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Bareboat Sailing Trips

Choose from one of the many trips available on your bareboat charter.

Martha’s Vineyard, Nantucket...
Day 1Sail from Newport to Cuttyhunk (28nm)
Day 2Cuttyhunk thru Quicks Hole to Oak Bluffs, Martha’s Vineyard (28nm)
Day 3Lay day…explore the island by rental car, moped or bike.
Day 4Sail from Oak Bluffs to Nantucket (30nm)
Day 5Sail from Nantucket to Menemsha Basin (49nm)
Day 6Sail from Menemsha Basin to Jamestown Island –
www.ConanicutMarina.com (36nm)
Day 7Sail to Newport (3nm)…top off water and fuel and return boat clean by 12:00 Noon.

Or stay an extra day or two in one of your favorite ports & create your own trip!!

map-trip1-large

Block Island, Martha’s Vineyard...
Day 1Sail from Newport to Block Island. (25nm)
Day 2Sail from Block Island to Cuttyhunk. (40nm)
Day 3Sail from Cuttyhunk to Edgartown. (25nm)
Day 4Lay day… Explore the island by car, moped or bike.
Day 5Sail from Edgartown to Menemsha Basin. (25nm)
Day 6Sail from Menemsha to Newport and have dinner in Newport (30nm)
Day 7SSail around Newport and return boat clean and fueled up.

Or stay an extra day or two in one of your favorite ports & create your own trip!!

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Martha's Vineyard Sunrise

Martha’s Vineyard Sunrise

Padanaram, Martha’s Vineyard, Nantucket...
Day 1Sail from Newport to Menemsha Basin, Martha’s Vineyard (38nm)
Day 2Sail from Menemsha Basin to Edgartown (25nm)
Day 3Sail from Edgartown to Nantucket. (20nm)
Day 4Sail from Nantucket to Oak Bluffs (30nm)
Day 5Sail from Oak Bluffs thru Quicks Hole to South Dartmouth (Padanaram) (25nm)
Day 6Sail from Padanaram to Newport and have dinner in Newport (30nm)
Day 7Sail around Newport and return boat clean and fueled up.

Or stay an extra day or two in one of your favorite ports & create your own trip!!

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Martha's Vineyard Sunrise

Martha’s Vineyard Sunrise

Montauk, New York, Block Island, Martha’s Vineyard...
Day 1 Sail from Newport to Block Island (25nm)
Day 2Sail from Block Island to Montauk, NY or Fort Pond Bay (20nm)
Day 3Sail from Montauk to Menemsha Basin, Martha’s Vineyard (63nm)
Day 4Sail from Menensha Basin to Oak Bluffs, Martha’s Vineyard (18nm)
Day 5Sail from Oak Bluffs thru Quicks Hole to Cuttyhunk Pond (28nm)
Day 6Sail from Cuttyhunk to Newport and have dinner in Newport (28nm)
Day 7Sail around Newport and return boat clean and fueled up.

Or stay an extra day or two in one of your favorite ports & create your own trip!!

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Martha's Vineyard Sunrise

Martha’s Vineyard Sunrise

Fishers Island, Greenport, Montauk, New York, Block Island...
Day 1 Newport to Fishers Island, NY… 49 miles
Day 2Fishers Island to Shelter Island, NY…24 miles
Day 3Shelter Island to Greenport…1 miles
Day 4Greenport to Montauk…24 miles
Day 5 Montauk to Block Island…24 miles
Day 6 Sail from Block Island to Newport and have dinner in Newport (25nm)
Day 7Sail around Newport and return boat clean and fueled up.

Or stay an extra day or two in one of your favorite ports & create your own trip!!

map-trip5-large

shelterisland-lg

2+-wks- Block Island, Montauk, Martha’s Vineyard, Nantucket...
Many of my customers who take a boat for 2 weeks or longer seem to like this itinerary in the Cape Cod area.

