Escape to the Cape for a long weekend with this three-day weekend Cape Cod itinerary. The secret about Cape Cod is out, making this New Englander’s summer getaway a not-so-hidden gem. Could you do Cape Cod as a day trip from Boston? Sure, you can, but you won’t enjoy it nearly as much as going for three full days to explore everything it has to offer. So, pack your bags and take your PTO to make the most out of a three-day weekend on Cape Cod.
For this itinerary, we will assume you have three full days in Cape Cod, arriving late on Thursday night and leaving late Sunday night or early Monday morning.
Let’s get into it.
Friday: Mid Cape
On your first day in Cape Cod, acquaint yourself with the area you’re staying in. If it’s your first time visiting Cape Cod, you should stay in Mid Cape. I recommend Barnstable, specifically Hyannis because it makes a great home base with easy access to beaches, grocery stores, main streets, whale watching, and more. Regardless of where you stay, there are a bunch of things to see and do in Mid Cape that you won’t want to miss.
Breakfast at Old King’s Coffeehouse
Start your day with breakfast at Old King’s Coffeehouse. Old King’s is a casual order-at-the-counter kind of place. They have great breakfast sandwiches and burritos that are both delicious and filling. Grab a coffee or a matcha latte and enjoy it there or take it to-go to enjoy on the beach.
Stroll down Main St. in Hyannis
After breakfast, take the opportunity to stroll down nearby Main St. Hyannis, the heart of the Mid Cape. On Main St., you’ll find souvenir shops, restaurants, bars, and cafes.
Find your Cape Cod dream house on a walk along the beach
Walking along the sand in Hyannis gives you a view of the ocean and Cape Cod cottages worth millions. Neighborhoods in Cape Cod are lined with picturesque cottages with wood siding that have been weathered down to a charming light gray color. The most famous Cape Cod cottages are in the Kennedy Compound near Eugenia Fortes Beach. This was the place the Kennedy family (like JFK and Jackie O) called home.
In Hyannis, you can walk along the coastline to hop from beach to beach. Start your beach walk by the Kennedy Compound or park at Keyes Memorial Beach and walk to Kalmus Beach. Kalmus Beach has a snack bar if you’re hungry.
Shop for souvenirs at Cuffy’s
Cuffy’s isn’t your typical souvenir store. It’s a candy shop, homeware store, and apparel boutique all in one. They even host activities and events for kids. It’s worth the stop if you’re looking for Cape Cod merch. It’s located in Dennis, off the main drag so stop on your way to dinner. At the end of the summer, they have a huge sale where you can get hats and sweatshirts at unbeatable prices.
Drinks and snacks at Summer Shanty
The Summer Shanty is a seasonal hotspot that’s only open during the summer months. It’s in Bass River Marina in Dennis with a view of boats coming in and out. They have a great selection of fun cocktails and small plates to sip and snack on in the afternoon. There is extensive outdoor seating and live music indoors on most days.
Watch the sunset at Parker’s River Beach
You can catch the sunset at the Summer Shanty or take a short drive to Parker’s River Beach for a more picturesque view.
Across the street from the beach is The Skipper Restaurant. It has a window that serves ice cream that you can enjoy on the beach. The Skipper can have a long wait for dinner on the weekends, but it’s worth it if you’re willing to wait.
Dinner at Captain Parker’s Pub
Enjoy a laid-back dinner at Captain Parker’s Pub. The interior of Captain Parker’s is decked out with patches from first responders. It has a homey pub feel with a nice outdoor patio. On busy weekends, there can be a wait but you can hang out at the outdoor par and gas fire pit to pass the time.
The lobster at Captain Parker’s Pub was great. Order the Lazy Man’s Lobster to enjoy lobster meat without the hassle of wrestling a lobster with claws. We also tried a Quahog, a clam stuffed with breadcrumbs and chorizo which is a Cape Cod specialty.
Saturday: Outer + Lower Cape
Spend your Saturday going from town to town to sightsee, eat, drink, and get a true feel of Cape Cod.
