Enchanted Islands of New England

September 9, 2022 thru September 16, 2022

Enjoy this perfect Autumn escape to coastal New England!

Enchanted Islands of New England Tour Presentation – click here to learn all about this tour and view pictures.




Roundtrip air transportation from Tucson to Boston*




Narragansett Bay Schooner/Yacht Cruise & Ferries


10 days, 9 nights

Activity Level 3



13 meals included




Livery service to/from your home included

Tour Highlights

  • Tour of Boston’s Historic Freedom Trail
  • Fenway Park Tour
  • Guided tour of Newport’s Ten Mile Drive
  • Admission to the Breakers Mansion
  • Narragansett Bay Schooner/Yacht Cruise
  • Round trip ferry to Block Island
  • Guided tour of Block Island
  • Round trip ferry to Martha’s Vineyard Island
  • Guided tour of Martha’s Vineyard
  • Guided tour of the Cape to Provincetown
  • Provincetown Whale Watch Cruise
  • Round trip ferry to Nantucket Island
  • Guided tour of Nantucket


  • Roundtrip air transportation from Tucson to Boston*
  • Transfers & motorcoach transportation
  • Pick-up/livery service
  • 7 nights lodging
  • Admissions & tours as described
  • Baggage handling
  • 13 meals (7 breakfasts, 1 lunches, 5 dinners including Huzzah! and a traditional lobster dinner)
  • Services of a Tour Director
  • Motorcoach refreshments
  • Taxes & gratuities for included items

Day 1 - Welcome to Boston & Coastal New England!

This morning we fly to Boston’s Logan International airport to begin our Islands of New England adventure! We’ll receive a warm greeting by our tour director and board our luxury transportation and shuttle to our Boston area hotel for a two-night stay. Take some time to relax and freshen up before enjoying a delicious welcome dinner this evening. (D)

Day 2 – Boston’s Freedom Trail, Fenway Park Tour & Huzzah!

Enjoy a hearty breakfast before we spend the day exploring Boston, the birthplace of American Freedom!  Tour along Boston’s famous Freedom Trail! See many historic sites while hearing tales of the brave Bostonians and Colonialists who dared to challenge Britain and helped establish the greatest republic in the world.  Enjoy free time for lunch on our own at Faneuil Hall Marketplace, which is as alive today as it was in 1742 when our nation’s fathers proclaimed it “The Cradle of Liberty.”  This afternoon, enjoy a private tour of Fenway Park for a enjoy a ‘once in a lifetime’ experience in the country’s oldest and most beloved ballpark, where the Babe pitched, The Kid hit, Yaz dazzled and Big Papi thrilled! Tonight, leave our 21st century troubles behind and join the Sons and Daughters of Liberty for the best hospitality in 18th century Boston! We’ll join Samuel Adams, John Hancock, Dorothy Quincy, Paul Revere and other prominent Bostonians for a night of colonial merrymaking, savory colonial dinner, authentic games, boisterous songs and cheerful dance in a spirited colonial tavern atmosphere! Huzzah! (B,D)

Day 3 – Newport Tour, Breakers Mansion & Narragansett Bay Cruise

This morning enjoy breakfast before departing for Aquidneck Island; more commonly known as Newport, Rhode Island – America’s first resort and yachting capital of the world. Begin with a tour along the magnificent Ten Mile Drive where we’ll step back in time to the opulent era of the Gilded age where elite families such as the Vanderbilt’s and Astor’s built their “summer cottages” to retreat from the city life.  After our tour, enjoy time along the waterfront for lunch and shopping.  This afternoon, tour the grand dame of all the Mansions – The Breakers. This 70 room Italian style Renaissance-style villa was built by Cornelius Vanderbilt II. We’ll finish the afternoon off aboard one of Newport’s classic schooners or motor yachts for a cruise around Narragansett Bay!  Check into the Newport Harbor Hotel for a relaxing two-night stay. Tonight, enjoy another delicious dinner at one of Newport’s fine restaurants. (B,D)

Day 4 – Block Island & Luncheon

This morning after breakfast, we’ll board the ferry for a ride to the famous Block Island.  This island, 12 miles off the coast of Newport, has been heralded as ‘one of the twelve best unspoiled area in the Western Hemisphere” and is known for its relaxed way of life. Enjoy a guided tour with spectacular views of the rolling dunes, dazzling beaches and Victorian village. Step back in time to a bygone era and enjoy lunch at one of the Islands grand hotels.  Return to our hotel in Newport and enjoy the balance of the day and evening on our own to dine at one of many of Newport’s great restaurants. (B,L)

