Destinations and Favorite Cruising Grounds

Below is merely a sample of the cruising ground available to our charter clients. There are many more, some hidden, some that should not be attempted without specific local knowledge.

As you can see, you can spend months cruising our area and still not see it all! If you need assistance planning your trip, let us know. We love to assist fellow sailors.

Buzzards Bay, Nantucket and Vineyard Sound


It is approximately a 4-5 hour sail from Cove Haven.  20-miles from Breton reef buoy.  The larger boats with masts taller than 65-feet must transit via the east or west passage of Narragansett Bay. Those with shorter masts can travel via the Sakonnet River.

Cuttyhunk Island is a very small island with a crowded a mooring field. The inside moorings can accommodate boats up to 50-feet. Larger boats must moor, or anchor, outside the entrance. Cuttyhunk is a very nice little town. Limited eating facilities, but what is there is excellent. Great place for a hike and to relax after your day on the water.

Quicks Hole

3.2 miles from Cuttyhunk. This is the safest passage between Buzzard Bay and Vineyard Sound. This is the only passage that we will allow unless you have written permission (more about that later). There is a great beach in Quicks Hole that is well protected from prevailing winds and good holding ground. The local islanders sometime close the beach to visitors, so please be respectful. It’s a great lunch spot, too.

Lambert’s Cove

7-miles from Quicks Hole passage or 6.5 miles from Menemsha. Nice lunch spot in Southwest winds. Day anchorage only.


6-miles from Quicks Hole. Interesting locations to visit. The narrow entrance has significant tidal current, so plan accordingly. Once inside, there are limited moorings, so boats are always rafted together. Don’t go unless you want close neighbors!

You can anchor outside in good holding ground, but it can be a bit rolly. Once inside the harbor, the dingy dock is immediately to port upon entrance. The town is a really fun visit. Excellent food establishments, and a very picturesque fishing town. Menemsha is known as a small fishing village within the town of Chilmark, part of Duke’s County, Massachusetts.

Vineyard Haven

13-miles from Quicks Hole. A large and easily accessible town and mooring field. It provides access to some nice restaurants, Black Dog among others. There are several areas to rent bikes, and bike touring the island is a great experience. This is a ferry landing port, so expect that traffic to disrupt your mooring on occasion.


6-miles from Vineyard Haven. A really nice spot to spend a few days. Moorings can be reserved in advance and there is a shore launch service that is inexpensive. Excellent beaches and good food can be had here.

Nantucket Harbor

18-miles from Edgartown. Plan at least two days on Nantucket as it takes awhile to get there. About 4-hours from Edgartown. We tend to discourage this a bit on one-week charters because it takes a long time to get there.

Requires good knowledge of tide and current charts. That four hour trip can take 6-8 if you don’t plan for the tidal currents. There is a lot of shoal water along the way, experienced sailors only! Once there, it is a really nice location. Great biking, beaches and good dining.

Hadley’s Harbor

13-miles from Cuttyhunk. A very protected mooring tucked well back into a protected location. There is no public access to shore except to Bull Island, but it’s a nice place to row a dingy and explore all the coves. Idyllic location with horses by the shoreline.

An excellent place to wait out weather. This is also a location for those that are awaiting favorable currents to pass through Woods Hole. We do not allow passage through Woods Hole unless you have significant experience and local knowledge, so discuss with us if you have interest in this.

Quissett Harbor

A quiet spot. No services, but sometimes that is exactly what you are looking for. Just Northeast of Woods Hole.

Red Brook Harbor, Cataumet

Nice overnight spot with two full-service boat yards. Good Dining.

Sippican Harbor, Mattapoisett and Padanaram

South Dartmouth. Moorings and town services including some fine dining.

New Bedford/Fairhaven

Anchorage behind hurricane barrier if you need protection in severe seas. Lots of history here. Interesting places to see and some good restaurants.

Narragansett Bay

Prudence Island/Potters Cove

A jewel of Narragansett Bay. Moorings inside Potters Cove are all privately owned, although tradition is that you can pick up if not occupied. Of course, if the rightful owner comes in, you have to look elsewhere. Limited or no room to anchor during peak seasons and especially on the weekends. It’s tough to get a spot here. But, if you do, it’s a great protected cove. Excellent hiking trails; but beware of ticks. The island is famous for its deer herd and deer ticks.

