Depending on where you are coming in from will depend on your departure day, time, and arrival method. This is my fiancé and I’s personal itinerary from our trip last summer, with a few tweaks! Plus I included a few other places to eat and things to do on the Cape.

Day 1: Travel Day + Arrival (Driving from North Jersey/NYC)

• Start drive around 9am north toward Cape Cod

• Depending on route - make a pit stop in Mystic, CT to stretch legs and get lunch at the famous Mystic Pizza!

  • From where we live, it takes about 2 hrs. 45 mins to get to Mystic

    • Dayne and I ordered small build your own ($14 before toppings) then walked down by the river to enjoy the weather and views

• If you’re looking for a little coffee pick me up you can check out: Mystic Depot Roasters, Lighthouse Bakery, Sift Bake Shop or for a little spooky witchy vibe visit The Cloak and Wand!

• Get back on the road and continue drive to Cape Cod (2 hrs. 25/30 mins.)

• First official stop on the Cape needs to be Cuffy’s located in Dennis!

  • This longtime establishment got a new look a few years ago, but it still has the same incredible coziness. This store has endless amounts of shirts, sweatshirts, hoodies, hats, and home decor items.

    • There is also a candy store attached where you can get some Saltwater Taffy or fudge for a little afternoon sweet treat

• Head to hotel or Airbnb

  • Where you stay is all dependent on what you want to do and how much you are willing to pay. Some places are much more expensive, while others can be pretty reasonable.

    • Here’s a great article by Adventurous Kate that breaks down the different areas of the Cape and you can decided which area is best for you, your family and friends.

• Dayne and I stayed here for four nights: Chatham Guest Rooms - East Room | 1409 Main Street, Chatham, MA 02633, United States

  • The fun twist? It was above a map shop on the main road heading into the Cape’s famous town of Chatham. The stay was comfortable, convenient, and very clean!

    • My rule of thumb for most trips is unless you are looking to make the accommodation a key part of your trip (cooking meals, doing laundry, hanging out), don’t go crazy with the hotel or Airbnb. I always look at reviews, safety reports, and proximity to restaurants/shopping when booking. However, if I am just paying for a clean, safe spot to sleep and keep my stuff, I don’t splurge.

If you are flying instead of driving:

• Fly into Boston Logan International Airport

• Once you get all your luggage and personal items situated, head for the rental car center or for Ground Transportation to take the bus out to Cape Cod.

  • More information on the Peter Pan bus line is here.

    • If you aren’t meeting any friends or family on the Cape that have a car, I would recommend renting one as Ubers/Lyfts/Taxis can be sparse or very expensive. Also the Cape is easier to explore if you have a rental car.

  Now let’s jump back into Dayne and I’s long weekend itinerary

• Freshen up for dinner

• Head over to Mac’s Chatham Fish & Lobster

  • Can be pricey (as most restaurants on the Cape are) but in our opinion it is so worth it! The lobster rolls and chowder were top-tier. Not to mention they get your food out to you so quickly, so five stars for the customer service!

• After you finish up dinner, continue your drive down Main Street and head into the heart of Chatham

  • There are a few municipal parking lots throughout the town - plus street parking.

• Get out, enjoy a nice walk down Main Street and be sure to start at the bottom of the hill so you can check out the shops on your way up.

• At the top of the hill, there is a delicious homemade ice cream shop called Buffy’s Ice Cream that needs to be on your list.

  • My family and I have been coming here since I was three years old - this is actually where I had my first big girl cone (only for me to roll the ice cream scoop right off the cone onto the ground)

• Don’t feel like you need to rush your Chatham experience (you’ll be back)

• Head back to hotel or Airbnb and gear up for an early morning

Day 2: Whale Watching and Baseball

• Get up early, get dressed

  • Be sure to bring a sweatshirt or wear warmer clothes and closed toe shoes! Out on the water, it can get pretty chilly. Especially when they increase the speed!

    • Other things to pack: water, camera, sunscreen, snacks (if you are particular - they do have food to buy on board), sunglasses

      • Also, if you get sea sick easily this might not be for you. Unless you have a remedy that works! The few times I have done this experience the water has mostly been calm so I didn’t encounter any motion sickness

• Head out around 7:30am and head toward Whale Watching cruise site

  • Hyannis Whale Watcher Cruise - Barnstable

    • $75 a person for 4 hours

    • You should try to get there 30 minutes early as the boat starts boarding an hour ahead of departure time (ours was 9am)

    • Here is a guide to parking near the cruise site

• When Dayne and I went, we parked our car about 10 minutes away and then grabbed some food and coffee from Nirvana Coffee

  • Highly recommend Nirvana Coffee’s breakfast sandwiches! It’s a cute, cozy shop right off Main St. in Barnstable

• Make sure you have all your personal items and your tickets ready to go when you start boarding

• Go enjoy the open ocean and keep your head on a swivel! Every time we have gone out with this cruise company, we have seen lots of humpback and minke whales

• Once your cruise is over - typically wraps up around 12:30/1pm - it’s time to figure out where to eat lunch!

