Islands of New England 2027 | Awaken Travel Club
A white lighthouse on Nantucket at sunset, with sailboats in the harbor

2027 Tour Pick #2

Islands of New England

Lighthouses, lobster feasts and ferry rides to two famous islands.

Newport, Cape Cod, Nantucket & Martha’s Vineyard | Hosted by Cindi & Denise

✈️ Flights + the ride to the Atlanta airport included

Length8 days, 7 nights
RouteProvidence to Boston
Signature stay4 nights at a beachfront Cape Cod resort
Included10 meals

The trip

Why we love this one

If your idea of a perfect trip is lighthouses, salt air and a really good lobster dinner, this is the one. We spend three nights in Providence, Rhode Island, with a day in Newport touring The Breakers, the grandest of the Gilded Age summer mansions.

Then it is four nights at a beachfront resort on Cape Cod, with ferry days to Nantucket and Martha’s Vineyard, a lobster boat ride in Plymouth Harbor, a stop at Plymouth Rock, and a farewell lobster feast. Just two hotels, so there is no packing up every morning, and plenty of time by the water.

A New England beach at sunset
The lighthouse at Nantucket Harbor
The Breakers mansion in Newport
Gingerbread cottages on Martha’s Vineyard
Fresh lobsters on a lobster boat
Dune grass above an ocean beach
The river walk in downtown Providence
Fishing boats in a Cape Cod harbor

The highlights

What we'll do together

The white lighthouse at the entrance to Nantucket Harbor

Nantucket by ferry

Cobblestone Main Street, the harbor, free time to shop, and the Whaling Museum with its 46-foot whale skeleton.

Colorful gingerbread cottages with hanging flower baskets on Martha’s Vineyard

Martha’s Vineyard

A ferry ride to the Vineyard for its famous gingerbread cottages and an old whaling port lined with sea captains’ homes.

The Breakers mansion in Newport, Rhode Island

Newport’s Gilded Age

A drive down Bellevue Avenue past the grand summer “cottages,” then a tour of The Breakers, the Vanderbilts’ 70-room mansion.

Gloved hands sorting fresh lobsters on a lobster boat

Lobster, start to finish

Watch a captain pull up a lobster trap in Plymouth Harbor, see Plymouth Rock, then celebrate with a farewell lobster feast.

The route

Where the road takes us

Map of the route: Providence, Newport, Plymouth, Cape Cod, Nantucket & Hyannis, Sandwich (optional), Martha’s Vineyard, Boston
1
2
3
4
5
6
7
8
  1. 1ProvidenceDays 1 to 3
  2. 2NewportDay 3
  3. 3PlymouthDay 4
  4. 4Cape CodDays 4 to 7
  5. 5Nantucket & HyannisDay 5
  6. 6Sandwich (optional)Day 6
  7. 7Martha’s VineyardDay 7
  8. 8BostonDay 8

Ferry rides to Nantucket and Martha’s Vineyard.

Day by day

Your itinerary

  1. 1

    Day 1: Providence, Rhode Island

    Arrive in Providence, the capital of Rhode Island. Nothing is scheduled today, so dinner is on your own.

    Stay: Aloft Providence Downtown
  2. 2

    Day 2: Providence

    A morning drive around the city with our tour manager, past Brown University and Waterplace Park. In the afternoon, pick your own adventure: a guided walk through Providence’s architecture and hidden corners with a local guide, or time in the RISD Museum of art and design. Tonight, a colonial-style welcome dinner together.

    Stay: Aloft Providence DowntownMeals: Breakfast, Dinner
  3. 3

    Day 3: Newport

    A day trip to Newport, the old colonial port that became the summer playground of America’s richest families. We ride down Bellevue Avenue past its mansions, then tour The Breakers, the Vanderbilt family’s 70-room summer home. Back to Providence for the evening.

