Cape May

Bicycle Tour of Cape May, NJ and Lewes, DE

A 5 Day Cycling Vacation on the Atlantic Coast

Cape May, New Jersey and Lewes, Delaware: two delightful beach communities and vibrant towns that are best explored by bicycle.  Both communities include state parks, lighthouses, beaches, museums and more.  Conveniently connected by the Cape May - Lewes Ferry, these wonderful communities are combined in our latest itinerary.

Note:  This page is under construction.  Check back soon for more details and images.

Book this Tour

Cape May

Lewes, DE

Tour Difficulty



5 Days, 4 Nights


Inn at Canal Square

Nearest Airport



From $2675 per person


5/8/22 - 5/12/22 9/25/22 - 9/29/22 10/2/22 - 10/6/22

Tour Status

Two spots have opened up on each tour date. Please email or call a.s.a.p. if interested.
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Lewes, DE has been a favorite overnight destination for us for many years. We are delighted to add this new itinerary with a second night in Lewes and our first adventure in Cape May.
Greg and Anne

ItineraryDownload Itinerary

Day 1

20–30 miles, easy

We'll meet in the charming town of Lewes, DE near Delaware Bay.  First settled by the Dutch in 1631, Lewes calls itself "The First Town in the First State."  After lunch and orientation, we will jump on our bikes to explore Cape Henlopen State Park and the Rehoboth Beach boardwalk.  Cycling in the area has been greatly enhanced by new paved trails and wide paved shoulders on roadways.  Our group dinner tonight will definitely include fresh local seafood.

Day 2

25–50 miles, easy

Explore the Delaware country roads and a magnificent new rail trail today.  Multiple route distance options are available to satisfy varying riding styles.  We'll make our way through the communities of Georgetown and Milton, the latter being the home of wildly successful Dogfish Head Brewery.  Take a few minutes for a beer tasting before cruising back in to Lewes.

Day 3

15–35 miles, easy

We'll take the Cape May - Lewes Ferry across Delaware Bay this morning.  Upon arrival in Cape May, we'll have the chance to bike to the Lighthouse, explore the beautiful Victorian town and walk the beach.

Day 4

25–47 miles, easy

Today offers the opportunity to bike as little or as much as you please.  The loop route of 47 miles includes the waterfront communites of Wildwood, Stone Harbor and Cape May Courthouse.  There will be ocean and bayside views to enjoy along a strikingly diverse route.  Route extensions are available to make this a metric century, and leapfrog shuttle options can whittle it down a shorter ride as desired.

Day 5

5–25 miles, easy

On our final day, rise early to take a bike ride on the Cape May promenade overlooking the Atlantic Ocean, and around town before everyone wake up.  After breakfast at The Virginia, we'll cruise over to the ferry dock for our return to Lewes.


$2,675 - $2,775
Single Room Supplement

What's included in your Tour Price

Tour prices are per person rates and include all of the following:

  • Lodging costs (double occupancy rooms), including all taxes/fees
  • All breakfasts and most lunches
  • All dinners described in the tour itinerary. Please note: alcoholic beverages are not included.
  • 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 were noted
  • Transportation back to starting point
  • Costs for any special activities such as canoeing, kayaking, sailing, or rafting where noted
  • Carolina Tailwinds t-shirt or day bag, water bottles, complimentary photo cd of your tour on request.

Please Note:

All lodging costs are based on double occupancy. The single room surcharge rates are shown above.

Single travelers who desire a roommate match will be paired with other tour guests of the same gender in a room with two beds, if available. If a match can't be found for a single traveler, a single occupancy surcharge will be assessed. To find out if a roommate match is available, call us. We will be happy to put you on a wait list for a match if one is not already available.

Single travelers may request a private room, subject to availability, and to the single room surcharge rate payable in full at the time of the reservation.

Transportation to the tour starting point, including airfare and any airport transfers, is not included in the tour price. We can assist you with making any airport transportation arrangements or advise you on the nearest and most convenient airport. See more airport and airport shuttle information on our FAQ page or on the individual tour pages.

Alcoholic beverages at restaurants are not generally included . A separate beverage tab may be run for anyone who would like a drink with dinner. Settling this tab will be the responsibility of the individual participants.

