Cape Cod

Flights into Boston would be much cheaper. I’d prob base in Yarmouth again if I went back. It’s very close to Hyannis (where the ferries run) but very quiet. You’ll def want to drive the entire cape though. Chatham is a little more $$$ than Yarmouth but is a lot prettier with more charm imo. The skipper restaurant and chowder house in s Yarmouth was really good. I spent a day in Martha’s Vineyard and enjoyed it. I rented a car once I got off ferry and drove around the entire island. Would def like to check out Nantucket if I went back. That about all I’ve got.

Arrival: Boston (BOS) vs Providence (PVD)
—Providence (TF Green) is smaller, less crowded, easier parking, faster security, and about 80 mi from Cape—roughly 1.5–2 hr drive
—Boston Logan typically has more flight options and often cheaper tickets, though busier ().
—Recommendation: Choose Providence if ease & speed matter; pick Boston if your flights are better or cheaper.

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Day 1–3: Cape Cod Highlights

Day 1: Outer Cape – Provincetown
—Morning: Drive to Provincetown, climb the Pilgrim Monument and stroll Commercial St .
—Lunch: Casual seafood—The Lobster Pot or Ceraldi
—Afternoon: Beach at Race Point, gallery-hopping at the Art Association & Museum.
—Dinner: Try The Canteen, Spiritus Pizza for late-night slices
—Stay: Boutique hotels like Salt House Inn or Awol

Day 2: Mid Cape – Hyannis & Chatham
—Morning: Ferry departures are here, visit the Kennedy Hyannis Museum.
—Lunch: Spanky’s Clam Shack for chowder or fried clams
—Afternoon: Drive to Chatham for its lighthouse and Main St charm.
—Dinner: Mac’s Fish & Lobster in Chatham .

Day 3: Cape Cod National Seashore
—Morning: Hike the Great Island trail near Wellfleet
—Lunch: Mac’s Seafood in Wellfleet.
—Afternoon: Relax at Cahoon Hollow Beach; oysters and dinner at The Wellfleet Pearl
—Evening: Explore Sandwich (oldest town) or Dexter Grist Mill if time allows .

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Day 4–7: Martha’s Vineyard (4 Nights)

Day 4: Oak Bluffs & Film Legacy
—Morning: Ferry to Vineyard; explore the colorful gingerbread cottages at Oak Bluffs.
—Lunch: Red Cat Kitchen: playful, fresh plates
—Afternoon: Visit “Jaws bridge,” South Beach, and town hall in Edgartown…movie-buff musts
—Dinner: Detente or waterfront Dock Street in Edgartown .

Day 5: Edgartown day
—Morning: Lighthouse sightings and boutique shopping.
—Lunch: Nancy’s seafood or Giordano’s for lobster rolls .
—Afternoon: Relax at Moshup Beach in Aquinnah before catching sunset.
—Dinner: Outermost Inn for fine dining views .

Day 6: Vineyard culinary loop
—Morning: Farm-to-table snack at local farms.
—Lunch: John’s Fish Market or classic Sandy’s Fish & Chips
—Afternoon: Sample drinks & sandwiches in Menemsha Harbor.
—Dinner: Chilmark Tavern or The Covington, local favorites

Day 7: Island leisure
—Morning: Rent bikes, explore trails or take a lighthouse tour.
—Lunch: Atria Burgers or Sweet Life
—Afternoon: Afternoon at the beach or Flying Horses Carousel.
—Dinner: Casual seafood at Nancy’s on the Water or jerk at Chef Deon’s Kitchen

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Day 8–9: Nantucket (2 Nights)

Day 8: Arrival & Downtown
—Ferry or short flight early morning to Nantucket.
—Brunch: Island Kitchen: beloved all-rounder .
—Afternoon: Visit Brant Point Lighthouse, browse Whaling Museum & shops.
—Dinner: Seafood at Brant Point Grill or creative plates at The Nautilus

Day 9: Beach + Brewery vibe
—Morning: Beach time at Jetties or Surfside
—Lunch: Sandwich-to-go from Something Natural or Walter’s Deli
—Afternoon: Visit Cisco Brewer for beer, live music, food trucks
—Dinner: Dine waterfront at Galley Beach or Or, The Whale

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Day 10: Return & Final Cape Day
Ferry back to Cape in the morning.
—Midway lunch at Spanky’s or revisit favorite.
—Afternoon: Leisure in Falmouth or Sandwich.
—Drive to airport-ready town; return vehicle and fly from PVD or BOS depending on flight.

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Tips & Tricks
—Book ferry & accommodations early, especially in summer.
—Rent a car on Cape Cod for island transfers; on the islands, bikes + local buses suffice.
—Check Jaws anniversary events on MV—tours and photo ops .
— Pack layers, coastal wind can be chilly even in July.
— Peak dinners need reservations at Nautilus, Brant Point, Outermost.

There are several posts on here. I’ve got some feedback as well. Abita likely to have feedback on Logan v PVD. Ten days may be a lot unless you want to to stay on one of the islands for part of the trip. Or you can do a couple days in Boston on the front or the back.

My folks had a place in Harwich Port for 30+ years. We finally sold a couple years ago. Probably my favorite place to visit.
Partial to Harwich Port and Chatham. Prefer Nantucket over Martha’s Vineyard.

Yarmouth is not a bad place to stay as it’s a bit central. Can have some traffic though as it’s closer to Hyannis which is more commercial. I’d plan to spend time toward Chatham and the seashore. P-Town is nice too.
Depending on budget, Chatham Bars In is great. Chatham Wayside is cheaper. Other poster mentioned Truro. Mom always loved that place.

I will say this - Eagle Wing Inn in Eastham is pretty nice. Owner is great. Stayed there the week I had to move my mother to memory care in Louisiana. Enjoyed it and very well located.

For Martha’s Vineyard I prefer Edgartown. Nantucket, I’d rent a jeep and go to Sconset beach. Can also drive to the point and see the seals. That’s very cool but have to drive on the beach which is not the easiest.

For airports, I’ve done both. Since Big Dig I’ve preferred Boston for the nostalgia of it since I am from there. Better schedules and airfare too.

For food, Chatham Bars Inn. Veranda is nice. Wild Goose Tavern in Chatham. Brax in Harwich. Embers is good pizza but I’m old school and prefer George’s. Sundae School in Harwich Port or Dennisport. Best ice cream ever. O’er the Whale on Nantucket. Red Inn in Provincetown. Owner is from NOLA. For lobster roll, Chatham Fish Pier is the best per the wife (no pics). They have other stuff too but we always stop there.

National seashore is awesome. Whale watch out of P-town. For Nantucket, you can catch ferry out of Harwich Port. Hyannis will get you ferry to Martha’s Vineyard. Car rental on the Vineyard creates major parking issues. Easier on Nantucket if you drive around. If you stay in town I’d pass on a rental. Partial to Murray’s Toggery Shop. Great clothes and I have several sets of Nantucket reds. Whale museum is cool too.

Understand May is a bit early as kids don’t get out of school until June. Some places may not be open every day or as late in the day as they normally are in the summer. Do some checking on that.

Great place to visit. Have a great time.

Thanks to all.

Great reply's.