Have you been confined to your 700 square foot prison, err I mean palace in the city? Or has spending too much time in the house with the kids got you ready to put them up for sale on Facebook Marketplace? Then it's time to change up the scenery and head out! “But where should I go suitabull? I’m afraid to breathe in the recycled air of 40 other people on a plane for 2 to 4 hours, so that a wrap for the Bahamas!” Well, I'm a style guy not a travel agent, but I can definitely give you the scoop on my trip to Martha's Vineyard, which turned out to be the perfect place at the perfect time and only a half tank of gasoline away from where I live in New York! Come with me as I share my experience from, what to pack, to where I stayed and how to keep sane on the way there!
How it Started
I’ll start by saying that this is the first official family trip taken since my new little guy Lucas arrived last August. Usually around this time of year, my wife and I are harder to find around town than a clean bathroom at a gas station, because we drop the kiddy (Micah) at my parents’ house and make moves to somewhere tropical. It’s a time that we look forward to every year, where it’s just her and I, celebrating our wedding anniversary and celebrating freedom! But not this year, due to the Coronavirus. We’ve spent every moment with our children and in the spirit of “sheltering in place”; we haven’t dropped them off with the grandparents or anyone else to spoil them rotten in our absence, for fear of unknowingly spreading or acquiring the virus. So we loaded up the SUV and hit the road to Martha’s Vineyard (more on the road trip in a bit). We didn’t imagine there was anywhere we could go, until an impromptu conversation with a friend whom I found out was heading to Martha’s Vineyard. After that we decided to plan a very last minute trip to hold on to our last hope of normalcy.
What/Where is Martha’s Vineyard Anyway?
For those that don’t know, Martha’s Vineyard is an approximately 100 square mile island off the coast of Massachusetts, sitting in the Atlantic Ocean and is arguably one of the hottest US summer destinations. At the Northern part of the Island is Tisbury, to the Northeast is Oak Bluffs, Southeast is Edgartown (with Chappaquiddick island off the coast) and to the West are Chilmark and Aquinnah. Its neighbors are Nantucket, the Elizabeth Islands. The island is dotted with quite a few lighthouses, has plenty of beaches to choose from (go figure, it is an island!) and some of the best lobster you’ll taste in the US. The island is welcoming to all, from past presidents, to entertainers and vacationers from all ethnic backgrounds. However, it wasn’t always that way. In the late 1800’s and early 1900’s decedents of slaves bought property in the only part of the Vineyard where they were welcomed, Oak Bluffs. Since that time Oak Bluffs has become a destination for affluent African American Families, politicians, lawyers etc., and would serve as a place where African American could catch up on the current happenings in the country and network amongst their circles.
Planning and Prep
After my friend gave me the scoop on how to grab accommodations and more importantly, booking the ferry across from the mainland to the island, I booked it within 5 days of our convo (2 days before we left). Shout out to Mary M. for the intel! Since it was meant to be, we were blessed to find a 2-bedroom guesthouse in West Tisbury (booked via AirBnB) and reserved a steamboat ferry, for our vehicle and us. If you don't book a spot on the ferry with the Steamship Authority, you ain't going nowhere! With the short timeframe we had a tall task ahead of us. Though we would’ve preferred to stay in Oak Bluffs due to the historical aspect, Tisbury was central enough to reach anywhere on the island quickly!
Being a project manager in my other life, I had to have my list of items to bring! The challenge in bringing the kids was that we had a playpen, and a myriad of baby stuff to bring to ensure Lucas’ safety. So packing the car was more like playing a real live game of Tetris.
Food—We decided to prepare most of our meals ourselves once we got there, so we loaded up the coolers with lamb, burgers, dogs and everything else that would last a family of 4 for the next 4 days. And unless we wanted a screaming baby and whining adolescent in our face, we made sure to bring all essential baby foods, formula, oatmeal and snacks and beverage with us. And to ensure that we stayed sane, a little wine and adult beverages for the adults. Red bulls were also essential for the 4 and a half hour drive from Long Island, New York to the ferry in Massachusetts.
Clothes, What and How to Pack—With this being my first time to the Vineyard I had to show out, so what did I pack? Unfortunately I couldn’t bring the closet, but I’m a light packer anyway, from my management consulting traveling days (Check out the movie “Up In the Air” with George Clooney for context). For my luggage, I chose a carry-on sized pully suitcase, which fit everything perfectly without taking up too much space in the SUV. Here’s the line-up.