Bicycle rental is available as an option (prices above). We have road touring bikes and hybrid bikes for your use and invite you to forego the hassle of transporting your bike to and from the starting point. Click here for more information on the equipment available for your use.

Want to know more about our polices, terms and conditions? Click here to review our deposit requirements, cancellation policy and more.

We will be happy to address any additional concerns or questions you may have.
Simply e-mail us at our Contact Us page, or call us at 1-888-251-3206 (local number is 336.794.1054). Ready to make your
reservation? Click here to reserve a spot online, or call us at 1-888-251-3206 (local number is 336.794.1054).

Travel Insurance: We strongly encourage you to consider travel insurance. You may research and compare competing travel insurance policies at websites such as


Inn at Canal Square

Nights 1 & 2

The Inn at Canal Square, Lewes, DE.  Overlooking the Lewes Harbor in the heart of Historic Lewes, this upscale inn is 1.4 miles from Lewes Beach.  22 tastefully furnished and generously sized rooms feature private balconies, harbor views, minifridges and coffeemakers. Outstanding dining and unique shopping are within easy walking distance.

The Virginia Hotel

Nights 3 & 4

The Virginia Hotel sets the standard for luxury hotels in Cape May, New Jersey. An impeccably restored 1879 landmark building, history combines with modern day amenities and superior service to provide guests with a unique, adults-only hotel experience. The Virginia is located just a block from the beach, offering vacationers a haven of beautiful design, unrivaled comfort and friendly, attentive service.



The terrain is entirely flat.  Mileage each day will range from 25 – 55+ miles, at your option.  As with all Carolina Tailwinds tours, you can take advantage of the support van to "leap frog" ahead on the route.

All of the routes are on country back roads or busier roads with bicycle accommodation, and the scenery is beautiful.  This area has many roads with wide pave shoulders and paved bicycle paths, and we have incorporated them into our routes.  That being said, any rider enrolling in this tour should be comfortable and competent biking on public roadways with traffic.

Tour Point of Origin:

The Inn at Canal Square, 122 Market Street, Lewes, DE 19958

Getting to the Tour Start (Lewes, DE)

Driving: Approximate drive time to Lewes--

  • Annapolis, MD:  1.5 hours
  • Raleigh, NC:  6.5 hours
  • Washington, DC:  2.25 hours
  • Philadelphia, PA:  2.5 hours

Planning your drive:  If coming from the south, be careful to avoid rush hour in the Norfolk area.  Besides that, look forward to the Chesapeake Bay Bridge and Tunnel, an engineering marvel.  Check for weather related delays in advance:  EZPass accepted. 


Salisbury Regional Airport (SBY)  1 hour driving from Lewes
Service by American affiliate Piedmont Airways.  All flights through Philadelphia or Charlotte.
Rental cars available from Avis and Enterprise

Wilmington Airport (ILG)  1.5 hours driving from Lewes
Service by Frontier through Orlando
Rental cars available

Thurgood Marshall International Airport  (BWI)  2.5 hours from Lewes
Service by all major airlines and rental car companies.

Parking: We have arranged for complimentary long term parking for the duration of your tour in Lewes. 

Arrival/Departure Timing

In order to participate in the Day 1 meeting and bike ride, please plan to arrive in Lewes no later than 11:30 a.m. (10:30 a.m. if renting a bike).

 On Day 6, we will return to Lewes between 12 and 1:00 pm.  Flights should be booked for the following day. 


Extend Your Vacation

Before or after our activity packed tour, you may want to tack on a few days. 

Cape Charles, VA:  If driving from the south, consider an overnight or two in lovely Cape Charles on the lower Delmarva Peninsula.  For years a sleepy little town, it has recently emerged as a favorite waterfront getaway with new restaurants, breweries, upscale lodging and more.  2.75 hours drive from Lewes.

Annapolis:  If driving or flying through BWI, Annapolis is a logical place to explore on your own.  Downtown is historic and walkable, and home to the state capitol, U.S. Naval Academy and a beautiful waterfront.

Brandywine Valley:  If driving from the north or flying through ILG or PHL, you may want to explore the regional attactions:  
Longwood Gardens, the Winterthur Museum, Hagley Museum and the historic Brandywine Battlefield.


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