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Newport & Nantucket Sound

Welcome friends - Newport, Rhode Island is one of the global centers for sailing with a maritime heritage unmatched by many. Sailing Collective Travel Co. looks to our backyard to create memorable sailing voyages and we’re excited to announce the latest in our journey: The Newport to Martha’s Vineyard Expedition

There will be the sea - there will be lobsters - there will be oysters - there will be nature and there will be paradise. We’ll enjoy local restaurants at the mariners wharf and drop anchor in secluded coves to jump off our sailboat and enjoy the seas. The white sand beaches of Martha’s Vineyard will be a highlight along with so many more opportunities to feel free.

Dates

August 17th — 24th 2025

8 days, 7 nights

Location

Nantucket Sound & Newport, RI
United States

Availability

0 Double Cabin

0 Single Cabin

Price

$5100 Single Cabin price per cabin

$7800 Double Cabin price per cabin

Itinerary

Day 1: Enjoy a beautiful evening at the docks in the center of downtown Newport located at Christie’s Landing. Walk from the boat to the restaurants on Thames Street which is the central hub for seaside restaurants and nightlife in Newport.

Day 2: Set sail from Newport early morning bound for Menemsha, Martha’s Vineyard, and anchor off the seaside town where the movie Jaws was filmed. This is a quiet lowkey fishing village offering a look into the relaxed culture on Martha’s Vineyard. There is plentiful fresh seafood alongside stunning white sand beaches home to dunes along the waterfront.

Day 3: Make the passage through Vineyard Sound towards the famous island of Nantucket where we spend a night at anchor and explore the historic homes and towns on the island. We’ll enjoy fresh oysters and explore the vibrant and exclusive seaside communities on the island.

Day 4: We’ll sail back to Martha’s Vineyard and spend a day in the main town of Oak Bluff on the island. There are shops and restaurants that line the old seaside town where we will explore and adventure.

Day 5: Sailing west towards mainland, we’ll sail to the quiet island of Cuttyhunk Island which is the outermost island of the Elizabeth Islands. This small island has plenty of adventures with rocky beaches lined with modest summer homes.

Day 6: Sailing back towards Newport, we’ll explore Jamestown on Conacicut Island, the second largest island in Narragansett Bay. This island captures a rustic style with much to explore throughout this sleepy seaside island. There are a variety of restaurants and bars to explore with some fantastic beaches to enjoy as well.

A one-week voyage starting from NEWPORT will circumnavigate the south coast of Cape Code exploring the marvelous islands of Nantucket, Martha's Vineyard, Cuttyhunk, and the Buzzards Bay Coast.

Alternative itineraries with a NEWPORT port of call:

[a] Block Island, Fishers Island, Montauk, Mystic (7-days)

[b] Buzzards Bay, Cape Code Bay, Providence Town, Playmouth, Gloucester, Falmouth (7-days, 10-days to include Nantucket and Martha's Vineyard)

[c] Newport to Casco Bay, Maine roundtrip (13-days)

The weather & itinerary is dictated on the weather and may vary based on your captain's decision. Safety is our top priority and inclement weather can interfere with sailing to Nantucket.

Crew

Jon Bickford

Captain

A native to Maine and unabashed thalassophile, Jon has worked on the water for over 12 years and has sailed over 15,000 miles. On land he has walked the width and breadth of two nations and has lived in cities from New York to Honolulu to Bangkok. While solo journeys have incredible value, for him, it is the communal expeditions in outdoor settings that have defined Jon’s time in the wilderness as they provide the rare combination of camaraderie and growth that only can be known through group adventure. He holds a USCG masters license, and has participated in international competitions on traditional 18th century wooden Bantry Bay Gigs, canoed Alaska's Inside Passage rain forest, and operated a marine research vessel for Cornell University. When not on the move, he enjoys living in small island communities off the New England coast.

Flannery Klette-Kolton

Culinary Director and Chef

Despite my tiny frame, I am an eater and food is always on my mind! I love every element of the food experience, from shopping the finest the farmers market has to provide to the preparation of an exquisite meal. A hostess at heart, it is the sensual and intimate aspect of dining that remains most important to me. I always keep in mind that overall indulgence is exemplified through flawless service and genuine hospitality. I believe that food has the capacity to fascinate and surprise, and I am not one to resist sharing my discoveries with any innocent bystander who has a set of ears, an open mind, and an empty stomach.

Newport Trip Details

ARRIVAL AND DEPARTURE

Embark: 7:00 pm on the first day of the charter - First night spent at the marina in Conanicut Marina in Jamestown, Rhode Island Disembark: 9:00 am on the final day of the charter

AIR TRAVEL

Logan International Airport (BOS) - the airport is a two-hour drive by car or scuttle.
Rhode Island T. F. Green International Airport - 45 minute taxi to Newport

MARINA AND STARTING LOCATION

Your crew will be onboard to welcome you at:

Conanicut Marina

20 Narragansett Avenue, Jamestown, Rhode Island 02835

You will receive communication from them prior to the trip with contact information and exact location details of where to find the boat.

GRATUITY Tipping your captain and crew is welcomed. If you are satisfied with your service, the industry standard for yacht charters ranges from 10-20% of the cost of the charter. Gratuity is split evenly between the crew and can be paid via cash, check, Venmo, or PayPal. Please contact your Sailing Collective Journey Coordinator if you have any questions.

10% - Standard good time on holiday with good service.
15% - Exceptional service on your holiday with exceptional service!
20% - Extraordinary experience and your crew sent the voyage to the moon and back!!

Provisioning Sailing Collective will provision your journey with local foods and produce. Cooking Aboard: Your Sailing Collective chef/crew is incredibly talented and can handle the group's needs with ease. We are all about participation and learning, so if you'd like to help, just ask and we'll get you involved! Collective groups may choose to dine out more times than scheduled if the group or individuals choose.

Included in provisioning package*:

7 Breakfasts, 6 Lunches, 3 Dinners (or similar), Light Snacks, Water, Coffee & Tea

* Subjected to change

Dietary Restrictions We can accommodate as long as we know in advance! It is important to notify us of any dietary restrictions ahead of time and include full details in the Guest Form that you will fill out prior to the start of the trip.

Sailing a group journey is a collective experience calling us to ebb and flow with the tides of the group. While alcohol and soft beverages are not included, we find a well curated bar shared across the group works out best. We offer two beverage during group journeys packages during the course of the week:

$150 for wine, beer, spirits and soft beverages
$75 for soft beverages and under 5 alcoholic drinks.

*Private charters, beverages are billed to the charter

You can also choose to bring your own beverages on board at no cost. Beverages through our package options will be provisioned for by your crew based on the preferences shared in your guest forms. Alternatively, if you plan to purchase your beverages separately, it is best to stock up before we depart the marina! Private Journey guests will receive information from crew about alcohol provisioning, which we can handle on your behalf. Morning beverages and water are included for all guests.

Please confirm your package choice within your guest form so your crew can plan accordingly!

ADDITIONAL COSTS We recommend planning on having at least $300 – $600 in spending money depending on spending habits. You will be responsible for paying for: