Romantic Things to Do on Cape Cod

Cape Cod is very relaxed but lively. It has the character to provide the best backdrop for some of the most romantic moments you will have with your partner. Whether you want to take a calming evening stroll along a scenic path, enjoy a day/evening at a world-class spa, enjoy ice cream and mini-golf, or get lost in a deep conversation in a romantic Italian restaurant, the Cape has you covered.

Here are just a few of the many romantic things you can do on Cape Cod.   The Cape has so many great destinations and activities to experience.  It would be impossible to cover them all.  So, here are some of the great romantic date-night ideas the Cape has to offer.  

An Evening Walk Down Commercial Street, Provincetown

Commercial Street is the main street in Provincetown. It is lined with cool restaurants, homes, gift shops, art galleries, and clothing stores. There’s a lot to do here and it can provide an excellent backdrop for a relaxed romantic evening stroll with your partner.

The street is always bustling with life till late in the evening. The evenings are warm in the summer and a cool breeze sweeps the street thereby providing the perfect conditions to enjoy the outdoors. Several restaurants along the street have outdoor seating spaces which make for great spots to people watch or observe the goings-on in the street.

The street attracts both tourists and locals in the evenings. You will see many locals cycling down the street. You will also see many people walking their dogs. If you have a dog, bring them with you as most of the outdoor restaurants are pet-friendly and stock pet treats.

 

Sunset Cruise in Hyannis & Little Pleasant Bay

Very few experiences are as calming as an evening cruise on beautiful Cape Cod waters. Bay Spirit Tours and Hy-Line Cruises have been offering well-reviewed evening cruises that are guaranteed to provide you and your partner with a romantic time on the water.

The Bay Spirit Tours provides a 75-minute cruise on a 63-foot motor catamaran from the Ocean Street Dock near the Bismore Memorial Park. They play light music and have a bar down below where patrons can buy wine, beer, and mixed drinks as well as non-alcoholic beverages and snacks.

Visit their website at https://bayspirittours.com/  for updated cruise descriptions,  departure times, and pricing.   

You should arrive at the dock a half-hour before departure time to pay, check-in, and collect your boarding pass. You will be allowed into the boat 15 minutes before the scheduled departure time. You can reserve a spot by calling them on 508-771-0107.

Hy-Line Cruises provides a 90-minute sunset cocktail cruise out of Hyannis that will provide you with a great opportunity to witness the beautiful sunset over Lewis Bay and Hyannis Harbor. The cruise is available subject to weather conditions starting mid-June till the end of summer.  The cruise features a little background music and a cash bar serving both alcoholic and non-alcoholic drinks as well as snacks.   Visit their website at Hy-Line Cruises for updated cruise descriptions,  departure times, and pricing.   

 

Plan a Surprise Trip to Martha’s Vineyard

If you want to surprise your partner with an excellent trip while on the Cape, a visit to Martha’s Vineyard would be just perfect. The island is just a 45-minute ferry ride from Woods Hole which can be easily accessed by car from wherever you are on the Cape.

You can leave your car or bring it with you to Martha’s Vineyard if you book a space for your car on the ferry in advance. If you're doing a day trip or traveling light, you don't need a car on the Vineyard.   The Martha’s Vineyard Transit Authority operates a bus service that will take you to most points of interest on the island.

Steamship Authority’s ferry has excellent ferry service to Vineyard Haven or taking the Hy-Line ferry from Hyannis for a one-hour trip to Oak Bluffs. The Hy-Line ferry has more luxuries and does not ferry cars.

You will find lots of interesting things to do and places to explore while on Martha’s Vineyard. If you use the Steamship Authority ferry, you can start the tour by taking a walk through the beautiful Vineyard Haven Village. Off Main Street, there is a calm beach and park called Owens Park for you to relax and recharge. You should also consider visiting the Old School House Museum.

Edgartown has lots of beautiful architectural masterpieces under the care of the Vineyard Trust that are worth a visit. Vineyard Trust (vineyardtrust.org) offers affordable guided group walking tours of the landmarks that have been part and parcel of the town’s storied past. You can also arrange private tours by appointment.

Oak Bluffs has the Flying Horses Carousel which is arguably one of the oldest attractions of its kind in the country. The carousel was first built in Coney Island in 1876 and then moved to Oak Bluffs in 1884. If you have young children with you, they will definitely love it. If you want to spend time on the beach, Inkwell Beach and Joseph Sylvia State Beach are perfect. Also, there is a small business right off State Beach that rents kayaks and paddleboards. You can enjoy some time on the water kayaking on the beautiful Sengekontacket pond.

