Day by Day Itinerary

Chesapeake Bay Bicycle Tour 2015

Countries   USA
Tour Length   6 days
Dates Of Tour   Sunday, May 3, 2015
Sunday, May 10, 2015
Sunday, September 27, 2015
Sunday, October 4, 2015
(All dates are Sunday-Friday tours.)
Type of Tour Road (Guided)
Price $2,025 ($100 discount applies to reservations paid in full 180 day prior to the tour date. )
Family Friendly
Age of Participants Mixed
Gender Basis Mixed
# of Participants (max) 18
Language English
Sleeping Accommodations   
Luggage Support
Sag Wagon Along the Way
Total Trip Mileage    300 Miles
Average Daily Mileage    50 Miles Per Day
Longest Single Day 62 Miles
Total Trip Altitude Gain +0 ft
Single Day Altitude Gain   +0 ft
Overall Difficulty Rating   Beginner, Intermediate
Cost of Trip without Airfare per person  $2,125
Cost of Trip with Airfare per person   n/a
Single Supplement $450
  • Lodging costs (double occupancy rooms), including all taxes and fees
  • Three outstanding dinners at three of the finest restaurants on the Eastern Shore.
  • Breakfast daily
  • Lunch every day but one
  • Morning and afternoon snacks
  • Route planning and detailed daily area maps
  • Guide support along the route
  • Van support along the route
  • Luggage transfer
  • Fees for all ferries, tolls for all highways and any park entrance or guided tour fees where noted
  • Transportation back to starting point
  • Costs for any special activities such as canoeing, kayaking, sailing or rafting
  • where noted
  • Complimentary photos of your tour, Carolina Tailwinds t-shirt, and water bottles
  • Perfect cycling conditions on flat Eastern Shore farmland and coastline
  • Fresh gourmet seafood
  • Beach-combing and plenty of relaxation

Beginning and ending in historic Chestertown, MD this tour also spends one night in Lewes, DE, one night in Berlin, MD, and two in the picturesque waterfront town of St. Michaels, MD.

In a region defined by the numerous exquisite tidal rivers that drain into the Chesapeake Bay and the shimmering beauty of undeveloped seashore on the Atlantic Ocean, miles of flat coastal cycling await you. Views of rural farmland, Chesapeake Bay skipjacks and sailing craft, fishing boats, and quaint communities greet you along the way.

Day 1   Bike to Rock Hall, MD
Day 2   Cross the Peninsula to Historic Lewes
Day 3   Delaware Seashore
Day 4   Blackwater Wildlife Refuge and the Oxford Ferry
Day 5   A Day to Do What You Want
Day 6   Return to Chestertown
Additional Activities During Trip
Optional paddling, maritime museum tours, birding.
Countries Visited  
  • USA
    • Delaware
    • Maryland
Cities Visited   Chestertown MD, Lewes DE, Berlin MD, St. Michaels MD
Early Bird Discount

The earlier you enroll, the better your price. Your discount when you pay in full 6 months prior to your tour is $100, 5 months = $75, 4 months = $50, and 3 months = $25.


• Nights 1: Brampton Inn, Chestertown, MD. Located on 20 acres of woodland and gardens, the Branpton Inn has been described by the NY Times as "...meticulously restored, utterly quiet, in a pastoral setting. The perfect base for exploring the Eastern Shore." You may want to add a night here to the beginning or end or your tour.

• Nights 2: The Inn at Canal Square, Lewes, DE. Located on the waterfront in the heart of Historic Lewes, The Inn at Canal Square offers its guests comfort coupled with seaside charm.

• Nights 3: The Atlantic Hotel, Berlin, MD. Each room is beautifully furnished with antiques and unique in its decor. Rich green and burgundy, delicate rose and aqua, and deep mahogany tones all help transport you to a gentler time and quieter place.

• Nights 4 & 5: The Five Gables Inn, St. Michaels, MD. In the heart of historic downtown, this inn is a haven for relaxation, featuring twenty well-appointed rooms, an Aveda Concept Spa, an indoor pool, sauna and steam room.


Designed for flexibility, our routes offer 15 - 50+ miles each day (at your option). Stronger cyclists may bike over 50 miles on each day of the tour, including up to 75 on two days. Less ambitious cyclists take advantage of short cuts and "leap frog" van shuttles along the route to tailor the route to their needs. Because the route distance options are so flexible, this is one of the best tours for bicycling companions of differing riding styles.

The terrain is flat, making it accessible to all ability levels. Strong coastal winds sometimes present a minor challenge, but they are just as likely to propel us along our route! Along the way, observe coastal wetlands and rural farmland as we bike the scenic backroads of Maryland and Delaware.


We have a new fleet of road bikes featuring custom steel frames and Shimano 105 components. We also have a fleet of high quality Cannondale and Fuji hybrid (flat handlebar) bikes. You are welcome to bring your own saddle and/or pedals for installation on a rental bike.


This tour destination is easy to reach by car or by air. If flying, Baltimore/Washington International Airport (BWI) is usually the best bet. From there, an inexpensive airport shuttle can take you to nearby Annapolis, MD. If you spend the night prior to the tour in Annapolis, Carolina Tailwinds will provide the remaining shuttle from there to Chestertown on the first morning of the tour.

Company Name Carolina Tailwinds
Country     USA
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