Romance on the Eastern Shore

The Perfect 3 Days Away

Whether you’re celebrating a honeymoon, anniversary, birthday, or simply being in love, Chesapeake Bay is an ideal destination for romance, and Great Oak Manor is the perfect setting for your special occasion. Want to get away with your one and only? All you have to do is select your favorite romantic room, pick your dates, and pack your bags! Leave the planning to us; check out our 3-day itinerary filled with our top recommendations for romance on Maryland’s Eastern Shore…
Couple and their dog enjoying the sunset views from Great Oak Manor's beach front property

Collage of romantic room, complimentary cruiser bikes, couple on sunset cruise, and couple enjoying the views from Great Oak Manor

Day 1: Welcome to Your Getaway

    • Check in to your home away from home for the next three days and settle in to your inviting and spacious room or suite, complete with luxurious modern amenities.
    • Start the trip off on the right note with our Romance Package, warmly welcoming you to your space with sparkling wine, chocolate truffles, and flowers.
    • Head into Chestertown for dinner. We recommend The Kitchen at the Imperial or Fish Whistle!
    • Pour the wine and take your glasses out to the gazebo on property. A sunset toast is in order as you commemorate your time away together.

Day 2: Cruise by Bike & Boat

    • Wake up to a farm-fresh breakfast and take in morning bay views as you enjoy your first meal of the day.
    • Take our complimentary cruiser bikes out and explore the bay’s coastline and beautiful countryside.
    • Head into Historic Chestertown for lunch and do some shopping (ask us for self-guided tour maps).
    • End the evening with a romantic dinner cruise on the Chester River, courtesy of Chester River Packet Company, before heading back to the Manor for undoubtedly a peaceful night’s sleep after a day in the sunshine.

Day 3: Beach + Bay Day

    • After another delicious breakfast, you’ll be fueled for more fun in the sun!
    • Stroll down to our private beach to relax or if you’re feeling active, please use our complimentary gear for kayaking and paddle boarding.
    • We can pack you a picnic to take with you or have it waiting for you when you return to enjoy outside in one of the many secluded spots on the grounds.
    • Head down to the Eastern Neck National Wildlife Refuge to discover a special part of the bay and its diverse wildlife. Explore on your own or take part in the sanctuary’s varied activities.
    • Visit Rock Hall and explore this charming water town, known as the “Pearl of the Chesapeake.” Enjoy live music and some of the best seafood in Maryland.
    • Stick around and set sail with Blue Crab Charters. Book our Sunset Sail Package and we’ll take care of the reservations, and put together a wine & cheese basket to enjoy on the water!
    • Head back to the Manor for a nightcap around the fire pit as you reflect on your time spent on the bay.

Day 4: Until Next Time!

    • Before you check out, savor your last Great Oak breakfast and bay views.
    • Go back for a last stroll along the beach or peaceful moment in the gazebo to enjoy your coffee and simply being in the moment together.
    • Maybe get some last-minute souvenirs in town before heading back to reality.

What are you waiting for? Book your romantic getaway at Great Oak Manor today and look forward to a few days away with your love on the bay! We can’t wait to host you both.