The Great Escape

If you're well prepared, a three-day weekend on the water is a great way to unwind.

January 4, 2012


bimini, beach, palm tree, water, sailboat

I don’t know about you, but lately a two-day weekend just doesn’t cut it. With social and family commitments, chores to do and errands to run, I inevitably find myself wishing I had one more day to just relax when Sunday evening rolls around. If you can find an extra day and go cruising, leaving your life ashore often magically makes three days feel like five! And no matter what shoreline you’re near, there’s probably an itinerary that will do the trick. Here are three sample trips to get you off the dock and in vacation mode (and see a complete resource guide here).

A Southern Escape: Bimini to Gun Cay to Cat Cay, Bahamas (101 nm round-trip)
Boaters in south Florida have a lot of options when choosing where to go for a few days of R&R. Gunnar Christensen, a professional captain and president of All Points Energy, which specializes in the maritime aspects of renewable energy, has a favorite itinerary. “In south Florida,” says Christensen, “‘go west, young man’ does not apply … unless you like airboats and boas.”

When he thinks of great three-day weekends in south Florida he pulls out his passport, gets a custom decal for easy re-entry and heads east to the Bahamas.


For a jaunt to this area you need to do some planning. In the winter the seas can build to dangerous heights when the northerly winds kick in, so the best time to make this voyage is in the spring and summer when it’s easier to find a weather window. From Miami to Bimini is about a 43 nm run, so get an early start across to maximize your time in the islands. Once you’re there, the cruising distance between islands is minimal.

Bimini (25°43’10.08″N 79°16’12.76″W) is popular with anglers and spring break students — in other words, people go there to fish hard and play hard. Snorkeling, diving, dolphin encounters and, of course, deep-sea fishing are popular here. Bars outnumber restaurants two-to-one so you won’t go thirsty — check out the End of the World Bar in Alice Town. The Bimini Big Game Resort and Marina is a good place to eat, as is the Bimini Beach Club Restaurant.

When you’re ready to unwind, head south to Gun Cay (25°34’57.20”N 79°17’53.58”W). It’s less than a 10 nm run. The main attractions here are beautiful scenery and great snorkeling. It’s a wonderful place to throw out the hook, but look out for the stone ledge on the east side of Gun Cay, which won’t hold your anchor if it blows.


Cat Cay (25°33’20.91″N 79°16’44.30″W) is a privately owned club that welcomes cruisers who need to clear in through customs, or who want to refuel or come ashore to dine. “Beware of high prices and the air of superiority you might encounter,” Christensen warns, and when you’ve had enough, check out any of the small cays south of Gun Cay and Cat Cay — they’re almost always deserted and you can have them all to yourself.

A New York Getaway: Sag Harbor to Shelter Island to Greenport (23 nm round-trip)
Boaters in the Northeast face an embarrassment of riches when it comes to cruising options. But one of my favorites is a relaxed trip on Long Island’s East End. Sag Harbor (42°00’21.40″N 72°17’42.83″W) has more than enough to keep you entertained all weekend: great shopping, fine dining, the Whaling Museum and an art-house movie theater as well as live shows at the Bay Street Theatre and a wonderful public library. If you’ve got 21 feet of vertical clearance, head under the bridge and anchor in Sag Harbor Cove for up to 72 hours. Call the launch on Channel 9 for a ride into town.

Do your provisioning at Schiavoni’s and the liquor store nearby, or stop and grab a burger or great mussels at the Corner Bar. For something a little less traditional, I like Dockside, which is just down Bay Street and features more inventive cuisine. Leaving might be hard, but since you’ve got a boat, head north to Shelter Island.


If you’re looking for peace and quiet, Shelter Island’s Coecles Harbor is a great spot. Also lovely is the sleepy Victorian town of Shelter Island Heights. But I like to head past there and anchor off Sunset Beach (41°04’27.10″N 72°21’58.49″W). Aboard, you’ll have your own lovely island. Hop into the dinghy and head for the bright yellow- and white-striped beach umbrellas, and you’ll feel like you’re in St. Tropez. The glamorous and happening Sunset Beach restaurant is an Andre Balazs hot spot that transports you to the Med with its cool Euro vibe. Though the check is usually obscene, I’ve always found it enough fun to be worth every penny!

You might find that wandering the less than 2 miles west to Greenport (41°06’00.83″N 72°21’29.28″W), above, for simpler pleasures is the perfect antidote to last night’s fun. Greenport is an old fishing town on Long Island’s North Fork, and it has a laid-back, more rustic feeling than its South Fork counterparts but plenty of charm. Good restaurants, an antique carousel, Preston’s ship chandlery and proximity to the great farm stands and vineyards of the North Fork add to the appeal.

California Dreamin’: Santa Barbara to the Channel Islands to Oxnard (72 nm round-trip)
West Coast folks have their own favorite haunts, but one that wafts back to us repeatedly on the East Coast centers on the Channel Islands. Susan Scheer, a filmmaker and the owner/operator of Phantom, a 90-foot expedition yacht that’s available for research, documentary and diving charters in Central America, spent years in Santa Barbara and filled us in on her favorite jaunt.


“What’s great about Santa Barbara (34°24’19.30”N 119° 41’29.27”W) is it has so much to offer. It is a beautiful, old Spanish-flavored city and there is something magical about the light here.” Scheer keeps a sailboat in Santa Barbara. “The harbor is unique — it has a commercial fishing fleet alongside multimillion-dollar yachts and a racing fleet, as well as the old live-aboards. … Orca is right next to the transient dock, and I have seen cruisers from all over the world spend a night or two and fall under the spell of the Santa Barbara coastline.” This haven of tranquility is located just 90 miles from the hustle and bustle of Los Angeles, yet there are festivals, the famous sidewalk art sales, whale watching, kayaking, mountain climbing and horseback riding. “If you can think of it, you can find it in Santa Barbara,” Scheer promises. For good places to eat and drink in the harbor, she recommends world-famous Endless Summer Bar Cafe and Brophy Bros.

Roughly 25 miles offshore, the Channel Islands National Marine Sanctuary (34°9’32.74”N 119°13’25.25”W) await. Five of these islands — Anacapa (above), Santa Cruz, Santa Rosa, San Miguel and Santa Barbara — make up the United States’ 40th national park. The Santa Barbara Channel is a very busy shipping area, and the ever-shifting weather conditions can be challenging. There are no public moorings or all-weather anchorages around the islands, and Santa Rosa and San Miguel islands often have strong winds. Park authorities recommend that one person stay on board the boat at all times. That said, these islands are absolutely stunning and well worth the trip. They’re under strict ecological protection, so you’ll need a permit to land. For more information on the various islands and park procedures, visit

Wind down your three-day weekend with a trip back to shore and Oxnard’s Channel Island Harbor. Oxnard (34°9’32.74”N 119°13’25.25”W) is a laid-back beach town that’s a popular weekend getaway for Los Angelenos and home to the California Strawberry Festival. Check out the Carnegie Art Museum; take a wine, chocolate and cheese tour; or just try the popular Fishermen’s Catch restaurant that overlooks the channel.

For all of these trips, preparation is not only key, but half the fun. Plan your course, check the weather, make sure your boat is ready, and file a float plan. Then turn off your cell phone and watch three days of decompression work their magic.

View a complete resource guide here.


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