Boston, Cape Cod and Newport
Plus Nantucket & Martha’s Vineyard
September 7 - September 13, 2026Our tour from Boston to Newport via Cape Cod begins in one of America's oldest and most charming cities, with a city tour and time to explore the historic "Freedom Trail." We then make our way to Cape Cod to stay in Hyannis, which is a great jumping off point for visits to both Nantucket and Martha's Vineyard. Our final stop is Newport, a shining gem in the coastal crown of New England. The summer mansions of well-known families of the early 1900s are truly a sight to behold. Our favorite is "The Breakers," a modest 70-room "summer cottage." Come see for yourself why this is one of our favorite trips for the variety of sights and experiences, all in proximity to one another.
Boston, Cape Cod and Newport
September 7 - September 13, 2026Highlights
- Walk Boston's Freedom Trail
- Ferry to Martha's Vineyard & Nantucket
- Visit the John F. Kennedy Presidential Library
- Tour Newport's "The Breakers" Mansion
- Stroll around Newport
- Time to explore personal interests
- Suggestions for additional things to see
- And More... See itinerary for details
Activity
Read more about WTT Activity Levels
- 60% Easy
- 40% Moderate (3-4 hour walking tour)
Your Responsibilities as a Solo Traveler
As a solo traveler you are responsible for yourself, your possessions, your physical fitness, and all other aspects related to participation in the WTT tour you have chosen. Be sure to read the itinerary closely to better understand the physical requirements necessary for the tour.
WTT tours are not suitable for anyone whose mobility is challenged or compromised. If you struggle with walking, standing or negotiating stairs or if you are in doubt as to your ability to meet the physical activity requirements, you should not sign up for this trip.
Itinerary
Monday, 07 September 2026: Arrive Boston; Welcome Dinner (D)
Schedule your arrival no later than 4:30pm and take local transportation to the hotel. The tour begins in the lobby of the hotel at 6:00pm. We will get better acquainted during our Welcome Dinner and discuss the week's upcoming adventures. Overnight Boston - 2 nights
Tuesday, 08 September 2026: Walking Tour of Boston's Freedom Trail; Afternoon at Leisure (L)
Put on your walking shoes and grab breakfast on your own this morning before we meet up with our local guide to walk a good portion of Boston's 2.5-mile Freedom Trail that connects 16 nationally significant historic sites. As our guide re-familiarizes us with the finer points of American revolutionary history, we'll follow the literal red line throughout historic Boston. Afterward, we'll have lunch together and the rest of the day is yours to enjoy. You might want to walk more of the Freedom Trail, poke around Faneuil Hall and the Quincy Market, or make your way across the Charles River to snap a picture of yourself at Harvard in Cambridge. There are so many things to do in this historic city. Your WTT Tour Leader will have a sightseeing itinerary if you wish to spend the day with her.
Wednesday, 09 September 2026: JFK Presidential Library; Plymouth; Hyannis (D)
Grab a quick breakfast on you own before we head out of Boston this morning. Our first destination is the John F. Kennedy Presidential Library and Museum, where we enter the re-created world of the Kennedy Presidency for a “first-hand” experience of JFK’s life, legacy and leadership. It's then onto Plymouth, to step back in time and mark the Pilgrims' 1620 landing. We’ll enjoy dinner together this evening before arriving in Hyannis, the commercial hub of Cape Cod. Overnight Hyannis – 3 nights
Thursday, 10 September 2026: Day Trip to Martha's Vineyard (B)
We travel by high-speed ferry to Martha's Vineyard for a day of exploration. We land in Oak Bluffs, noted for its "gingerbread" cottages, and take a sightseeing tour that encompasses several of the island's most popular towns. We will learn about the history of Martha's Vineyard, the diverse culture and lifestyles of each of the six towns on the island, and how the island has come to be what it is today. We return by ferry to Hyannis later this afternoon.
