The countdown for the Martha’s Vineyard season in August always starts when the temperature gets warmer. Although we try not to rush the precious months of June and July, we have to admit summer in the Vineyard is always on our mind, especially since UPTOWN Vineyard and the Rocket Mortgage UPTOWN House are the premier events of the season. Now that August is underway, it is a fair time to prepare for your trip. Having gone to the Vineyard since I was a child, I know what items are critical for your drive up and stay on the island.

The first must-have is a cargo carrier for your vehicle. Transporting yourself, your family, and your belongings onto the Vineyard will take up more space than anticipated. And you may have to account for certain items that may not be sold on the island. A vehicle cargo carrier ensures you have enough room to sit comfortably in the car and pack everything you need. 

MeeFar Car Roof Bag, $140

The day before your trip, shop at your local grocery store. It is best to do most of your grocery shopping before leaving because groceries are more expensive and scarce on the island. This leads me to the second thing you should definitely pack for your Martha’s Vineyard vacation … 

A cooler is absolutely essential. On the drive up, the cooler will prevent your groceries from spoiling. When you get on the island, you can use it to carry snacks, sandwiches, alcohol, or anything else you’d like to keep cool at the beach or the pool. 

Igloo 60 Quart Latitude Roller Cooler, $55

There are many beautiful beaches in Martha’s Vineyard. While you may not need to bring sand to the beach, there are a few essentials that will make your beach day more pleasant. Be sure to pack portable chairs, a sturdy blanket, an umbrella, towels, canvas bags, and sand toys.

WEKAPO Beach Blanket, $30 

Mupater 4-Fold Patio Chaise Lounge Chair, $54 

Fun Little Toys Beach Sand Toy Set, $23

There will undoubtedly be days in which the weather keeps you indoors. Playing cards or games like Rhyme Antics, Apples to Apples, or Wits and Wagers will keep your friends and family busy until the sunshine returns.

Bicycle Standard Rider Back Playing Cards, $5

I won’t go as far as to tell you what to wear on the Vineyard, but I will warn you that packing the right clothes is essential. It is important to remember that it may be warm during the day, but Martha’s Vineyard is an island. This means it gets very cool at night. You also have to remember your activities will take you beyond the beach, so if working out, golfing, biking, or even partying are on your itinerary, pack clothing accordingly. Also, consider that the Vineyard is the perfect setting to rep your alma mater and/or sorority or fraternity.

In addition, you’ll be extremely mad at yourself if you forget the equipment necessary for your activities, like golf clubs or a bicycle. (Pro tip: If you prefer to rent a bike, make sure to book your reservation before leaving home.)

Top Flite 2022 XL 13-Piece Complete Set, $250

Schwinn Loop Adult Folding Bike, $400

One thing that’s sure to happen in Martha’s Vineyard is running into family and friends. And you never know when someone may have to crash with you. If the couch is already occupied at bedtime, then be prepared for an unexpected guest by packing a blow-up mattress.

King Koil Luxury Air Mattress Queen with Built-in Pump, $150

While there may be many other obvious packing items to take to Martha’s Vineyard, these are all items I highly recommend as a seasoned Vineyard goer. With these items, you are set for a successful stay on the Vineyard.