Caribbean Cruises from Boston

As Fall approaches and our Boston weather is heading from bad towards "miserable", many Bostonians dream of going south like the birds. This is actually good timing as there are a number of cruise lines moving their Northern ships south for the Caribbean season.

These so-called repositioning cruises can be an exceptional bargain.  Some  of these cruises have fewer stops but at almost half-price and with the wind blowing cold outside, this really sounds good..

The Caribbean weather in early Fall is particularly appealing since it is still warm but not hot as in Summer.  The temperature is perfect for spending time on the beach or exploring the many islands. 

Boston is a great starting point for a cruise to the Caribbean. You may want to add a few extra days at the beginning to explore Boston, one of the most historic and walkable cities in the US.

So, next Fall, when you are walking on the beach in the Caribbean, think of us poor Bostonians shivering away.

 

 

 

 

Itinerary Example: Holland America - 14 Night Southern Caribbean

Day 1 - Boston
Beautiful, walkable city with many attractions and historic sights.  Boston has beautiful parks, waterfront and riverfront, as well as museums, aquarium and excellent shopping.  Known for its great seafod restaurants.

Day 2 - At Sea

Day 3 - Kings Wharf, Bermuda
This tropical island paradise is most famous for its great climate and outstanding pink coral beaches. Once a British colony,  Bermuda is a gem in the middle of the Atlantic that will please you with its European architecture and charm.

Day 4 - At Sea

Day 5 - At Sea

Day 6 -Charlotte Amalie, St. Thomas
Shopping capital of the Caribbean, that draws many visitors each year to buy goods duty-free. Also known for scuba diving, golf courses, picture-perfect beaches and spectacular nightlife.

Day 7 - Philipsburg, St. Maarten
Tropical Island with friendly people, pristine beaches and exceptional food and shopping. Famous among diving enthusiast.

Day 8 - Castries, St. Lucia
Lush unspoiled tropical island with majestic mountains, spectacular waterfalls and breathtaking beaches.

Day 9 - Bridgetown, Barbados:
The British roots are still strong on this island and you may find cricket and afternoon tea right next to classic sand beaches and jungles. Go on an island tour or explore the many attractions in town.

Day 10 -At Sea

Day 11 - Willemstad, Curacao
Old Amsterdam is still alive in this historic quaint harbor town. Browse through its many excellent shops and then relax with a drink made of the famous Curacao liqueur on one of the verandas.

Day 12 - At Sea

Day 13 - At Sea

Day 14 - Half Moon Cay, Bahama
A private island with access for cruise ships only. It is known for its pristine beauty and crystal-clear turquoise waters, powdery white sand beaches, and lush tropical surroundings.

Day 15 - Ft. Lauderdale, Florida
Arrival time is at 7 am, followed by checkout. Disney World, Sea world and many other world-famous amusement parks are a short trip away.Take a tour at Cape Canaveral, where the space program started.
 

  

 

Cruises from Boston to the Caribbean - 2025

DateCruiseStopsLinePriceDetails