Eastern Shore Vacation Rentals

July 4th Holiday Dinner Cruise
2023-07-04 18:00 - 22:00 UTC
Take a relaxing 3-hour cruise and dinner on one of the most exciting attractions offered on Maryland’s Eastern Shore! Followed by a beautiful display of fireworks!!
The boat offers a fully enclosed lower deck with heating and air conditioning, as well as a covered upper deck with a great view of the river.
Catered by Suicide Bridge Restaurant and features local seafood and Eastern Shore favorites including dinner Choice of one Prime Rib & Crab Cake or Lemon Chicken & Crab Cake. Dinner Side: Potato of the Day, Green Vegetable, Dessert and Non-Alcoholic Beverage
Full Cash Bar on Board as well!

Berlin Fireworks
2023-07-03 20:30 - 21:00
Fireworks start at dusk. Bring lawn chairs, blankets and enjoy. Heron Park is open for viewing.

Event Deta

Fireworks Near You 2023
2023-07-01 20:30 - 2023-07-04 21:00
Add a little extra sparkle and excitement to your vacation with the local area’s fireworks!

Special 4th of July Fireworks Cruise
2023-07-01 20:00 - 22:00
Saturday July 2, 2022 8 PM to 10 PM, $150 per person plus tax and gratuity.
Join us for the ultimate Independence Day celebration and Sail Selina the Ultimate St Michaels 4th of July Fireworks Boat Tour!
Watch in awe as the stunning St. Michaels 4th of July fireworks reflect over the serene Miles River, creating a magical experience you won’t forget. Savor the moment with an open bar featuring the finest icy cold beer, red & white wines, or better yet, champagne. Feel truly pampered on this exclusive excursion.

Book now to secure your spot, as this small-group experience with only 6 guests always sells out fast!
Please call to book us at (410) 726-9400.

Sail on the Skipjack Nathan (July 1st)
2023-07-01 10:00 - 12:00
Nathan sails from May through October. Each sail is two hours long and generally includes an oyster dredging demonstration. Sails are unique depending on wind, weather, captain and crew.
Advance reservations are recommended and accepted online use the link below, until midnight of the day before the sail. We carry up to 20 passengers per trip and the boat leaves the dock promptly on schedule.
Booking – Skipjack Nathan (skipjack-nathan.org)

Adults
Children Aged 4–12
Children Under Age 4

$40.00
$15.00
Free

St. Michaels Ghost Walk - Spirits of Rowdy Women
2023-06-21 20:00 - 2023-11-05 22:00
The walk begins in front of the Chesapeake Bay Maritime Museum and makes its way through around the St. Michaels harbor and around St. Michaels historic downtown. Visit an old cemetery and hear stories about St. Mary’s Square where ghosts of unremembered dead once haunted a school that was on the Square. Visit the Victoriana Inn where a spirit of a former guest is still trying to pay his bill. Learn about the ghost in St. Michaels Town Hall, the house of a steamboat captain and a site that was once a brothel is said to still be “active.” The walk is about 1.5 miles and lasts about an hour and a half.

MEETING PLACE: Meet 15 minutes before the start of the tour in front of the Chesapeake Bay Maritime Museum entrance.
TIME & WEATHER: Ghost Walk begins on time. We walk in all kinds of weather except heavy rain and thunder storms. Dress for the weather and be aware that each ghost walk takes at least an hour and covers between 1 and 1.5 miles.

Bring your umbrella if it looks like rain.
Wear comfortable shoes.
Bring a flashlight.
Bring a camera. That’s part of the fun.

Visit (chesapeakeghosts.com) to explore more haunted areas all over the eastern shore!

Father’s Day Riverboat Cruise
2023-06-18 14:00 - 17:00
Take a relaxing 3-hour cruise on one of the most exciting attractions offered on Maryland’s Eastern Shore!
The boat offers a fully enclosed lower deck with heating and air conditioning, as well as a covered upper deck with a great view of the river.
Catered by Suicide Bridge Restaurant and features local seafood and Eastern Shore favorites including Prime Rib & Crab Cake or Lemon Chicken & Crab Cake with Vegetable, Potato & Dessert with Full Bar on Board!