 

If it’s interesting for you, you can check out the harbors in the Cruising Guide or on ‘Google Images.’

Friday, 17:0060 minute charter check out, then load your gear & food. Go into town for dinner and walk around & explore.
SaturdaySail out in the morning to Cuttyhunk Pond. Possible breakfast at the Cuttyhunk Fishing Club (28nm)
SundaySail over to Oak Bluffs – beaches, fishing, restaurants & maybe rent a Jeep and explore the island. (28nm)
MondayLay day – explore beaches & the famous The Black Dog Tavern
TuesdaySail to Nantucket – beaches, seal watching, rest. & rent a Jeep & drive on the beach to Great Point. (30nm)
WednesdayLay day – Children’s Beach, Whaling Museum, The Summer House, Galley Beach
ThursdaySail to Edgartown – South Beach, take the Chappaquiddick Ferry by Jeep & explore ‘Chappy’ & beaches. (20nm)
FridaySail to Menemsha BRIGHT and grab a mooring. – beaches, restaurants (BYOB), star watching at night time. (25nm)
SaturdayTaxi to Gay Head Cliffs (Aquinnah) for the best food & views on the island. You can see NY, CT, RI & MA.
SundaySail to Westport, MA – beach, fun harbor to dinghy around, The Back Eddy Restaurant. (25nm)
MondaySail to New Harbor, Block Island – Beaches, Horseback riding, fishing & restaurants. (36nm)
TuesdayLay day – explore the island.
WednesdaySail to Montauk, New York – beaches, fishing, sunset & restaurants. (21nm)
ThursdaySail to Newport -prevailing winds from the SW & return to the mooring by 19:00, then go into town for dinner. (42nm)
FridayPower to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 12:00 noon.

map-trip6-large

The MAPTECH / Embassy Cruising Guide for the ‘New England Coast’ will help you fine tune it even more.

We keep copies of the Cruising Guides on the boat.

2+-wks- New York City, Shelter Is., Fishers Is., Montauk, Block Is...
Friday, 17:0060 minute charter check out, then load your gear & food. Go into town for dinner and walk around & explore.
SaturdaySail out in the morning to Fisher’s Island, New York. If you’re hungry, visit the Pequot Restaurant for food, drinks & music. (49nm)
SundaySail over to Sunset Beach, Shelter Island – beach & food. (28nm) Then, power across the channel and dock in Greenport for the night & visit Claudio’s. (2nm)
MondayLay day – explore the village, boatyards and beaches of Greenport, New York.
TuesdaySail to Port Jefferson Harbor, NY – food, drinks & view. Try The Fifth Season or Lombardi’s On The Sound. (67nm)
WednesdaySail to City Island, New York – food, drinks & Minneford Marina. (37nm)
ThursdayPower thru Hell’s Gate to New York City and dock at Liberty Landing Marina or The North Cove Marina. (24nm)
FridayLay day – take the ferry across the Hudson River to New York City and explore!
SaturdayAnother lay day (remember to take a photo at the helm Sunday with the Statue of Liberty in the background!)
SundayPower back thru Hell’s Gate to City Island or Mamaroneck for the night. Fun harbor to dinghy around & explore. (24nm)
MondaySail to Essex, Connecticut (sail and power on the FRESH water river). Essex Island Marina. (89nm)
TuesdaySail to Montauk, New York – Montauk Marine Basin. (33nm)
WednesdaySail to New Harbor, Block Island, Rhode Island – beaches, fishing, sunset & restaurants. (24nm)
ThursdaySail to Newport -prevailing winds from the SW & return to the mooring by 19:00, then go into town for dinner. (24nm)
FridayPower to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 12:00 noon.

map-trip7-large

The MAPTECH / Embassy Cruising Guide for the ‘Long Island Sound’ will help you fine tune it even more.

We keep copies of the Cruising Guides on the boat.

2+ wks- Boston, Provincetown, Nantucket, Martha’s Vineyard, Cuttyhunk Is...

