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New England Fall & Caribbean Cruise

Boston, Massachusetts To Miami, Florida,
Onboard - Insignia
28 Nights
Includes 10 night New England Falls Tour

2025

Oct , 17

Package Price Starts From
£4579
New England Fall & Caribbean Cruise
Friday 17 October, 2025
Duration: 28 Nights
Boston, Massachusetts To Miami, Florida
Onboard - Insignia
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Embark on a journey that combines the best of two seasons. Start with a 10-night tour through New England’s stunning fall landscapes — from Boston’s rich history to Maine’s rugged coastlines, the White Mountains, and the charm of Cape Cod. Then, set sail on a 16-night Holland America cruise, visiting Bermuda and some of the Caribbean’s most beautiful islands, including St. Barts, Antigua, St. Lucia, and Barbados, before finishing in Miami. It’s a unique way to experience the vibrant colors of autumn and the warmth of the tropics, all in one unforgettable trip.

What's Included

Flights

London Heathrow to Boston

Miami to London Heathrow

Hotels

1 Night in Boston at TBC

1 Night in Portland at TBC

1 Night in Bar Harbor at TBC

2 Nights in Bretton Woods (White Mountains) at TBC

1 Night in Newport at TBC

2 Nights in Cape Cod at TBC

2 Nights in Boston at TBC

1 Night in Miami at Sole Miami

Tours

Cape Neddick Lighthouse and Kennebunkport - Boston - Portland

Acadia National Park - Portland - Bar Harbor

Flume Gorge Canyon - Bar Harbor - White Mountains

Tour of The White Mountains - White Mountains

Tour of Newport - Newport

Cape Cod at Leisure - Cape Cod

Tour of Plymouth - Cape Cod - Plymouth - Boston

Cruise

Island Inspiration on Oceania Cruises on ship Insignia
Click here for full cruise details

Pre Cruise Itinerary

Starting on Friday 17 October, 2025

Flights

Fri, Oct 17, 2025,
From: London Heathrow to Boston

Hotel

Fri, Oct 17, 2025,
Location: Boston
Name: TBC
Duration: 1 Nights

Excursion

Sat, Oct 18, 2025,
Tour: Cape Neddick Lighthouse and Kennebunkport

Along the route north of Boston lies over centuries of history as well as some of the East Coast's finest beaches and seascapes. After passing through Portsmouth, the oldest community in New Hampshire knows for its thriving fishing community and historic buildings, you will stop at New England's most iconic light that sits on the summit of Cape Neddick, a small off-shore rocky island. The Cape Neddick Lighthouse (also called 'the Nubble') is considered the most photographed lighthouse in America. Your next stop will be Kennebunkport. Kennebunkport is a small, charming coastal town and home to the palatial summer estates of prominent politicians, including the 41st U.S. President, George Herbert Walker Bush. You will experience first-hand why it was voted 'the place to be all year'. From Kennebunkport, it's on to Portland, Maine's largest city. You will enjoy the beauty of this coastal region, including lighthouses and local lobster fishermen. Afterwards, you are free to explore Portland, stroll the cobblestone streets of Portland's famous Old Port waterfront and perhaps you may wish to enjoy the famous Maine lobster roll!

Hotel

Sat, Oct 18, 2025,
Location: Portland
Name: TBC
Duration: 1 Nights

Excursion

Sun, Oct 19, 2025,
Tour: Acadia National Park

Journey to the North today to the "Crown Jewel of the North Atlantic Coast": - Acadia National Park. Situated on the coast of Maine and home to stunning landscapes and diverse wildlife, Acadia National Park is beautiful year-round and gorgeous in every season. You'll pass through quaint villages where local fishermen mark their grounds with colorful buoys prior to arriving in the small town of Bar Harbor. Known for its stunning coastal beauty, Bar Harbor has a world renowned ambiance that blends seashore community, Downeast character, and the fresh Maine Lobsters. Your afternoon is free to explore the quaint village of Bar Harbor on your own. Galleries, boutiques line the village of Bar Harbor.

Hotel

Sun, Oct 19, 2025,
Location: Bar Harbor
Name: TBC
Duration: 1 Nights

Excursion

Mon, Oct 20, 2025,
Tour: Flume Gorge Canyon

Travel inland and head for the White Mountains, the "rooftop of New England". This journey will take you through the pristine and scenic woodlands along the Kancamagus Highway to Franconia Notch which is an eight mile pass between two mountain ranges, both known for their renowned foliage areas and natural landscapes. Be prepared for a miraculous view which is the natural wonder in Franconia Notch State Park, the Flume Gorge State Park. The Flume Gorge is a natural gorge extending 800 ft horizontally at the base of Mount Liberty in Franconia Notch State Park, New Hampshire.

Hotel

Mon, Oct 20, 2025,
Location: Bretton Woods (White Mountains)
Name: TBC
Duration: 2 Nights

Excursion

Tue, Oct 21, 2025,
Tour: Tour of The White Mountains

The White Mountains of New Hampshire are a wonderful place to escape, explore and create unforgettable memories. Experience towering peaks, stunning scenery unrivaled anywhere in the Northeast, spectacular waterfalls and tax-free shopping. Enjoy a visit to a local Maple Farm and watch how the famous 100% pure Maple Syrup is being made. Tradition pairs with the latest advancements in technology to produce the finest maple syrup and product from the healthiest trees.