Murder Mystery Dinner Cruise (June 17th)
2023-06-17 18:00 - 21:00
Take a relaxing 3-hour cruise and live show on one of the most exciting attractions offered on Maryland’s Eastern Shore!
The boat offers a fully enclosed lower deck with heating and air conditioning, as well as a covered upper deck with a great view of the river.
Catered by Suicide Bridge Restaurant and features local seafood and Eastern Shore favorites including Dinner Choice of one Prime Rib and Crab Cake or (2) Lemon Chicken and Crab Cake
Dinner Side: Potato of the Day, Green Vegetable
Dessert
Non-Alcoholic Beverage

Sail on the Skipjack Nathan (June 17th)
2023-06-17 13:00 - 15:00

Annapolis Juneteenth Parade & Festival
2023-06-17 12:00 - 14:00
Come out and join us for our FREE 2nd annual parade and festival on Saturday, June 17, 2023! There will be TWO main stages this year, featuring headliners Avery*Sunshine, Koryn Hawthorne, Pastor Mike Jr., Beverly Crawford, the Chuck Brown Band, and a host of local talent! Fireworks will immediately follow the show!
PARADE- SATURDAY, JUNE 17, 2023​
SUSAN CAMPBELL PARK | CITY DOCK | ANNAPOLIS, MD​
LIBATION CEREMONY: 11:50 AM
PARADE STEPOFF: 12:00 PM SHARP

FESTIVAL-SATURDAY, JUNE 17, 2023
1:00 PM
BATES ATHLETIC COMPLEX
935 SPA ROAD | ANNAPOLIS, MD 21401

Delmarva Pride Presents 2nd Annual Drag Show
2023-06-16 19:00 - 21:00
If you attended last year’s event, you know this show is going to be a wonderful night of entertainment fit for a queen!
As part of its Annual Pride Weekend, the Delmarva Pride Center is presenting its Second Annual Pride Drag Show, hosted by none other than our own Eastern Shore Darling, Miranda Bryant.
Bring your adult friends, your dollars bills, and come see our queens! 100% of ticket sales will go to support the work of the Delmarva Pride Center.
Doors will open at 6:30 p.m. with the show starting at 7 p.m.
Tickets: $30 Tables/Mezzanine; $20 Upper Balcony
All seats for this performance are reserved. The Avalon Theatre is handicap accessible. If you require special seating accommodations, please contact the Avalon Box Office directly 410-822-7299.
Cash bar available.

35th Annual Antique & Classic Boat Festival and Coastal Artisans Fair
2023-06-16 10:00 - 2023-06-18 17:00
One of the largest classic boat shows in the Mid-Atlantic region. On Father’s Day weekend! Featuring the theme, “Your First Love,” members of the Antique & Classic Boat Society-Chesapeake Bay Chapter will show approximately 100 antique and classic cruisers, runabouts and racers in water and on land. Other attractions include educational seminars, maritime vendors, juried artists, nautical flea market, children’s activities, free boat rides, Field of Dreams (boats for sale), great food & more.

Friday, June 16 – 10am-5pm
Saturday, June 17 – 10am-5pm
Sunday, June 18 – 10am-3pm
(All tickets are good for two days. Purchase now for Friday-Saturday or Saturday-Sunday.)

Delmarva Pride Festival
2023-06-16 - 2023-06-18
Delmarva Pride 2023 Delmarva Pride takes place over the weekend 16th to 18th June 2023.

Waterfront Wine & Jazz Dinner
2023-06-14 17:30 - 20:30
Guest( 10 per table) will be greeted with a choice of our sparkling Rosés, Slipstream or Moondance(new), while you settle in, laugh with friends, and feel your entire self begin to relax as you soak in the views accompanied by the melodies of our jazz trio.
Part of the before dinner experience will include wine tasting stations so you can explore all the varietals our beautiful island vineyard helps us create. The coastal soil and fresh bay and river winds leave their special mark on each and every bottle and we want you to have the opportunity to immerse yourself in the full experience.