If it’s interesting for you, you can check out the harbors in the Cruising Guide or on ‘Google Images.’

Friday, 17:0060 minute charter check out, then load your gear & food. Go into town for dinner and walk around & explore.
SaturdaySail out in the morning to Cuttyhunk Pond. Possible breakfast at the Cuttyhunk Fishing Club or sail to Padanaram and have dinner at the Black Bass Grille (www.BlackBassma.com) (28nm)
SundaySail to Cape Cod Canal, power thru the Canal and then sail to Scituate, Ma and visit Riva Harbor side Bar & Italian Food. (69nm)
MondaySail to Boston and stay at Boston Waterboat Marina (www.bostonwaterboatmarina.com) (30nm)
TuesdayLay day…explore Boston
WednesdaySail thru Cape Cod Bay to Provincetown, located on the tip of Cape Cod. – beaches, whales, restaurants, people watching, star watching at night time. (58nm)
ThursdaySail to Nantucket (85nm)
FridayLay Day…explore Nantucket
SaturdaySail from Nantucket to Edgartown, Martha’s Vineyard. (20nm)
SundaySail from Edgartown to Menemsha Basin, Martha’s Vineyard. (25nm)
MondaySail to New Harbor, Block Island, RI – Beaches, Horseback riding, fishing & restaurants. (49nm)
TuesdayLay day – explore the island.
WednesdaySail to Montauk, New York – beaches, fishing, sunset & restaurants. (21nm)
ThursdaySail to Newport -prevailing winds from the SW & return to the mooring by 19:00, then go into town for dinner. (42nm)
FridayPower to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 12:00 noon.

map-trip8-large

Bareboat Sailing Trips

Choose from one of the many trips available on your bareboat charter.

Martha’s Vineyard, Nantucket...
Day 1Sail from Newport to Cuttyhunk (28nm)
Day 2Cuttyhunk thru Quicks Hole to Oak Bluffs, Martha’s Vineyard (28nm)
Day 3Lay day…explore the island by rental car, moped or bike.
Day 4Sail from Oak Bluffs to Nantucket (30nm)
Day 5Sail from Nantucket to Menemsha Basin (49nm)
Day 6Sail from Menemsha Basin to Jamestown Island –
www.ConanicutMarina.com (36nm)
Day 7Sail to Newport (3nm)…top off water and fuel and return boat clean by 12:00 Noon.

Or stay an extra day or two in one of your favorite ports & create your own trip!!

map-trip1-large

Block Island, Martha’s Vineyard...
Day 1Sail from Newport to Block Island. (25nm)
Day 2Sail from Block Island to Cuttyhunk. (40nm)
Day 3Sail from Cuttyhunk to Edgartown. (25nm)
Day 4Lay day… Explore the island by car, moped or bike.
Day 5Sail from Edgartown to Menemsha Basin. (25nm)
Day 6Sail from Menemsha to Newport and have dinner in Newport (30nm)
Day 7SSail around Newport and return boat clean and fueled up.

Or stay an extra day or two in one of your favorite ports & create your own trip!!

map-trip2-large

Martha's Vineyard Sunrise

Martha’s Vineyard Sunrise

Padanaram, Martha’s Vineyard, Nantucket...
Day 1Sail from Newport to Menemsha Basin, Martha’s Vineyard (38nm)
Day 2Sail from Menemsha Basin to Edgartown (25nm)
Day 3Sail from Edgartown to Nantucket. (20nm)
Day 4Sail from Nantucket to Oak Bluffs (30nm)
Day 5Sail from Oak Bluffs thru Quicks Hole to South Dartmouth (Padanaram) (25nm)
Day 6Sail from Padanaram to Newport and have dinner in Newport (30nm)
Day 7Sail around Newport and return boat clean and fueled up.