Day 5 – Martha’s Vineyard Island & Cape Cod

Following breakfast, we’ll check out of our hotel and depart for the beautiful sandy shores of Cape Cod where we’ll board the ferry for a cruise to the beautiful island of Martha’s Vineyard Island.  Once an early refuge for coastal ship traffic, it blossomed into a whaling community in the 18th and 19th century and evolved to what is now a popular resort destination of today, where even US President’s chose to vacation!  Explore the diversity of its island towns, take a walk along our pristine shores, and step back in time to a more leisurely pace.  Enjoy a guided tour of Oak Bluffs which is noted for its collection of small Carpenter Gothic cottages clustered in the Methodist Camp Meeting Grounds, and Edgartown, known for is stately Greek revival homes built by sea captains of years ago. This afternoon, cruise back to the mainland and arrive to the Hyannis Harbor Resort, overlooking lovely Hyannis Harbor, for a relaxing three-night stay. Take some time to relax and freshen up before enjoying dinner together. (B,D)

Day 6 – Chatham, Outer Cape & Provincetown Whale Watch

Following breakfast, we’ll depart with our tour guide for a fun-filled day touring the lower and outer Cape! Begin touring through the charming seaside village of Chatham with a picture stop at the Chatham Light.  Continue on to Provincetown – the tip of the Cape, and spend some time browsing around the downtown waterfront area with all its artistic and eclectic shops. This afternoon, choose between an exciting Whale Watch Cruise to view these magnificent mammals frolic and feed in their ocean playground! Enjoy dinner at our leisure this evening at one of the harbor front restaurants. (B)

Day 7 - Nantucket Island

This morning after breakfast, we will board the ferry and cruise to the enchanting Island of Nantucket, fondly known as “The Gray Lady”. Once the whaling capitol of the world in the 1800’s, it has since evolved into a popular ‘hide away’ vacationing spot for the wealthy. Enjoy Nantucket’s charm with its cobblestone main street, narrow roads, simple Quaker-style homes and handsome houses dating back to the whaling days of the early 19th century. Enjoy a guided tour of this beautiful island with views sandy beaches, historic lighthouses, charming villages and coastal beauty. Enjoy some free time to venture through the many charming shops and galleries before returning by ferry back to the mainland. Tonight, we’ll feast on a traditional Cape Cod lobster dinner at one of the Cape’s popular seafood restaurants! (B,D)

Day 8 - Hyannis & Sandwich, Depart for home

This morning before saying farewell to Cape Cod, enjoy a tour of Hyannis with a picture stop to the JFK Memorial and Korean War Memorial overlooking beautiful Veterans Beach.  Continue touring through Sandwich, Cape Cod’s oldest town, with views of Shawme Pond, Dexter Grist Mill and Sandwich Village. Return to Boston’s Logan International Airport for our departure home taking with us fun-filled memories of our Islands of New England vacation! (B)

Pleasurebent Tours reserves the right to make changes to this itinerary when necessary for the proper handling of the tour.

Package Pricing

$4,356 per person

Double occupancy

Deposit: $200

$5,166 per person

Single occupancy

Deposit: $200

Price Includes

Roundtrip air transportation from Tucson to Boston*
Transfers & motorcoach transportation
Pick-up/livery service
7 nights lodging
Admissions & tours as described
Baggage handling
13 meals (7 breakfasts, 1 lunches, 5 dinners including Huzzah! and a traditional lobster dinner)
Services of a Tour Director
Motorcoach refreshments
Taxes & gratuities for included items

Booking Policy

We pride ourselves on great service and an enjoyable experience for all and will go over our booking policies after you make your request for booking. If you’d like to learn more about our booking policies before your trip, give us a call at (520) 325-8839, or visit our Booking Policies page. Click here for more information on our booking policies.

Travel Insurance

We recommend that all travelers purchase a travel protection plan to help protect themselves and their trip investment. Travel protection plans can provide coverage for trip cancellation, trip interruption, emergency medical expenses and emergency evacuation/repatriation, trip delay, baggage delay, and more. For your convenience, we offer the following plan for this tour:


360° Adult Group Choice Flyer– Provides an overview of benefits and coverage limits

360° Adult Group Choice Policy – Provides the full coverage term details, including exclusions and limitations.

Contact us to purchase. If you have questions about coverage, please review the policy or contact Travelex Insurance Services at 888.574.7026 or email 360group@travelexinsurance.com. Travelex Insurance Services, Inc. CA Agency License #0D10209. Travel Insurance is underwritten by Berkshire Hathaway Specialty Insurance Company; NAIC #22276. RWF


Level 3: Moderate

Expectations: Expect a moderate amount of walking. There will be time to rest on the coach and between attractions. To enjoy this tour, you should be prepared to walk slightly longer distances, climb stairs and tolerate periods of standing, for example on city walks, sightseeing stops or ship excursions. The daily pace and timing can fluctuate significantly between longer and shorter travel days, with additional activities possibly occurring in the early morning or evening. There may be some changes in altitude or temperatures.