Lower Half—In the middle of 90+ degree heat, shorts were essential. So I brought a pair of blue striped, and Watermelon (you can go out there without these). I wore a pair of Khaki chinos on the drive down, but also packed a pair of slate blue chinos. And for the beach, a pair of swim trunks.
Upper Half—What’s the use in bringing the watermelon shorts if you’re not going to pair it with the blue button up with the marlin overlay, so in the suitcase it went. I also packed a Hawaiian/floral shirt, a couple of pastel colored T-shirts and a couple of henleys (striped and solid) for that nautical vibe.
Is it the Shoes—Fellas, you know how I feel about shoes. They can either make or break an ensemble, so I brought a few. I wore a pair of navy suede driver moccasins with red laces (settin’ it off), which I wore again while there. I also pack a pair of tan suede driver moccasins (multi purpose), and a pair of Bahamas blue hard bottom loafers with brown tassels (the secret weapon). For the beach, I made sure to have a pair of slides on deck and some sneakers for working out.
Hat Game—I kept it light and only brought one, but made sure the color (beige with a denim blue ribbon) was versatile enough for all of my style choices.
Grooming—The essential toothbrush, toothpaste, deodorant, lotion (can’t be ashy on the beach), wave cap, and beard trimmer, were all included in the suitcase
Note: Packing clothes for a trip is strategic give yourself options, by actually laying out the outfits before you pack them, ensure that some pieces are interchangeable, and most importantly, iron before you pack. You don’t want to get caught out there looking like someone tried to fold your shirts into a paper airplane. In case you forget or don’t have time to iron, you could hang your clothes up in the bathroom once you get to your destination and let the hot shower steam out those wrinkles.
Road Trip
The trip was actually pretty easy and only took 4 and a half hours with 3 stops in an SUV. We arrived at the ferry early, which is recommended due to the long lines, so we waited about 40 minutes, before boarding and spend another 40 minutes aboard for our trip from mainland Massachusetts to Martha’s Vineyard. It’s an island, so the only way to get there is by ferry, boat or small airplane. Thankfully the kids stayed asleep for most of the ride so it allowed for some time with the wife. When she finally tapped out, I got to spend time with my 90’s hip-hop playlist. Once we arrived at the dock, it was another 10 minutes to our final destination. For those wondering about cleanliness and safety, what made us we felt very comfortable about the cleanliness of the accommodations, since its owner is very environmentally conscious and had air purifiers in ever room prior to, and during our stay.
When You Get There
Make sure you check out some of these famous sights below.
Lighthouse—Any lighthouse will suffice, since all have closed off entry at the moment due to COVID. We spent most of our time in Oak Bluffs, so we hit East Chop Lighthouse, which overlooks Vineyard Haven Harbor.
Oak Bluffs—As a black family I felt a sense of pride as I spent time in Oak Bluffs and absorbing the history. Hit the Gingerbread style cottages, Inkwell Beach (there was a movie named after it, starring Larenz Tate), and Circuit Ave for eating and shopping!
Circuit Ave in Oak Bluffs is home of Murdock’s Fudge, C’est La Vie, the only black owned souvenir shop on the strip, and the “Black Dog” store.
Lobster Rolls—Make sure to pick up a lobster roll at Lookout Tavern (Also in Oak Bluffs), which argues to have the best on the island. Make sure you get it warm!
South Beach (Edgartown)—As the name implies it’s on the Southern end of the island and the sandy beaches are beautiful, but the waves can get a bit choppy. If you can’t swim, just plan on getting your ankles wet, that undertoe is serious!
We didn’t get to hit the “West side” of the island (respect to Snoop), but we’ll save that for the next trip.
Reflecting back, it was definitely a trip to remember. If you’re looking for somewhere to get away, I highly recommend it, for families, small groups or a couple’s getaway. The Vineyard vacation vibes were tranquil, the family was safe and as always I had an opportunity to flex these style muscles in a new location. Funny enough on the drive home, I stopped at a rest stop in Connecticut, and a gentlemen stopped to complement my ensemble, so of course I thanked him! Then immediately hit him with the contact info. Even on vacation, a man’s work is never done when the goal is to uplift the world, once style session at a time. For more insight on Martha’s Vineyard or style tips on how to stand out once you’re there, give me a shout at contact@suitabull.com. Hopefully I’ll run into some of you on the next visit to Martha’s Vineyard. Until then…
Stay Suitabull Guys.