First course:
Maryland Artisan Goat Cheese, Vermont Sharp Cheddar Fig Jam, Dried Fruits, Seedless Grapes Sliced Baguettes
Salad course:
Mache, Arugula, Mizuna, Red Oak Leaf, Watercress Baby Red Romaine and Frisee Burgundy Amaranth Heirloom Tomatoes and Julienne of Cucumber Blossoms Lemon-Dijon Vinaigrette Dressing
Main Course – your choice of:
Roasted Fillet of Chesapeake Bay Rockfish with Jumbo Lump Maryland Crabmeat Savory Lemon Soufflé Bundle of Haricots Verts Dauphinoise Potato Medallion
Sea Salt and Cracked Black Pepper Roasted Tenderloin of Beef, Medium Rare with Shallot-Wild Mushroom Pinot Noir Sauce Deep Fried Shoestring Sweet Potato Garnish Bundle of Haricots Verts Dauphinoise Potato Medallion
Oven Roasted Vegetables with Extra Virgin Olive Oil & Fresh Garlic Eggplant, Zucchini, Yellow Squash, Portobello Mushrooms, Italian Cipollini Onions Sweet Red and Yellow Peppers Sage Parmesan Polenta and Fresh Basil
And…DESSERT:
Fresh Strawberry Shortcakes English Shortcake Coulis of Fresh Raspberry Whipped Sweet Cream

The Berlin Farmers Market
2023-06-11 08:00 - 2023-09-24 14:00
Only market in the heart of downtown Berlin featuring more than 30 farmers, bakers, food cultivators and more. Shops in the downtown also open early on Sundays.
Live music starts at 10am. Free to attend, free to park!

Farms:

Bennett Orchards: Peaches and Blueberries (in season only)
BayBees Farm: Honey
Assateague Farm: Flowers
Bratten Farm: Locally Grown Produce
Cross Farms: Locally Grown Produce
(Shawn Cross, Market Manager)
Goat Plum Tree Farm: Lettuces, in season fruit and mushroom logs
Splendid Earth Acres Farm: Locally Grown Produce
The Bay Mushrooms Farm: Variety of locally grown mushrooms
6 Kings Farm: Lamb and beeswax products
The Good Farm: Locally grown plants and herbs
Beckys Beanz: Locally grown plants, garden flowers, produce
Marshall Creek Farm: Goat milk items and hand-made wool products
Truitt Farm: Handcrafted hot sauces from their pepper farm

Featuring:

The Buzz Meadery: Variety of locally made mead
Mandala Pies: Pies made from scratch
Little Green Witch Apothecary Teas
Beehouse Soap
Iron Skillet Coffee
Una Bella Salute: Downtown shop offering olive oils and vinegars
baked dessert café: Downtown bakery offering desserts, breads, granola, more
Del’Vecchios Bakery: Variety of baked goods, cookies, breads, more.
Home Canning Classics: Jams, jellies, pickled items, more
Honey Water Candles: Soy candles from local Berlin shop
Lyon Rum: Variety of rum distilled in Easton MD
Bleached Butterfly: Flower arrangements from local Berlin shop
KMBelz Pottery: Locally made pottery
Mother Flowers: Flowers
Sweet Tater Treats for Animals: Locally made for a variety of pets
Clare’s Nutty Concoctions
The Street Kitchen: Food Truck
Krave Gluten Free Bakery
Gather Bakery: Alfajores, Savory Biscuits made from scratch
Pearl Moon Face Painting
Gilberts Provisions: Fresh baked bread, breakfast burritos

Sail on the Skipjack Nathan (June 10th)
2023-06-10 13:00 - 15:00

Tall Ship Kalmar Nyckel Sails in Cambridge (June 4th)
2023-06-04 10:00 - 12:30
Come sail away with Kalmar Nyckel for a 2.5-hour sail and have an adventure of a lifetime!
The Tall Ship of Delaware returns to Cambridge, MD on Friday, June 2 through Sunday, June 4. Discover the remarkable story behind Kalmar Nyckel, a full-scale replica of the merchant ship that brought Swedish settlers to North America in 1638.
Day sails on the Kalmar Nyckel offer a unique, hands-on experience where adventure and education come together. You can haul lines, set sails, and hear tales from the crew, or simply relax and enjoy the ship. Kids will enjoy a scavenger hunt and pirate story (costumes welcome).
Tickets are limited and available online (KalmarNyckel.org/explore) or by calling 302.429.7447 for $65 per adult and $40 per child 12 and younger. Advance reservations are highly recommended. The schedule is weather dependent.

