A Romantic Cape Cod Weekend Getaway: The Definitive Guide

People who work in the hotel industry – that’d be us – read a lot of travel stories about Cape Cod and, unfortunately, we are left with the impression that the person who wrote the story doesn’t actually know the Cape very well. Should the title of a travel story include the phrase “in Cape Cod,” we instantly know the writer isn’t local. We may also gnash our teeth just a bit. (One is never “in” Cape Cod: one is “on” Cape Cod.) We live here, and we have all of the insider info about Cape Cod that will ensure a fun, relaxing and authentic experience.

So, here is our suggested itinerary for a romantic weekend on Cape Cod.

Friday

Like any devoted employee, you and your beloved have opted to sneak out of work after lunch and get on the road by noon, which means that your sleek digs at our Wellfleet hotel should be ready for check-in when you arrive at 3:00-ish. Drop your bags, freshen up and head for Wellfleet Pearl.

The Pearl has a happy hour from 3:00 to 5:00 pm every day; seven days a week thru the third week of September; Wednesday – Sunday until they close for the season after OysterFest. This happy hour is popular with an older crowd — think Gen X and Millenials rather than Gen Z. A live local band gets people out on the dance floor. Attractively priced Wellfleet oysters and lobster rolls keep people in their seats. You had us at the $28 lobster roll. If you are planning on dining out this evening, consider splitting the lobster roll.

You can start your gallery hopping early at The Frying Pan Gallery next door to Pearl. Metalsmith Steve Swain’s wall installations of “schoolies” are absolutely beguiling. Smaller metalworks and paintings by local artists are also available.

Once you are sufficiently happy, head back to the hotel for a proper freshen-up and a little relaxation. Should you be in the mood for a laidback dinner – you did work today – Mac’s Shack is that just-right blend of Cape Cod casual and exceptional food. It is also so the place to be, so you may have to wait for a table. Have a drink at the bar, or take in the view of Duck Creek and Uncle Tim’s Bridge outside and the wait will fly by.

You can’t go wrong with Mac’s oysters (even if you had oysters at Pearl; you are in Wellfleet, after all) and the Braised Cod Cheeks to start. For dinner, consider going the traditional route with a boiled lobster. Yes, it’s messy, but oh-so delicious, and diving into a lobster while wearing a plastic bib makes for an awesome photo op. Their Asian-inspired dishes are also stellar. Mac’s closes for the season in late October.

What you decide to do next will depend on your age and your stamina. If, after dinner, you are brimming with energy, you are clearly on the younger side, so it’s time to head to the Beachcomber. Let your hair down (literally or metaphorically) with a Goombay Smash and some quality time on the dance floor. Should you be ready to really rage, drop your car at Endless Coast and Uber to the Beachcomber and back. Those Goombay Smashes pack a punch.

For a low-energy way to end the evening, head to Emack & Bolio’s on Main Street for ice cream. An après-dinner ice cream is very much a Cape Cod tradition, which means the calories don’t count. Grab a cone and stroll through the charming village. Check out the shops and galleries you may hit later, or head down to the harbor for sunset. End your evening with a glass of wine in the front of the fire in our backyard.

Saturday

This is your one full day on the Cape. Let’s make the most of it.

Early risers should absolutely consider watching the sun come up at either Marconi Site (below) or Marconi Beach. The dramatic spectacle is worth getting up for.

Spending the day in Provincetown is a great option. Hop over to our Provincetown daytrip story for detailed suggestions on what to do. A whale watch is as incredible as you imagine, so worth the investment of your time.

Should you care to spend the day in around the Wellfleet area, read on. If you’re P-town-bound, skip the next few paragraphs.

If the weather is good, we suggest a quick breakfast.

For exquisite French baked goods, PB Boulangerie is the place to be. Don’t let the lengthy queue scare you off. The wait is worth it. You may want to order more than one pain au chocolat or almond croissant, not because they’re small, but because they are so good you’ll want a second.

With so-so weather, treat yourself to a relaxed sit-down breakfast at either Van Rensselaer’s or Harrigan’s Café. Harrigan’s has a cozy diner atmosphere. Van Rensselaer’s is more of a proper restaurant.

Much of the Cape’s allure is its natural beauty. As long as it isn’t actively raining, we’re hitting the trail. An absolute fave is the Mass Audubon Wellfleet Bay Wildlife Sanctuary. The walk out to the boardwalk alone is the worth price of the very reasonable admission. We came upon a flock of snowy egrets on our last walk, with several adults attending to their nestlings. The “half heart” tree on the Silver Spring Trail is just made for a romantic photo op. You can easily see all you need to see at Wellfleet Audubon within a couple of hours.

