the Shore
Higgins & Spencer Inc
What to Pack
Packing for a laid-back, charming coastal town is all about effortless style, comfort, and a few practical essentials. Think breezy layers for waterfront walks, versatile pieces for boutique hopping, and accessories that keep you comfortable while lo...
A little denim dress is my whole personality. So timeless and classic, dress up or down. I love this particular silhouette.
Azure Dress - Dusk Dive Wash
A really great casual but elevated bag for a shopping day!
Italian Leather Handwoven Sling Bag in Cognac
Perfect for strolling the waterfront or dining at a local café, and easy to layer with a cardigan.
Tall mini dress in linen
Easy to slip on with a dress or linen shorts or a skirt. Love the cognac color so much!
RUDIE SANDALS COGNAC LEATHER
I love my compression packing cubes and I don't know what I would do without them. I love this coastal blue too!
Eco Compression Packing Cubes (6-pack) in Blue
Perfect for a costal town! Love the gold details and just a slight heel to feel elevated.
Farrow Saddle Leather Sandals | Dolce Vita
I love this bag because I feel like I can dress it up or dress it down. The textures are perfect with the different materials and I am such a gold girlie!
Tan Nina Crossbody
This dress and this color...I die! The neckline is gorgeous and the skirt is just full enough.
Cherry Wells Dress
This just screams coastal charm to me. I love the large long handle and the weave is so pretty.
Hat Attack Sorrento Tote - Natural
I always try and just bring my everyday jewelry with maybe one or two dinner pieces that are special. This case helps me keep it to a minimum.
Leather Jewelry Travel Case in Nude
The sandel I've been wearing all summer long. Still look new and so comfortable!
Women's Collin Double Buckle Footbed Sandals
I always pack a white button down shirt because I use it as a way to stay warm at dinner or just to wear with some chic shorts.
100% European Linen Long Sleeve Shirt in White