

take a virtual tour of our boats
Bareboat Sailing Trips
Choose from one of the many trips available on your bareboat charter.
Day 1 | Sail from Newport to Cuttyhunk (28nm) |
Day 2 | Cuttyhunk thru Quicks Hole to Oak Bluffs, Martha’s Vineyard (28nm) |
Day 3 | Lay day…explore the island by rental car, moped or bike. |
Day 4 | Sail from Oak Bluffs to Nantucket (30nm) |
Day 5 | Sail from Nantucket to Menemsha Basin (49nm) |
Day 6 | Sail from Menemsha Basin to Jamestown Island for a late lunch – www.ConanicutMarina.com (36nm), then motor over to your mooring in Newport by 7 pm and enjoy your last night (Thursday) in fabulous Newport! |
Day 7 | Power to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 11am. |
Or stay an extra day or two in one of your favorite ports & create your own trip!!
Day 1 | Sail from Newport to Block Island. (25nm) |
Day 2 | Sail from Block Island to Cuttyhunk. (40nm) |
Day 3 | Sail from Cuttyhunk to Edgartown. (25nm) |
Day 4 | Lay day… Explore the island by car, moped or bike. |
Day 5 | Sail from Edgartown to Menemsha Basin. (25nm) |
Day 6 | Sail from Menemsha to Newport and have dinner in Newport (30nm) |
Day 7 | Power to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 11am. |
Or stay an extra day or two in one of your favorite ports & create your own trip!!
Martha’s Vineyard Sunrise
Day 1 | Sail from Newport to Menemsha Basin, Martha’s Vineyard (38nm) |
Day 2 | Sail from Menemsha Basin to Edgartown (25nm) |
Day 3 | Sail from Edgartown to Nantucket. (20nm) |
Day 4 | Sail from Nantucket to Oak Bluffs (30nm) |
Day 5 | Sail from Oak Bluffs thru Quicks Hole to South Dartmouth (Padanaram) (25nm) |
Day 6 | Sail from Padanaram to Newport and have dinner in Newport (30nm) |
Day 7 | Power to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 11am. |
Or stay an extra day or two in one of your favorite ports & create your own trip!!
Martha’s Vineyard Sunrise
Day 1 | Sail from Newport to Block Island (25nm) |
Day 2 | Sail from Block Island to Montauk, NY or Fort Pond Bay (20nm) |
Day 3 | Sail from Montauk to Menemsha Basin, Martha’s Vineyard (63nm) |
Day 4 | Sail from Menensha Basin to Oak Bluffs, Martha’s Vineyard (18nm) |
Day 5 | Sail from Oak Bluffs thru Quicks Hole to Cuttyhunk Pond (28nm) |
Day 6 | Sail from Cuttyhunk to Newport and have dinner in Newport (28nm) |
Day 7 | Power to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 11am. |
Or stay an extra day or two in one of your favorite ports & create your own trip!!
Martha’s Vineyard Sunrise
Day 1 | Newport to Fishers Island, NY… 49 miles |
Day 2 | Fishers Island to Shelter Island, NY…24 miles |
Day 3 | Shelter Island to Greenport…1 miles |
Day 4 | Greenport 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 7 | Power to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 11am. |
Or stay an extra day or two in one of your favorite ports & create your own trip!!
If it’s interesting for you, you can check out the harbors in the Cruising Guide or on ‘Google Images.’