Kent Island Farmers’ Market
2023-06-03 15:30 - 2023-11-25 18:30
With over 30 local vendors at KENT ISLAND FARMERS’ MARKET at Cult Classic Brewery Year-round every Thursday. Hours 3:30- 6pm through Spring, Summer and Fall. January through March 3:30- 5:30. Experience local selection of seasonal fruits and vegetables. Hand crafted jewelry, crafts, home decor and more! Homemade baked goods, beauty products, local breweries and restaurants all at your fingertips.

Annapolis Pride Parade & Festival
2023-06-03 12:00 - 19:00
With over 6,000 people in attendance, 2019 launched the Inaugural Annapolis Pride Parade & Festival– a visual dreamscape of the human spirit at its best. People, children, and pets of every walk of life dress in their rainbow finest and line the sidewalks of West Street to witness a dazzling parade of floats, dancing spirit dragons, musicians, motorcycles, and more. It was a day of pure love and joy – many community members couldn’t believe their eyes at the crowds.

PARADE
Time: Begins at Noon on June 3rd
Where: West Street, Amos Garrett Boulevard to Calvert Street, Clay Street
FESTIVAL
Time: 12 pm to 7 pm
Where: West Street, between Calvert Street and Church Circle, The People’s Park, and adjacent parking lots

St. Michaels Brewfest 2023
2023-06-03 12:00 - 16:00
On June 3rd, from 12:00 pm – 4:00 pm come out to the St. Michaels Brewfest 2023!
They offer Three Pouring Venues, Over A Dozen Breweries, Art, Glassware, Food, and more!
Tickets are limited and can be purchased on the website below, Offering General admission and a VIP cruise tickets are still available!

St. Michael’s Brewfest – St Michaels Brewfest 2023

Sail on the Skipjack Nathan (June 3rd)
2023-06-03 12:00 - 15:00

Tall Ship Kalmar Nyckel Sails in Cambridge (June 3rd)
2023-06-03 10:00 - 12:30

Easton Farmers Market
2023-06-03 08:00 - 2023-12-16 13:00
From local produce growers to watermen, from bakers to crafters and local artisans, the Easton Farmers Market provides an entire meal, home décor and unique gift items in a friendly and festive environment. The market is open every Saturday from April 15 to December 16, 2023 at 8 a.m. to 1 p.m. Live music starts at 10:30 a.m.
Parking is available for free directly across the street from the market via Brewers Lane. The market is a walkable distance to shops, galleries, restaurants, and the historic Avalon Theatre.

Chesapeake Bay Champagne Sunset Sail
2023-06-02 17:30 - 19:30
Looking to go sailing at sunset while sipping champagne? This is the sunset champagne charter for you!
Come join us for a relaxing 2 hour cruise near Annapolis. Your St Michaels MD sail boat ride includes a personalized tour with our first class captains & crew on all our boating trips including our romantic sunset champagne cruise. Unique, upscale, and exclusive, the luxury sailing yacht Selina II limits her passengers to just 6 guests for an intimate taste of the history of sailing. With Freshly varnished mahogany and brightly polished brass let the premier charter boat St Michaels, MD help you sail into another time and place.
Per person: Starts at $115
Private charter minimum 2 people: Starts at $675

Max 6 passengers: Must be 21 or older to consume adult beverages.
Check-in time: 15 minutes prior to departure
Children: Please note that while this excursion is primarily an adult experience, well-behaved children are more than welcome to join in on the fun. The Coast Guard considers every kid no matter how young or how little to be a passenger, and as such require their own ticket.
Parking: Free parking where we are parked at the Harbour Inn, 101 N Harbor Road, St Michaels MD 21663. If there are no spaces available, then there is parking on the side streets and along the waterfront down past where the work boats tie up.

