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Upper Chesapeake Bay Boat Tours

The best out of 27 boat tours in Upper Chesapeake Bay - enter dates to check availability

Upper Chesapeake Bay Boat Tours

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Top Boat Tours in Upper Chesapeake Bay

Upper Chesapeake Bay: 27 boats available

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    • Comfortable cruising with upper level

    Embark on an unforgettable maritime adventure with Hot Pursuit Charter Fishing LLC! Based in beautiful Edgewater, our 1993 Markley Custom vessel is your ticket to an exhilarating day on the water.

    "We booked Don and the Hot Pursuit for a corporate boating event to watch the Blue Angels." —⁠ Denise,

    trips from
    US $550

    Screaming Eagle Charters

    Bozman
    4.8
    /5
    (166 external reviews)

    Step aboard Screaming Eagle Charters—a classic 2010 Trojan Sportfish ready to show you the best of Neavitt and the Chesapeake Bay! With room for up to 6 guests, this well-equipped vessel is powered by a reliable 380HP Cummins diesel inboard and crui

    "We were looking for people who new the area well, and this was the right team." —⁠ Leigh,

    trips from
    US $400

    Patch on Water

    Washington
    +3

    Step aboard Patch on Water, a stylish 2007 Sea Ray 300 DA Motor Yacht, and enjoy a memorable day on the waters of Washington with up to 8 guests.

    trips from
    US $800

    Chasin Fins

    Cambridge

    Step aboard Chasin Fins, a sleek 2019 Key West 239 FS Center Console ready to take you on unforgettable adventures from beautiful Cambridge.

    trips from
    US $250
    +3

    FishPit Charters invites you to explore the stunning Nanticoke waters aboard a fully restored 1999 Maycraft 2300 Pilot House — a versatile and comfortable vessel perfect for both adventure and relaxation.

    trips from
    US $299

    Beach Bum Charters LLC

    King George
    4.9
    /5
    (5 external reviews)

    Get ready for an unforgettable day on the water with Beach Bum Charters LLC! Based in King George, this 2000 May-Craft 2700 Pilothouse comfortably welcomes up to six guests and is powered by a 300 HP Suzuki outboard, reaching speeds of up to 30 knots.

    trips from
    US $250
    +2

    Floating Kneads Charters is based on Baltimore's scenic Inner Harbor and can accommodate six (6) guests. Intimate and exclusive experiences on the water, by design.

    "I would highly recommend this trip arund the Harbor relaxing calm and peaceful on the water." —⁠ Tanya,

    trips from
    US $650

    Rowe Boat Sportfishing & Excursions

    Rock Hall
    5.0
    /5
    (57 external reviews)

    Step aboard Rowe Boat Sportfishing & Excursions, a beautifully restored 1990 Markley Pilot House Downeast, offering the perfect blend of classic charm and modern comfort.

    trips from
    US $700

    Experience an unforgettable adventure aboard Bay Hunter Charters, a spacious and well-equipped 45ft Downeast vessel based in Shady Side.

    trips from
    US $450
View all boat rentals
See all 27 boats in Upper Chesapeake Bay

Frequently Asked Questions about Boat Tours in Upper Chesapeake Bay

According to customer reviews, some of the most popular boat tours in Upper Chesapeake Bay are:
Full list of top boat tours in Upper Chesapeake Bay
According to customer reviews, some of the most popular boat tours in Upper Chesapeake Bay are:
Full list of top boat tours in Upper Chesapeake Bay
The average price for a private 4 hour Upper Chesapeake Bay boat trip is US $589, while an 8 hour private trip will cost you US $1,903 based on prices on BoatBooker.com.
The average price for a private 4 hour Upper Chesapeake Bay boat trip is US $589, while an 8 hour private trip will cost you US $1,903 based on prices on BoatBooker.com.
The top 5 boating-related activities in Upper Chesapeake Bay are:
The top 5 boating-related activities in Upper Chesapeake Bay are:
The top 5 most popular boat types you can rent in Upper Chesapeake Bay, by number of boats available are:
The top 5 most popular boat types you can rent in Upper Chesapeake Bay, by number of boats available are:
The top 5 most popular boat categories you can rent in Upper Chesapeake Bay, by number of boats available are:
The top 5 most popular boat categories you can rent in Upper Chesapeake Bay, by number of boats available are:
According to customer reviews on BoatBooker.com, some of the best rated boat tours in Upper Chesapeake Bay are:
According to customer reviews on BoatBooker.com, some of the best rated boat tours in Upper Chesapeake Bay are:
The average price of boat tours in Upper Chesapeake Bay is:
  • 2-hour boating trips – US $643
  • 3-hour boating trips – US $1,276
  • 4-hour boating trips – US $985
  • 5-hour boating trips – US $700
  • 6-hour boating trips – US $1,900
  • 8-hour boating trips – US $975
The average price of boat tours in Upper Chesapeake Bay is:
  • 2-hour boating trips – US $643
  • 3-hour boating trips – US $1,276
  • 4-hour boating trips – US $985
  • 5-hour boating trips – US $700
  • 6-hour boating trips – US $1,900
  • 8-hour boating trips – US $975
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Boating in Upper Chesapeake Bay

Upper Chesapeake Bay is where sheltered waters, scenic river mouths, and charming harbor towns come together for unforgettable days on the water. From the wide Susquehanna River delta to the winding Sassafras, Elk, Bohemia, and North East Rivers, you’ll find calm, protected routes ideal for families, first-time boaters, and seasoned captains alike. Upper Chesapeake Bay boating charters make it easy to explore quiet coves, sandy shorelines, and tree-lined bluffs that glow at sunset.