Friday, 17:00 | 60 minute charter check out, then load your gear & food. Go into town for dinner and walk around & explore. |
Saturday | Sail out in the morning to Cuttyhunk Pond. Possible breakfast at the Cuttyhunk Fishing Club (28nm) |
Sunday | Sail over to Oak Bluffs – beaches, fishing, restaurants & maybe rent a Jeep and explore the island. (28nm) |
Monday | Lay day – explore beaches & the famous The Black Dog Tavern |
Tuesday | Sail to Nantucket – beaches, seal watching, rest. & rent a Jeep & drive on the beach to Great Point. (30nm) |
Wednesday | Lay day – Children’s Beach, Whaling Museum, The Summer House, Galley Beach |
Thursday | Sail to Edgartown – South Beach, take the Chappaquiddick Ferry by Jeep & explore ‘Chappy’ & beaches. (20nm) |
Friday | Sail to Menemsha BRIGHT and grab a mooring. – beaches, restaurants (BYOB), star watching at night time. (25nm) |
Saturday | Taxi to Gay Head Cliffs (Aquinnah) for the best food & views on the island. You can see NY, CT, RI & MA. |
Sunday | Sail to Westport, MA – beach, fun harbor to dinghy around, The Back Eddy Restaurant. (25nm) |
Monday | Sail to New Harbor, Block Island – Beaches, Horseback riding, fishing & restaurants. (36nm) |
Tuesday | Lay day – explore the island. |
Wednesday | Sail to Montauk, New York – beaches, fishing, sunset & restaurants. (21nm) |
Thursday | Sail to Newport -prevailing winds from the SW & return to the mooring by 19:00, then go into town for dinner. (42nm) |
Friday | Power to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 11am. |
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.
Friday, 17:00 | 60 minute charter check out, then load your gear & food. Go into town for dinner and walk around & explore. |
Saturday | Sail out in the morning to Fisher’s Island, New York. If you’re hungry, visit the Pequot Restaurant for food, drinks & music. (49nm) |
Sunday | Sail 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) |
Monday | Lay day – explore the village, boatyards and beaches of Greenport, New York. |
Tuesday | Sail to Port Jefferson Harbor, NY – food, drinks & view. Try The Fifth Season or Lombardi’s On The Sound. (67nm) |
Wednesday | Sail to City Island, New York – food, drinks & Minneford Marina. (37nm) |
Thursday | Power thru Hell’s Gate to New York City and dock at Liberty Landing Marina or The North Cove Marina. (24nm) |
Friday | Lay day – take the ferry across the Hudson River to New York City and explore! |
Saturday | Another lay day (remember to take a photo at the helm Sunday with the Statue of Liberty in the background!) |
Sunday | Power back thru Hell’s Gate to City Island or Mamaroneck for the night. Fun harbor to dinghy around & explore. (24nm) |
Monday | Sail to Essex, Connecticut (sail and power on the FRESH water river). Essex Island Marina. (89nm) |
Tuesday | Sail to Montauk, New York – Montauk Marine Basin. (33nm) |
Wednesday | Sail to New Harbor, Block Island, Rhode Island – beaches, fishing, sunset & restaurants. (24nm) |
Thursday | Sail to Newport -prevailing winds from the SW & return to the mooring by 19:00, then go into town for dinner. (24nm) |
Friday | Power to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 11am. |
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.
If it’s interesting for you, you can check out the harbors in the Cruising Guide or on ‘Google Images.’
Friday, 17:00 | 60 minute charter check out, then load your gear & food. Go into town for dinner and walk around & explore. |
Saturday | Sail 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) |
Sunday | Sail to Cape Cod Canal, power thru the Canal and then sail to Scituate, Ma and visit Riva Harbor side Bar & Italian Food. (69nm) |
Monday | Sail to Boston and stay at Boston Waterboat Marina (www.bostonwaterboatmarina.com) (30nm) |
Tuesday | Lay day…explore Boston |
Wednesday | Sail thru Cape Cod Bay to Provincetown, located on the tip of Cape Cod. – beaches, whales, restaurants, people watching, star watching at night time. (58nm) |
Thursday | Sail to Nantucket (85nm) |
Friday | Lay Day…explore Nantucket |
Saturday | Sail from Nantucket to Edgartown, Martha’s Vineyard. (20nm) |
Sunday | Sail from Edgartown to Menemsha Basin, Martha’s Vineyard. (25nm) |
Monday | Sail to New Harbor, Block Island, RI – Beaches, Horseback riding, fishing & restaurants. (49nm) |
Tuesday | Lay day – explore the island. |
Wednesday | Sail to Montauk, New York – beaches, fishing, sunset & restaurants. (21nm) |
Thursday | Sail to Newport -prevailing winds from the SW & return to the mooring by 19:00, then go into town for dinner. (42nm) |
Friday | Power to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 11am. |
Bareboat Sailing Trips
Choose from one of the many trips available on your bareboat charter.
