Evenings to Remember: After-Hours Adventures on the Boston Harbor Islands
When the sun dips below the horizon and the island day-trippers head home, the Boston Harbor Islands truly begin to shine. This summer, Boston Harbor Now invites you to stay a little later and experience a side of the Harbor that few ever see.
From Prosecco to sunsets to seafood feasts, our 2025 after-hours programming brings a sense of wonder and celebration to the water.
Whether you’re a local looking for a new way to enjoy your summer evenings or a visitor eager to make your trip unforgettable, these experiences offer the perfect escape from the ordinary.
Spectacle Summer Nights
Imagine watching the sunset orange glow of the city skyline while live music floats through the evening air. That’s Spectacle Summer Nights, a special after-hours event series that lets you explore Spectacle Island long after most have headed back to shore. Lounge on the beach, take a twilight hike, enjoy pop-up performances, and sip on drinks from 67 Degrees Brewing as the skyline lights up. For the first three dates, we’ll have a pop-up from Luke’s Lobster, while ZaZ will provide food for Caribbean Night. These nights feel like a private island getaway just minutes from downtown Boston. With several Summer Nights opportunities throughout the season, you’re sure to find a night that fits in your schedule:
Saturday, July 12: Spectacle Summer Nights Season Opener – Help us kick off the summer with live music, lawn games, and s’mores on the beach!
Saturday, July 26: Spectacle Summer Nights: Nerd Night – To all our fellow nerds, this one’s for you. There will be trivia and board games—plus, costumes are encouraged in celebration of the 250th anniversary of the events that led to the American Revolution.
Saturday, August 9: Spectacle Summer Nights: Jazz Night – What’s better than relaxing on an island while listening to live jazz?
Saturday, August 23: Spectacle Summer Nights: Caribbean Night – We bring the Caribbean Islands to the Boston Harbor Islands with Caribbean food and music!
Prosecco Picnics
New for 2025, Prosecco Picnics on Spectacle Island are the ultimate elevated evening escape. Grab a curated picnic, toast with bubbly, and stretch out on a blanket as sailboats drift by and the sun melts into the harbor. With stunning views and unbeatable vibes, it’s a romantic date night, friends’ night out, or solo self-care moment all in one. These will fill up quickly, so book yours now:
Thursday, July 17 Prosecco Picnic
Thursday, July 31 Prosecco Picnic
Sunset Lobster Clambakes
Back by popular demand, our Lobster Clambakes turn Spectacle Island into a one-of-a-kind New England dining experience. Enjoy a full spread of classic seafood boil favorites – lobster, clams, corn, potatoes, and more – served piping hot against the backdrop of Boston Harbor, the city skyline, and the setting sun. Add in a harbor cruise to and from the island, and it becomes a dinner experience that’s as delicious as it is unforgettable. There are three chances to join this unique culinary experience throughout the summer, so don’t miss out on this unforgettable opportunity:
Thursday, July 24 Sunset Lobster Clambake
Thursday, August 7 Sunset Lobster Clambake
Thursday, August 21 Sunset Lobster Clambake
Friday Night Sunset Lighthouse Cruises
Step aboard a Friday Night Sunset Lighthouse Cruise for a 2.5-hour evening journey through Boston Harbor, featuring panoramic skyline views and up-close looks at historic lighthouses like Long Island Head Light, Graves Light, and Boston Light, the oldest continually used lighthouse in the country. With expert narration, a cool harbor breeze, and golden hour lighting, it’s the perfect mix of history, scenery, and serenity to start your weekend off right. Check the schedule to book your cruise now—the dates for 2025 Friday Night Sunset Lighthouse Cruises are July 11, July 25, August 8, and August 22.
Don’t miss your chance to see the Harbor in a whole new light. Your best summer nights are waiting just off the coast.