Massachusetts Cape and Islands Tour – Discover Coastal Charm

Discover the pristine beauty and captivating charm of Massachusetts on our six-day extended Cape and Islands tour. Experience the best that New England has to offer while discovering hidden scenes and beloved landmarks in this dreamy coastal tour. We’ll take you to both the iconic Nantucket Island and picturesque Martha’s Vineyard, with plenty of time to explore the quaint towns, beaches, wines, and sights that make these destinations so uniquely special. Discover them all by bike or boat, meeting locals along the way who can provide insights into the area’s real flavor. We invite you to experience our backyard where untamed serenity meets New England culture – from peaceful lighthouses and winding woodlands paths to bustling art galleries and fine dining – all richly steeped in history. Do more than just imagine it; come explore for yourself! Start at the tip of Cape Cod in fascinating Province Town. Bike spectacular trails in the 4,000 acres Province Lands. Pedal through maritime forests and emerge onto an open, vast dune system with farreaching views of the ocean. These parabolic dunes, some reaching 100' in height, are unique to the Cape in this part of the world. Stop at the visitor's center offering stunning 360° views of this extraordinary landscape. See Race Point Beach and Light and pedal alongside Herring Cove Beach on returning to Provincetown. Bike along the coast through classic Cape towns including the seaside artist community in Wellfleet. Explore another part of the Cape Cod National Seashore while pedaling past Nauset Light, Nauset Beach and Coast Guard Beach. Visit the Salt Pond Visitor Center to learn about the seashore’s unique ecosystems and enjoy panoramic views of marsh, ocean, bogs, pond and woodlands. Finish in Chatham, among the most picturesque towns on the Cape. Enjoy dinner at Chatham’s most acclaimed restaurant. Cycle a short loop viewing the Chatham Fish Pier, Chatham Lighthouse, the US Coast Guard Station and beautiful Chatham Light Beach. Walk an oceanside trail in the Monomoy National Wildlife Refuge to see sensational views and beaches where gray and harbor seals haul-out. Watch for seals frolicking in the shallow waters. Pedal past quaint shingled cottages and magnificent seaside estates. The afternoon in Chatham is free to enjoy as you wish. Relax at the beach or inn pool, explore the many unique boutiques and art galleries, take a seal-watching cruise or explore more of the area by bike. Enjoy dinner on your own with fine options just a walk away. Pedal on bike paths and roads to Saquatucket Harbor, then board the ferry to Nantucket, once the whaling capital of the world. Discover the beautifully preserved village architecture that looks almost as it did 200 years ago and explore cobblestoned streets lined with gas lamps. Pedal bike paths to pristine beaches and stately lighthouses while enjoying breathtaking views along the way. After exploring Nantucket, ferry to Martha’s Vineyard and view the renowned Gingerbread Cottages in Oak Bluffs. Pedal a seaside bike path to the handsome colonial era village of Edgartown. Enjoy dinner on your own with many excellent options to choose from. Continue the exploration of Martha’s Vineyard and discover quintessential fishing villages, island farms and miles of beaches. Visit the Mytoi Gardens on the stunning Chappaquiddick Island. Swing back to Edgartown for lunch before a quick ride to South Beach. Travel back to Oak Bluffs through Edgartown. View the meticulously preserved mansions built by whaling captains. Relax at the inn pool enjoying a drink from the poolside bar, or stroll the charming streets of town, lined with fine boutiques and art galleries. Enjoy dinner together at an excellent Oak Bluffs restaurant. This morning, take one last ride on Martha’s Vineyard, pedaling flat bike paths through Oak Bluffs to Vineyard Haven. Bike a quiet road to West Chop embraced by soft sand dunes and framed by the sparkling Atlantic. Pedal back to the inn, then depart for the mainland where you may wish to spend a bit of time exploring Woods Hole, a charming fishing village which is home to numerous shops, cafes and the Woods Hole Oceanographic Institution. Your guides will return you to your car or to your transportation to Boston. By tour’s end, you will have experienced much of the finest of Cape Cod and the Islands and this extraordinary place will certainly have captivated your heart. Confirmation will be received within 48 hours of booking, subject to availability Not wheelchair accessible Near public transportation Not recommended for pregnant travelers No heart problems or other serious medical conditions Travelers should have a moderate physical fitness level