As much as I try to avoid routines, you can always find me lunching at the same crêpe joint every Saturday with my weekend Financial Times (and always a Bloody Mary to start and a macchiato to end). After last summer’s solo trip to Shelter Island and the North Fork of Long Island, I left knowing this would become an annual summer visit. This year, however, I enticed my two favorite foodie soul mates, Celia and Adria, to join me.

Arriving in Greenport precisely at noon on a sultry July summer day, we were all ready to enjoy a relaxing drawn-out meal. The plan was to stick around town, eat, then take the ferry across the bay to check into our hotel on Shelter Island. Before coming out, I had called on a few trusted Long Island wine friends for the latest “best of” list. Many of the recommendations came with specific names of people to ask for. This was the case with Scrimshaw. My instruction read: “You should visit Rosa Ross at Scrimshaw, too, right on the water.” At first I interpreted Rosa Ross as the name of a restaurant and Scrimshaw as the town. But luckily, Adria quickly pointed out that Scrimshaw is actually a restaurant right here at the piers in Greenport. So, off we went knocking on Rosa’s door.

Greeting us with grace and enthusiasm, Rosa quickly seated us at her intimate and seashore-quaint seventy-seater dining room. My most memorable tastes from this estival meal were the Widow’s Hole oysters with Asian mignonette ($15 for half a dozen) and the stilton salad with croutons, roasted tomatoes and white balsamic dressing ($9), accompanied by the 2003 Lenz Estate Bottled Gewürztraminer ($34). This combination proved to be the perfect harbor-side lunch.

For dinner, we had booked the newly-opened and highly-recommended North Fork Table & Inn. As loyal fans of Gramercy Tavern, we were excited to taste Claudia Fleming’s new outpost. Right after we were seated and deep into studying our menus, wine director Mike Mraz (formerly of Hearth) came by to say hi. We were both surprised and thrilled to see a familiar face. After perusing through the wine list in search of a local wine to try, I realized I had tasted most of the wines in this category.

As I was eager to try something new, Mike proposed a Pinot Noir from the Niagara Escarpment. Okay, so it’s not local per se, but it’s still New York State. I said yes to the 2004 Warm Lake Estate ($85). Given that the Niagara Escarpment is similar in climate and soil to Burgundy,  Pinot is a variety that should do well in this little discovered region. The wine was seductive by sight, a dirty medium rose color, but at the same time incredibly light to the point where you’d imagine a wine lacking in character and taste. Mike explained that the region experienced heavy rainfall in 2004, resulting in the diluted appearance of the wine that year. The nose promised lots of spice and bright red berries, and the taste followed through with more layers of complexity after each sip. However, the general consensus was that the wine reached an apex then started to falter slowly, leaving us all a bit disappointed in the end. Having said this, I was happy to have tried the wine and would happily re-taste wines from Warm Lake — the winery name leaves a bit more to be desired — in the future. My only criticism would be the QPR (Quality-Price Ratio). The wine did not meet my expectation for a whopping eighty-five dollars. By the way, rumor has it that Paul Grieco, general manager of Hearth, has been itching to get this wine on his list.

The following day was dedicated to winery visits. We started from the western-most estate, Roanoke Vineyards in Riverhead. A newcomer to the community, Roanoke advantageously has a top winemaker, Roman Roth of Wölffer Estate, on board. Here, we met Nena, a grade school teacher on summer break pouring wines at the tasting room. After a run through the two Chardonnays, one rosé and two Bordeaux blends, my thumbs-up went to the 2003 Roanoke Blend One ($30), made of 48% Cabernet Sauvignon, 30% Merlot and 22% Cabernet Franc. This one-hundred-percent French-oaked red was velvety, well-integrated and elegant. It made me think burgers but not for that particularly grueling summer day when we were all just craving a good white or sparkler with some oysters for lunch. A bit of chitchat gave away that Nena’s husband, Lenn Thompson, is a food and wine writer based in the area. He has his own website at Lenndevours.com. Although I never got to meet him in person, I am very excited to have met a Long Island wine writer friend via e-mail. Lenn is a great source for New York wines.

Next was a visit to a staple of mine: Macari Vineyards. In fact, I had just brought a bottle of their 2005 Sauvignon Blanc ($16) to Shanghai for a blind tasting with my wine group there. Not surprisingly, none of my fellow wine-loving members could guess the provenance even though they knew it was distinctly a Sauvignon Blanc. At the end, this Long Island wine shocked more than a few disbelievers! I related this to Alexandra Macari who turned out to share my love for champagne. We ended up comparing notes on a few of our favorites. The Billecart-Salmon rosé was a top contender for both of us in the category of rosé bubblies. Re-tasting through the Macari lineup reminded me of my love for their meritage wine: Bergen Road ($40). This predominantly Merlot blend with a good portion of Cabernet Sauvignon and a splash of Malbec just has a very distinct character; it is full-bodied but understated. The vintage I tasted was the 2001, which is drinking beautifully, but I’m sure it could be kept for a few more years down the road.