You’ll explore the majority of the Cape by driving to your furthest point and working your way down. It takes about an hour to drive from Barnstable to Provincetown on the tip of the Outer Cape. To make the most of your Saturday start early to accomplish as much as possible on this jam-packed day.
That Planner Friend Tip: You could divide the plan for this day by doing one Outer Cape day for Provincetown and the National Seashore and another Lower Cape day where you explore Chatham and Harwich at a slower pace.
Breakfast at Three Fins Coffee Roasters
Before you leave Mid Cape, get your coffee fix by stopping at Three Fins Coffee Roasters in West Dennis. Three Fins Coffee Roasters is in a large industrial-like space off the main drag. They have a selection of pastries to pair with your coffee.
If you’re looking for a full sit-down breakfast, I recommend trying Hangar B Eatery in Chatham. Here, you can watch airplanes take off and land at the Chatham Municipal Airport. This breakfast spot is small and very popular so be prepared to wait.
Go to Provincetown…or don’t
After breakfast, you’ll want to drive to the furthest point on your road trip adventure. For most people that would be Provincetown also known as P-town. This quintessential Cape town is famous for being the real place where the pilgrims on the Mayflower landed in 1620 and for its proud LGBTQ+ community. If it’s on your bucket list, you should totally go. There are cute shops, picturesque homes, and a lively Commercial St.
In my humble, honest opinion, I believe Provincetown is a tourist trap. In the summer, Commercial St. gets overcrowded and you’ll spend at least $20 on parking. There are much more charming and laid-back main streets in the Cape for you to explore.
Sip wine at Truro Vineyards
Your Cape Cod adventure truly begins in the beach town of Truro. Truro’s land is mostly protected by the National Park Service as a part of the Cape Cod National Seashore. It’s also home to the best vineyard on Cape Cod.
Truro Vineyards is a small winery serving both red and white wine and spirits from their new distillery. If you want to taste multiple wines in a wine flight, you’ll need to make a reservation in advance and book a table on Tock. Reservations can be made for groups of up to eight people.
If you’re a larger group or don’t want to bother with reservations, you can head to the back patio bar in the vineyard for wines by the glass. In the vineyard, there are food trucks, cornhole, and plenty of seating. Be mindful that it gets crowded on holiday weekends so try to get there early.
Late lunch and drinks at the Beachcomber
The Beachcomber is a classic beach bar in Wellfleet. It’s on Cahoon Hallow Beach on the Cape Cod National Seashore, which makes for a beautiful view while you wait for a table. The Beachcomber is a lively spot that gets rowdy on holiday weekends (in a fun way) and hosts live music shows. We visited the Beachcomber for a late lunch and tried steamers, a classic Cape Cod dish of clams with butter.
It is $30 to park at the Beachcomber but those $30 go toward the price of your meal. This $30 does not apply to alcohol so you’ll want to spend at least $30 on food to get your money back.
Another place to try in Wellfleet is Mac’s Shack and Mac’s On the Pier. They’re both in the actual town of Wellfleet on opposite ends of Main St.
Explore Nauset Lighthouse and Coast Guard Beach
If you see any lighthouse in Cape Cod, it has to be Nauset Lighthouse. It’s the quintessential American lighthouse in red and white. It’s the lighthouse pictured on Cape Cod Kettle Cooked Potato Chips.
The next beach over from Nauset Light Beach is Coast Guard Beach, an expansive beach with breathtaking views. Nauset Light and Coast Guard Beach are both located on the Cape Cod National Seashore, so you’ll need to pay $25 for a pass.
That Planner Friend Tip: If you visit beaches on the National Seashore after 5 p.m., you may get away with not paying the $25 fee because an attendant might not be there anymore.
Stroll down Main St. Chatham
The next stop on your Cape Cod road trip is Chatham, a cute town in the Lower Cape. Chatham has a main street with a bunch of shops and places to stop in. The Chatham Squire is a famous spot for a pint and going out.