Friday, 11 September 2026: Day Trip to Nantucket (B)
Today is another ferry, this time to Nantucket, a tiny picturesque island off the coast of Cape Cod with a history of seafaring greatness. This island was once the greatest whaling center in the world. More than 800 homes built between 1740 and 1840 by brave whaling men still stand, lovingly preserved. Upon arrival, we'll enjoy a narrated tour and after our tour there will be some personal time to explore the island further before heading back to the mainland. We return by ferry to Hyannis.
Saturday, 12 September 2026: Newport & The Breakers; Farewell Dinner (B,D)
This morning we pack up and head to the adorable seaside town of Newport, Rhode Island. During the Gilded Age, America's wealthiest families flocked to the City by the Sea, making the area their summertime playground. We begin with a tour of The Breakers, the 70-room “summer cottage” of Cornelius Vanderbilt II. From here you may choose to visit other mansions or explore the town on your own. There is a wonderful 3.5-mile walk along the sea wall that offers panoramic ocean views, crashing waves and a glimpse of the dozen mansions that front this area. Your Tour Leader can offer additional suggestions. Late this afternoon, we will regroup to make the hour-long drive to Providence and enjoy our Farewell Dinner together. Overnight Providence Airport Area - 1 night
Sunday, 13 September 2026: Return Home from Providence (B)
Sadly, our time together has come to an end. Make your return flight home at your convenience. The airport is less than 10 minutes from the hotel. Each traveler should determine when they need to depart the hotel based on flight time, allowing approximately 1.5 - 2 hours at the airport.
Boston, Cape Cod and Newport
September 7 - September 13, 2026Pricing
Room Share
$3,394.00Single Room
$4,596.00Non-Members
ADD $50.00Status of this Tour
Trip Full, Accepting Standbys
Tour Pricing Includes
- All meals and activities expressly listed in the itinerary, PLUS...
- All tipping of local guides
- WTT Tour Leader to enhance the individual & group experience
- Arranged room sharing with another solo traveler
- Travel Dollar credits (a benefit of WTT membership) toward future travel with WTT
Not Included In The Price
- Airfare and other transportation from your home and return to your home,
- Airport transfers
- Meals and activities not specified in the itinerary,
- Any personal expenses,
- Any gratuities for WTT Tour Leader
- Trip Cancellation / Trip Interruption Insurance
Payment Dates -and- Cancellation Terms for This Tour
You have 3 days to cancel and receive a refund. Thereafter, the amount required at time of reservation is non-refundable and the following cancellation penalties will be enforced.
Wednesday, 11 Mar 2026: Last day $250 deposit can be converted to a credit for use on a new reservation; thereafter the deposit is forfeited.
Tuesday, 9 Jun 2026: Balance Due. Cancellation after this date but before Friday, 24 Jul 2026 results in a cancellation penalty of 50% of your Total Tour Cost.
Friday, 24 Jul 2026: Cancellation on or after this date results in a cancellation penalty of 100% of your Total Tour Cost.
Using Parked Credits: If traveler cancels during the 3-day cancel without penalty period, used credits will be re-parked with the original expiration date(s). Thereafter, cancellation will result in forfeiture of the total amount of parked credits used. If applicable, additional cancellation penalties will be assessed based on date of cancellation.
To Cancel: Should you need to cancel after
your space on this tour is confirmed, you must use the Cancellation Form. Cancellation penalties are based on the date we receive your
cancellation form. No other method of communicating a cancellation will be accepted.
Insurance Reminder
Trip Cancellation / Trip Interruption Insurance is not included in the cost of the tour. It is your responsibility to determine the amount and type of coverage you require to recoup some or all of your travel investment, whether you cancel, are unable to complete the tour, or the tour cannot operate. Section 4.0 of WTT Terms & Conditions explains what will happen to your payments in the unlikely event that your tour cannot operate.
WTT is not licensed to sell travel insurance. You can purchase travel insurance from any provider you choose. To get an idea of rates, please go to NTA Travel Protection Plan (Enter 206063 for the "Tour Operator Location #") or TravelGuard.