Well, literally down the road from Macari was Lieb Family Cellars, the winery that brought me out to this wine region last summer. Since then, I’ve been spotting Lieb’s winning Pinot Blanc on quite a number of highly-coveted wine lists and, most impressively, it often holds a proud place on the by-the-glass section. Recent spottings include Union Square Café, King Cole Bar in the St. Regis, The Modern, Ducasse and Le Bernardin. I love three of Lieb’s whites the best: the 2002 Blanc de Blancs sparkling wine (a wonderfully crisp purely Pinot Blanc bubbly) ($35), the 2004 Reserve Pinot Blanc (which I serve regularly at cyn-et-vin corporate tastings) ($18) and the 2003 Reserve Chardonnay (my favorite Chardonnay on this trip) ($18). To top things off, I always enjoy catching up with Gary Madden, the general manager, who is the dynamic force behind this stellar winery.

We left Lieb planning to taste some wines at The Tasting Room in Peconic, but it turned out to be closed that day. This is where my favorite Long Island Cabernet Franc from Schneider Vineyard and Merlot from Sherwood House can be found. Fortunately both wines are readily available back in the City. Schneider is similar to Lieb in that you see it a lot at top establishments (both restaurants and retailers).

So, we headed further south to the highly-reputed Lenz Winery, also in Peconic. Again, this top producer is seen across the board on the wine lists of all the top tables we visited. I am especially enamored — as were Celia and Adria — by their Gewürztraminer. It’s tropical yet crisp; a winning combination. This is a wine that I’d easily keep a case of in the house year-round. As for the sparkling wines, I found the 1999 Cuvée sparkling wine ($30) a bit one-dimensional but enjoyed it as an accompaniment the next day with my light seafood meal at the Seafood Barge. I regret not having tried the 1994 RD sparkler ($50), as I’m sure it would have had more development and complexity. (RD = recently disgorged; I am reminded of my recent visit to Champagne when I visited Bollinger, which is known for its RD wines.). Of Lenz’s famous Merlots, all three of us preferred the 2000 Estate Selection ($23) to the 2000 “Old Vines” at twice the price ($55).

After a full day of tasting (and spitting…well, I’d say on occasion if at all) and no lunch, we dropped by The Frisky Oyster to indulge in some early-evening appetizers. Ever a staple, I still vouch for the roasted corn soup with frizzled leeks ($8) and tempura zucchini blossom stuffed with goat cheese ($12). For me, the dining space covered in full-blown red flower blossoms on white wallpaper is still the most gorgeous interior in town (see image above). I love the bar area looking into the dining room, and I discovered this time that it is just as mesmerizing looking out onto the bar area from the dining room!

We then were intent on checking out a new addition to Greenport: Vine Wine & Café. Many of our trusted contacts had suggested a visit to the only wine bar in town. Alexandra Macari had especially tipped me on the sparkling flight. I was thrilled to see that the wine list not only had a good selection but also had tasting/glass/bottle options. Although we didn’t get to try everything, here is what I am looking forward to ordering on my next trip: local oysters (Pipes Cove or Widow’s Hole) ($2.50/piece) followed by a sliced beef tenderloin sandwich with horseradish and raw onions ($15) (sounds racy good!). I’d pair the oysters with a glass of cava from Paul Chenaut ($8) or with the Blanc de Blancs from Leclaire Gaspard ($20), and the beef with the 2003 Shinn Estate Vineyards Merlot ($12) or the 2002 Anton Bauer Pinot Noir ($14). Both the cheese selection (with a couple of local samples) and the cookie plate (all from local purveyors) were fantastic, period. Oh! And owner Joe, fellow Manhattanite turned Greenporter to fulfill his true calling, is a fellow champagne enthusiast. I say cheers to that!

On our last day, right before departing we were told by our friend Eugenia not to miss the scones from Aldo’s, Too. So we made our last quick stop at Aldo’s, where Celia ended up picking up all three of the scones that were left, and I ordered a macchiato. Aldo asked whether I’d had a real macchiato before. I assured him I’m not a Starbucks girl, but that didn’t seem to convince him of much. He explained that macchiato means “stain” in Italian and proceeded to show me how and what a proper one should taste like. When I asked for sugar after getting my coffee, he took back my cup and told me, “sugar is not necessary, let me fix it for you.” A couple of chocolate shavings later, he handed me the perfect macchiato. And I must say, this weekend when a friend called to ask me where I like to go for coffee in the City, I sadly told her that the best one I’ve had recently was at Aldo’s in the North Fork. Turns out her family summers in Greenport and they have been fans of Aldo’s for years!

It was at Aldo’s that we also met Mike Osinski, who cultivates Widow’s Hole oysters right on the water, two-minutes from the coffee shop. This really wrapped things up for me since Mike’s oysters at Scrimshaw were my first taste of North Fork on this trip. Chatting with Aldo and Mike at the big coffee table in the front of the store, I felt like we were visiting with friends in their kitchen rather than sitting at a coffee shop we’d never been in before. Hey, if you had been on this trip you’d surely make this a summer habit, too, right?