Treat yourself to ice cream at Buffy’s Ice Cream, a homemade ice cream shop that serves famous ice cream bars. (An ice cream bar is similar to an ice cream sandwich but in a square shape.) Buffy’s is in a small cottage at the end of Main St. in Chatham. It’s the perfect sweet treat to cap off your day of adventuring and snacking.
Still hungry?
We were full after eating along the Cape all day but here are some dinner options that are on my list to try:
- Embargo
- The Naked Oyster
- The Pheasant
- Crisp
- The Brewster Fish House
Sunday: Beach Day + Whale Watching
After a busy day exploring the Cape, it’s time for some well-deserved relaxation. On your last full day, spend the day at the beach before going on a sunset whale watching cruise.
Relax on the beach
Let’s be honest, Cape Cod’s beaches can’t compare to the turquoise waters of the Caribbean and they aren’t trying to. Cape Cod beaches are a great place to relax with a book and feel the cool ocean breeze while lying in the sun. The water is warm enough to swim in but cold enough to cool you off after hours in the sun.
Do not swim in the water if you see a seal in the water because it means a shark might be lurking nearby. The beaches on the Cape Cod National Seashore are more likely to have sea life because they’re along the Atlantic, while beaches in Mid Cape are along Cape Cod Bay and Nantucket Sound are calmer.
Disclaimer: If you’re not accustomed to jumping into cold North Atlantic waters, you will likely find the water too cold.
The best beach to relax at on the Cape is the beach that’s within walking distance of where you’re staying. If you need to drive to a beach, it’ll cost $20 to park your car. Some Airbnbs include beach passes with your stay, which grants you access to any county beaches.
In Hyannis, we would hang out at Keyes Memorial Beach near the Kennedy Compound. It was very laid back but did not include a snack bar.
Lunch at Black Cat Tavern
The best lobster roll I had on Cape Cod was at Black Cat Tavern. It’s because they make no compromises. They pile the lobster onto a buttery roll that makes for a delicious roll that’s a bang for your buck.
The Black Cat Tavern is located right across the street from the ferry stop in Hyannis. It’s right next to Black Cat Harbor Shack which is a more casual lunch spot owned by the same people. You can’t go wrong at either spot because it’s basically the same menu.
Go on a sunset whale watching cruise
Hit two birds with one stone on a sunset whale watching cruise out of Hyannis. There are two big whale watching companies on Cape Cod: Dolphin Fleet Whale Watch in Provincetown and Hyannis Whale Watcher Cruises. During the peak of high season (late June-Labor Day), Hyannis Whale Watcher Cruises advertises a sunset whale watching cruise where you can see whales and the sunset. The cruise leaves around 3:30 or 4 p.m. and arrives back to shore soon after sunset.
Tickets for whale watching a big cruise like this are $75 per person for four hours. There are also smaller private boats for up to 6 people that will take you whale watching for a higher price tag. The benefit of going on a big cruise boat is there’s a snack bar with food and drink. Plus, you’re less likely to get seasick on a bigger boat.
The whale watching cruise takes you to the Stellwagen Bank National Marine Sanctuary between Boston and Provincetown to see all kinds of marine wildlife from whales to seals to rare sunfish. You never know what you’re going to get. The good news is the sunset is always guaranteed.
Dinner at Añejo
On Main St. in Hyannis is Añejo, a Mexican restaurant and bar with an expansive interior and back patio. The back patio area and lounge is a great place to grab a margarita while you wait for your table to be ready. Añejo serves your typical Mexican fare like tacos, enchiladas, and more. They also have a location in Falmouth.
More things to add to your Cape Cod itinerary
- Cape Cod Lavender Farm
- Cape Cod Rail Trail
- Explore Falmouth and Maspeth on the Lower
- Take a day trip to Martha’s Vineyard
For the top 10 things to do in Cape Cod, check out this blog post.
For more helpful information on each part of the Cape and where to stay, read this Cape Cod Travel Guide. I’m happy to answer any questions in the comments below.
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