Top 5 most romantic places to propose on Cape Cod

For most people, asking the big question at the right time and choosing the right place to do it is almost as important as the wedding itself. If you plan a proposal, you want to be sure that it’s everything they dreamed of. You found the perfect ring, you are ready to pop the question, and finally, you must decide where you want it to all go down.  

Cape Cod might be just the right place! Known for its beautiful coastline, charming towns, and romantic B&Bs, such as The Old Harbor Inn in Chatham, Cape Cod makes for the perfect place to start your new life together. Plan a trip to Cape Cod this spring or summer and plan the most romantic proposal to create memories that will last a lifetime. Here are the top 5 most romantic places to propose on Cape Cod.

  1. Chatham Lighthouse Beach

Imagine soft sand, breathtaking ocean views, historic lighthouse…there is nothing more picturesque and romantic than getting engaged on the beach. Located just a short mile from the Inn, this enchanting location would be the perfect backdrop for your proposal. Let us pack a picnic basket for you filled with local Champaign, chocolate-covered strawberries, and little nibbles for you to enjoy at the beach. Take them on a romantic beach walk as you both marvel at the ocean, pop the champagne, and pop the question. Also, consider investing in a proposal photographer to capture that precious moment. Let us arrange a romantic dinner following the proposal where you can continue the celebration.

  1. Sandwich Boardwalk

Plan a day trip to Sandwich, drive down the historic route 6A and explore the quaint downtown, the Heritage Museum & Gardens, and grab lunch at a true English tearoom. At the end of the day walk hand in hand down Sandwich’s famous boardwalk and plan to watch Cape’s most stunning sunset. This romantic, secluded and intimate location allows you to enjoy the natural beauty of Cape Cod. The long-wooded bridge over the water leads to one of the most beautiful beaches on Cape Cod and makes for a proposal straight out of the movies.

  1. Biking Trail

The great outdoors on Cape Cod can be the perfect backdrop for your proposal. Cape Cod has miles of trails designed just for cycling. Rent bikes from a local shop, pick your favorite trail, and hit the road, biking leisurely along the coastline, through lush wooded areas or through picturesque towns. Stop for a break at a scenic lookout point or a local lighthouse and pop the question. After the proposal, visit a local winery for a tour and tasting for a toast to a beautiful future together.  

  1. Pilgrim Monument – Provincetown

Enjoy this piece of history, and the picturesque location of the Pilgrim Monument. Walk to the top of the tower, 350 feet above sea level to witness breathtaking views of Provincetown, the Atlantic, and the beautiful Cape Cod landscapes. Take your loved one up to the very top of the tower, and mark the beginning of your new lives together where the pilgrims once marked the beginning of their new lives in the new world.  

  1. Island Proposal

How about popping the question on one of the local islands; Nantucket or Martha’s Vineyard? The islands are all about living lavishly by the ocean, from celebrities to presidents that choose to vacation here, these islands are on most people’s bucket list to visit. The islands are easily accessible from The Old Harbor Inn, you can either take a ferry or fly over in less than an hour. Once on the island, you will find many beautiful backdrops for you to get down on one knee. On Nantucket, popular spots for proposals are Brant Point Lighthouse, the Whaling Museum observation deck, or the famous Cisco beach. On Martha’s Vineyard, Aquinnah Beach & Gay Head Cliffs, Black Dog Tavern, or the Flying Horses Carousel.  Pick the perfect spot and as the sun falls behind the horizon, pull the ring out, and ask your love to share forever.

Finding the perfect spot and planning the proposal can be stressful and overwhelming. Let us take the stress off your shoulders with our Engagement Escape Package! We will take care of all the arrangements, the little details, and make sure it’s as perfect as you imagined it! Chatham is the perfect town for a romantic getaway and there is no better place than The Old Harbor Inn to feel relaxed, at home, and taken care of. There is nothing like spending a romantic weekend together after your engagement. Enjoy each other’s company and unwind in one of our luxury suites before going home to announce the big news to friends and family.

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