Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in Saint Michaels…
    3. /Water Activities
    4. /Boat Tours
    5. /Private Sunset Cruise on the Miles River in St. Michaels
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Destinations
    • Categories
    • Experience Gift Cards
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Gallery image

    Private Sunset Cruise on the Miles River in St. Michaels

    Share a sunset with the people who matter most

    Duration

    2.5 hrs

    Ideal For

    Up to 6 people

    Includes

    Private cruise, bottled water

    Highlights

    Step aboard Sweet Tilly for a private evening cruise from St. Michaels harbor onto open water. Settle into an unhurried ride with your group as daylight gives way to evening.

    • Look out over the Miles River at sunset
    • Capture golden-hour photos from the water
    • Celebrate a proposal, anniversary, or birthday aboard

    What's Included

    • Deck chairs
    • Bluetooth speakers
    • Complimentary bottled water
    Split the cost with your group

    This booking is for the whole experience, which fits up to 6 guests.

    From$72per person
    Split with

    Cancellation Policy

    Cancel up to 48 hours before departure for a full refund. Cancellations within 48 hours receive a credit and are rescheduled for the next available date. If the captain cancels due to weather or other safety concerns, you'll receive a full refund.

    Product ID: AACEHV

    FAQs

    The cruise accommodates up to six passengers.

    Yes. Bring your own wine or champagne to enjoy during your sunset cruise.

    Wear weather-appropriate clothing. Bring sunglasses, sunscreen, and any personal items you need for comfort.

    Meeting details

    South-end marina slip at St. Michaels Harbour Inn, Marina & Spa, 101 North Harbor Road, Saint Michaels, MD 21663

    Experience provided by Escape by Boat

    Related locations

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Private Charter

    $435

    Fits up to 6 guests · 2.5 hrs

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Nearby activities

    Chesapeake Bay Day Sail on a 1935 Ketch in St. Michaels
    Sailing

    Chesapeake Bay Day Sail on a 1935 Ketch in St. Michaels

    Sail a Historic 1935 Ketch on the Miles River

    5.0 • 1.4K reviews
    $131/ person
    Blackwater Refuge Bike Rental in Cambridge
    Bike Rentals

    Blackwater Refuge Bike Rental in Cambridge

    Pedal refuge and marsh roads with a bike, helmet, and map

    4.9 • 556 reviews
    $23/ bike
    Cambridge Haunted High Street Ghost Tour
    Ghost and Haunted

    Cambridge Haunted High Street Ghost Tour

    Hear true local ghost stories on a nighttime walk through historic Cambridge

    4.6 • 137 reviews
    $27/ person
    Annapolis Naval Heritage Guided Tour
    Historical Tours

    Annapolis Naval Heritage Guided Tour

    Discover Annapolis's Navy culture, history, and Chesapeake character

    5.0 • 52 reviews
    $1,547
    Fall Foliage Cruise in Kent Narrows
    Boat Tours

    Fall Foliage Cruise in Kent Narrows

    Cruise Chesapeake Bay waterways with fall views and complimentary warm apple cider

    5.0 • 37 reviews
    $45/ person
    Chesapeake Bay 60' Yacht Charter
    Yacht Charters

    Chesapeake Bay 60' Yacht Charter

    Cruise Chesapeake Bay aboard a 60-foot Viking with captain, crew and fuel included

    4.7 • 199 reviews
    $4,095& up