Condé Nast TravelerAug 10, 2026
The 10 Best Road Trips on the East Coast for Every Season
From the tip of Cape Cod to the tip of the Florida Keys, these itineraries prove there's never a bad season for an East Coast road trip.
23 things in this story
- Truro VineyardsSightwines and spirits crafted from maritime-grown grapes
- Elsewhere
- KaiaRestaurantBoston, United Statesstandout Aegean cooking
- Gifford HouseGuest houseProvincetown, United Statessquarely in the gay thick of it with nightlife
- Dolphin Fleet Whale WatchAttractionProvincetown, United Statesset out for whale watching
- Crown & AnchorGuest houseProvincetown, United StatesDance floors, pool decks, and a stage that’s seen things.
- A-HousePlaceProvincetown, United Stateslate-night destination
- Equality TrailTrailBoston, United Statescommemorates people and places central to Boston's LGBTQ+ history
- Cape Cod Lavender FarmSightHarwich, United Statespick lavender and browse house-made products
- Atlantic White Shark ConservancyPlaceChatham, United Statesjoin expedition tracking great white sharks
- Cape Cod National SeashoreNature reserveProvincetown, United Statesride through towering dunes
- Art's Dune ToursPlaceProvincetown, United Statesride through the towering dunes
- Boatslip Tea DanceFestivalProvincetown, United Statesan enduring LGBTQ+ tradition overlooking the harbor
- Spiritus PizzaRestaurantProvincetown, United Stateslate-night slice
- DesnudaRestaurantBoston, United Stateslistening bar pairing inventive cocktails and small plates
- Love FarmsRestaurantDennis, United Statescelebrates region's bounty with farm-grown ingredients
- LuneRestaurantDennis, United Statesever-changing menu, earned James Beard Award semifinalist nod
- Sal's PlaceRestaurantProvincetown, United Stateswaterfront institution serving classic Italian comfort food
- Provincetown Portuguese BakeryBakeryProvincetown, United Statesget favorites before they disappear
- The Whitney HotelHotelBoston, United Statesintimacy in Boston
- Raffles BostonHotelBoston, United Statesultra-luxury in Boston
- The Liberty Hotel, a Luxury Collection HotelHotelBoston, United Statesreimagined former Charles Street Jail
- Sleep at Sal'sHotelProvincetown, United Stateswaterfront retreat includes nightly dinners, beach access
- Post Office CaféRestaurantProvincetown, United States