Day 1 | Sail from Newport to Cuttyhunk (28nm) |
Day 2 | Cuttyhunk thru Quicks Hole to Oak Bluffs, Martha’s Vineyard (28nm) |
Day 3 | Lay day…explore the island by rental car, moped or bike. |
Day 4 | Sail from Oak Bluffs to Nantucket (30nm) |
Day 5 | Sail from Nantucket to Menemsha Basin (49nm) |
Day 6 | Sail from Menemsha Basin to Jamestown Island for a late lunch – www.ConanicutMarina.com (36nm), then motor over to your mooring in Newport by 7 pm and enjoy your last night (Thursday) in fabulous Newport! |
Day 7 | Power to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 11am. |
Or stay an extra day or two in one of your favorite ports & create your own trip!!
Day 1 | Sail from Newport to Block Island. (25nm) |
Day 2 | Sail from Block Island to Cuttyhunk. (40nm) |
Day 3 | Sail from Cuttyhunk to Edgartown. (25nm) |
Day 4 | Lay day… Explore the island by car, moped or bike. |
Day 5 | Sail from Edgartown to Menemsha Basin. (25nm) |
Day 6 | Sail from Menemsha to Newport and have dinner in Newport (30nm) |
Day 7 | Power to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 11am. |
Or stay an extra day or two in one of your favorite ports & create your own trip!!
Martha’s Vineyard Sunrise
Day 1 | Sail from Newport to Menemsha Basin, Martha’s Vineyard (38nm) |
Day 2 | Sail from Menemsha Basin to Edgartown (25nm) |
Day 3 | Sail from Edgartown to Nantucket. (20nm) |
Day 4 | Sail from Nantucket to Oak Bluffs (30nm) |
Day 5 | Sail from Oak Bluffs thru Quicks Hole to South Dartmouth (Padanaram) (25nm) |
Day 6 | Sail from Padanaram to Newport and have dinner in Newport (30nm) |
Day 7 | Power to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 11am. |
Or stay an extra day or two in one of your favorite ports & create your own trip!!
Martha’s Vineyard Sunrise
Day 1 | Sail from Newport to Block Island (25nm) |
Day 2 | Sail from Block Island to Montauk, NY or Fort Pond Bay (20nm) |
Day 3 | Sail from Montauk to Menemsha Basin, Martha’s Vineyard (63nm) |
Day 4 | Sail from Menensha Basin to Oak Bluffs, Martha’s Vineyard (18nm) |
Day 5 | Sail from Oak Bluffs thru Quicks Hole to Cuttyhunk Pond (28nm) |
Day 6 | Sail from Cuttyhunk to Newport and have dinner in Newport (28nm) |
Day 7 | Power to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 11am. |
Or stay an extra day or two in one of your favorite ports & create your own trip!!
Martha’s Vineyard Sunrise
Day 1 | Newport to Fishers Island, NY… 49 miles |
Day 2 | Fishers Island to Shelter Island, NY…24 miles |
Day 3 | Shelter Island to Greenport…1 miles |
Day 4 | Greenport 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 7 | Power to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 11am. |
Or stay an extra day or two in one of your favorite ports & create your own trip!!
If it’s interesting for you, you can check out the harbors in the Cruising Guide or on ‘Google Images.’
Friday, 17:00 | 60 minute charter check out, then load your gear & food. Go into town for dinner and walk around & explore. |
Saturday | Sail out in the morning to Cuttyhunk Pond. Possible breakfast at the Cuttyhunk Fishing Club (28nm) |
Sunday | Sail over to Oak Bluffs – beaches, fishing, restaurants & maybe rent a Jeep and explore the island. (28nm) |
Monday | Lay day – explore beaches & the famous The Black Dog Tavern |
Tuesday | Sail to Nantucket – beaches, seal watching, rest. & rent a Jeep & drive on the beach to Great Point. (30nm) |
Wednesday | Lay day – Children’s Beach, Whaling Museum, The Summer House, Galley Beach |
Thursday | Sail to Edgartown – South Beach, take the Chappaquiddick Ferry by Jeep & explore ‘Chappy’ & beaches. (20nm) |
Friday | Sail to Menemsha BRIGHT and grab a mooring. – beaches, restaurants (BYOB), star watching at night time. (25nm) |
Saturday | Taxi to Gay Head Cliffs (Aquinnah) for the best food & views on the island. You can see NY, CT, RI & MA. |
Sunday | Sail to Westport, MA – beach, fun harbor to dinghy around, The Back Eddy Restaurant. (25nm) |
Monday | Sail to New Harbor, Block Island – Beaches, Horseback riding, fishing & restaurants. (36nm) |
Tuesday | Lay day – explore the island. |
Wednesday | Sail to Montauk, New York – beaches, fishing, sunset & restaurants. (21nm) |
Thursday | Sail to Newport -prevailing winds from the SW & return to the mooring by 19:00, then go into town for dinner. (42nm) |
Friday | Power to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 11am. |
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.