Or stay an extra day or two in one of your favorite ports & create your own trip!!

map-trip3-large

Martha's Vineyard Sunrise

Martha’s Vineyard Sunrise

Montauk, New York, Block Island, Martha’s Vineyard...
Day 1 Sail from Newport to Block Island (25nm)
Day 2Sail from Block Island to Montauk, NY or Fort Pond Bay (20nm)
Day 3Sail from Montauk to Menemsha Basin, Martha’s Vineyard (63nm)
Day 4Sail from Menensha Basin to Oak Bluffs, Martha’s Vineyard (18nm)
Day 5Sail from Oak Bluffs thru Quicks Hole to Cuttyhunk Pond (28nm)
Day 6Sail from Cuttyhunk to Newport and have dinner in Newport (28nm)
Day 7Sail around Newport and return boat clean and fueled up.

Or stay an extra day or two in one of your favorite ports & create your own trip!!

map-trip4-large

Martha's Vineyard Sunrise

Martha’s Vineyard Sunrise

Fishers Island, Greenport, Montauk, New York, Block Island...
Day 1 Newport to Fishers Island, NY… 49 miles
Day 2Fishers Island to Shelter Island, NY…24 miles
Day 3Shelter Island to Greenport…1 miles
Day 4Greenport to Montauk…24 miles
Day 5 Montauk to Block Island…24 miles
Day 6 Sail from Block Island to Newport and have dinner in Newport (25nm)
Day 7Sail around Newport and return boat clean and fueled up.

Or stay an extra day or two in one of your favorite ports & create your own trip!!

map-trip5-large

shelterisland-lg

2+-wks- Block Island, Montauk, Martha’s Vineyard, Nantucket...
Many of my customers who take a boat for 2 weeks or longer seem to like this itinerary in the Cape Cod area.

 

If it’s interesting for you, you can check out the harbors in the Cruising Guide or on ‘Google Images.’

Friday, 17:0060 minute charter check out, then load your gear & food. Go into town for dinner and walk around & explore.
SaturdaySail out in the morning to Cuttyhunk Pond. Possible breakfast at the Cuttyhunk Fishing Club (28nm)
SundaySail over to Oak Bluffs – beaches, fishing, restaurants & maybe rent a Jeep and explore the island. (28nm)
MondayLay day – explore beaches & the famous The Black Dog Tavern
TuesdaySail to Nantucket – beaches, seal watching, rest. & rent a Jeep & drive on the beach to Great Point. (30nm)
WednesdayLay day – Children’s Beach, Whaling Museum, The Summer House, Galley Beach
ThursdaySail to Edgartown – South Beach, take the Chappaquiddick Ferry by Jeep & explore ‘Chappy’ & beaches. (20nm)
FridaySail to Menemsha BRIGHT and grab a mooring. – beaches, restaurants (BYOB), star watching at night time. (25nm)
SaturdayTaxi to Gay Head Cliffs (Aquinnah) for the best food & views on the island. You can see NY, CT, RI & MA.
SundaySail to Westport, MA – beach, fun harbor to dinghy around, The Back Eddy Restaurant. (25nm)
MondaySail to New Harbor, Block Island – Beaches, Horseback riding, fishing & restaurants. (36nm)
TuesdayLay day – explore the island.
WednesdaySail to Montauk, New York – beaches, fishing, sunset & restaurants. (21nm)
ThursdaySail to Newport -prevailing winds from the SW & return to the mooring by 19:00, then go into town for dinner. (42nm)
FridayPower to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 12:00 noon.

map-trip6-large

The MAPTECH / Embassy Cruising Guide for the ‘New England Coast’ will help you fine tune it even more.

We keep copies of the Cruising Guides on the boat.

