Date Ideas
in Boston, MA (showing 1 - 9 out of 9)

Dinner and a movie are always great date night options. But after a while, date night can end up turning into a routine more than a fun outing. If you’re looking for date ideas, whether for a first date with a partner or a night away from the kids with your spouse, check out our options below.

We’ve found the best spots near you to give you the variety you have been craving for. Think outside the box and dare to try something different for your next date night! Turn a regular night into one to remember forever.

Gondola di Venezia

96 Beacon St
Boston, MA 02108   Directions

(617) 876-2800


Experience a romantic outing in Italy without ever leaving the city with Gondola di Venezia. You'll be seated in an authentic gondola and you'll set out on an excursion on the Charles River; on your ride you'll be able to sip champagne or wine as you're serenaded by one of the talented musicians. Start date night out right on a trip with Gondola di Venezia.

Green Street Grill

280 Green St
Cambridge, MA 02139   Directions

(617) 876-1655


Plan a romantic dinner date at the Green Street Grill. This restaurant has been a fixture in the city since the Great Depression, and is a local favorite that's known for putting a new spin on comfort foods and all-time favorites. After dining on one of the eatery's signature dishes, stick around for drinks; Green Street is proud to feature an award-winning cocktail menu and a variety of craft beers.

L.A. Burdick Handmade Chocolates

220 Clarendon St
Boston, MA 02116   Directions

(617) 303-0113


Ryles Jazz Club

212 Hampshire St
Cambridge, MA 02139   Directions

(617) 876-9330


Live music, drinks, dinner, and dancing are all part of the fun at Ryles Jazz Club. The club's two floors feature a variety of music genres, from jazz and blues to R&B and Latin tunes. Heat things up while dancing to Brazilian music on Wednesdays, or get close on the dance floor as you salsa and merengue on Thursdays. If you're in it for the jazz though, you'll want to be in attendance on Sunday night. This sultry venue is the perfect place for your next romantic date.

Samuel Sewall Inn

143 Saint Paul Ave
Brookline, MA 02446   Directions

(617) 713-0123


Spirit of Boston

200 Seaport Blvd
Boston, MA 02210   Directions

(866) 310-2469


There's not much that could be more romantic than a date on the water. Plan your next date night with a Spirit of Boston sunset dinner cruise on the beautiful Boston Harbor. As you dine on a buffet of sumptuous foods you'll enjoy taking in the view of the city from the luxury ship; after dinner you'll have plenty of opportunities to get close with drinks and dancing. For an extra romantic moment, toast to your love while experiencing the view from the ship's outdoor deck.

Swan Boats

4 Charles St S
Boston, MA 02116   Directions

(617) 522-1966


While you're hanging out in the Boston Public Garden, take a ride on the city's signature Swan Boats. The boats are the only ones of their kind in the world and they float the waters of the Public Garden lagoon. A ride on one of these boats is the best way to see all of the attractions in and around America's first botanical garden.

The College Club

44 Commonwealth Ave
Boston, MA 02116   Directions

(617) 536-9510


Spend a romantic weekend at a cozy getaway guest room at the Bed and Breakfast at 44 Commonwealth Avenue, located at The College Club. The 11 rooms are all restored and boast “vintage charm with modern convenience”. You'll feel like you're in a 19th century love story during your stay here.

Thinking Cup

165 Tremont St
Boston, MA 02111   Directions

(617) 482-5555


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