Summer fills up faster than it should. The good hotels get booked, the charter boats sell out, and the restaurant everyone’s going to be talking about stops taking reservations. Before you know it, it’s somehow June, and you’re scrambling. If you’re looking for ideas for summer vacations that are actually worth the effort, I’ve been thinking a lot about where I want to go — and more importantly, making sure I don’t end up somewhere I settled for because I waited too long. These are the seven summer trip ideas I’d start booking now, while there’s still time to do them right.
Boston
A long weekend in Boston is one of the best summer vacation ideas on the East Coast, easy to underestimate and hard to forget. Start in the North End: espresso martinis and lobster tails (the pastry kind, just to be clear) are non-negotiable. Catch a Red Sox game at Fenway, which is worth doing at least once in your lifetime. If you’re feeling crazy, splurge for Green Monster seats. Close out the weekend with a lobster roll at Yankee Lobster and a Sam Summer at Barking Crab with the harbor glistening in front of you. You’ll be enunciating your a’s and dropping your r’s in no time.
Alaska
If you’ve been putting off Alaska, this is the summer trip to finally make happen. Landscapes that feel too wild to be real? Check. Hitting your 10K step goal without even trying on a morning hike? Check. Kayaking through a glacier-filled national park? Check. Casting a reel and catching your dinner? Check.
Speaking of which, if you’re a seafood lover, you’re in the right place. Alaska is the seafood capital of the world for good reason — fresh halibut, salmon, and Alaskan king crab are all on the table, and all of the above is the right answer. When dinner is done, do as the locals do and end your night at a dive bar. A personal favorite is the Salty Dog in Homer, where the floors are worn and nearly every crevice is covered in dollar bills. Fair warning: you may close the place down.
Willamette Valley
If you’re considering Napa or Sonoma for your summer vacation this year, it’s worth looking at Willamette Valley instead. Oregon wine country is stunning, unhurried, and a fraction of the price, without sacrificing any of the good stuff. Stay at Deux Vert Vineyard, a small family-owned vineyard available on Airbnb or VRBO, complete with a pool, fire pits, a putting green, and even a bocci court. Spend your days sipping at local vineyards such as Fairsing, Four Graces, or J. Christopher, and start one morning at the McMinnville Farmers Market. Just plan on leaving with more bottles than you intended.
Nantucket
Nantucket doesn’t need much of an introduction, so I’ll just direct you where to go instead. Rent bikes and ride out to Madaket for lunch at Millie’s; the fried oyster tacos are worth the trip alone. For the island’s best lobster roll, go straight to 167 Raw. What sets 167 Raw apart from the rest? The perfect mayo-to-lobster ratio (this is important), and they don’t skimp on the lobster either.
Plan to spend at least one afternoon at Cisco. Yes, you’ll encounter your fair share of ‘Chads,’ but the scene can’t be beat — picnic tables packed, live music buzzing, and cute dogs everywhere you turn. Book Nautilus for dinner if you can get in, and time a reservation at Straight Wharf for golden hour on the harbor. Last but not least, don’t leave without a Crucumber martini at Cru. It’s a very particular kind of perfect.
Cuttyhunk
There are very few places left that feel genuinely untouched, and Cuttyhunk is one of them. No cars, no itinerary, no pressure — just a small island off the coast of Massachusetts operating on its own quiet frequency. Expect slow mornings, long beach days, and golf carts as your only mode of transport.
Cuttyhunk has a fiercely loyal community of regulars who’d rather keep it off the radar, and after spending time here, it’s easy to understand why. There’s no dress code, no scene, and nobody’s trying to be seen. Oysters here are pulled straight from the water and shucked in front of you. No frills, just fresh. Come here when you need to actually decompress.
Mackinac Island
I haven’t been to Mackinac yet, but it’s on the shortlist for a girls’ trip this summer. Much like Cuttyhunk, there are no cars on the island. Just bikes, horses, and an easy pace that feels increasingly hard to find. The whole island has a preserved, almost time-capsule quality, with Victorian-era storefronts lining the main street and a general sense that not much has changed here in a very long time. The Grand Hotel is the landmark stay, all white columns and sweeping porch views, and the fudge shops are famously hard to walk past without stopping. Consider this one on my radar — and maybe yours too.
Croatia
Save this one, plan it properly, and go. It’s one of the summer vacation ideas I keep recommending to anyone who asks — best experienced as a slow island hop, starting in Split and working your way down the coast. Dinner at Bokeria in Split will set the tone immediately. Order whatever your server suggests and don’t second-guess it. From there, make your way to Hvar. Check into Palace Elisabeth (located just steps from the marina), spend an afternoon exploring the Pakleni Islands, and don’t leave without dinner on the patio at Giaxa. If you can swing a stop in Korčula on your way to Dubrovnik, do it. The island is reminiscent of Dubrovnik, with a fraction of the crowds.
End your island-hopping adventure in Dubrovnik, but keep it to one night. Walk the city walls, enjoy dinner at Michelin-starred Restaurant 360, and end the night at Buža Bar, a literal hole in the wall built into the cliffs above the Adriatic. The islands are the real story — Dubrovnik is just a beautiful way to close it out.
Any one of these summer vacations will deliver. The only mistake is waiting too long to book.
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