See Cape Cod from the Sky

When looking for an outside-the-box activity to enjoy on a clear sunny day, a helicopter tour of beautiful Cape Cod is a strong contender. Cape Cod is already amazing from the ground; imagine taking in all this beauty from the sky in the company of your loving partner?

This is a whole different experience. It’s nothing like seeing the area on a commercial airliner as you land at the airport. First, a helicopter will allow you to fly low close to the ground. You will see more of the Cape than you have ever seen before. The details are incredible from the sky.

Relative to the cost of a helicopter tour in the big cities, a helicopter tour on the Cape is comparatively affordable. Consider starting your tour at Ryan Rotors in Plymouth, MA. There are lots of well-reviewed affordable charter services there. They have a variety of customizable tours that are guaranteed to offer you a great time. Depending on your budget, you can even tour the whole of New England if you so wish.

If for some reason you don’t fancy helicopters, you can charter a small fixed-wing airplane from Stick ‘n Rudder Aero Tours. Stick ‘n Rudder Aero Tours. offer tour options ranging from a 15-minute ride exploring Pleasant Bay and Chatham to a 30-minute ride that takes you over the Lower Cape, Chatham, Orleans and Provincetown Area to a 55 min flight that covers the Lower Cape, Monomoy Island where you'll see Lighthouses and maybe even some sharks!    The offer flight packages in their Skyhawk Plane and their Bi-Plane.   The planes have different seating capacity, so please visit Stick ‘n Rudder Aero Tours website for tour and seating info...  The great thing about this tour group is that all of their prices are per trip, not per person so you will pay the same amount whether you are going alone or with your partner.

 

Go on a Horseback Riding Adventure

When the sun is up and your appetite for adventure is rising, you will do yourself a great service to experience the Cape’s magnificent trails and beaches on horseback. Very few places offer as much of a variety in real estate to go horseback riding on.

The shoreline in southeastern Massachusetts stretches some 560 miles. The Cape Cod National Seashore alone stretches 40 miles. Further, there are beautiful trails in the impressive 4200-acre Sandy Neck Beach Park that are very friendly to horseback riding.  Also, in the mid-Cape, there is the Cape Cod Rail Trail that stretches some 22 scenic miles and will take you through the towns of Wellfleet, Eastham, Dennis, Orleans, Brewster, and Harwich.

If horseback riding interests you, here's a few places that offer lessons and trail adventures:
Emerald Hollow Farm (Brewster) (For Beginner Lessons):
If you’ve never ridden horses before or you are inexperienced and you wish to polish your skills, The Emerald Hollow Farm in Brewster is a teaching and training facility.   They do not offer trail rides or pony rides and all lessons are by appointment only. 

Haland Stables (Falmouth):
Haland Stable offers horseback riding lessons and pony rides for children and adults.  They provide a safe, caring and healthy environment for both horse and rider..   They provide lessons and pony rides are conducted around the perimeter of their large grass field.   Please visit their website  http://www.halandstable.com/  for up to date hours and availability.  

Ridge Valley Stables (Grafton, MA) (For Proper Trail Rides):
For proper trail rides, you will have to step out of the Cape to the nearby Grafton Town. Ridge Valley Stables in Grafton is one of the best horseback riding companies in Massachusetts and they offer riding lessons, pony rides, and trail rides.
There are lots of good riding trails in Grafton and surrounding areas. You can ride in the forests, in the open field, or along the lakes. You can ride through the inner Cape and make it to the sandy dunes of Sandy Neck Beach. They have excellent trail guides on staff to ensure you have a safe riding adventure in Grafton and the inner Cape.

Enjoy an Intimate Private Wine Tasting Experience

In the small undisturbed town of Truro, you will find one of the Cape’s best attractions – the Truro Vineyard. It is open daily most of the year and located between Wellfleet and Provincetown.  Please visit their website https://trurovineyardsofcapecod.com/ for updated events, hours of operation, and wine/spirit availability.    

Truro’s popular vineyard welcomes visitors to their tasting room to sample their wines which have a characteristic intense flavor. Flights change weekly – ask the server which wines are being offered on the tasting week you get to visit the vineyard.

For an intimate wine experience- Truro Vineyards Custom Tasting Experience is a two-hour private tasting experience that's held on the private rooftop deck or a table among the vines.  The resident expert will guide you through a tasting of five hand-selected wines paired with an artisanal cheese plate. Depending on the wine you like the most; you will get a full pour of your favorite Truro Vineyard wine. You will also be offered a Truro Vineyards wine glass to take home. Remember to make a reservation a few days in advance if you want a private tasting experience.  see https://trurovineyardsofcapecod.com/ for details and book your experience.   

