“Bay to Ocean Tour #1”: May 4-10, 2025
The LOVE sign that sits on the beach in Chesapeake Bay in Cape Charles VA
Experience the unspoiled beauty of Virginia’s Eastern Shore
We are excited to offer you an unforgettable experience on Virginia's Eastern Shore with our bicycle tours. Our tours are perfect for adventure seekers and nature lovers who want to take in the beauty of the Chesapeake Bay and the Atlantic Ocean while getting some exercise.
During our tours, we will be staying in two charming coastal towns: Cape Charles and Chincoteague. Both towns have a rich history and offer stunning views of the Chesapeake Bay and Atlantic Ocean. In Cape Charles, you will find yourself surrounded by quaint Victorian homes, beautiful beaches, and a bustling downtown area filled with unique shops and restaurants. Chincoteague, on the other hand, is known for its wild ponies and offers a more laid-back atmosphere with breathtaking sunsets over the bay.
One of the highlights of our bicycle tours is the food. As avid seafood lovers ourselves, we make sure to take our guests to only the best seafood restaurants in the area. From fresh oysters to mouthwatering crab cakes, you will have plenty of opportunities to indulge in delicious local cuisine. We believe that experiencing a destination also means experiencing its food culture, and we can't wait to share it with you.
No Eastern Shore visit would be complete without taking in Tangier Island and Chincoteague Island. This tour includes two boat tours over the course of our time together so you can learn more about the area.
Ability Level: 2-3 (lightly travelled roads, moderate distance)
Mileage: 30-50 miles per day with SAG options
Terrain: Coastal and therefore flat with wind. All paved surfaces.
Cost: $2,495 Double occupancy. Single supplement is only an additional $500. Registration fee is $500 to hold your spot and the balance can be paid up until 30 days prior to arrival. A $200 early bird discount will be applied if you register before 12/31.
Our rider meeting in Cape Charles
Additional Ride Information
Wow Factor:
Immerse yourself in the beauty of unspoiled nature
Feast on fresh soft-shell crab and fresh oysters
Relax on a boat cruise around Chincoteague
Ride through pastoral farmland on lightly traveled roads
What You’ll Get:
All-inclusive bicycling vacation including concierge services
Exceptional guides who ensure you are safe and having a great time
Four days of cycling around beautiful coastal villages
Six nights in the best hotels/B&Bs three of those nights will be in a waterfront hotel with balconies.
All transportation for you and your bike
Valet service for your luggage
Shuttle service
Breakfast each morning
Healthy snacks, water and ice at scheduled rest stops
Delicious picnic lunches
Four dinners at locally owned restaurants
Free time to stroll small towns, exploring shops, museums, restaurants, breweries and wineries
Incredible SAG support with a bike mechanic.
Incident medical insurance and first aid supplies in all support vehicles
Things to note
Helmets are required. NO EXCEPTIONS!
You do need to have two spare tubes. Our mechanic is just a phone call away if you need a flat tire fixed.
Please have your bike serviced/setup prior to joining us so that you know your equipment is ready to ride!
gratuity for the support team is customary for full-service tours. Please bring cash.