Friday, 17:00 | 60 minute charter check out, then load your gear & food. Go into town for dinner and walk around & explore. |
Saturday | Sail out in the morning to Fisher’s Island, New York. If you’re hungry, visit the Pequot Restaurant for food, drinks & music. (49nm) |
Sunday | Sail 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) |
Monday | Lay day – explore the village, boatyards and beaches of Greenport, New York. |
Tuesday | Sail to Port Jefferson Harbor, NY – food, drinks & view. Try The Fifth Season or Lombardi’s On The Sound. (67nm) |
Wednesday | Sail to City Island, New York – food, drinks & Minneford Marina. (37nm) |
Thursday | Power thru Hell’s Gate to New York City and dock at Liberty Landing Marina or The North Cove Marina. (24nm) |
Friday | Lay day – take the ferry across the Hudson River to New York City and explore! |
Saturday | Another lay day (remember to take a photo at the helm Sunday with the Statue of Liberty in the background!) |
Sunday | Power back thru Hell’s Gate to City Island or Mamaroneck for the night. Fun harbor to dinghy around & explore. (24nm) |
Monday | Sail to Essex, Connecticut (sail and power on the FRESH water river). Essex Island Marina. (89nm) |
Tuesday | Sail to Montauk, New York – Montauk Marine Basin. (33nm) |
Wednesday | Sail to New Harbor, Block Island, Rhode Island – beaches, fishing, sunset & restaurants. (24nm) |
Thursday | Sail to Newport -prevailing winds from the SW & return to the mooring by 19:00, then go into town for dinner. (24nm) |
Friday | Power to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 11am. |
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.
If it’s interesting for you, you can check out the harbors in the Cruising Guide or on ‘Google Images.’
Friday, 17:00 | 60 minute charter check out, then load your gear & food. Go into town for dinner and walk around & explore. |
Saturday | Sail 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) |
Sunday | Sail to Cape Cod Canal, power thru the Canal and then sail to Scituate, Ma and visit Riva Harbor side Bar & Italian Food. (69nm) |
Monday | Sail to Boston and stay at Boston Waterboat Marina (www.bostonwaterboatmarina.com) (30nm) |
Tuesday | Lay day…explore Boston |
Wednesday | Sail thru Cape Cod Bay to Provincetown, located on the tip of Cape Cod. – beaches, whales, restaurants, people watching, star watching at night time. (58nm) |
Thursday | Sail to Nantucket (85nm) |
Friday | Lay Day…explore Nantucket |
Saturday | Sail from Nantucket to Edgartown, Martha’s Vineyard. (20nm) |
Sunday | Sail from Edgartown to Menemsha Basin, Martha’s Vineyard. (25nm) |
Monday | Sail to New Harbor, Block Island, RI – Beaches, Horseback riding, fishing & restaurants. (49nm) |
Tuesday | Lay day – explore the island. |
Wednesday | Sail to Montauk, New York – beaches, fishing, sunset & restaurants. (21nm) |
Thursday | Sail to Newport -prevailing winds from the SW & return to the mooring by 19:00, then go into town for dinner. (42nm) |
Friday | Power to the fuel dock, remove trash, top off water, dinghy & diesel. Remove gear & depart boat by 11am. |

take a virtual tour of our boats
AVAILABLE CHARTERS
Now taking reservations for May, June, July, August, Sept. & Oct. 2025 charters.
Google Maps Harbor Views
Check out interactive maps of New England’s harbors.
Specials
Early May, late-Sept. & Oct. weekend or mid-week special 2-day rate starting from $2,000. Additional days can be added at $700 per day during early May, late-Sept. & Oct.
Testimonials
