The Experience Collection

Depart from local marina or private dock and cruise toward a curated waterfront destination — whether docking at Annapolis for lunch near City Dock, enjoying fresh Maryland Blue Crabs at a local crab house in Kent Island, or arriving in style at Harbor East for an upscale dining experience along Baltimore’s Inner Harbor.

Unwind with a leisurely cruise back across the Bay, where open water, coastal breezes, and unhurried conversation set the tone for a relaxed and refined return.

Depart from a local marina or private dock and settle in as your private yacht charts a course toward one of the Bay’s most charming waterfront destinations.

Cruise to historic Annapolis, where cobblestone streets, boutique shops, and harborfront dining create the perfect blend of sophistication and maritime heritage. Or journey to picturesque St. Michaels, known for its refined yet relaxed atmosphere, celebrated restaurants, and scenic harbor views.

For a quieter, storybook escape, explore the timeless charm of Oxford or the laid-back coastal beauty of Tilghman Island, where working waterfronts and hidden culinary gems offer an authentic taste of the Eastern Shore.

Dock for a leisurely waterfront lunch, stroll through charming streets, toast the day with handcrafted cocktails, and savor the unhurried rhythm of life along the Bay. As the afternoon light softens, enjoy a relaxed cruise back across open water.

Depart from a local marina or private dock, relax and unwind on an evening cruise along the Chesapeake Bay.

Enjoy stunning sunset views, scenic waterfront towns, and optional wine and light bites—perfect for couples, friends, or small groups.

3-Day Chesapeake Bay Voyage

Escape for a long weekend of scenic cruising, charming waterfront towns, and relaxing yacht life. Enjoy overnight stays aboard your yacht—anchored in peaceful coves or docked at local marinas—while exploring Annapolis and St. Michaels. Perfect for couples, friends, or small groups seeking a curated Chesapeake Bay adventure.

Sample 3-Day Itinerary

Day 1 – Departure & Sunset Evening

• Board your private yacht at a local marina or private dock

• Champagne welcome and vessel orientation

• Evening cruise with light hors d’oeuvres as the sun sets

• Overnight anchored in a quiet cove or docked at a nearby marina

Day 2 – St. Michaels Exploration

• Morning cruise to St. Michaels

• Explore the charming town, visit local galleries, shops, and historic sites

• Lunch at a waterfront café or onboard

• Optional afternoon kayaking, paddleboarding, or short sailing excursion

• Dinner at a curated local restaurant or onboard

• Overnight docked at St. Michaels Harbor

Day 3 – Annapolis & Crab Feast

• Morning cruise back toward Annapolis

• Explore the historic waterfront or enjoy a short stroll along the docks

• Enjoy a classic Chesapeake crab feast for lunch, onboard or at a local waterfront restaurant

• Leisurely afternoon cruise back to your departure marina

7-Day Chesapeake Bay Curated Charter

Set sail for a week of scenic waterways, charming waterfront towns, and hidden coves. Enjoy overnight stays aboard your yacht—anchored in peaceful bays or docked at local marinas—while exploring historic Annapolis, St. Michaels, Cambridge, Oxford, and beyond. Savor leisurely cruising, local cuisine, and optional water sports or wine tastings. Relax, explore, and make the Chesapeake your private playground.

Sample 7-Day Itinerary

Day 1 – Departure & Sunset Welcome

• Board your private yacht at your chosen marina (Annapolis, Kent Island, or Harbor East, Baltimore)

• Champagne welcome and vessel orientation

• Evening sunset cruise with light hors d’oeuvres

• Overnight anchored in a serene cove or docked at a nearby marina

Day 2 – Historic Annapolis

• Morning cruise to Annapolis

• Stroll the historic district, visit local shops and markets

• Waterfront lunch or dinner at a curated seafood restaurant

• Evening cocktails onboard

• Overnight at Annapolis Marina or anchorage

Day 3 – Kent Island & Secluded Coves

• Leisurely cruising with stops for swimming or paddleboarding

• Picnic lunch onshore in a quiet bay

• Sunset drinks aboard the yacht

• Overnight anchored in a scenic cove or at Kent Island Marina

Day 4 – St. Michaels Exploration

• Cruise to St. Michaels

• Explore charming shops, galleries, and historic sites

• Optional kayaking, paddleboarding, or guided sailing excursion

• Dinner at a local bistro

• Overnight docked in St. Michaels Harbor

Day 5 – Oxford & Tilghman Island

• Morning cruise to Oxford

• Stroll the waterfront, visit local art galleries, and enjoy a seafood lunch

• Afternoon sail to Tilghman Island for tranquil bay views

• Sunset cocktails aboard your yacht

• Overnight anchored near Tilghman Island

Day 6 – Cambridge & Dorchester County

• Cruise to Cambridge, MD

• Explore the historic waterfront, canal walk, and charming streets

• Optional visit to local distilleries or museums

• Dinner at a curated waterfront restaurant

• Overnight docked at Cambridge Marina or anchored nearby

Day 7 – Scenic Return & Farewell

• Leisurely morning cruise with photography stops along the Chesapeake

• Brunch at a waterfront café or marina

• Return to departure marina for disembarkation

Optional Enhancements: Onboard chef-prepared meals, curated wine or cocktail pairings, fishing excursions, paddleboarding or kayaking, and special celebration packages.

🥂 Intimate Celebrations
Celebrate birthdays, anniversaries, or milestones aboard your private yacht. Toast with champagne, enjoy curated dining, and take in the scenic Bay views for a truly memorable occasion.

🍽 Dinner Parties & Culinary Cruises
Host an elegant onboard dinner with a private chef, wine pairings, and personalized menus. Perfect for small groups seeking an unforgettable dining experience on the water.

💍 Engagements, Elopements, Micro-Weddings & Vow Renewals
Pop the question, exchange vows, or renew your love with the Chesapeake as your backdrop. Your captain is fully licensed to officiate the ceremony, and we provide an intimate, private setting with options for floral arrangements, photography, and curated dining.

📸 Photo & Lifestyle Shoots
Capture stunning images of engagements, family portraits, or personal branding. The Bay offers dramatic sunsets, charming waterfront towns, and serene coves for the perfect backdrop.

🎉 Custom Private Experiences
From milestone celebrations to themed cruises, we work with you to design a unique and unforgettable charter tailored to your vision.

🛩 Blue Angels – Annapolis (Half-Day)
Catch the Blue Angels from the best seat on the Bay. Cruise to prime viewing spots, enjoy light brunch or snacks onboard, and soak in the thrill before returning to the marina.

⚓ USNA Commissioning Week – Annapolis (Half/Full-Day, Multi-Day, Weekly)
Experience Annapolis’ most celebrated week from your private yacht. Stay onboard instead of a hotel or Airbnb, with a dinghy for trips into town. Enjoy Parade of Ships views, scenic Bay cruising, and curated dining.

⛵ Annapolis Power & Sail Boat Shows (Morning, Daytime, Evening)
See the show from the water with front-row views of the latest vessels. Combine cruising with onboard lunch, cocktails, or short walking tours of the show docks.

🎉 CBMM Festivals – St. Michaels (Day or Weekend)
Immerse yourself in festival energy while relaxing on your yacht. Dock overnight for weekend escapes, explore local exhibits, enjoy live music, and take optional dinghy trips or water adventures.