Curator’s statement
As a lifelong Bostonian, the Cape has held a special place in my heart since I was a child. The only issue was the beach. I never really enjoyed it. As an adult, I learned to love the Cape from a different angle. I’m thrilled to help those who want to explore this beautiful part of New England without too much sand in their shoes.
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Day 1: Arrival
Chatham's Hydrangeas
Plan to arrive at your hotel around lunch time — this will give you plenty of time to cross the bridge (Sagamore or Bourne) and not stress about the ride. Check in, explore the property and go out for lunch. Plan to spend the afternoon strolling down Main Street in Chatham. Grab lunch at any place that looks good. Impudent Oyster is a great spot (a little more upscale) that serves lunch or dinner or grab a quick sandwich at Chatham Cookware if you want to spend more time shopping/browsing. There are cute shops up and down Main Street — enjoy it!
After stopping back at the hotel to freshen up, grab a drink at the hotel bar and then head to dinner. If you are in the mood for Italian, check out Buca’s Tuscan Roadhouse - authentic Italian food with great service and even better bread.
Day 2: Provincetown
Bikes on Herring Cove Beach in Provincetown
Day two is all about the part of the “arm” you haven’t driven through yet. Get in your car and head towards Provincetown. Stop at Three Fins Coffee Roasters to caffeinate for the ride.
Once in P-Town, find a parking spot and plan to explore. There are great art galleries, boutiques and incredible food. The Canteen has a great menu with some classics and some not-so-classic options. Plus, you can pick up your food and then grab a spot in their backyard that opens up to the Bay. I’d recommend renting a bike and heading out to Herring Cove Beach or Race Point Beach (even if you don’t like the sand, these are beautiful spots). Before starting your ride home, if you need another coffee — check out Kohi.
If you decide to stay in P-Town for an early dinner, as you head home, check out Wellfleet Cinemas to see if there is a movie that catches your eye. An old-fashioned drive-in movie theater, this is a great option with or without kids.
If you come home during the day, take your time and stop at Nauset Lighthouse in Eastham or venture into Orleans.
Day 3: Boating
Today we’re going on a boat! The Cape has two islands right of the south coast - Martha’s Vineyard and Nantucket. Both are incredibly beautiful, charming, and very special — it’s up to you which one catches your eye. There is a ferry from Harwich Port (closer to Chatham) to Nantucket, so that might win out just for convenience. You don’t need your car for either so find a place to park and enjoy the freedom. Take in the salt air as you are on the water and prepare for a day of shopping, ice cream, great food, and biking (if you are up for it again) around the islands. If you aren’t sure which island to choose — let me know and I can help you decide!
On your way back, dinner can be at your hotel or try Mooncusser’s Tavern in Harwich Port.
Day 4: Farewell
It’s our last day down the Cape — get up nice and early to finish packing and check out. Before you cross over the bridge, we’ve got more of the west side of the Cape to check out.
Depending on your stamina (or your driver’s interest in long drives) you have two options:
The easier option is to head towards Hyannis and drive towards the airport — no, you aren’t flying home (unless… you are?). Instead, you are going to Pain D’Avignon - an incredible Parisian boulangerie right next to the airport. They have a full sit-down restaurant or you can grab bread or baked goods at the counter. They’ve also opened a pizza place next door!
Hop on Rt 6 north and right before the Sagamore Bridge, you’ll come to Sandwich, MA. Stop at Heritage Museum & Gardens — a gem down the cape with an old car museum, gorgeous gardens and outdoor art.
Once you’re done with all that walking, you’re ready for the final bite or brew before your weekend is fully over. Sandwich has a variety of places for lunch (Cafe Chew, Moto Pizza and Off the Grid are some of my favorites). If you want to sneak in one last incredible view, head to Tree House Brewing for a pint and snag an Adirondack chair to take in the scenery.
If you are ready for a longer ride (and/or plan to take the Bourne Bridge home), put Woods Hole in your GPS. Head to the Woods Hole Science Aquarium or just enjoy the main street (be sure to check out the famous Pie in the Sky Bakery). If you want a more substantial bite to eat before heading off on the road, you can swing back towards Falmouth. Stop at Simply Divine Pizza (believe me, sharing a slice is more than enough!)
Need to know
A note about traveling to Cape Cod: The Cape is long, with really only one road that will take you all the way to it's farthest point. The travel time will vary depending on where you are headed (and when you go). My recommendations in this guide place you in the middle of the Cape (just at the tip of the “elbow” if you are looking at a map), so you can explore all parts without too long a drive. I always recommend a car for exploring (I can help you rent one if you need it!) but there are a few ways to get down the Cape. A car (or a bus) is convenient but depending on when you go (and where you go), there can/will be traffic. Just build it into the plan and you’ll be fine. Alternatively, there is a seasonal train from Boston that brings you to Hyannis (the Cape Flyer) or you can take the ferry from Boston to Provincetown.
There is a lot to do down the Cape - mini golf, Glass Museum, festivals (especially in the summer and fall). It’s great for a romantic getaway, a girls weekend, or a trip with the kids. You just need to know someone who knows the Cape to truly get the most out of it.
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Joanna Vinick
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