A local’s guide to exploring and relaxing in the best towns on Cape Cod, Martha’s Vineyard and Nantucket.
Total Days: 7 days | Accommodations: Hotels | Traveled with: Family | Transportation: Car rental on the Cape and MV. Bike riding in Nantucket | Type of Trip: Beaches and scenic New England attractions and seafood | Highlights: Chatham Bar’s Inn, sandy beaches and sunset drinks, MV road trip and Nantucket bike ride
I grew up on Cape Cod during the summers and spent a lot of time on the islands. Though it’s impossible to visit all the towns, I’ve included the best representation in this 7-day itinerary for first-time visitors. This is targeted to summer vacations, but this guide could also work in the spring and fall. Just less time sunbathing on the beach! FYI: almost all dinner spots should be reserved beforehand!
DAY 1
At a glimpse: Exploring the Main Street in Chatham
Travel agenda: Welcome to Chatham! Once checked-in to your hotel, make your way to the Main Street in town. Main Street holds the key to my heart, as well as some adorable and quirky stores like Goodies, Where the Sidewalk Ends bookstore, Mermaids on Main, Mark August and Ducks in the Window (just as it sounds!) Gould and Chase Park are right off the main streets and worth a walk through. The Godfrey Windmill built in 1797 is sometimes open for tours in Chase Park as well.
Dinner is at Bluefins Sushi, a well-regarded restaurant with locals and visitors alike. Chatham Squire is just a few doors down and a fun pub for after-dinner drinks. If you have room, the clam chowder is widely hailed as some of the best on the Cape.
Tip: If you don’t have a car, the best neighboring rental places are at the Hyannis Airport or in Orleans. Drop off can be in Falmouth!
DAY 2
At a glimpse: Chatham brunch, beach and clam bake experience
Travel agenda: Enjoy a unique brunch at Hanger B Eatery, located on the second view of a small airport building where you can watch the Cessnas or Biplanes take off. If you want a bird’s eye view of the Cape, the airport also offers tours!
After, head to Lighthouse Beach for beautiful views and a white sandy retreat. From there, it’s a short but scenic walk to the Harding Beach Point via Monomoy Nature Trail.
Dinner is more of a New England experience tonight. Enjoy a Clam Bake at the Chatham Bars Inn. Attendees feast on lobster, corn, potatoes and clams, all of which are locally caught or grown around Chatham. This is an easy bucketlist “check”!
DAY 3
At a glimpse: Drive to Osterville, then stay in North Falmouth
Travel agenda: PSA for coffee snobs: Snowy Owl Coffee Espresso Bar off of Main Street specializes in a good cup of coffee. Sit and enjoy in their courtyard. Chatham Cookware is the spot for pastries.
Pack your bags! Falmouth Heights is the next Cape destination. About halfway through the drive stop in to the quaint Osterville town. For lunch, opt for the very best pizza at Crisp Flatbread. THEN you’re going to stop for ice cream at the local favorite Four Seas. Grab a pint of Chocolate Chip to go. You’re on vacation after all! If you’d like to drive to the water and see the Kennedy Compound (from a distance though you can walk the beach next to it!) it’s just a 8-minute drive from here.
Once in Falmouth Heights, enjoy some relaxing time by visiting Old Silver Beach or a less obvious and more tranquil option: The Knob peninsula. For some physical activity, the Shining Sea Bikeway stretches from North Falmouth to Woods Hole. The 10.7-mile former railroad path features bird sanctuaries, marshes, cranberry bogs and sea views.
Instead of post-dinner drinks, plan on unofficial happy hour drinks at the Chart Room. Hidden away in a marina, sunset drinks “on the shells” don’t get much better. For the real deal experience order a mudslide! From there, take an Uber or designated D.D. to Epic Oyster for oysters, clams casino and other New England specialties.
DAY 4
At a glimpse: Salty day on the water, kayaking and picnicking
Travel agenda: Sleep in today! When it’s time for breakfast head to Dean’s Market. Pick up provisions for lunch as well. Then drive 20 minutes to hidden gem Waquoit Bay with sheltered beaches, marches and Washburn Island, a protected reserve with wooded trails. Explore via kayak or SUP. It’s a 45-minute paddle from the town boat ramp to the island. Cape Cod Kayak offers kayaks and stand up paddleboards and delivery! It’s a cool spot for shellfishing, sailing, water-skiing and fishing on the calm waters.
Drive back to home-base to get ready for the night. The Popponesset (Poppy) Marketplace is a 20-minute drive from Falmouth. I grew up biking to the marketplace. It’s a small neighborhood spot with lots of character and little boutique stores. Right in the center is the Raw Bar and THIS is where you order the Lobster Roll. It’s an institution and worth the wait! For a drink after, walk just a few minutes to the water. If you’re under 30 head to The Lure, if you’re over walk next door to The Inn bar instead!
DAY 5
At a glimpse: Ferry to Martha’s Vineyard, road trip around the island and stay in Oak’s Bluff
Travel agenda: In the morning, be ready to go early to drop off the car rental in Falmouth! It should help knowing the first stop is for a coffee and pastry at Pie in the Sky Bakery. Just around the corner, hop on the ferry (no later than the 8:15am) to Martha’s Vineyard from Woods Hole. Upon arrival, make a run to the iconic and original Black Dog Tavern. Located just a parking lot away from the restaurant, many others will have the same plan. There may be a wait, so during this time you can stroll the beach.
