Recommended plan: Drive to Orleans and rent bikes at Orleans Cycle (http://www.orleanscycle.com/). Bike along the Cape Cod Rail Trail to Coast Guard Beach (https://www.nps.gov/caco/planyourvisit/coast-guard-beach-eastham.htm). There is a beautiful ~2 mile bike path offshoot from the Cape Cod Rail Trail that takes you to this beach. Type 2 fun people (if you don’t know what this means, this plan isn’t for you probably): Drive to Orleans and rent bikes at Orleans Cycle. Bike along the Cape Cod Rail Trail to the Beachcomber!
Best beaches: Coastguard beach, Nauset beach Things to see: Nauset Lighthouse Drive to and hike at the Cape Cod National Seashore which has beaches, lighthouses, hiking, and the Beachcomber bar. Recommended plan: Drive to and park at the Salt Pond Visitor Center, Eastham. Hiking trails leave from here for brief exploration. Then drive to the Nauset Lighthouse. This is a great beach for hanging out for a while. If you have time, head to the Beachcomber bar. If the weather is nice, the parking lot can be busy!
Recommended plan: Park at Paine’s Creek Beach parking. In September it will be free to park. If the lot is full, you can go to Mant’s Landing or Saint’s Landing beaches. If it’s high tide, you can swim on the beach. If it’s low tide, you can walk out ~1 mile and swim out there, and explore the flats (tons of wildlife)!
Stroll and window shop in classy Chatham Recommended plan: Park at any public parking lot or street parking in Chatham. Grab a coffee from Snowy Owl and window shop. Grab a tiki drink at Apalya. There are also nearby beaches to explore.
Recommended plan: If you don’t like salty water, Cape Cod has nice ponds for swimming and hanging out that are usually not crowded. Pleasant Lake and Nickerson State Park are both nice!
Recommended plan: If you want to explore a famous Cape Cod town, drive up to Provincetown for Portuguese food and window shopping. Warning that the drive is not short from West Dennis!
Classic Cape Cod Shopping
Sesuit Harbor Cafe (lunch/dinner)*** Mac’s Chatham Fish and Lobster (lunch/dinner)* Aplaya Tiki Bar (lunch/dinner)* Mad Minnow (lunch/dinner) Land Ho (rainy day) (lunch/dinner) Grumpy’s (breakfast)
Peacemaker (breakfast) Kate's Fried Seafood & Ice Cream (lunch/dinner) Pleasant Lake Pizza Shark (lunch/dinner) Mom & Pops Burgers (lunch/dinner) Sir Cricket’s Fish and Chips Hot Chocolate Sparrow (coffee/dessert)** Snowy Owl (coffee)**
Sundae School** Kate's Fried Seafood & Ice Cream (lunch/dinner)**
Devil’s Purse** The Beachcomber*** Hog Island Perks Coffee Shop & Beer Garden (in Harwich, which has a nice, tiny downtown and ‘nightlife’, to the extent that exists on the Cape) Treehouse (on your way to or off Cape Cod near the bridge)