2+-wks- New York City, Shelter Is., Fishers Is., Montauk, Block Is...
Friday, 17:0060 minute charter check out, then load your gear & food. Go into town for dinner and walk around & explore.
SaturdaySail out in the morning to Fisher’s Island, New York. If you’re hungry, visit the Pequot Restaurant for food, drinks & music. (49nm)
SundaySail over to Sunset Beach, Shelter Island – beach & food. (28nm) Then, power across the channel and dock in Greenport for the night & visit Claudio’s. (2nm)
MondayLay day – explore the village, boatyards and beaches of Greenport, New York.
TuesdaySail to Port Jefferson Harbor, NY – food, drinks & view. Try The Fifth Season or Lombardi’s On The Sound. (67nm)
WednesdaySail to City Island, New York – food, drinks & Minneford Marina. (37nm)
ThursdayPower thru Hell’s Gate to New York City and dock at Liberty Landing Marina or The North Cove Marina. (24nm)
FridayLay day – take the ferry across the Hudson River to New York City and explore!
SaturdayAnother lay day (remember to take a photo at the helm Sunday with the Statue of Liberty in the background!)
SundayPower back thru Hell’s Gate to City Island or Mamaroneck for the night. Fun harbor to dinghy around & explore. (24nm)
MondaySail to Essex, Connecticut (sail and power on the FRESH water river). Essex Island Marina. (89nm)
TuesdaySail to Montauk, New York – Montauk Marine Basin. (33nm)
WednesdaySail to New Harbor, Block Island, Rhode Island – beaches, fishing, sunset & restaurants. (24nm)
ThursdaySail to Newport -prevailing winds from the SW & return to the mooring by 19:00, then go into town for dinner. (24nm)
FridayPower to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 12:00 noon.

map-trip7-large

The MAPTECH / Embassy Cruising Guide for the ‘Long Island Sound’ will help you fine tune it even more.

We keep copies of the Cruising Guides on the boat.

2+ wks- Boston, Provincetown, Nantucket, Martha’s Vineyard, Cuttyhunk Is...

If it’s interesting for you, you can check out the harbors in the Cruising Guide or on ‘Google Images.’

Friday, 17:0060 minute charter check out, then load your gear & food. Go into town for dinner and walk around & explore.
SaturdaySail out in the morning to Cuttyhunk Pond. Possible breakfast at the Cuttyhunk Fishing Club or sail to Padanaram and have dinner at the Black Bass Grille (www.BlackBassma.com) (28nm)
SundaySail to Cape Cod Canal, power thru the Canal and then sail to Scituate, Ma and visit Riva Harbor side Bar & Italian Food. (69nm)
MondaySail to Boston and stay at Boston Waterboat Marina (www.bostonwaterboatmarina.com) (30nm)
TuesdayLay day…explore Boston
WednesdaySail thru Cape Cod Bay to Provincetown, located on the tip of Cape Cod. – beaches, whales, restaurants, people watching, star watching at night time. (58nm)
ThursdaySail to Nantucket (85nm)
FridayLay Day…explore Nantucket
SaturdaySail from Nantucket to Edgartown, Martha’s Vineyard. (20nm)
SundaySail from Edgartown to Menemsha Basin, Martha’s Vineyard. (25nm)
MondaySail to New Harbor, Block Island, RI – Beaches, Horseback riding, fishing & restaurants. (49nm)
TuesdayLay day – explore the island.
WednesdaySail to Montauk, New York – beaches, fishing, sunset & restaurants. (21nm)
ThursdaySail to Newport -prevailing winds from the SW & return to the mooring by 19:00, then go into town for dinner. (42nm)
FridayPower to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 12:00 noon.

map-trip8-large

take a virtual tour of our boats

Learn More

Available Charters

Now taking reservations for May, June, July August, Sept. & Oct. 2017 charters.

Google Maps Harbor Views

Check out interactive maps of New England’s harbors.

Specials

Weekly rate of $3,500 May 21 thru mid-Sept on our Beneteau 42’s.
Late Sept. or Oct. weekend specials from $1,500.