If you’re more of a beach person than a trail person, you have come to the right spot. Lecount Hollow Beach is less than two miles from Endless Coast, and Cape Cod National Seashore’s Marconi Beach is less than four miles. Go sit in the sand and just be.

Next stop, Wellfleet Center. Once you take the left off of Route 6 to head into town, you will quickly come upon Uncle Tim’s Bridge, an iconic landmark. Parking is in a small dirt lot just past the bridge. The bridge crosses over to Cannon Hill. It’s tiny, but there is a nice elevated spot on the far side with a bench positioned to appreciate the view.

Okay. It’s decision time.

Assuming you left Endless Coast at about 9:00 a.m., it is probably just about noon by now. If you didn’t have much of a breakfast, it may be lunch time. If you prefer a later lunch, you have an hour or two.

Spend this hour or two exploring the galleries of Wellfleet. Commercial Street, which leads down to the pier, has several. Left Bank Gallery is one of the largest and has a selection of jewelry, pottery and glass pieces in addition to a huge selection of paintings. Wouldn’t a painting be the perfect way to remember your trip to the Cape for years to come?

Also on Commercial Street is the Works Gallery, which represents Paul Suggs, one of the most respected painters currently working on the Cape. His work just is Cape Cod; think Hopper for a more modern time. Pottery handcrafted by Anne, his wife, is also available, as is handmade jewelry.

Lunch Suggestions:

If the weather is nice, head to Mac’s On the Pier for an ultimate sand-in-the-toes clam shack kind of lunch. This is the more casual sister restaurant of Mac’s Shack, and it sits right in the sand overlooking the harbor. Amazingly, their fried seafood is gluten free and it’s amazingly good. The grilled swordfish or tuna sandwiches (as in tuna steak, not canned tuna) are excellent. But our go-to choice is the tuna poke bowl. It is the best we’ve found on the Cape. Add a side of fries and an ice-cold craft beer to complete this decadent meal.

For a leisurely lunch served with a proper glass of wine, the terrace at Winslow’s Tavern is a lovely option. Start with one of the unique Wellfleet oyster dishes, such as roasted with lemon-rosemary butter or Tabasco lime butter. We highly recommend a glass of Champagne to go with. The entrées offer a blend of French dishes, classic Cape food with a twist, and hefty sandwiches.

A large lunch coupled with a glass of wine or two may mean it’s nap time. By all means, nap. You are on vacation, remember? Go back to the hotel for a dip in our indoor pool or relax with a book on one of the sofas in our backyard.

If relaxing just isn’t your thing, may we suggest a boat ride? Wellfleet Marine Boat Rentals, located on the town pier, will rent a power boat for as little as an hour. This is unheard of the Cape. Grab a 16-foot bowrider for an hour or two and zip out to Jeremy Point and tool around the harbor. By all means, bring a beer or two along; be safe, be responsible, and the guys on the dock are more than okay with it. You can see all there is to see in under two hours and have plenty of time to relax and shower before dinner.

If you skipped Winslow’s Tavern at lunchtime, put it on your short list for dinner. Other options include The Wicked Oyster, housed in a historic home and oozing in romantic, rustic elegance, and CShore Kitchen & Bar which has a slick, lively atmosphere inside, and fireside seating outside. The ramen bowls are a signature dish at CShore. Opt for the added tuna and you’ll be in heaven.

Another cone at Emack & Bolio’s? Another stroll along the harbor? Another glass of wine in our backyard? The night is your [Wellfleet] oyster.

Sunday

After breakfast, there is one more not-to-be-missed destination: Cape Cod National Seashore’s Atlantic White Cedar Swamp Trail. Parking is in the same lot as Marconi Site. The hike is just over a mile. It’s tough to describe; kind of an eerie-yet-beautiful “Where the Wild Things Are” vibe. You have to experience it to understand its awesomeness.

If it’s time head home, you’re headed in the right direction. If you’re more of a meanderer, mosey on down to Eastham and check out the Fort Hill Area. The Fort Hill trail is just a mile. The adjacent Red Maple Swamp trail tacks on another half mile or so. The Red Maple Swamp Trail is reason enough to visit the Cape in the fall. Yeah, it’s that beautiful.

We hope you had a fantastic weekend on Cape Cod. Until next time!