Cape Cod + Islands Guide

The gateway to Cape Cod, straddling both sides of the Cape Cod Canal. More of a pass-through than a destination.

The oldest town on Cape Cod with a charming village center, heritage museums, and beautiful boardwalk beach.

The Upper Cape's best beach town with a walkable village, excellent Sound-side beaches, and easy ferry access to Martha's Vineyard.

Home to South Cape Beach State Park and Mashpee Commons. More residential, with good Sound-side beaches.

The largest town on Cape Cod, encompassing Hyannis, Centerville, Cotuit, Osterville, and Hyannisport. Hyannis is the commercial hub with the best shopping, restaurants, and Nantucket ferry access. Kennedy family heritage.

Split between Route 28 commercial strip and the quieter Route 6A historic district. Bass Hole boardwalk is a hidden gem.

A town of two coasts: bay-side Dennis with stunning sunsets and Nantucket Sound-side Dennis with warm swimming. Cape Playhouse adds culture.

A quiet, family-friendly town with warm Sound-side beaches and Harwich Port's small but charming village center.

The bay beach capital of Cape Cod. The Brewster Flats at low tide are a mile-wide wonder. Quiet, charming, and deeply family-friendly.

The jewel of Cape Cod. A picture-perfect New England village with upscale shops, excellent restaurants, a working fishing fleet, and the iconic lighthouse.

The crossroads of the Lower Cape with access to both epic Nauset Beach and serene Skaket Beach sunsets. More relaxed and practical than Chatham.

Gateway to the Cape Cod National Seashore with some of the Cape's best ocean beaches and pristine freshwater ponds.

An artsy, oyster-loving town with excellent ocean and bay beaches. Wellfleet Drive-In and the gallery scene give it a bohemian charm.

The quietest town on the Outer Cape. Rolling dunes, isolated beaches, and an "end of the world" feeling. Edward Hopper's favorite.

The most vibrant, inclusive, and unique town on Cape Cod. World-class dining, art galleries, whale watching, and legendary nightlife at the tip of the Cape.

The smaller, more uniform island 30 miles south of the Cape — a single town with cobblestone streets, gray-shingle architecture, and several outlying village beaches (Sconset, Madaket, Surfside, Cisco).

The year-round port of Tisbury — the working ferry terminal, the island’s largest year-round commerce, and a quieter harborfront than Oak Bluffs.

The Vineyard’s party-and-Gingerbread village — Methodist Camp cottages, the Flying Horses carousel, and the only real bar scene on the island.

The whaling-era anchor village of Martha’s Vineyard — white clapboard captains’ houses, a working harbor, and the island’s most photographed village center.

The agricultural heart of the Vineyard — the Saturday farmers’ market, Lambert’s Cove Beach, and the island’s pastoral interior.

Rural, dramatic up-island Vineyard — Menemsha fishing harbor, Lucy Vincent’s cliff-backed beach, and the island’s darkest night skies.

The Vineyard’s westernmost town — Wampanoag tribal land, the famous Gay Head clay cliffs, and the lighthouse at the island’s western tip.