Historic waterfronts add to the appeal. Cruise past Havre de Grace’s landmark lighthouse views, drift by the canal-side architecture of Chesapeake City on the C&D Canal, or drop anchor near Elk Neck State Park to swim, picnic, and photograph ospreys and herons. With marinas, fuel docks, and transient slips conveniently spaced along both shores, it’s simple to plan a relaxed day trip or a full weekend of hop-on, hop-off exploring.

Upper Chesapeake Bay boating charters cater to every style of adventure. Choose a leisurely sightseeing or sunset cruise, book a nature-focused outing through marsh-lined backwaters, or opt for a captained day that links waterfront eateries with strollable historic districts. The Bay’s gentle chop and short distances between highlights mean more time enjoying the ride and less time underway.

Season by season, the scenery changes but the draw remains the same: easy navigation, abundant wildlife, and welcoming ports. Whether you’re celebrating with friends, entertaining family, or just chasing a quiet cove, Upper Chesapeake Bay boating charters deliver the perfect blend of access, variety, and small-town charm—right where the rivers meet the Bay.

What people said about boating in Upper Chesapeake Bay

  • 5.0
    /5
    (3 Hour – Sunset Wine Cruise)

    Great Local Team

    It's a changeable time of year and can be cold--or hot. Weather is tough, but the captain is flexible.
    Leigh F.
    Leigh F.
    Reviewed on May 22, 2026

How people rated boat trips in Upper Chesapeake Bay

  • Hot Pursuit Charter Fishing LLC
    Hot Pursuit Charter Fishing LLC
    Boat rentals in Upper Chesapeake Bay
    5.0
    /5
    (3 Hour – Scenic Cruise)

    Such a fun experience

    Captain Don and his wife Madie are amazing! The boat ride was so fun, and they were incredibly professional, welcoming, and safe!
    Shefali J.
    Shefali J.
    Reviewed on Jun 25, 2026
  • Burton Charters, Inc
    Burton Charters, Inc
    Boat rentals in Upper Chesapeake Bay
    5.0
    /5
    (4 Hour – Lunch and Swimming)

    Bucket Lister

    An amazing day that far exceeded all our expectations. We plan to be back yearly!
    Paula T.
    Paula T.
    Reviewed on Jun 12, 2026
  • Screaming Eagle Charters
    Screaming Eagle Charters
    Boat rentals in Upper Chesapeake Bay
    5.0
    /5
    (3 Hour – Sunset Wine Cruise)

    Great Local Team

    We were looking for people who new the area well, and this was the right team. Highly recommend. Would book again.
    Leigh F.
    Leigh F.
    Reviewed on May 23, 2026
  • Hot Pursuit Charter Fishing LLC
    Hot Pursuit Charter Fishing LLC
    Boat rentals in Upper Chesapeake Bay
    5.0
    /5
    (6 Hour Trip – Weekday (copy))

    Great Blue Angels Day Event

    We booked Don and the Hot Pursuit for a corporate boating event to watch the Blue Angels. Don was very professional, personable and easy going. The boat was very spacious and fit our need perfectly. He was very responsive ahead of the trip when I had questions and needed coordination with the caterer. We had a great spot on the Severn River and the team had a perfect day!
    Denise Z.
    Denise Z.
    Reviewed on May 21, 2026
  • Hot Pursuit Charter Fishing LLC
    Hot Pursuit Charter Fishing LLC
    Boat rentals in Upper Chesapeake Bay
    5.0
    /5
    (3 Hour – Scenic Cruise)

    Great outing for an 80th Birthday celebration!

    Captain Don was great. The trip was all we hoped it would be. Captain Don was verry flexible and accommodating. We had several different age groups and they all enjoyed the trip.
    Crumback A.
    Crumback A.
    Reviewed on May 13, 2026
  • Screaming Eagle Charters
    Screaming Eagle Charters
    Boat rentals in Upper Chesapeake Bay
    5.0
    /5
    (3 Hour – Sunset Wine Cruise)

    Fun and easy!

    We found the booking process extremely easy, communication clear, and had a beautiful sunset cruise. Thank you!
    Nancy L.
    Nancy L.
    Reviewed on Apr 3, 2026
  • Hot Pursuit Charter Fishing LLC
    Hot Pursuit Charter Fishing LLC
    Boat rentals in Upper Chesapeake Bay
    5.0
    /5
    (3 Hour – Scenic Cruise)

    Wonderful Day

    The captain couldn’t have been more accommodating. We booked this boat for a family gathering and celebration of life for a deceased loved one. The day was spectacular with loved ones reuniting by the beautiful view of the light house and bay. Would definitely charter this boat again.
    Carolyn H.
    Carolyn H.
    Reviewed on Oct 27, 2025
  • Hot Pursuit Charter Fishing LLC
    Hot Pursuit Charter Fishing LLC
    Boat rentals in Upper Chesapeake Bay
    5.0
    /5
    (3 Hour – Scenic Cruise)

    A beautiful ride

    My family had a beautiful 3-hours boat cruise in this beautiful boat. We had a good time and the captain was very nice, respectful and polite. It was an enjoyable experience for my family. Thank you captain Don.
    Afam E.
    Afam E.
    Reviewed on Aug 2, 2025
  • Burton Charters, Inc
    Burton Charters, Inc
    Boat rentals in Upper Chesapeake Bay
    5.0
    /5
    (Special 2 hour trip for Brandy Starheim)

    We loved our day on the Kimberly Ann!

    Jim, James and Kimberly were amazing. Everything was perfect…amazing boat, safe and friendly crew and a perfect tour of the lighthouse. We even got to stop for a little dip in the water. Thank you!!
    Brandy S.
    Brandy S.
    Reviewed on Jun 29, 2025