Cruises from Boston to Caribbean Ports

Find best cheap prices for these repositioning cruises!

Cruises from Boston to Caribbean destinations are for "repositioning" - and this means you'll stop at lots of interesting ports as well as having days at sea.  Best of all, if you're looking for Caribbean cruises, this is where you'll find them!

Caribbean cruises from Boston for repositioning happen because the cruise ships need to move from one seasonal location to another.  In late October, Royal Caribbean's Jewel of the Seas makes a repositioning cruise from Boston to varous Caribbean ports, and then back to Tampa, where she offers Caribbean cruises all winter.

Because repositioning cruises mean lots of days at sea, cruise companies entice passengers aboard by stopping at interesting ports along the way - including some not usually found on regular cruises.  As an added enticement, they offer very cheap cruise prices.

Boston locals know that these repositioning cruises to Caribbean ports are some of the best deals around - so I'm going to share some insider tips about:

• Where to find repositioning cruises from Boston to Caribbean destinations
• How to find the cheapest cruise prices and discounts
• Ports of call on cruises from Boston to the Caribbean - what you'll discover, what you can do

Where to find cruises from Boston to the Caribbean

For 2011, only 1 of the cruises departing from Boston offers a repositioning cruise to Caribbean destinations - but it is a very special one. 

Royal Caribbean's Jewel of the Seas also offers a cruise from Boston to Caribbean Island destinations on the way to her winter port of Tampa, departing in late October.

During this 15 day, 14 night cruise, Jewel of the Seas stops at several Eastern and Southern Caribbean ports. 

The most convenient place to learn more about these cruises from Boston to Caribbean ports and find the cheapest cruise prices is at CruiseCompete.com.  Just let them know which cruise you want, and they'll show you competing rates from independent travel agents right on the CruiseCompete website.  Then you can select the quote you like best and contact the agent to book your cruise.

Here's a tip based on my own cruise experiences:  Get your travel agent to book a hotel room for you for a day or 2 at the other end of the cruise before you fly back to Boston.  It's like getting an extra vacation!  Plus, I've discovered that travel agents who do lots of cruise bookings can get very low hotel and flight rates when they bundle them with a cruise, plus usually some "extras," like airport transfers to your cruise ship or hotel. 

When you're booking a cruise or comparing cruise costs, find out if all items are included, such as port taxes, sales taxes, tips (if these get added on to your bill, they're not optional!), and any other charges.  These are not usually included with the cheapest cruise prices that you'll see advertised on the web, and they can add up fast. 

Ports of call on cruises from Boston to the Caribbean

When you take Jewel of the Seas' repositioning cruise from Boston to the Caribbean, you'll stop at some familiar ports such as St. Thomas and Orangestad, as well as others that you may have never heard of. 

Cruise companies usually vary the ports on each trip to add to the excitement and adventure.

Here are the ports you will get to visit. 

Eastern and Central Caribbean cruise ports

Charlotte Amalie, St Thomas, US Virgin Islands

This beautiful port city on the south side of St Thomas is the capital of the US Virgin Islands, and the most popular cruise port in the Caribbean. 

Stroll along Main Street's tax-free shops, take an open-air taxi to the gorgeous white-sand beach at Magens Bay to swim and snorkel, and visit historic St Thomas Synagogue, 2nd oldest under the US flag.

Basseterre, St Kitts and Nevis

Capital of the Federation of Saint Kitts and Nevis and site of the 2007 World Cricket Cup matches, Basseterre lies between the calm waters of a bay and lush green hills and mountains rising up behind it. 

Explore the shops in The Circus, a tourist-oriented area, or Independence Square, where you'll find a cathedral and older historic buildings.  

Photo credit Boby Fume

Castries, St Lucia

As a major cruise ship Port of Call for St Lucia, Castries offers tax free shopping and plenty of restaurants serving local and international cuisine. 

Enjoy shopping and a meal, or take a water taxi or visit nearby towns or tour the rest of the island...or throw your swimsuit into a bag and head to one of the spectacular nearby beaches.

Photo credit D G Brown

Bridgetown, Barbados

Bridgetown, capital and largest city in Barbados, is known for duty free shops along Broad Street, with smaller boutiques located on Swan Street, Roebuck Street, and Tudor Street.  At the very top of Broad Street sit the impressive Parliament Buildings.

