Coastal Highlights

Self-Guided Multi-Sport Adventure


Have you ever had the opportunity to travel with a local? Have them show you the sights, take you to their favorite restaurants and pubs. Our new self-guided multi-sport adventures let you discover Maine from a local’s perspective. We have created a five-day fun-filled adventure. In addition to arranging activities and hotels, we will share with you our favorite spots along the way, for food, drinks, view, and more.

  • Enjoy Five Days Exploring Maine
  • Bike Acadia’s Carriage Roads
  • Sail on Penobscot Bay
  • Hike for Amazing Ocean Views

2021 Dates

Starts any Sunday, May through October

Price $1395.00 per person



Day 1 Bike to Lighthouses-Portland

Arrive in Portland, Maine and stop by our bike rental shop the Portland Encyclepedia where will set you up with bikes and a trunk mount bike rack. From our shop, we will send you to visit three lighthouses and enjoy Portland’s best lobster roll.

Activity: Cycling 15 miles
Lodging: The Portland Regency
Meals: Breakfast

Day 2 Heading to Camden

Leaving Portland head to mid-coast Maine and pause to hike Morse Mountain. More of a hill than a mountain you will enjoy ocean views and the opportunity to walk on a beach. After hiking continue north to the Picturesque town of Camden where you will finish your day sailing on Penobscot Bay.

Activities: Sailing and Hiking
Lodging: The Hartstone Inn
Meals: Breakfast

Day 3 Hiking and travel to Bar Harbor

Begin your morning with an easy hike for panoramic views. See the islands of the Blue Hill Archipelago, Penobscot Bay, and the mountains of Acadia National Park. Plan to arrive in Bar Harbor early enough to walk the shore path and explore the town.

Activities: Hiking
Lodging: The Sand Bar Cottage Inn
Meals: Breakfast

Day 4 Acadia’s Carriage Roads

Picture breathtaking scenery, gentle grades, and car-free cycling, and you have Acadia’s famous carriage roads. A gift of John D. Rockefeller to help the people of America enjoy Acadia’s beauty the carriage roads offer the opportunity to cycle through stately forests of pine and birch and to enjoy panoramic views of Mount Desert Island.

Activity Cycling: 12 to 35 miles
Lodging: The Sand Bar Cottage Inn
Meals: Breakfast

Day 5 Sea Kayaking

Join your guide for a morning of paddling the waters of Blue Hill Bay. If you are lucky you will see seals, dolphins, and bald eagles. After kayaking, return to Portland or extend your stay for more exploration.

Activity: Kayaking
Meals: Breakfast



Browse Trips


  • Four nights’ lodging
  • All lodging taxes and gratuities
  • Four breakfasts
  • Hybrid Bike Rental with helmet
  • Trunk mount bike rack
  • Sailing and kayaking
  • Detailed route notes and maps
  • Summer Feet Souvenirs – a cycling water bottle and t-shirt (available in men’s and women’s fit)


Price: $1395 Per person

Ask A Question