Bristol, Rhode Island

Home of the famous Herreshoff Marine Museum and the America’s Cup Hall of Fame. There are limited moorings here, so call ahead! The anchorage has good holding ground but is exposed to southerly breezes. The town has a number of excellent eating and shopping to experience.

Battleship Cove, Fall River

Limited mooring, so call ahead. But, an amazing place to visit. There are many events and you can even tour the battleship itself. More information is available at

Wickford, RI

Very nice place to stop over for the night. Brewers Marina has transient slips if you call ahead. Moorings are usually available as well. Everything is an easy walk to town. The harbor is known to have shoal areas and can have significant boat traffic. It is a very boat friendly community.


A refuge close to Newport, but without as much boat traffic. You can usually get a mooring here if you a call ahead. Town is very nice, walkable and plenty of good eating. There is some spectacular scenery on the island, Beavertail State Park, Fort Wetherill, and others. It’s worth a visit.


Has many amenities for the visiting yachtsman. Shopping, eating and of course the tremendous history of sailing. This is a town that is built around boating so you can find anything you want here. It is difficult to get a mooring here, and the anchorage is usually quite full.

Long Island Sound

Block Island

Located 10-miles off Point Judith, it is a one-day sail from Cove Haven. Moorings are available in New Harbor, Salt Pond, on a first come, first-serve basis. There are ninety owned by the town and can accommodate boats up to 50-feet. They are usually all taken early in the morning during peak season.

There is an anchorage, about 75-acres in size. However, you will be anchoring in deep water with poor holding ground. One person must remain on board at all times if anchored here. Slips are available, for a high price, and are usually noisy.

Having said all that, the beaches are excellent, food is great, and there is plenty to do on the island. Baked goods are delivered fresh each morning throughout the mooring and anchorage area by a local vendor. Biking and hiking opportunities abound on the island. There is another harbor on the east side of the island, Old Harbor, that has a very limited anchorage.

Fishers Island, NY / Stonington, CT

This is either a very long day of sailing from Cove Haven, or perhaps broken up into two days with a stopover at Point Judith or Block Island. It is 30-miles from Pt. Judith.

Stonington Harbor is protected by a breakwater and has an excellent anchorage as well as a mooring field. The town of Stonington Borough is a favorite. Excellent eating establishments and shops. If going here please utilize your Eldridge and time your passage though Watch Hill passage at slack tide. If planning a trip to this area, contact us to discuss. It is a very nice cruising ground but a lot of current, and rocks abound!

West Harbor on the west end of Fishers Island is a nice anchorage with great views. It is protected in all but north winds. We have been asked about going from Stonington to Watch Hill Harbor. Please discuss with us first. You really need local knowledge to do that one.

Montauk, New York

18-miles from Block Island. There is an anchorage and limited moorings in Lake Montauk. A narrow approach and heavy boat traffic can make this a challenge. There is shoaling in the rear of the entrance as you enter the lake basin itself. If you have a shallow draft vessel it can be a very nice anchorage.

Recommendation is to try to obtain a mooring or transient slip ahead of time and plan your approach carefully. Fort Pond Bay is adjacent to the entrance to Montauk and is protected from all but NW winds. It is a deep anchorage, with deep water close to shore, so you have to take that into account. Montauk is a famed fishing village with plenty of dining and other establishments to satisfy that desire.

Longer, Two-Week Cruising Destinations

New York

There is a myriad of interesting ports of call in the NY area. It takes time to get there, the winds are not always the best and the currents must be understood. Having said that, you can easily spend a week in the lower Long Island Sound area, going from port to port. Stop to see New York City and the yachts lined up in Manhattan. Plenty of options any time you sail to New York.

Provincetown, Mass.

This is an interesting destination. It requires a longer transit through the Cape Cod Canal and up through Cape Cod Bay. Usually an overnight at the entrance to the canal at Onset or the Falmouth area, waiting to have the tidal current through the canal in your favor. DO NOT transit the canal if you do not understand the tidal currents there! Discuss with us if going through.

Cape Cod is known for its nice beaches. A trip to Provincetown is a good destination for that. There is a good, semi-protected anchorage there, as well as moorings available. The town itself is unique. It’s nice experience for all to observe the diversity in culture and lifestyles. Excellent dining can be had here as well.