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Saint Michaels

St. Michaels is a small historic town on Maryland’s Eastern Shore, located in Talbot County along the beautiful Chesapeake Bay. Originally a ship-building and seafood-processing center, it has evolved into a charming destination known for its maritime heritage, waterfront views, and boutique-style atmosphere.

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Featured Trip Itineraries

How to Spend the Day in St. Michaels, Maryland

Recommendations

Culture4.7/5

Chesapeake Bay Maritime Museum

Located in the charming town of St Michaels, the Chesapeake Bay Maritime Museum is an enthralling maritime oasis. Dive into the region's rich nautical heritage as you explore interactive exhibits, restored vessels, and breathtaking waterfront views. From oyster dredging to boatbuilding, this living museum invites you to feel the wind in your hair and discover the wonders of the Chesapeake Bay.

Culture4.5/5

St Michaels Museum

Step back in time and experience the charm of St Michaels Museum! Tucked away in the heart of St Michaels, Maryland, this delightful museum offers a fascinating peek into the town's rich history. Wander through exhibits showcasing the maritime heritage and learn about the intriguing tales of its inhabitants. With its quaint location on Chestnut Street, this is a must-visit spot for history buffs and curious travelers alike!

Landmark4.5/5

St. Michaels Farmers Market

Step into the vibrant St. Michaels Farmers Market and brace yourself for a delightful gastronomic journey! Nestled in charming St. Michaels, MD, this lively market offers a kaleidoscope of fresh produce, local goodies, and a feast for the senses. Sample mouthwatering delicacies from talented artisans, meet friendly vendors, and soak up the lively atmosphere. A must-visit for foodies on the move!

Culture4.7/5

1879 Hooper Strait Lighthouse, CBMM

The 1879 Hooper Strait Lighthouse, housed at CBMM, is an iconic maritime landmark that offers visitors a glimpse into Chesapeake Bay's rich history, complete with stunning views and a charming architectural design.

Culture4.8/5

Classic Motor Museum of St. Michaels

Discover the Classic Motor Museum of St. Michaels, where a captivating collection of vintage automobiles and unique memorabilia brings the golden age of motoring to life, making it a must-visit for motor enthusiasts and history buffs alike.

Self Care5/5

The Mill Salon + Apothecary

Discover unique beauty treatments and artisanal apothecary products at The Mill Salon + Apothecary, where historic charm meets modern wellness, making it a must-visit gem in St. Michaels, MD.

Landmark5/5

Town of St. Michaels, Maryland

Nestled on the Eastern Shore, the town of St. Michaels enchants visitors with its charming waterfront, rich maritime history, and quaint boutiques, making it a perfect escape for those seeking coastal beauty and cultural treasures.

Outdoor

Navy Point

Nestled in St. Michaels, MD, Navy Point offers stunning waterfront views, historic charm, and a vibrant community atmosphere, making it a must-visit destination for those seeking tranquility and coastal allure.

Landmark4.7/5

Miles River Yacht Club

Nestled along the stunning Miles River, the Miles River Yacht Club offers breathtaking views, vibrant sailing events, and a rich nautical heritage, making it a must-visit destination for boating enthusiasts and socializers alike.

Landmark5/5

MILES RIVER MARINE

Nestled in St. Michaels, MILES RIVER MARINE offers a blend of maritime heritage and stunning waterfront views, making it a must-visit for boat enthusiasts and those seeking a unique coastal experience.

Outdoor4.7/5

Waterfront Park

Waterfront Park in St. Michaels offers stunning views of the Chesapeake Bay, charming waterfront trails, and vibrant gardens, making it a perfect spot for leisurely strolls and picturesque sunsets.

Culture4.4/5

Christ Church, St. Michael's Parish

Nestled in St. Michaels, MD, Christ Church captivates visitors with its stunning Gothic architecture and rich history, offering a serene atmosphere and beautiful waterfront views that make it a must-visit landmark.

Self Care4.4/5

St. Michaels Harbour Inn, Marina & Spa

St. Michaels Harbour Inn, Marina & Spa is a charming waterfront retreat in the picturesque town of St Michaels, Maryland. With luxurious accommodations, a scenic marina, and rejuvenating spa treatments, this hidden gem is the perfect escape for travelers seeking relaxation and adventure on the Chesapeake Bay. Get ready to unwind and indulge in waterfront bliss!

Eat$$$$3.9/5

The Crab Claw

Welcome to The Crab Claw in St Michaels, MD! This charming seafood joint on Burns St will make your taste buds dance. Feast on mouthwatering crab dishes while enjoying picturesque waterfront views. Known for their stellar service and cozy atmosphere, it's the perfect spot to indulge in local Chesapeake Bay flavors. Don't forget to crack open a cold one and savor the deliciousness!

Eat4.7/5

Ava's Pizzeria & Wine Bar - St. Michaels

Craving a slice of heaven in St. Michaels? Look no further than Ava's Pizzeria & Wine Bar on 409 S. Talbot St. Indulge in delicious wood-fired pizzas and sip on local wines in a cozy atmosphere. Don't miss out on this hotspot for a tasty meal after exploring the charming town. Cheers to good food and good vibes!