Boston, Cape Cod and Newport
September 7 - September 13, 2026Flights, Transfers & Lodging
Arrival & Departure Information
Travelers will make their own air arrangements as follows:
When searching for flights for this trip, be sure to search "Multi-city" or "Multiple Destinations." For comparison, you may also want to search for one-way fares.
Arrival Airport: BOS - Boston, MA (Logan Int'l Airport)
Arrival Date: Monday, September 7. Arrive no later than 4:30pm.
Arrival Transfer: Use local shuttle or taxi service. Details provided in Final Travel Instructions.
Departure Airport: PVD - Providence, RI (Providence - T.F. Green Airport)
Departure Date: Sunday, September 13th. Depart at your convenience.
Departure Transfer: Use local shuttle or taxi service. WTT Tour Leader will assist in coordinating ride sharing.
When to Book Your Air
Once you have booked your flights (or other transportation arrangements), use the Travel Arrangements Form to send WTT your flight details. Use the same form to update your information should it change.
Airport Transfer Information
When arrival transfers are not included: WTT will provide suggestions to get to the hotel in your Final Travel Instructions about 2-3 weeks before the start of the tour. You'll also be able to see who else is arriving at the same time if you want to coordinate ride-sharing to the hotel.
Don't Worry. We're Expecting You: One of the reasons we ask for your travel arrangements is so we know when you're arriving and can approximate when you should be at the hotel. Your Final Travel Instructions will have instructions on what to do and who to contact if your flight is delayed.
Lodging / Hotels
Hyannis: Anchor In Hotel
Providence: HGI - Providence Airport/Warwick
Whenever possible, we choose hotels that are near the city center and/or where there are things to do and places to eat within walking distance of the hotel. When the chosen hotel is not within walking distance of much, transportation options, at the traveler's expense, are typically available.
In the unlikely event WTT is unable to provide the hotel accommodation(s) listed, for whatever reason, WTT will substitute similar quality accommodation(s) at no additional cost to the traveler.
Want to Arrive a Day Early?
Worried about possible flight delays? Consider arriving one day before the official tour start date. Many of our travelers choose this optional service. Your pre-tour package includes:
- The room (standard check-in times apply)
- Optional activity suggestions prior to tour
$198.00 Roomshare pp $394.00 Single Occupancy
The pre-tour package is an optional service. Rates are established at time of tour posting. Early check-in is solely at the discretion of the hotel and cannot be arranged in advance.
Early Arrival Hotel: This tour uses the same hotel used on the first night of the tour.
Boston, Cape Cod and Newport
September 7 - September 13, 2026Destination Information
What do others say about this tour and traveling with WTT?
How Does Room Sharing Work?
On the Reservation Form there are 3 choices regarding room-sharing.
Note: Certain room-types may be unavailable at the time you make your reservation. If a room-type is unavailable the choice will be greyed out.
- Select "Yes, I want to share a room" and WTT will assign you a roommate when Final Travel Instructions are sent.
- You can specify a roommate by entering her name where indicated. If your named roommate is not on the tour, for any reason, WTT will assign you a roommate unless you pay to have your own room, if available.
- Select "No, I do not wish to share a room" if you want to have your own room. Additional costs apply.
- All shared rooms have 2 beds
- All shared rooms are non-smoking
- No special requests about your roommate can be accommodated
- See "Frequently Asked Questions" TAB for more details
How Active is this Tour?
- 60% Easy
- 40% Moderate (3-4 hour walking tour)
Your Responsibilities as a Solo Traveler
As a solo traveler you are responsible for yourself, your possessions, your physical fitness, and all other aspects related to participation in the WTT tour you have chosen. Be sure to read the itinerary closely to better understand the physical requirements necessary for the tour.
WTT tours are not suitable for anyone whose mobility is challenged or compromised. If you struggle with walking, standing or negotiating stairs or if you are in doubt as to your ability to meet the physical activity requirements, you should not sign up for this trip.
