Step off the Freedom Trail and Boston changes. Acorn Street in Beacon Hill is red brick and cobblestones, gas-lit at night, looking more or less as it did two hundred years ago. The North End has trattorias with tables on the street. The Harbor gives you open water and skyline at once.
That's what makes it work for a proposal. The history is close enough to touch. The water is never far. It's a compact city you can walk, which means you can cover a lot of it in a weekend and find the right moment without having to engineer the whole thing.
Boston Proposal Ideas
The combination of culture, history, and scenery means that Boston is a fabulous city for a weekend away and is packed with ideal proposal locations. Whether you choose the romantic atmosphere of Beacon Hill with its gas lamps and cobbled streets, the Italian vibe of North End, or the trendy setting of Newbury Street, Boston is a superb place to wander about hand in hand and discover your own perfect place to propose.
Iconic Proposal Locations in Boston
Acorn Street, Beacon Hill. Photo: Abdullah / PexelsWhen we imagine Boston the image that most often springs to mind is Acorn Street in Beacon Hill. A cobbled street with brick built row houses which some people suggest is the most photographed street in the U.S. It is certainly a pretty spot for a romantic walk and could be a great place for an evening proposal. If you’re planning a winter proposal, check out the Commonwealth Avenue Mall, a strip of park that runs down the center of Commonwealth Avenue, as the trees there form a beautiful pathway when they are lit up with Christmas lights.
Another iconic location in Boston is the Hatch Shell, or Edward A. Hatch Memorial Shell, an outdoor concert venue located at the Charles River esplanade. There are often free concerts at the Hatch Shell during the summer months and the grass pavilion in front of the stage is a great place to chill out with your girlfriend. For the ultimate in Boston icons, consider proposing at the legendary Fenway Park but only if your girlfriend is a big Red Sox fan and you think she’d be happy with a public proposal. Think about proposing during a ballpark tour and the Winter Lights Show if you’re not sure about proposing during a game.
Boston Common, the oldest park in the U.S. and the starting point of the Freedom Trail, along with its more picturesque neighbor Boston Public Garden, would both be ideal places for an iconic Boston proposal. Take a swanboat ride at the lagoon in the Public Garden or go ice skating on the Frog Pond on the Common. For an unusual outdoor proposal location why not visit the Arnold Arboretum of Harvard University in the Jamaica Plain area of Boston? There are innumerable beautiful locations within its boundaries for a unique proposal.
Proposing on the Water in Boston
Boston Harbor. Photo: Mohan Nannapaneni / PexelsBoston Harbor has a charm all of its own and there are plenty of ways to propose on and around this historic location. You could make a day of it and take a cruise out around the Boston Harbor Islands, or check out some of Boston’s historic sites including the lighthouse and Old North Church where two lanterns were famously hung to show that the British were invading by sea. A sunset cruise is also a great option and the patriotic among you will enjoy the USS Constitution’s sunset cannon fire.
If you’d rather stay off the water there are plenty of locations along its edge that would make great proposal spots such as Carson Beach in South Boston, a sandy beach with a pier and lovely views of Boston Harbor. The Charles River is also a picturesque spot for a proposal, whether you have a picnic on the esplanade, cross over the footbridge to Cambridge, or simply take an evening stroll along its banks.
Proposing with a view of Boston
The Boston skyline. Photo: philevenphotos / PexelsFor a spectacular view over Boston and, on a clear day, the surrounding 100 miles, View Boston at the Prudential Center offers a 360-degree panorama from the top of the tower. It is open daily until 10 PM, with last entry an hour before closing. After you propose up there, head back down for dinner in Back Bay.
If you’d like to get out of town but still propose with a view of Boston, there are a couple of places you could go. Just 15 miles from Boston, the World’s End Reservation features rolling hills and rocky shorelines which offer sweeping views of the Boston skyline. Whether you take a summer walk, or go cross country skiing in winter, this area of natural beauty is extremely romantic. You could also consider Robbins Farm Park in Arlington Heights, which is an ideal picnic spot overlooking the landmarks of Boston.
Romantic Restaurants in Boston
New England cuisine traditionally relies heavily on seafood and dairy products, and each area has its own specialties with Boston being well known for clams and haddock as well as baked beans and various pastries. However, strong European influences have also shaped Boston cuisine, and in today’s multicultural city you can find fantastic food from across the globe. Here are some restaurants you might like to try by area:
Restaurants in Back Bay
Grill 23 & Bar on Berkeley Street has been a Back Bay institution since 1983, and in its clubby, wood paneled dining room you can order dry aged steaks, fresh seafood, and rich sides. Check out Deuxave at the corner of Commonwealth and Massachusetts Avenues for refined French American cooking built on local ingredients. Finally, if you’d like to splash out on hearty Northern Italian cuisine, Davio’s Steakhouse on Arlington Street offers traditional pastas, lobster risotto, homemade sausage, and of course superb steak.