Take a tour to explore different sides of Barbados - perhaps an eco tour to see the beauty of the island, a Black Culture tour to explore its African heritage, or a distilleries tour to see how rum is made.

Southern Caribbean cruise port

Oranjestad, Aruba, Netherlands Antilles

Orangestad, capital and most important city of Aruba, features lovely pastel Dutch Colonial Revival houses, as well as a few original buildings now turned into restaurants, museums, and boutiques.

Although shopping is wonderful, nearby beaches, swimming, and water sports are the real attractions.  Aruba, along with nearby Curaçao and Bonaire, is known as a diver's paradise due to the coral reefs, wrecks, and colorful tropical fish species.  Don't dive? Take an underwater submarine sightseeing tour.

Options beyond cruises from Boston to Caribbean ports

Don't forget . . . if the departure dates for ths cruise from Boston to Caribbean ports doesn't work out for you, remember that you can easily fly to other US port cities and hop on a Caribbean cruise all winter.  You can find tons of great options.

Or if you want to explore other inexpensive repositioning cruises, just ask your travel agent.  Almost all cruise ships all over the world get repositioned at one time or another.  If you're looking for really cheap cruise prices and a bit of adventure, check them out!

To whet your appetite for these cruises, here are some of the other ports visited during previous years on cruises from Boston to Caribbean destinations:

Eastern and Central Caribbean cruise ports

Saint Croix, US Virgin Islands

When cruise ships pull into the deep water port at Frederiksted on the west end of this lovely mountainous island, passengers go by taxi to Christiansted. 

Walk along streets near the water lined with pastel-colored buildings built in the 18th century by African slaves, visit historic buildings in the Christiansted National Historic Site, charter a boat and go scuba diving . . . or just enjoy lunch in a charming restaurant.

Tortola, British Virgin Islands

Surrounded by white sand beaches, blue water, and blue skies, Tortula is a former volcano, with lush green foliage covering its mountainous slopes.  

Swim, windsurf, sail, or kayak . . . or just relax with your drink at a beachside bar.   You'll find plenty of chic boutiques, and shopping couldn't be easier - the US dollar is the official currency, even though the island is British.

Antigua

Antigua is both an island and along with nearby Isle of Barbuda, a country.  Offshore banking, internet gambling, 2 medical schools, and luxury tourism fuel the economy.   You'll love the white sand beaches, sailing, snorkeling, and diving. 

For a change of pace, try hiking, birdwatching, or an eco-tour.  If you enjoy spectator sports, watch a cricket game or tennis match.

Philipsburg, Sint Maarten, Netherlands Antilles

With just over 1,300 residents, Philipsburg is located on the Dutch side of Sint Maarten (Saint Martin), an island in the Netherlands. 

Now part of the Kingdom of the Netherlands, the Dutch half of the island is slated to gain independence on October 10, 2010.   Enjoy shopping on Front Street, visit nearby Butterfly Farm, relax on the beach, and explore historic Fort Amsterdam and Fort Willem.  (Photo courtesy of digitalfilmphoto)

Roseau, Dominica

Roseau is the capital of Dominica, considered the most pristine of all the Caribbean islands, with its steep mountains and extensive rainforest.  Take a tour to Boiling Lake, where escaping volcanic gases produce bubbles and clouds of steam.

In Roseau, enjoy French colonial and modern buildings, and shop near the end of the dock when you disembark.  Other interesting spots include Old Market Plaza (once a slave market), the Roseau Museum, and Botanical Gardens (head up Queen Mary Street).  (Photo courtesy of Jean & Nathalie)

San Juan, Puerto Rico

Bustling San Juan, the capital and largest city in Puerto Rico, was founded by Spanish Conquistadors in 1521 (it's even older than Boston!). 

Visit Old San Juan to see Spanish Colonial buildings, narrow cobblestone streets, massive wall sections, and even 16th and 17th century forts.

Head to the Condado neighborhood just east of Old San Juan to enjoy swimming, surfing, and kite surfing.  If you love gardens, take a cab to the Botanical Garden at the University of Puerto Rico and enjoy the lush tropical plantings. (Photo courtesy of D'Arcy Norman)

Semana, Dominican Republic

Located on a beautiful mountainous peninsula covered with rainforests and surrounded by crystal-clear water, Semana boasts some of the world's best whale-watching. 

