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Newport Leisure Charter Itinerary | Vacation Vibes

Get ready for an epic 8-night Newport Leisure Charter Itinerary, where you can kick back and cruise at a laid-back pace. This itinerary is about taking it easy, enjoying sightseeing, rocking some watersports, and exploring cool spots with the tender.

Newport Leisure Charter Itinerary

Day 1 | Newport to Cutty Hunk, MA

Start with a relaxing two-hour cruise from Newport Harbor to the historic Cuttyhunk Island in the Elizabeth Islands group. Cuttyhunk Island takes the crown as the farthest island in the Elizabeth Islands group.

Kick back in the charming harbor, do some fishing, or hit the scenic hiking trails. Feeling adventurous? Try jet skiing or kayaking. Keep your eyes peeled for cute seals lounging in the sun at Gull Island.

Day 2 | Cuttyhunk, MA

Embrace the tranquility and spend the whole day soaking up the peaceful ocean vibes of Cuttyhunk. It’s like finding a secret hideaway surrounded by stunning nature.

If you’re up for it, dive into some watersports like jet skiing or kayaking. Take a hike, enjoy the scenic views, and let the stress melt away. And hey, don’t miss checking out the seals at Gull Island—they’re adorable!

Day 3 | Vineyard Haven, Martha’s Vineyard

After a leisurely breakfast, cruise for about one and a half hours from Cuttyhunk to Vineyard Haven. This happening seaside town is begging to be explored. Catch a play at the Martha’s Vineyard Playhouse or take a leisurely walk to the iconic West Chop Lighthouse.

The town is full of unique shops, so treat yourself to a little retail therapy. Grab a light lunch at the cozy Little House Cafe. When you’re done, head back to your yacht for watersports action and play with those fabulous water toys.

Days 4 and 5 | Nantucket, MA

Ahoy, Nantucket! You’ve got two days to soak up the awesomeness of this captivating island. There’s so much to see and do here that you won’t want to rush. Explore the town’s historical museums, take island tours, or show off your ice skating skills.

Dinner in town or on your yacht will be a treat. The next day, cruise around the local waters and keep your eyes peeled for majestic whales and playful seals.

Days 6 and 7 | Edgartown, Martha’s Vineyard, MA

Days 6 and 7 are all about Edgartown on Martha’s Vineyard. There is so much to see and do here that you need two days to do it justice. Start by exploring the town center, where you’ll find whaling captains’ homes now inns, restaurants, and cool shops.

Jump into some watersports or revisit any spots you missed on the first day.

Day 8 | Oak Bluffs, Martha’s Vineyard, MA

You still have a full day of your Newport leisure charter itinerary! Cruise a short distance to the busy town of Oak Bluffs. Get ready for a good time! Check out the legendary gingerbread cottages—they’re officially called the Martha’s Vineyard Camp Meeting Association but known as The Campground.

Stroll through Ocean Park, fly a kite at the historic gazebo, and ride the oldest carousel in the US—the Flying Horses Carousel.

Hungry? Restaurants and bars line Oak Bluffs Harbor, while water sports and fishing charters offer a thrill. Don’t miss the North Bluff seawall. Also, hit up the town’s shops, restaurants, cafes, and ice cream spots. And if you’re feeling artsy, catch an exhibition, reading, or concert at Featherstone Center for the Arts.

Day 9 | Newport, RI

Wrap up your Newport Leisure Charter itinerary with a relaxing three-hour cruise from Oak Bluffs back to the fabulous city of Newport. It’s time to say goodbye to the yacht and hold onto those amazing memories of your coastal journey.

Disembark your Newport Leisure Charter Itinerary.