What is the Group Size?
You will be introduced to the WTT Tour Leader when you receive your Final Travel Instructions, about 2-3 weeks before the tour begins.
Learn about your fellow travelers after final payment by visiting MyWTT. Room sharing assignments will be listed in the Final Travel Instructions.
What meals are included and how are dietary restrictions accommodated?
Each day of the itinerary lists the included meals for that day (B,L,D,O=Other). When a meal is not included, the WTT Tour Leader will have suggestions for where to eat.
You do not have to dine alone unless it is your personal choice. You'll most likely be dining with new acquaintances you've made, or you can join the Tour Leader.
Dietary Restrictions: Vegetarian and gluten-free dietary restrictions can be accommodated on this tour with limited selections.
What clothing and items should I pack for this trip?
For This Trip You May Want—
- One smart-casual outfit if you’d like to dress up a bit for dinners.
- Lightweight but warm jacket/sweater for the cool mornings and evenings.
- Raincoat, poncho or travel umbrella, just in case.
Good Packing Habits—
- Bring what you need to get a good night's sleep, such as ear plugs, white noise generator, sleeping aids, etc. Unfamiliar noises of all types can disrupt your rest.
- Pack a limited amount of comfortable, casual clothing that layer and coordinate. Your fellow travelers will not mind or even notice – seeing you in the same clothing.
- Bring only two pairs of everyday shoes: one pair of well-broken-in walking shoes, and a second pair that could do double-duty as a walking shoe or a slightly dressy shoe.
- Pare down your beauty regimen to the bare minimum and always pack travel-sized toiletries.
- Pack medication in your carry-on and pack only as much as needed for the duration of your tour plus a few extra days as a precaution.
What are the luggage restrictions for this tour?
We will use the WTT Coach. Luggage restrictions are driven by the physical space limitations of the vehicle and the requirement that travelers manage their belongings on their own.
- It is best to travel as lightly as possible. Most travelers regret when they have packed too much.
- You may bring one suitcase plus small shoulder bag/day pack/purse.
- Maximum suitcase size: 22-24 inches in height. This is the size of bag that fits into the overhead bins of aircraft. Suitcases larger than this will not fit properly in the WTT coach; don't bring them.
- The weight of your bag should not exceed 30 pounds as you will need to lift it into the coach luggage compartment.
- You are responsible for managing your own belongings. We expect you to take your belongings from the coach to your room and to bring it back to the coach and load it on days we change hotels. We do not provide luggage pulls; they are not safe and are inconvenient. The possibility of steps exist at most hotel entrances.
How much money should I bring on this tour?
What are the tipping guidelines for this tour?
- You are responsible for tipping waitstaff, porters, or other individuals who provide a service to you at the hotel, or other public locations.
- You may want to tip your WTT Tour Leader for an outstanding job. The amount is entirely a personal preference. If you'd like a guideline, consider $8-$10 per day.
Can I transfer my deposit to another tour?
To get off this tour and register for another tour, you must follow these steps - in the order shown:
2) WAIT before submitting your new reservation! You must receive the Cancellation Confirmation email before submitting your new reservation. This can take up to 2 business days. The Cancellation Confirmation email will list the amount of parked credits from this tour that are now available to use on a new reservation.
3) COMPLETE the new Reservation Form and USE the parked credits towards your deposit on the new tour.
Note: If you used Parked Credits to pay the deposit on this tour, these credits cannot be used a second time and are not eligible to be transferred.
What happens if I need to cancel this tour?
Boston, Cape Cod and Newport
September 7 - September 13, 2026STANDBY REQUEST FORM
1)There is no obligation to take the tour if you submit a standby request. 2)If an opening occurs, WTT will email you based on the room-type available. 3)WTT membership is not required to go on standby, however we do notify our members ahead of non-members.
Our Promise to You
It doesn’t matter which tour you choose.
You’ll find your people and make memories that last a lifetime.