St. Michaels Yacht Wine Tasting Cruise
2023-06-02 15:00 - 2023-10-29 17:00
Enjoy a truly unforgettable wine tasting experience on the Chesapeake Bay with Sail Selina II. Our 2-hour St Michaels, MD wine tasting cruises are the perfect way to indulge in the basics of wine tasting while taking in breathtaking views of one of the most picturesque waterfronts in America. With limited availability for just six guests per excursion, our wine cruises are perfect for a special girls night out or with your sweetheart.
Experience the rich aromas and flavors of 3 reds and 3 whites, including a stunning Italian Pinot Grigio that will transport your senses to the breathtaking vineyards of Italy. Capt Iris lovingly handpicks a constantly changing selection of global wines, ensuring that each excursion with us is a unique, personalized adventure that you’ll remember for years to come.

$95 per person, minimum 2 guests (+tax/tip)
Private charter up to 6 guests $545 (+tax/tip)

Plus there is a 10% amusement tax in St. Michaels harbor, and a customary 20% tip for the crew.
Wine Cruises are available Sun-Sat 12:30-2:30pm and 3:00-5:00pm.
Sail Selina wine cruise is located in St Michels MD, just an hour from Annapolis, making it the perfect day trip to share with loved ones or make it a special girls night out.
Limited to just 6 guests for a truly personal experience.

Parking: Free parking where we are parked at the Harbour Inn, 101 N Harbor Road, St Michaels MD 21663. If there are no spaces available, then there is parking on the side streets and along the waterfront down past where the work boats tie up.

Beer: Sometimes there is someone in your group who would just rather drink beer. That’s OK too, just let us know and we will be happy to give them a beer tasting tour while you sip your wine.

St. Michaels Yacht Beer Tasting Cruise
2023-06-02 15:00 - 2023-10-29 17:00
Available per person or Private Charter
Join us for an unforgettable experience on our ice-cold Beer Tasting Cruises Be prepared for an unforgettable adventure on our beloved historic yacht Sail Selina II. Indulge in the aroma, taste, and quench your thirst with our cold, refreshing beers.
A 2-hour tour on our beautifully kept sailing boat offering a luxurious and comfortable sailing experience. Guests have consistently praised the impeccable condition of the sailboat, making it the perfect setting for a memorable trip on the water.

Person

Per person Starting at $90- $115

Private Charter

Private Charter starting at $675

Max 6 passengers: Must be 21 or older to participate in the beer tasting portion of this trip
Children: Kids of all ages are welcome aboard the Selina II. Example, mom, dad, and their six-month-old are three guests, not two.
Cancellation 24/72 hrs: Reservations made on a per person basis cancellation is 24 hrs. Private Charters are 72hrs.
Parking: Free parking where we are parked at the Harbour Inn, 101 N Harbor Road, St Michaels MD 21663. If there are no spaces available, then there is parking on the side streets and along the waterfront down past where the work boat tie up.

Wine: Wine is available for any guest who may prefer this.

WINE TASTING CRUISES

Tall Ship Kalmar Nyckel Sails in Cambridge (June 2nd)
2023-06-02 13:00 - 15:30

Cambridge Farmers’ Market
2023-06-01 15:00 - 2023-11-04 18:00
Operating May through November in 2023, Every Thursdays from 3pm – 6pm, the Long Wharf Farmer’s Market is a local favorite! What’s better than a waterfront Farmer’s Market?
The market is situated in the Long Wharf park, nearby public parking. The market is within walking distance to the Municipal Marina, Skipjack Nathan, the replica Choptank River Lighthouse and downtown Cambridge along historic brick-paved High Street.
Approximately 18 or more vendors can be found throughout the season, including many local Dorchester and Eastern Shore regional farmers, crafters, and specialty food vendors.

Crab Feast Cruise
2023-06-01 12:00 - 2023-08-31 15:00
Take a relaxing 3-hour cruise on one of the most exciting attractions offered on Maryland’s Eastern Shore!
The boat offers a fully enclosed lower deck with heating and air conditioning, as well as a covered upper deck with a great view of the river.
Catered by Suicide Bridge Restaurant and features local seafood and Eastern Shore favorites including Steamed Crabs, Crab Soup, Fried Chicken, Clam Strips, Fresh Local Corn, Coleslaw, Dessert and Non-Alcoholic Beverage

Sail on the Skipjack Nathan (May 27th)
2023-05-27 13:00 - 15:00
