Sailing Excursions and Boat Tours on the Chesapeake Bay

For guests who want to make a full day of it, the Cruise and Clays excursion combines two of the Eastern Shore's finest outdoor pursuits in a single guided outing. Cruise the Chesapeake Bay aboard our Hinckley Five Star yacht, then head to The Point at Pintail to test your aim with a morning of sporting clays. This guided excursion pairs a scenic motor yacht ride from the Inn with a timeless outdoor tradition, blending maritime leisure with friendly competition on land. The day's top shooter takes home a commemorative keepsake clay, and the whole experience wraps up well before the afternoon. It is one of the most distinctive half-day excursions available from any waterfront resort on the Chesapeake Bay.

The Details

• Available Saturdays and Sundays.
• Approximately four hours, departing at 8:45 am and returning early afternoon.
• $350 per person, inclusive of taxes, fees, and gratuities.
• Operates rain or shine with covered stations and sheltered transport; all participants must be over 95 pounds and complete a waiver.
• Sundays only: late checkout at 2 pm for guests booked on this excursion.
• Food and beverage selections are available upon request. Please contact Guest Services for the Boat Menu offerings.

Our Guest Services team is happy to assist with your reservation at 443.258.2228 or [email protected]

The Sailmate Experience is designed for guests who want more than a passenger seat on the water. Set sail on a genuinely hands-on private sailing lesson where you and your group can learn the fundamentals of sailing in an unhurried, personal setting on the Miles River. Whether you have never set foot on a sailboat or are simply looking to sharpen skills you already have, this experience is led by one of our experienced captains and tailored to your comfort level from the first line cast off the dock. Available for groups of 2 to 6 guests, the Sailmate Experience is one of the most personal ways to connect with the nautical heritage of St. Michaels, Maryland and the Chesapeake Bay.

The Details

• 2-hour private sailing lesson: $800, plus tax. Gratuity not included.
• Add an extra hour for $100 plus tax, allowing time for lunch (lunch sold separately).

Connect with our Guest Services Team and explore what's available during your stay! Call 443.258.2228 email or [email protected].

One of the most sought-after excursions at Inn at Perry Cabin takes guests from the Miles River all the way to Annapolis by boat, navigating some of the most scenic stretches of the Chesapeake Bay along the way. Aboard the 55-foot Hinckley Five Star motor yacht, the Explore the Chesapeake voyage departs from the Inn's private dock and charts a course toward Kent Narrows, around the majestic Love Point, and beneath the iconic Chesapeake Bay Bridge before arriving in downtown Annapolis for a tour of the city by water. 

On the return, the route passes the historic southern end of Kent Island, through the Eastern Bay, and back along the Miles River to home port at the Inn. For guests who want more time in Annapolis, the extended 6-hour option allows a proper stop in the city to shop, dine, or walk through its historic streets before boarding for the return voyage. This is the most complete boat tour of the Annapolis and Chesapeake Bay area available from a hotel dock on the Eastern Shore.

The Details

Explore the Chesapeake

• $2200- 4 hours / plus 10% fuel and 16% Tax (does not include gratuity). Choose to include a box lunch from our boat menu and enjoy it at your convenience.

Explore the Chesapeake with Annapolis Visit

• $2800- 6 hours / plus 10% fuel and 16% Tax (does not include gratuity; dockage rates may apply).

Extend your tour duration by 2 hours and take a break in Annapolis to shop, dine, or wander through its historic streets.

Interested in exploring what's available during your stay and making a reservation? Our guest services team is at your service at: 443.258.2228 or [email protected].

For guests who want to slow down and let the natural beauty of the Eastern Shore come to them, the Wye Island Experience is one of the most quietly spectacular outings available from the Inn. Guests choose their preferred mode of exploration, paddleboard or kayak, and board Starchaser, the Inn's 28-foot Zodiac, for the journey to Wye Island on the Wye River. 

Once there, the water is calm, the wildlife is abundant, and the shoreline of the Eastern Shore stretches out without interruption. Great blue herons, osprey, and bald eagles are regular companions on this route in season. This excursion is available to both overnight guests and day visitors and is a genuinely rare way to experience the unspoiled natural landscape that surrounds St. Michaels, Maryland.

The Details

• Available Tuesdays and Thursdays from May through October.
• Requires a minimum of 2 guests and maximum of 6 guests.
• $85 per person, Plus Tax and Gratuity.
• Three (3) hour exploration from 8 am to 11 am.
• Includes water, Gatorade, and power bars. 

Interested in exploring what's available during your stay and making a reservation? Our guest services team is at your service at: 443.258.2228 or [email protected].

Step aboard the Stanley Norman Skipjack and you are stepping into one of the most authentic pieces of living maritime history on the Chesapeake Bay. Built in 1902 and among the last of her kind, the Stanley Norman carries more than 120 years of history in her hull and rigging. She was built when skipjacks ruled the Chesapeake and oystermen worked the Bay's reefs from before sunrise to after dark in search of its prized bounty. On the Skipjack Legacy Voyage, guests embark on a one-and-a-half-hour sailing along the tranquil Miles River while our knowledgeable captains share the full story of the Stanley Norman and the fascinating history of oystering in the Chesapeake Bay region. The Stanley Norman is listed on the National Register of Historic Places and is one of the last surviving skipjacks in Maryland. Sailing her on the same waters she once worked is an experience with no real equivalent anywhere else on the Eastern Shore. For each ticket purchased, $10 is donated to 4ocean to support ocean cleanup and marine conservation.