    Stay: Aloft Providence DowntownMeals: Breakfast
  4. 4

    Day 4: Plymouth & Cape Cod

    On to Plymouth, where the Pilgrims came ashore in 1620. We cruise the harbor on a lobster boat while the captain pulls up a trap and explains how lobstering works, then visit Plymouth Rock. This afternoon we check in to a beachfront resort on Cape Cod for four nights.

    Stay: Sea Crest Beach Resort, FalmouthMeals: Breakfast
  5. 5

    Day 5: Nantucket & Hyannis

    A ferry to Nantucket. Free time for cobblestone Main Street, the harbor and the famous Nantucket baskets, then the Whaling Museum and its 46-foot whale skeleton. Back on the Cape, a stop at the Kennedy Memorial in Hyannis, then dinner together at a local favorite.

    Stay: Sea Crest Beach Resort, FalmouthMeals: Breakfast, Dinner
  6. 6

    Day 6: Cape Cod, your way

    Your choice today: relax at the resort’s pool and private beach, or ride along to Sandwich for the Heritage Museums & Gardens, 100 acres of gardens and collections, and the Sandwich Glass Museum with its glassblowing. The evening is free.

    Stay: Sea Crest Beach Resort, FalmouthMeals: Breakfast
  7. 7

    Day 7: Martha’s Vineyard

    A ferry to Martha’s Vineyard to see the island’s highlights, from the colorful gingerbread cottages to the old whaling port and its sea captains’ homes. Back on the Cape, a farewell lobster feast.

    Stay: Sea Crest Beach Resort, FalmouthMeals: Breakfast, Dinner
  8. 8

    Day 8: Cape Cod to Boston

    After breakfast, we head to Boston, where the tour ends.

    Meals: Breakfast

Hotels listed are the current plan and can change to a similar hotel.

The details

What's included

Included

  • ✓Your flights, plus the ride from the Chattanooga area to the Atlanta airport
  • ✓7 nights in two hand-picked hotels: 3 in downtown Providence and 4 at a beachfront resort on Cape Cod
  • ✓10 meals: 7 breakfasts and 3 dinners, including a welcome dinner and a farewell lobster feast
  • ✓A professional tour manager with the group the whole way
  • ✓Motorcoach travel between every stop, plus the ferries to Nantucket and Martha’s Vineyard
  • ✓Guided sightseeing and admissions: a Providence city tour, The Breakers in Newport, a lobster boat cruise in Plymouth Harbor, Plymouth Rock, the Nantucket Whaling Museum and the Kennedy Memorial in Hyannis

Not included

  • –Tips for your tour manager and motorcoach driver
  • –Meals not listed in the day by day
  • –Optional add-ons and anything on your free time
  • –Travel insurance (we strongly recommend it)

The pace

Moderate. Expect walking on cobblestone streets and island sidewalks, getting on and off ferries and boats, and some stairs. Day 6 can be an easy day at the resort if you want it.

Fall 2027 departures

Dates

Oct 1 - Oct 8, 2027

Oct 7 - Oct 14, 2027

Oct 8 - Oct 15, 2027

Oct 14 - Oct 21, 2027

Oct 22 - Oct 29, 2027

✈️ Every tour includes your flights and the ride to the Atlanta airport. We are finalizing group pricing now and will share it soon.

October is shoulder season on the Cape and the islands, with fewer summer crowds.

A New England beach at sunsetDune grass above a wide ocean beachThe Providence skyline along the riverFishing boats in a harbor on Cape Cod

Tour 2 of 3

Is this the one?

This is one of three tours on the club's 2027 shortlist, and you get a say in which one we take first. Cast your vote on our club poll. It only takes a second!

The other two picks

Traveling with you

Your hosts

Cindi Sanden

Cindi Sanden

Denise Karnes

Denise Karnes

Cindi and Denise started the Awaken Travel Club because travel is better with people who get it. We handle the planning, the questions and the details, so all you have to do is pack and come along.