Edgartown: Preppie Paradise - Sail Magazine

Edgartown: Preppie Paradise

These days, instead of sailing on a small boat with college kids playing hooky from their summer jobs, I’m often on a slightly more comfortable boat with friends playing hooky from slightly more stressful jobs. But what hasn’t changed is that Edgartown remains the quintessential summer cruising destination.
Author:
Publish date:
Edgartown

A lot has changed since I first sailed into Edgartown Harbor in the late 1980s. Back then I was squandering my youth sailing, going to the beach and waiting tables on Cape Cod. When the cutest waitress in town asked if I’d like to sail with her from Wellfleet down to “the Vineyard” on her father’s Hunter 25, I said “You betcha!” I was a bit disappointed when I met the other Ray-Ban bespectacled guys in her crew, but I was still psyched for the adventure—even if I was never going to get the girl.

These days, instead of sailing on a small boat with college kids playing hooky from their summer jobs, I’m often on a slightly more comfortable boat with the girl I was meant to get and with friends playing hooky from slightly more stressful jobs. But what hasn’t changed is that Edgartown is only a short hop from mainland Massachusetts and remains the quintessential summer cruising destination.

Nothing really compares to sailing past the colorful cabanas of the Chappaquiddick Beach Club and the stubby lighthouse at the harbor entrance on a sunny summer afternoon. Once you’ve dodged the car ferry that constantly zips back and forth across the channel, you’ll be directed via VHF to pick up a mooring that’ll set you back a cool $40 a night. But it’s well worth it, as the inner harbor is connected to Katama Bay, and the current is strong. Be warned that while the mooring field is quite large, it fills up on busy summer weekends, so it’s a good idea to reserve a spot well in advance (edgartownharbor.com). 

From there, Edgartown is an easy launch ride away, or you can take your chances finding a spot for your tender at the small dinghy dock in town. Either option lands you right in the center of the action, where you’ll see plenty of happy tourists, preppie locals, an occasional celebrity and maybe even a sitting President (he usually comes in August). Edgartown is a great place to explore on foot and shop for souvenirs and stylish clothes, if you’re into that kind of thing; there’s also a wide variety of restaurants to satisfy your gastronomical cravings. However, I’ve always found the best way to explore both the town and its environs is by bicycle. These can be rented right on Main Street (marthasvineyardbike.com) and are the perfect way to get the blood flowing after a long stint in the cockpit. 

One of my favorite rides is along the bike path out to South Beach. I also love slowly spinning around the uber-charming neighborhood over by Eel Pond off North Water Street. If you really want to get away from the boat and the “hustle and bustle” of town, you can take your bike on the ferry over to remote Chappaquiddick and ride all the way across the island out to East Beach. It’s a bit of a workout, but even when Edgartown is chock-a-block with tourists, you usually can have a good portion of the beach all to yourself. 

Lots of cool summer destinations offer stunning natural beauty, a great harbor, a sophisticated local community and first-rate shops and restaurants, but none do it quite like Edgartown. The only “problem” is you can’t experience all of this preppie paradise has to offer in one short weekend. I’ve been back several times since that eye-opening cruise back in the ‘80s, and it gets better every time.

Related

01b_WALKING-KEDGE-OUT-cmykpromo

Getting More Use From Kedge Anchors

If you are cruising, you need at least two anchors on board for the simple reason that you must have a backup. Imagine having to slip your anchor on a stormy night with other boats dragging down on yours, or having your rope rode severed by some unseen underwater obstacle, ...read more

SailAwayCharter

How-to: Navigating on a Bareboat Charter

So you graduated from navigation class where you practiced dead reckoning, doubling the angle on the bow and maybe even celestial nav, and you now feel well prepared for your first charter trip. Well, you won’t be doing any of that on vacation—not past the first day, anyway.Most ...read more

04-Turtle-rescue

Turtle Rescue in the Vic-Maui

Strange and often wonderful things can happen in the course of an offshore sailboat race, and one of the strangest and most wonderful things we’ve heard of recently took place during the 2,300-mile 2018 Vic-Maui race, from Victoria, British Columbia, to Lahaina, Hawaii.It ...read more

dorcap-open-blue

ATN Inc: Dorcap

COOL SLEEPYou’re fast asleep in a snug anchorage, forehatch open to catch the breeze, when you’re rudely awakened by a sneaky rain squall. Now you’re not only awake and wet, you’re sweltering with the hatch closed. Sucks, right? That’s why ATN came up with the Dorcap, an ...read more

HIGH-RES-29312-Tahiti-GSP

Ask Sail: Who has the right-of-way

WHO HAS RIGHT-OF-WAY?Q: I sail in Narragansett Bay, which is a relatively narrow body of water that has upwind boats generally going south and downwind boats generally going north. When sailboats are racing, the starboard tack boat has the right-of-way over the port tack boat, so ...read more

albinheaters

Albin Pump Marine: Marine Water Heaters

IN HOT WATERSweden’s Albin Pump Marine has introduced its line of marine water heaters to the United States. Complete with 130V or 230V AC electric elements, the heaters can be plumbed into the engine cooling system. They feature ceramic-lined cylindrical tanks in 5, 8, 12 and ...read more

03-squalls4

Squall Strategies

Our first encounter with a big squall was sailing from San Diego to Ensenada, Mexico. We left at 0200 to ensure we’d get into Ensenada before our 1300 haulout time. The National Weather Service had forecast consistent 15-20 knot winds from the northwest, which was perfect for the ...read more