After a filling breakfast, explore Vineyard Haven. Some of the best stops include Alley’s General Store, Green Room, Bunch of Grapes bookstore and CB Stark Jewelers for local vineyard jewelry. This is also where to pick up the authentic merchandise at the Black Dog General Store. Next, book a car at the A-A Island rental shop.
Tip: Plan for a full day car rental and go for the Jeep! It’s an additional $25 to drop off at the Oak Bluffs location where you’re spending the night.
Head Southwest to the other side of the island, with first stop at Squibnocket Beach. This newly renovated beach is finally open to the public. Then drive the final 10 minutes to Gay Head Light, a 1799 lighthouse surrounded by the dramatic Aquinnah Cliffs and a sandy beach below. FYI: the beaches here are clothing optional!
Tip: These beautiful MV landmarks are not great for swimming, but the scenery is outstanding.
From here, drive through West Tisbury to Edgartown. You can stop at the lookouts over Menemsha Pond or the Island Alpaca Company. In Edgartown, wander the quaint streets and boutique stores. A good lunch stop is Rosewater Market for sandwiches, salads and pastries. More importantly, save room for dessert: Murdick’s Fudge is a landmark in MV and you can watch it being made at a nearby table. Samples are always offered! Or if you prefer ice cream, Mad Martha’s will do the trick!
Finally, drive the 15 minutes to Oak’s Bluff where you will spend the night. Make sure to take the route that features the Jaw’s Bridge. If you want to stop, it’s technically not permitted but it’s an MV right of passage to jump off the bridge!
Drop off the car at the A-A Island Auto Rental located right in town on Circuit Ave Extension. Check in to your hotel and get ready for the evening. Flying Horses is the nation’s oldest platform carousel, originally located on Cooney’s Island in 1876. The beautifully crafted wooden horses and brass ring game make this a fun stop for all ages. Seriously, it can get competitive! Around sunset, check out Circuit Ave and Trinity Park where you can find 318 of the original 500 “Gingerbread House” cottages that remain today.
Dinner is at the Red Cat Kitchen, serving respected seasonal comfort food. For a beverage after dinner walk just one block down Kennebec Ave to Offshore Ale Co. Before retiring, stroll across the street to Back Door Donuts. This hidden gem is open until 1am and serves hot, melt-in-your-mouth doughnuts for a late-night snack.
DAY 6
At a glimpse: Ferry to Nantucket, exploring town and bike ride to scenic town and beach
Travel agenda: Take the morning ferry from Oak’s Bluff to Nantucket! Drop off your bags at your hotel and pack a day bag with towel. Then walk to Handblebar, a little café for equally good coffee and ambiance. It’s also fitting with the theme for the day!
Then it’s time to explore what the locals call “town.” This historic district has more than 800 houses built in the 1700 and 1800s during the peak of the whaling business. Main, Federal and Centre are the main streets, but the side roads are worth investigating too. Nantucket Looms, Murray’s Toggery Shop, Milly and Grace, and Mitchell’s Book Corner are just a few favorites. Of course there are Nantucket gift shops all over and a Lilly Pulitzer and Vineyard Vines right up front if you want to look the part.
Next, pick up sandwiches and drinks at Provisions. Then walk just 5 minutes away to Young’s Bicycle Shop. The best way to get around the island is via bike. For a flat, scenic and 100% worth-it ride, bike 45 minutes east to the town of Siasonset, or Sconset! Most of the ride will be on the Sconset Bike path. Meander through the town with summer residences, mostly built during the 1900s. Have a picnic lunch on the beautiful white sandy beach.
From here, take a walk in the direction of the Sankaty Head Lighthouse on the Sconset Bluff Walk. This is a little-known path that provides views, gardens and a behind the scenes look at many of the amazing seaside residences. On the bike ride back to Town, take Sakatay Road to Polpis Road, which offers scenic marshes and cranberry bogs along the way.
Now you’ve earned dinner! Get ready at your hotel and then walk to Afterhouse Seafood Bistro & Wine Bar. A cozy and new-ish restaurant housed in a historic building. After, it’s a 5-minute walk to the Straight Wharf and the Gazebo right next door for drinks in a fun, laidback setting.
DAY 7
At a glimpse: Bike ride to Cisco Brewery
Travel agenda: Good morning! Sleep in and when you’re ready, hop on your bike for a refreshing 10-minute ride to Downyflake. Follow the smell of heavenly fresh doughnuts and then grab a seat at the 85-year-old-and-still-going-strong diner.
From Downyflake, it’s just a 15-minute bike ride to Cisco Brewery. Plan to be there when it opens to secure a table! This is a “must visit” destination for adults of all ages, not to mention kids and dogs are welcome too. The brewery has world-class beers (wines and spirits are available), a laid back ambiance and live music and is the perfect way to end your New England getaway. Food trucks are usually parked around the venue for sustenance.
Then bike back to the hotel to grab a ferry or flight home.
Love the itinerary, can you suggest hotels in each location?