• Here are some spots with high ratings:

  • Mattakeese Wharf Waterfront Seafood Restaurant

  • Osterville Fish Too

  • Dolphin Restaurant

• Dayne and I decided to go to a restaurant that was a childhood staples on the Cape: Captain Parker’s Pub in Yarmouth

  • It’s not a fancy restaurant but the food is really fresh, really good and it’s been there for a long time

• Following lunch you have some free time! You can either go to one of the many mini golf coursing on the Cape, head back to your hotel or Airbnb for a quick nap, head to the Cape Cod Mall and walk around, or head to a local beach to take in the sights

  • Here are some top recommendations for saltwater beaches near Yarmouth:

    • Seagull Beach

    • Parker’s River Beach

    • Bass Hole (Gray’s Beach)

    • Smuggler’s Beach (Bass River)

    • Thatcher’s Beach

    • Sea View Beach

Playball!

• A huge part of Cape Cod’s identity is the summer collegiate baseball league. Each year, hundreds of the best players from across the country are invited to play for one of ten teams the league has. The schedule consists of a 40-game regular season before the postseason begins in August. The culture of the Cape Cod League is truly special and something you should do more research on, if you aren’t familiar with it!

  • History of the Cape Cod League

  • Host families for the Cape League

  • The League’s Importance

• The schedule can be found here when they are in-season and the games can start as early as 4:30pm and as late as 7pm

  • It just depends on which team you want to see and be sure to factor in the time it takes to drive and park!

  • Oh and did I mention it’s FREE to attend the games?!

• I haven’t been to ALL of the fields/parks but the ones that I have gone to or have been recommended to check out are:

  • Chatham

  • Orleans

  • Yarmouth-Dennis

  • Harwich

  • Cotuit (close to Mashpee Commons which is an adorable area to go shopping and get some coffee/food!)

    • Another thing to keep in mind, a lot of the stadiums do not have seating or they have limited metal bleachers so if you have the chance to pick up some beach chairs or if your hotel/Airbnb provides them or towels, bring those!

    • Another note - not all of the fields/parks have food so my best piece of advice is to plan on bringing snacks and get something before or after. You could always pick up food and bring it to the field/park (sandwiches, pizza, take out)! Just be sure to clean up all of your trash afterward.

      • Chatham does have concessions so if you plan to go to a game here, you can get hamburgers, hot dogs, chips and drinks!

• As for where Dayne and I went during our trip, we headed over to Orleans (Eldredge Park) with a 6:30pm start

  • Since there were no concessions here (they did have Cape Cod League merchandise though) we decided to get a pizza afterward and head back to the Airbnb since we were wiped!

Day 3: Chatham and Baseball

• No need to rush into the day as we are staying local! So get up and get ready at your own pace

  • Be sure to dress in layers as being by the beach can be cooler and if you plan to stay for the baseball game it can be cooler

• Head into Chatham for the day

• Brunch at Wild Goose Tavern

  • Be sure to make reservations!

• Stroll Main Street and shop

  • You can truly get lost in these stores for hours as a lot of them are artisan stores, clothing boutiques or art galleries

• Grab coffee and snack from Cape Cod Coffee at the top of the hill (they had a coconut cold brew in season)

• Keep walking toward Lighthouse Beach and take in the scenery

• If you are up for a mid-afternoon beverage and want to relax at a five-star resort, head over the Chatham Bars Inn

  • This iconic property sits right on the water and not only has breathtaking views, it exudes coastal luxury

    • If that’s not your jam, there is a cozy dive bar right on Main Street called Chatham Squire

• Baseball game at 7pm - Chatham (Veteran’s Field)

• And what’s the best way to close out the night? Head up to Buffy’s Ice Cream post game

Day 4: Head Home

• Get up, pack up, check out

• On the drive out, stop into Mariner Cafe in Hyannis (at the time we went, they were featuring a delicious tiramisu latte)

• Head over to Kalmus Beach and soak up the last moments of the (hopefully) peaceful long weekend

If you are flying out instead of driving in:

• Make sure you leave early as the Cape is known to have horrible traffic on Sunday as everyone heads back home for the week ahead

• If you are taking the bus, just make sure you are there with plenty of time to load up

• Final piece of advice before flying home - try to get Kelly’s Roast Beef at Logan Airport - It’s truly delicious

  • My go-to order: Roast Beef Sandwich with a slice of provolone, a cup of clam chowder and a side of onion rings.

Towns, attractions and other fun things to check out:

Towns/Cities (on or near Cape)

• Martha’s Vineyard

• Nantucket

• Provincetown

• Sandwich

Attractions

Mashpee Commons

Food

Lobster Trap (Bourne)

Other