If you don't want to spend your port time lounging on the beach, this is a spot where taking a tour makes sense.  You'll have a lot to choose from - ecological tours to Los Haitises National Park, a private island "beach escape," whale watching tours, and a guided historical tour that includes a visit to a working marble mine.   Photo courtesy of Anthony Quintano.

St Kitts and Nevis

This 2-island nation, the smallest in the Americas, is part of the Leeward Islands and boasts an active volcano. 

With many pink-sand beaches, water activities are big here, but both islands also offer a range of unspoiled ecosystems.  Ecotourism is growing, and this is a port where you may want to take one of the guided tours and hikes into the rainforests and around archeological sites for a memorable experience in this beautiful paradise.  Photo courtesy of opusbei

Southern Caribbean cruise ports

Oranjestad, Aruba, Netherlands Antilles

Orangestad, capital and most important city of Aruba, features lovely pastel Dutch Colonial Revival houses, as well as a few original buildings now turned into restaurants, museums, and boutiques.

Although shopping is wonderful, nearby beaches, swimming, and water sports are the real attractions.  Aruba, along with nearby Curaçao and Bonaire, is known as a diver's paradise due to the coral reefs, wrecks, and colorful tropical fish species.  Don't dive? Take an underwater submarine sightseeing tour.

Curaçao, Netherlands Antilles

Despite over 60 places to dive and breathtakingly beautiful white sand beaches, Curaçao is relatively uncrowded and the perfect place to relax - or go sailing, windsurfing, or fishing.  

If you can tear yourself away from the water,  you'll also find spots for hiking and biking.  If you don't want to head out on your own, you'll find plenty of good guided tours.  In addition, capital city Willemstad offers high-end shopping and plenty of good restaurants.

Western Caribbean

Belize City, Belize

With ancient Mayan temples to explore, dense rainforests filled with numerous species of colorful tropical birds to visit, rivers for kayaking and tubing, and spas for relaxing, Belize offers plenty of options for everyone.

What the area is best known for, though, is the fabulous diving and fishing.  The longest barrier reef in the hemisphere is located here, along with the Great Blue Hole and numerous locations for snorkeling and scuba diving.  You'll have trouble deciding what to do - but if you haven't been here before, take a tour to get an overview of this fascinating area.

Costa Maya, Mexico

Around the port where the cruise ships dock, you'll find beaches, duty free shopping, kayaking, diving, and snorkeling. 

But what makes this area special are the nearby Mayan villages, reminders of an older civilization.  Visit the Chacchoben archeological site, and you can see ruins dating back to A.D. 200 - 700, reminders of earlier civilizations.  Or go on an ecological tour of the Sian Ka'an Biosphere Reserve.

Cozumel, Mexico

Cozumel Island, just off Mexico's Yucatan peninsula, is famous for its beaches, deep sea fishing, snorkeling, and scuba diving.  

Explore shops near the cruise port, visit Chankanaab Park and swim with the dolphins, and experience Maya Zone, a reproduction of an authentic Mayan Village. Or visit Discover Mexico, a cultural theme park about pre-Hispanic, Colonial, and modern Mexican history and archeology.

Roatan Island, Honduras

Swimming, snorkeling, or just sunbathing on the beach can keep you happily occupied on this Caribbean Island off the coast of Honduras.

Or tour nearby coral reefs in a semi-submersible glass-bottom boat, admire exotic butterflies and tropical birds in the Butterfly Garden, or go horseback riding on the beach.  For a more sedate visit, you'll find plenty of spa services at local resorts.

Santo Tomas de Castilla, Guatemala

Originally settled in the 19th century by Belgian pioneers, Santo Tomas is one of Guatemala's most important port cities. 

You can go on an eco-tour kayak trip and horseriding adventure, visit the Omagua Banana Plantation to see how Chiquita bananas are processed, visit a local school, and even go on a river cruise where you'll see a scenic gorge, gorgeous wild flowers, and maybe even monkeys.  Hop on a water taxi to Amitique Bay Resort for a BBQ lunch and enjoy the private beach, pool, and water slides.