Excursion

Wed, Oct 22, 2025,
Tour: Tour of Newport

Today we journey south and experience many miles of forest scenery before leaving New Hampshire. We then enter Rhode Island, the 'Ocean State',-home to spectacular coastal scenery and awe-inspiring architecture. We then arrive at our destination for today:,- Newport is considered by many as the Sailing Capital of the World. Here you may wish to explore Newport's natural beauty along its Cliff Walk. Here, between the pounding surf of the Atlantic Ocean and sprawling lawns, sit the famed Gilded Age mansions that once were the summer playgrounds for socialite families such as the Astor's and Vanderbilt's. Visit one of these opulent mansions for a glimpse into the lavish lifestyle.

Hotel

Wed, Oct 22, 2025,
Location: Newport
Name: TBC
Duration: 1 Nights

Hotel

Thu, Oct 23, 2025,
Location: Cape Cod
Name: TBC
Duration: 2 Nights

Excursion

Fri, Oct 24, 2025,
Tour: Cape Cod at Leisure

Today is your day to explore or to rest in the beauty of Cape Cod. Your Tour Director will have plenty of suggestions which may include, weather permitting, a ferry ride to Martha's Vineyard (optional, fee applies) that is known for its proud history and unique character or perhaps a journey to experience the magic of Provincetown, an oasis on the Cape that sits on the edge of the continent, 60 miles out of seas and is truly a small haven at the end of the world, with the most beautiful beaches of New England. Provincetown also offers a glimpse as the history and legacy of the US 35th president John F. Kennedy.

Excursion

Sat, Oct 25, 2025,
Tour: Tour of Plymouth

Today you will have the opportunity to visit Plymouth, the town where English colonists first made a home in New England. Discover Plymouth Rock, which was the landing place of the Pilgrims and the famous Mayflower (onboard admission not included), the ship that carried the Pilgrims from England to Plymouth before heading to Boston. Here you may retrace portions of the Freedom Trail which could include such experiences as a stroll beside Boston Common, King's Chapel, the Boston Massacre site and numerous pubs and taverns where America's Founding Fathers toasted freedom! Perhaps you may wish to try a local cup of clam chowder ("chowdah") while there. Explore Quincy Market, Boston's first marketplace from the 1800's, now home to boutiques, cafes and shops.

Hotel

Sat, Oct 25, 2025,
Location: Boston
Name: TBC
Duration: 2 Nights

Hotel

Wed, Nov 12, 2025,
Location: Miami
Name: Sole Miami
Duration: 1 Nights

Cruise Itinerary

Cruise Starts on Monday 27 October, 2025, Onboard: Insignia

CRUISE DAY

1 Boston, Massachusetts

Boston, Massachusetts

Mon, Oct 27, 2025

Arrives: 07:00am and Departs: 18:00pm

Port Information

CRUISE DAY

2

Newport, Rhode Island

Tue, Oct 28, 2025

Arrives: 08:00am and Departs: 17:00pm

Port Information

CRUISE DAY

4

Hamilton

Thu, Oct 30, 2025

Port Information

CRUISE DAY

5

Hamilton

Fri, Oct 31, 2025

Departs: 06:00am

Port Information

CRUISE DAY

5

Saint George

Fri, Oct 31, 2025

Arrives: 08:00am and Departs: 16:00pm

CRUISE DAY

8 Gustavia

Gustavia

Mon, Nov 03, 2025

Arrives: 08:00am and Departs: 18:00pm

Port Information

CRUISE DAY

9 Saint John's

Saint John's

Tue, Nov 04, 2025

Arrives: 07:00am and Departs: 17:00pm

Port Information

CRUISE DAY

10 Castries

Castries

Wed, Nov 05, 2025

Arrives: 09:00am and Departs: 20:00pm

Port Information

CRUISE DAY

11 Bridgetown

Bridgetown

Thu, Nov 06, 2025

Arrives: 08:00am and Departs: 19:00pm

Port Information

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Post Cruise Itinerary

Starting on Thursday 13 November, 2025

Flights

Thu, Nov 13, 2025,
From: Miami to London Heathrow

Pricing

Cruise Packages
Prices shown are based on 2 people sharing.
Cat Code Cat Description Price
G Inside Stateroom £4579
(Single Occ: £)
F Inside Stateroom £4739
(Single Occ: £)
D Ocean View Stateroom £4979
(Single Occ: £)
C2 Deluxe Ocean View Stateroom £5249
(Single Occ: £)
C1 Deluxe Ocean View Stateroom £5419
(Single Occ: £)
B2 Veranda Stateroom £6149
(Single Occ: £)
B1 Veranda Stateroom £6279
(Single Occ: £)
A3 Concierge Level Veranda £6419
(Single Occ: £)
A2 Concierge Level Veranda £6579
(Single Occ: £)
A1 Concierge Level Veranda £6719
(Single Occ: £)
PH3 Penthouse Suite £7479
(Single Occ: £)
S Solo Oceanview Stateroom £7519
(Single Occ: £7519)
PH2 Penthouse Suite £7709
(Single Occ: £)
PH1 Penthouse Suite £7879
(Single Occ: £)
VS Vista Suite £9869
(Single Occ: £)

Package Type:
Inside Stateroom

Exclusive Price:
£4579

(Single Occ: £n/a)
Need to Know:
Itinerary
Itinerary

Port order may vary by date of departure. Check your specific sailing for exact departure and arrival times. All times are local to the port. Itineraries are subject to change at any time without notice. View a list of tender ports.

EMBARKATION + DISEMBARKATION

Due to security reasons, all guests must be on board 2 hours before sailing on Day 1 of cruise. Disembarkation usually begins 2 hours after docking on final day of cruise.

Island Inspiration

Departing: Monday, 31st March 2025

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