7 Romantic Things to Do in Boston
Boston doesn’t get talked about as a romantic city the way Paris or Charleston does. That’s a mistake. It’s small, walkable and old, with gas lamps on brick lanes, a harbor that glows at sunset and a whole neighborhood that smells like garlic and espresso.
In this guide
- 1. Walk Beacon Hill after dark
- 2. Ride the swan boats in the Public Garden
- 3. Spend an afternoon at the Isabella Stewart Gardner Museum
- 4. Have dinner in the North End
- 5. Take a sunset sail on Boston Harbor
- 6. Wander the Arnold Arboretum in fall
- 7. End with a drink somewhere high up
- Where to stay as a couple
- When to go
- A few practical tips
- A simple two-day plan
- Common questions
Fall is the sweet spot. The leaves turn, the air is crisp and you have a real excuse to share a blanket. Here are seven romantic things to do in Boston, whether it’s a first date weekend or your tenth anniversary.
1. Walk Beacon Hill after dark
Beacon Hill is the Boston you see on postcards: steep lanes, brick row houses, black shutters and flower boxes. In the evening the gas lamps flicker on, and it feels like a film set.
Start at the top of Mount Vernon Street, then drift down to Acorn Street, a tiny cobbled lane that’s said to be the most photographed street in America. Finish on Charles Street, where the antique shops and little wine bars stay open late. Wear flat shoes. The cobbles are lovely and also a little brutal.
2. Ride the swan boats in the Public Garden
The swan boats have paddled around the lagoon in the Boston Public Garden since 1877. The ride is about 15 minutes, it costs a few dollars and it’s completely, gloriously cheesy. Do it anyway.
The boats run from spring to mid-September, so in fall you’ll walk the garden instead. That’s no loss. Cross the tiny suspension bridge, find the weeping willows by the water and grab a bench. The Make Way for Ducklings statues are near the corner of Beacon and Charles if you want a silly photo together.
3. Spend an afternoon at the Isabella Stewart Gardner Museum
This is the most romantic museum in the country, and I’ll defend that. Isabella Stewart Gardner built a Venetian-style palace to hold her art collection, then left instructions that nothing could ever be moved.
The heart of it is a glass-roofed courtyard filled with flowers that change with the seasons. Upstairs, the rooms are dim and intimate, with Titian and Rembrandt hanging next to old letters and lace. It’s also home to the famous empty frames from the 1990 art heist, which is a great story to whisper about.
4. Have dinner in the North End
The North End is Boston’s Little Italy, and it’s tailor-made for a date night. The streets are narrow, the restaurants are tiny and half of them seat fewer than 30 people. Book ahead for the popular places, or arrive early and put your name in.
After dinner, the great Boston debate begins: Mike’s Pastry or Modern Pastry for cannoli. Mike’s has the famous boxes and the long line. Modern is quieter and, honestly, a bit better. Get one from each and argue about it on the walk back.
5. Take a sunset sail on Boston Harbor
Seeing the city from the water changes how you feel about it. Several companies run sunset sails on tall ships and classic schooners from Long Wharf and Rowes Wharf, usually from May to October.
You’ll glide past the harbor islands as the skyline turns gold, and most sails let you bring a drink on deck. If you’re visiting late in the season, the harbor ferries to Charlestown are a cheap stand-in. A round trip costs very little and the view back to downtown is just as good.
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6. Wander the Arnold Arboretum in fall
If you’re in Boston in October, this is the one you shouldn’t skip. The Arnold Arboretum is a 281-acre park run by Harvard, and it’s free. In fall the maples, oaks and beeches go every shade of red and gold.
Walk up Peters Hill for a view of the skyline over the treetops, then take the long loop back past the ponds. It’s quieter than the Public Garden, so it’s easy to feel like you have the place to yourselves. The Orange Line gets you close, and it’s a pretty walk from Forest Hills station.
7. End with a drink somewhere high up
Finish the night with a view. Several hotel rooftops and bars in the Seaport and the Back Bay look out over the harbor or the Charles River. They aren’t cheap, but one drink each is plenty.
For something cozier, the bars in old Beacon Hill and the North End are dark, wood-paneled and perfect for leaning in close. FYI, Boston bars close earlier than you might expect, so don’t plan on a 3 a.m. last call.
Where to stay as a couple
Beacon Hill and the Back Bay are the most romantic bases. You’ll find small boutique hotels in old brownstones, and everything on this list is a walk or a short train ride away. The Seaport is more modern and has the harbor views, but it feels a bit like a business district after dark.
When to go
Late September to late October is the best time for a romantic weekend in Boston. The weather is cool and sunny, and the foliage peaks around mid to late October. Spring is lovely too, with magnolias on Commonwealth Avenue. Summer is busy and humid, and winter is cold but very cozy if you like fireplaces.
A few practical tips
Don’t rent a car. Parking is expensive and the streets are a maze. The T, Boston’s subway, gets you almost everywhere, and the center is small enough to walk. Book weekend dinners a week or two ahead, especially in October, which is one of the city’s busiest months.
A simple two-day plan
If you only have a weekend, here’s how I’d fit it together. On Saturday morning, walk the Public Garden and the Common, then spend the early afternoon at the Gardner. Head back to the hotel for a rest, then go out for dinner in the North End and finish with a stroll through Beacon Hill when the lamps are lit.
On Sunday, have a slow brunch in the South End, which is full of pretty brownstones and good cafes. Take the Orange Line out to the Arnold Arboretum for the afternoon, then come back in time for a sunset sail or a harbor ferry. End with a drink somewhere with a view. It’s a full weekend, but nothing about it feels rushed, and that’s really the goal on a romantic trip.
Common questions
Is Boston good for a romantic weekend?
Yes. It’s walkable, historic and full of cozy restaurants, and fall makes it even better.
What’s the most romantic neighborhood in Boston?
Beacon Hill, especially in the evening when the gas lamps are lit.
Are the swan boats open in October?
No. They usually run from mid-April to mid-September.
Is the Arnold Arboretum free?
Yes, it’s free and open every day from sunrise to sunset.
Do we need a car in Boston?
No. The T and your feet will cover everything on this list.