Eat$$$4.5/5

STARS Restaurant

Located in the charming town of St Michaels, Stars Restaurant is a hidden gem for hungry travelers. With a laid-back atmosphere and a hearty menu, this hotspot promises a lip-smacking culinary adventure. From their famous crab cakes to their indulgent desserts, every bite is a taste of Maryland's finest. Don't miss their delightful waterfront view - a perfect spot to unwind and enjoy life's little pleasures!

Eat$$$4.5/5

Carpenter Street Saloon

Looking to wet your whistle in historic St Michaels? Look no further than Carpenter Street Saloon! Nestled on Talbot Street, this lively joint offers a delightful mix of local brews, tasty pub grub, and toe-tapping live music. Whether you're a curious traveler or a local legend, this charming spot is the perfect pitstop for laughter, libations, and lasting memories. Cheers, mate!

Stays

Stay4.65/5

Inn At Perry Cabin

Welcome to the Inn At Perry Cabin, where relaxation meets charm in the heart of St. Michaels, Maryland. With its picturesque location on the Chesapeake Bay and a luxurious yet cozy atmosphere, this waterfront retreat is a dream come true. Enjoy sumptuous dining, stunning views, and a spa that will transport you to cloud nine. Get ready to unwind and indulge in true vacation bliss!

Stay4.5/5

Victoriana Inn

Welcome to Victoriana Inn, nestled in the charming town of St Michaels, Maryland. This whimsical B&B is a hidden gem, with cozy rooms adorned with vintage decor and stunning water views. Indulge in delicious homemade breakfasts before exploring the historic streets, or hop on a boat for a delightful Chesapeake Bay adventure. Unwind here and let Victoriana Inn transport you to a world of nostalgic charm.

Stay4.5/5

Old Brick Inn

Welcome to Old Brick Inn, a charming bed and breakfast nestled in the heart of St Michaels, Maryland. This historic gem is bursting with character, from the exposed brick walls to the cozy fireplaces. Indulge in a delicious homemade breakfast before exploring the picturesque harbor, trendy boutiques, and delicious seafood restaurants just steps away. A quirky and memorable stay awaits you here!

Self Care4.4/5

St. Michaels Harbour Inn, Marina & Spa

Stay4.7/5

Five Gables Inn & Spa

Nestled in the charming town of St Michaels, Five Gables Inn & Spa is a haven for weary wanderers. This whimsical retreat offers a blend of luxurious accommodations and rejuvenating spa treatments. Unwind in stylish rooms, indulge in sumptuous breakfasts, and pamper yourself with a heavenly massage. With its idyllic location and top-notch amenities, this gem promises a vacation you'll never forget!

Stay4.6/5

The Parsonage Inn

Welcome to The Parsonage Inn, a charming bed and breakfast nestled in the heart of St Michaels, MD. Step into a world of comfort and relaxation, with beautifully decorated rooms and a delicious homemade breakfast to start your day off right. Explore the quaint streets of this historic town, indulge in fresh seafood, and unwind with a sunset cruise on the Chesapeake Bay. Your perfect getaway awaits!

Things To Do
Provided by

Funfull FunPass - Delmarva

Unlock a year of unlimited fun with Funfull’s Delmarva FunPass! This isn’t just a discount—it’s your family’s ticket to adventure all year long. With one low price, you’ll enjoy daily visits to dozens of the best local attractions, including Altitude Trampoline Park, bowling alleys, mini golf, play centers, arcades, and more. And to make it even better, every FunPass comes with one free movie ticket each month, redeemable at Regal Cinemas—an extra $150+ value over the year! Traveling? Your FunPass goes with you. Your membership isn’t limited to Maryland’s Eastern Shore. As Funfull rapidly expands across the United States, your pass is accepted at hundreds of partner locations nationwide. That means whether you’re at home or on vacation, you’ll always have access to family fun—without paying extra. Why pay full price for one visit when you can unlock a full year of fun for less than the cost of a family night out? Join Funfull today and start making memories that last all year long.

$199.99

8760 h

Funfull Family Package Delmarva

Unlock a year of unlimited fun with Funfull’s Delmarva FunPass! This isn’t just a discount—it’s your family’s ticket to adventure all year long. With one low price, you’ll enjoy daily visits to dozens of the best local attractions, including Altitude Trampoline Park, bowling alleys, mini golf, play centers, arcades, and more. And to make it even better, every FunPass comes with one free movie ticket each month, redeemable at Regal Cinemas or Cinemark! Traveling? Your FunPass goes with you. Your membership isn’t limited to Delmarva. As Funfull rapidly expands across the United States, your pass is accepted at thousands of partner locations nationwide. That means whether you’re at home or on vacation, you’ll always have access to family fun—without paying extra. Why pay full price for one visit when you can unlock a full year of fun? Join Funfull today and start making memories that last all year long.

$699.99

8 h

Day on the Bay Cruise from Annapolis to St Michaels

Set sail across the scenic Chesapeake Bay to the charming village of St. Michaels, where travelers can immerse themselves in local culture, fresh seafood dining, boutique shops, and historic sites. Guests enjoy a complimentary non-alcoholic beverage during the cruise before spending around three hours ashore exploring the town before the return journey to Annapolis. Admission to the Chesapeake Bay Maritime Museum is included, making this sightseeing day trip an ideal way to experience Maryland's rich maritime history.