Have a Romantic Dinner at One of the Cape’s Best Restaurants

Cape Cod has a great selection of fine-dining restaurants. Whether you want a super casual dining experience or a romantic fine dining experience, the Cape has you covered. Instead of browsing through thousands of reviews on TripAdvisor and Yelp to find a good spot, start your search using the following four recommendations:

Cuvée at Chatham Inn (359 Main Street, Suite 2, Chatham, MA 02633): If you want to enjoy a romantic fine dining experience in Chatham, this is the restaurant for you. They have great 4-course menu options as well as the chef’s 7-course tasting menu. Go to Cuvée for globally inspired locally-tailored Cape Cod cuisine.

The Pheasant (905 Main Street, Dennis, MA 02638): For a casual, fun, yet romantic evening out in Dennis, The Pheasant on Main Street has you covered. Go to the Pheasant for refined American delicacies with French influences in a beautiful restaurant with a fireplace and garden.

Twenty Eight Atlantic (2173 MA-28, Harwich, MA 02645): This restaurant at the Wequassett Resort and Golf Club offers a formal 5-star fine dining experience with a stunning view of the water. They offer a coastal menu with most of the ingredients sourced locally from Cape Cod providers. For a romantic evening, request patio seating to fully enjoy the views.

 

Get a Waterfront Luxury Villa for the Two of You

Having a luxury waterfront property all to yourself sure beats staying in an inn and having to share resources with tens of other travelers. There are several waterfront properties on the Cape lining the beaches of Barnstable, Sandwich, Mashpee, and Bourne.

Cape Cod is a summertime beach destination so you might as well get a beachfront rental to get the most of your vacation. You will get to enjoy walking to the beach straight from the house while still being able to enjoy relative privacy due to the exceptional seaside landscaping most of the luxury Cape Cod beach properties have. With its sandy beaches and clear waters, the Cape Cod location will provide the perfect backdrop for a romantic time with your partner. You can spend your days swimming, lounging on the sand, surfing, or just luxuriating on the property while enjoying the views.

 

Get Pampered Together at the Spa

There are a few things you can do to unwind as a couple that are as relaxing as a couple’s massage session. Going to the spa as a couple is less intimidating than going alone and a lot of fun...  Spa days are not only beneficial for your physical well-being but also your mental health.

The Cape boasts of several independent spas as well as full-fledged spa resorts that provide a range of treatments including custom spa treatments that you can tailor to suit your needs as a couple. You can make a reservation with any of the following establishments:

1)  The spa at Ocean Edge Resort and Golf Club – 2907 Main St, Brewster, MA 02631. Email [email protected] or call (774) 323-6230 to make a reservation.

2) The spa at Chatham Bars Inn – 203 Seaview St, Chatham MA 02633. Call (508) 945-6737 to make a reservation.

3) Solstice Day Spa – 408 Main Street at Puritan Cape Cod, Hyannis, MA 02601. Call (508) 775-7400 to make a reservation.

4) Cape Cod Therapeutic Spa – 793 Iyannough Rd, Hyannis, MA 02601. Call (508) 771 7077 to make a reservation.

 

Rent a Boat for the Day

The ultimate romantic getaway on the Cape would probably be getting a boat and sailing into the horizon for a day cruise with your partner. You can craft whatever experience you want. Whether that be having elaborate meals in the sea, drinks, and music, or just a relaxed romantic time on the water.

The following companies offer boat charters and rentals on Cape Cod:
1)  Selkie Charters – 147 Lewis Bay Road, Hyannis, MA 02601. Call (508) 648 0670 to inquire.
2)  Down Cape Charters and Boat Rentals – 2173 MA-28, Harwich, MA 02645. Call (508) 241 4070 to inquire.
3)  Rock Harbor Charter Boat Services – 18 Bay View Dr, Orleans, MA 02653. Call (508) 255-9577 to inquire.
4) Lane Yacht Management Group – 22 Bayview Rd, East Sandwich, MA 02537. Call (508) 888-3209 to inquire.
5) Cape Cod Sailing Charters – Serves 02633 and neighboring areas. Call (508) 237 5467 to inquire.

Closing Thoughts

Cape Cod is full of fun activities to do YEAR ROUND There are lots of fun things that a couple can enjoy aside from the ten things I have listed above. Visiting Cape Cod art galleries as well as the Heritage Museums and Gardens should always be on your short list of things to do.  Landmarks such as the Pilgrim Monument in Provincetown or Cape Cod’s many lighthouses should also make for a fun-filled romantic day. 

There’s always a live show somewhere on the Cape on any summer evening that a couple can attend. To satisfy your sweet tooth, stop by any of the Cape’s great ice cream shops.  If you want some adventure, you can go skydiving in Barnstable or race each other on the Shining Sea Bikeway and the Cape Cod Rail Trail.