I enjoyed my trip to the Vineyard last year with Brian and Pam, and I’ve been thinking about getting a Jeep Wrangler for a while. Since the Vineyard is one of the places where you can rent a Wrangler, it made sense to me to kill two birds with one stone and go back and rent a Jeep to see how it felt.

I decided I wanted to do an overnight stay this time, so we’d have more time on the island. So I booked the rental and the hotel stay, and ferry tickets for Brian and myself.

Because of the location of the rental, and because we’d be starting from the Cape, we came into Oak Bluffs. The rental agency was right across the harbor, and we got a 2 door JK soft top, with the top down. The weather was gorgeous, which made it even nicer.

We started off, along Sea View Ave towards Edgartown. We found the ferry to Chappaquiddick, and Brian found that the best time to go over would be late in the day, so we decided to come back around 5 — we didn’t have to catch a ferry this time — and drove on, through the more rural towns on the southerly side, toward Aquinnah and Gay Head, trying out a couple of side roads toward the ocean that kind of petered out along the way.

At Gay Head, I decided to go inside the lighthouse this time. The view was great — you could see a couple of expensive houses nearby that were hidden from the road, which seemed to be a Martha’s Vineyard pattern — the island has a lot of very nice homes, but they are set back from the road so you can’t see them. At the top of the lighthouse, you can see the lighthouse lamp, and feel the heat coming off it.

After the lighthouse, we had lunch at the Gay Head restaurant, and decided to take a walk down to the beach. There were a ton of people there, and the water was very clean, so we decided to walk a ways…and discovered that once you walk far enough, it’s a nude beach. Brian noticed it first, and was absolutely scandalized.

Getting back to the Jeep, we headed back east along the perimeter of the island, to Menemsha Pond, and then circled back, around the pond, and wound up in Menemsha Harbor.

We continued to drive. It was great driving with the top off, and the Wrangler felt comfortable to drive. I want one. It wasn’t nearly as rough a ride as I’d been led to believe, and it handled well.

We continued around the perimeter of the island, looking into East Chop before getting back into Oak Bluffs. It was now around 4, so we checked into the hotel, and then headed over to Chappaquiddick.

You get to Chappaquiddick by taking a small, two car ferry the 500 yards or so across Katama Bay to the smaller island (technically, not an island since it’s joined to the main island by a barrier beach, but the beach is impassable) From there, there are a couple of Trustees of Reservations wildlife sites; one of which has the bridge Ted Kennedy drove off of.

We walked over the bridge, since the signs there state quite clearly that you will get stuck unless your tires are deflated and you have off-road gear. The rental forbade off-roading, and I didn’t want to deal with tire inflation anyway.

The beach was gorgeous – fine sand, clean, and not crowded. At about 5:30, there was one family there, playing in the ocean. Peaceful, quiet, no traffic sounds, just the beach. As we left, a kid rode over the bridge on a scooter with his girlfriend on the back. Sure enough, he got stuck shortly after he cleared the bridge.

From there, we circled the rest of Chappaquiddick. We saw osprey nests on poles, and a couple of birding preserves. Then it was time to head back to the main island for supper. Even at that hour, we had to wait for the ferry to make a couple of trips before it was our turn.

Edgartown at that hour turned out to be too busy to find a place to park, so we headed back to Oak Bluffs, parked along for the night along Ocean Park, and walked in search of a place to eat. We found a place, Coop de Ville, right along the harbor, and had supper with a view of the sunset.

After taking a couple of sunset pictures, I noticed the camera settings were wrong, and reset them. After the fact, I discovered the camera had been in a “scene” mode and all my Chappaquiddick pictures were posterized.

After supper, we went for a walk along the harbor. The harbor seemed to be a happening place, with tons of people around. We watched a ferry come in, and then walked over to see the gingerbread houses along Ocean Park. There was one Victorian there that was particularly impressive. From there, we just walked around the area.

The next day, we were up early. We still had the Jeep until 10, and I needed to refuel it. Checkout wasn’t until 11. So we had breakfast, got gas, then drove over to Vineyard Haven, saw some very nice homes, and then got out and walked around the harbor and village a little. From there, we had to drive into the interior of the island a bit, then back into Oak Bluffs to return the Jeep. We then did some shopping in town before picking up our stuff at the inn and checking out.

Brian may be retired from UPS, but he was fascinated to see a cargo boat pull into the harbor with a ton of UPS cargo. It was a bunch of air freight that had arrived too late to to make it onto the trucks ferried over, so it was sent separately, and then dropped off at the dock, where a UPS truck pulled up and loaded it all on for sorting and delivery

Finally, it was time to head back. Our ferry arrived just before it was scheduled to depart. Since we were leaving in the middle of the day, we had the boat mostly to ourselves for the trip back. Once there, we headed back to Eastham to drop off Brian, then I headed home to get ready for my next trip.