Restaurants in the North End
Few visitors that venture into the North End of Boston to eat are looking for anything other than superb Italian food, so here are a couple of the best choices in the area. Mamma Maria’s is consistently reported to be the best Italian Restaurant in the North End and specialties include Nantucket Bay scallops, Ipswich clams, and risotto with crab meat as well as their famous osso buco. Other excellent restaurants in the area include Prezza on Fleet Street, a dressier Italian kitchen with house made pastas and grilled steaks, and Giacomo’s Ristorante on Hanover Street which is always busy but worth the wait.
Restaurants in the South End
The fashionable South End of Boston has an eclectic mix of restaurants to choose from. For classic French cooking check out Aquitaine, a Parisian style bistro on Tremont Street known for its steak frites and duck confit. For Italian small plates Coppa is an intimate enoteca on Shawmut Avenue from chef Ken Oringer, and its patio is a good spot on a warm evening. For a proper celebration dinner, book Mistral on Columbus Avenue, a long running French Mediterranean restaurant and a longtime Boston favourite for celebration dinners.
Restaurants in Cambridge
Across the river in Cambridge, home of Harvard University, the best restaurants are equally diverse. On First Street you’ll find the Helmand Restaurant, an atmospheric Afghani restaurant with a traditional wood-fired brick oven. On Washington Street the Spanish restaurant Dali is a favorite for authentic tapas which is ideal for sharing. Finally, if you’re looking for fantastic seafood, Waypoint at the edge of Harvard Square serves a raw bar and coastal small plates, with dollar oysters early in the evening.
Romantic Activities in Boston
Once that sparkling diamond is firmly in place you’ll want a few additional activities up your sleeve to make your vacation one to remember. Here are some fun and romantic activities around Boston.
- Visit the Isabella Stewart Gardner Museum and enjoy the beautiful courtyard
- Ride the ferry from Charlestown Naval Yard to Long Wharf and cuddle up for warmth
- Take the North End Market Tour and sample delicious Italian food and wine
- Check out some street theater at the Faneuil Hall open marketplace
- Book a couples massage at Bella Santé, the Newbury Street day spa
- Enroll in a couples cooking class at the Cambridge School of Culinary arts
- Follow the footsteps of the world’s great musicians to Scullers Jazz Club
- Stroll around the New England Aquarium on Central Wharf and watch the penguins play
- Splash in the fountains at the Christian Science Center Plaza and enjoy the reflecting pool
- Enjoy eight blocks of salons and boutiques around Newbury Street
Where to Stay in Boston for Your Proposal Trip
There are plenty of romantic hotel choices in Boston whether you pick a small boutique hotel in Beacon Hill or a top class five star establishment in Back Bay, and most of the sights are accessible on foot from all hotel locations.
Boutique Hotels in Boston
If you’re looking for a boutique hotel in the popular Beacon Hill district of Boston the XV Beacon could well tick all the boxes. The Beaux Arts building stands at the top of Beacon Hill and its earth toned interior exudes luxury. Take advantage of the complimentary in-town Lexus service, Nespresso machines, in-room massage, beautiful roof terrace, and customized bath products.
The Clarendon Square Inn, located in the stylish South End of Boston is a luxurious historic townhouse which has been beautifully renovated with designer fabrics, limestone and marble bathrooms. Relax in the garden or rooftop terrace, which is complete with a Jacuzzi hot tub.
For a long established boutique hotel in Back Bay, close to Newbury Street, the Lenox Hotel offers everything you need for a romantic stay. The very fact that it was used in the filming of the 1970's 'Love Story' says it all; the hotel is an integral part of Boston history. Book a room that offers a working fireplace and a view of the Charles River.
Luxury Hotels in Boston
The Boston Harbor Hotel at Rowes Wharf is the perfect choice if you want to add a touch of luxury to your proposal vacation, and the striking arched building has become a Boston landmark. As well as the hotels own boutiques you can enjoy skyline or harbor views, and various award winning restaurants.
For somewhere special to stay in Back Bay, the Hotel Commonwealth is a fantastic choice for personal service and attention to detail as well as old world charm. Located on Kenmore Square, the hotel features striking interior design, spacious rooms and suites, imported Italian linens, luxury bath products, boutique shopping, and in-room spa services.
Like any large city the usual five star hotel chains have a presence. The Mandarin Oriental Hotel is located on Boylston Street in Back Bay and features art deco inspired interiors as well as a luxurious spa. Also located in Back Bay, overlooking Boston’s Public Gardens, the Four Seasons Hotel is designed to incorporate iconic Boston Hill influences and modern New England design in a neutral palette, and offers a superb eighth floor swimming pool with spectacular views.