Appropriate for: Most travelers beginning with those who are moderately fit, lead semi-active lives, are comfortable participating in long days of activities and expect some physical exertion.

Visit our Activity Level Ratings page under Plan Your Tour for full information on the ratings system.


For your reference, we send to you a detailed itinerary approximately 3-4 weeks prior to the scheduled tour departure. This has day-by-day times and events, hotel information where you can be reached in case of an emergency, and airline information.

The times listed on the itinerary are all approximate. We cannot be held responsible for schedule changes due to unforeseen circumstances with the weather, transportation agents, highway conditions, hotels or contracting agents.


It is always a good idea to carry on your person a list of medications that you are taking and an emergency contact phone number while you are traveling. And we suggest making a copy of the itinerary and provide it to a friend or family member.


You will be issued your boarding pass the morning of our departure, after your arrival at the Tucson International Airport. If you have a frequent flyer number, or a TSA number, please call our office at least 3 days prior to the tour to ensure we can note these in your reservation.

If you are joining the tour from locations other than Tucson, we make other arrangements for you to join the tour. Please call our office for more details.


Do not forget to bring your government issued picture ID to show at the airport. A Driver’s License or Passport is preferred. If you do not have the proper ID, the airline will turn you away.


We have arranged for handling for one piece of luggage per person regarding the skycaps (where available) and hotels. If you check through luggage note that the maximum weight for the checked piece of luggage is 50 pounds and maximum size is 62 inches (length + width + height). If your bag weighs over 50 pounds the airlines will levy an extra fee that you will be responsible to pay. If you feel the need to lock your checked through luggage and your bag is searched, your lock could be damaged in the process. You can purchase a TSA (Transportation Security Administration) accepted and recognized lock at any luggage store. Make sure you ask for a TSA approved lock. These locks are the kind that TSA screeners can open by using a special tool without breaking. Passengers can carry-on 1 bag (dimensions are limited to 10x16x24 inches), plus a personal type bag, like a purse. We advise that you pack your carry-on lightly. There are restrictions regarding your carryon baggage and contents due to enhanced security


On our scheduled airline for this tour, passengers are assessed a $30 fee per checked in bag, by the Airlines, upon checking in for the flight.


All hotel baggage handling fees are included. We also include basic gratuities for the Tour Director, Coach Driver, Livery Drivers and local Tour Guides. If someone has truly gone above and beyond additional tipping is permitted, but never required.


For your convenience, we have a (round-tour) door-to-door pickup service with each multi-day tour. (This service is not available to all clients depending on your location.) Approximately 2 to 3 days prior to the departure date you will receive a call from our office and we will tell you your assigned pickup time. (These times can vary up to 15 minutes depending on traffic.)


With passenger health in mind, we are not currently offering daily seat rotation. You will have an assigned seat and boarding order to allow for social distancing among passengers. At booking let us know if you prefer Front, Middle or Back of motorcoach. Each section comprises 4 to 5 rows. We will try to accommodate all requests. If we are unable to honor all requests, preference will be given based on date of your tour deposit.


If you would like to request special accommodations at the hotel(s) where we are lodging, please call us as soon as possible and we will forward these requests for you. The phone numbers of the hotel(s) where we are staying are listed on the itinerary.

Many hotels around the country have instituted a "reconditioning fee" of $300 or more that is levied upon a guest that smokes in a non-smoking room. If this occurs during our tour you will be responsible for paying this fee to the hotel prior to check-out.


We pay close attention to your requests but please realize that these are merely requests and cannot be guaranteed.


Pleasurebent Tours acts solely as an agent in arranging hotels, transportation, sightseeing, baggage-handling, and other services and does not assume any liability for injury, damage, loss or delay due to any act or default of any company or person. We, along with our subcontractors, reserve the right to make changes to an itinerary if it is necessary for the proper handling of a tour.


The average daytime high temperatures during our stay in New England is typically in the mid 60'’s and the average night-time temperature is usually low 50’s. When we are on the shore or on boat those temperatures may drop 5-10 degrees or more. Typically, we can expect some Fall storms. Please be sure to bring a sweater and / or rain jacket, along with good walking shoes and a hat. There are no dress codes for the areas we take you to on this tour.

Inquire About This Tour

Submit your inquiry for more information about a tour. We will get back to you with a (human) response as soon as possible. During the week that’s usually within a couple of hours. Evenings and weekends may take us a little bit longer. Please note that this is an inquiry for tour bookings only and does not constitute or confirm a reservation on a tour.
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Call 520.325.8839 to Book Today!

If you aren't ready to inquire by email or would rather call and speak to a team member, we look forward to hearing from you.

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