Testimonials

  • We booked a sailboat with a local Massachusetts broker and were informed a week before the charter that the sailboat was not available and she had no replacement. We were highly disappointed as my dad, brother and father in law were flying in from across the country to sail for a week. I went on-line and found Bareboat Sailing Charters-Newport. Brian was most accommodating and a pleasure to work with. He was able to offer us a Jeanneau 49’ Deck Salon. The boat was well equipped with many options that included (3) color GPS chart plotters and a 10’ dinghy. The 20 minute virtual tour video of the boat was great and allowed us to get familiar with the boat and its systems prior to beginning of our sailing adventure. We now have wonderful memories with my family sailing to the islands of Cuttyhunk, Martha’s Vineyard & Nantucket. Looking forward to our next charter with Brian @ Bareboat Sailing Charters. Many thanks from Alex and family!!

    Alex
  • My husband and I chartered a Beneteau 45′ for a week long trip to MV and Nantucket, and hired Captain Scott. We own the same boat on the Great Lakes and wanted to get experience sailing in New England. Our boat was clean and in tip-top condition. Scott was an invaluable instructor and our navigational skills improved immeasurably. The entire experience exceeded our expectations (sun every day helped!) I would not hesitate to recommend Bareboat Sailing Charters.

    Tracy
  • We have chartered many, many times (since 1985) from Bareboat Sailing Charters in Newport. Great boat with great weekly charter prices. The boat was well maintained and all systems were highly functioning. The boat was well equipped with many options that included (2) color GPS chart plotters and a 10’ dinghy. The 20 minute virtual tour video of the boat was great. After watching it, you feel like you already know the boat and its technology upon boarding. Thanks, Bareboat Sailing Charters for a memorable vacation!

    Daniel
  • A dream come true for Captain and crew! The Jenneau 439 we chartered from Bareboat Sailing was comfortable and perfectly suited for our group. The boat was well equipped and in great working conditon when we boarded. We spent the next 6 days bopping port to port around the Elizabeth Islands and Martha’s Vineyard. Bareboat Sailings crew made everything easy for first timers in that area. We’ll be back next year!

    Chip
  • “What a fantastic vacation”. We just returned from a wonderful vacation aboard the Beneteau 45 we chartered. There were two families onboard, but with 4 cabins there was plenty of room for everyone. The boat was equipped with all the electronics we could need and the chart plotter was especially useful during our week. The best part of the boat, according to my kids, was the hydraulic transom that lowered to create a great swim platform. Will charter again and again.

    Wendy
  • We rented July a Jeanneau 439 for 3 weeks to sail from Newport to New York and back. This long dream became really true. And thanks to Brian we were excellent prepared by several books, maps and most important by a super maintained ship equipped with everything we needed. I charted already boats all over the world, but here both the check-in and check-out was the easiest and fastest ever. Thanks for this great time!

    Karl
  • “Living the Dream!” My friends and I just booked our first charter with from Bareboat Sailing Charters to Nantucket last week. The boat was well maintained and all systems were functioning. The boat was well equipped with many options that included (2) color GPS chart plotters and a 10’ dinghy. The 20 minute virtual tour video of the boat was great. After watching it, you feel like you already know the boat & electronic when you board. Chalk up another great sailing vacation!!!

    John
  • This is my 5th time chartering through Bareboat Sailing. The boats are the best maintained of any I have chartered and I have been doing this for about 12 years. The checkouts and support from Brian and his crew are second to none. The boats are very well equipped, including chart plotters and radar. They also come with a dinghy and outboard. Like the boats they are always in good order…not necessarily a given in the charter industry. Simply put, Bareboat is one of the most professional organizations I have dealt with and I look I forward to many more trips with them in the future.

    Al
  • This outfit and the people behind are absolutely fantastic. I have chartered from them every year for the last 10-years and each time my expectations are far exceeded. The boats are always in excellent condition (with a noticeable and very well received emphasis on safety), the service and help we get along the way from Brian and his staff always goes above and beyond, and the area / region is not to be beat. You are virtually guaranteed to have a terrific experience if you choose Bareboat Sailing Charters.

    Ross