The Details

• Season start date to be determined.
• Every Wednesday, Friday and Sunday
• 5:30pm to 7:00pm (Wednesdays & Sundays)
• 4:30pm – 6:00pm (Fridays)
• $140 Per Person. A 20% gratuity will be automatically applied.
• Price includes beer, wine, and non-alcoholic beverages and dry snacks.
• $10 per ticket donated to 4oceans.

Interested in experiencing this beautiful vessel?  Connect with our  guest services team at 443.258.2228 or [email protected]. 

* Experience requires a minimum of 7 people. Less than 7 people will be offered a sailing experience on one of our sailboats.

Set sail for a one-of-a-kind Chesapeake Bay evening aboard the historic 1902 Stanley Norman Skipjack, where sailing, storytelling, and spirited sipping come together in a single remarkable voyage. The Rum Running on the Skipjack experience invites guests to learn the lore of this rare vessel alongside the fascinating and rebellious role rum played in the history of the Chesapeake Bay region, all while enjoying a curated tasting from Lyon Rum, a local, women-owned distillery based on the Eastern Shore of Maryland. 

The experience is timed perfectly to catch front-row views of the Wednesday Night Sailboat Races on the Miles River, one of the most beloved local traditions in St. Michaels. This is not a standard cocktail cruise. It is a genuine blend of maritime history, local craft spirits, and the kind of evening on the water that guests talk about long after they have returned home.

Details

• Available Wednesdays June - August
• 5:30 – 7:00 PM
• $150 per person, Plus Tax and Gratuity.
• Non alcoholic beverages and snacks included

Interested in joining the adventure or learning more?
Connect with Guest Services at 443.258.2228 or [email protected].

Ahoy, mates! Step aboard the historic 1902 Stanley Norman Skipjack for a genuinely rare autumn experience on the Miles River. The Experience on the Half Shell is a seasonal excursion available in October and November that gives guests the chance to dredge for oysters exactly as Chesapeake watermen did over a century ago, using the same traditional methods that made the Bay's oyster harvest famous throughout the Eastern Seaboard. After a hands-on dredging session on the oyster reef, the crew prepares freshly shucked oysters right on board, paired with beer, wine, and non-alcoholic beverages for the sail back to port. 

Whether you are docking with the Inn for the day or staying as an overnight guest, this is an authentic, hands-on connection to the traditions that shaped St. Michaels, Maryland and the entire Chesapeake Bay region.

Details

• Seasonal: October &  November
• Every Friday, Saturday, and Sunday
• 3:30pm to 5:00pm
• $150 per person, Plus Tax and Gratuity.
• Price includes: freshly shucked oysters, beer, wine, and non-alcoholic beverages.
• $10 per ticket donated to 4oceans.

Timeline

3:30 PM - All Hands on Deck for a Safety Briefing!
Gather ‘round as we go over the essentials for a safe voyage on the high seas!

3:35 to 4:00 PM - Set Sail with Complimentary Libations!
As we cast off from the dock, enjoy a selection of complimentary beverages while we cruise through the harbor. Listen closely as we regale you with tales of the local area and the storied history of our beloved town.

4:00 to 4:45 PM - Hoist the Sails and Head for the Oyster Reef!
With sails unfurled, we’ll chart a course to the oyster reef. Once we arrive, delve into the rich heritage of  the Stanley Norman and its legacy in the art of oystering. Our crew will provide hands-on tutorials about the dredging process, demonstrating how we bring the bountiful oysters aboard.

4:45 to 5:00 PM - Lower the Sails and Motor Back to Port!
As we make our way back to port, sit back and savor the taste of fresh oysters, expertly pre-shucked by our culinary team. Bon appétit!

Interested in this experience?  Connect with our  guest services team for details at  443.258.2228 or [email protected]. 

Skip the bridge traffic entirely and make your arrival at Inn at Perry Cabin the first unforgettable moment of your stay. The Skip the Bridge package brings guests from Pier 7 Resort Marina in Edgewater, Maryland directly to the Inn's private dock on the Miles River aboard our elegant 55' Hinckley Five Star yacht, gliding across the Chesapeake Bay with the Eastern Shore opening up ahead of you. 

This is not simply a transfer. It is the beginning of the stay itself, complete with Laurent Perrier Brut champagne and a cheese and charcuterie board on board, VIP check-in upon arrival, and a 2 pm late checkout on departure day. For guests who have made the drive across the Bay Bridge many times, arriving by private yacht is an entirely different introduction to St. Michaels and everything the Inn offers.

The Details

• 2-Night Stay in Luxury Accommodations.
• Laurent Perrier Brut champagne and Cheese & Charcuterie board.
• VIP check-in and 2pm late check-out.
• On & Off- Luggage Boarding Service.
• Complimentary parking at Pier 7 Resort Marina.
• Minimum 2-night stay required.
• Available for Friday arrival only.
• Maximum of six passengers on board.
• 1-bottle of champagne and 1-charcuteries board per 2-passengers booked.
• Pricing based on 2-guests. For Solo Travel contact Guests Services at 443.258.2228.

Additional Specifics

*The round-trip transfer departs for Inn at Perry Cabin from Pier 7 Resort Marina in Edgewater, MD. Pickup is at Pier 7 on Friday at 3pm. Your return to Pier 7 Marina from Inn at Perry Cabin is Sunday at 2pm.

To Book Skip the Bridge: Visit our Special Offers page.

Interested in a Private Boat Transfer or Customized Boat Experience? Please contact Guest Services at: 443.258.2228.