These luxe ships, which shuttle about 350 guests between islands, provide an intimate alternative to the hulking ocean liners carrying thousands. Best of all, there's nary a closet-sized cabin in sight -- the onboard accommodations are all spacious suites with incredible ocean views. silversea.com
The itinerary: Ten days from Fort Lauderdale, Florida, to Bridgetown, Barbados. This voyage passes through the U. S. Virgin Islands and the British Virgin Islands before heading down to southern Caribbean spots like St. Lucia and Grenada.
The excursion worth booking: A catamaran sail and shipwreck snorkel. After dropping anchor off St. Thomas in the USVIs, you'll board a catamaran and cruise over to the BVIs' Buck Island. There you can paddle around a sunken shipwreck before downing a Painkiller (the islands' signature rum punch).

Two of this company's three boats run Caribbean routes: a pair of gorgeous barques (sailing vessels with more than three masts) that are like floating five-star hotels. They're incredibly intimate -- one carries just 64 people, the other, 94 -- and are outfitted with Carrara marble, brass fittings, and antique furniture. seacloud.com
The itinerary: Eleven days from Santo Domingo, Dominican Republic, to St. John's, Antigua. This trip jumps from the DR to the British Virgin Islands, where several days are spent exploring islands like Jost Van Dyke, before departing for under-the-radar destinations like St. Kitts, Nevis, and Anguilla.
The excursion worth booking: A walk through the Cueva de las Maravillas (Cave of Miracles) in the Dominican Republic. This half-mile-long cavern is filled with cave drawings etched by Taino Indians.

These three sailing yachts, which can accommodate anywhere from 148 to 312 people, depending on the boat, are known for their beautiful sky-high sails. All staterooms are decked out with L'Occitane bath goods, Bose SoundDock speakers, and portholes. windstarcruises.com
The itinerary: Seven days starting and ending in Bridgetown, Barbados. This trip loops around to hit French islands St. Martin, St. Barts, and the Iles des Saintes near Guadeloupe, plus unexpected ports like Pigeon Island off St. Lucia.
The excursion worth booking: A tour of the Brimstone Hill Fortress and Colonial Plantation House on St. Kitts. The island is known for its British colonial architecture, and this tour will take you to historic government buildings, one of the Caribbean's best-preserved fortresses, and a still-working plantation.

Stately midsize boats (one carries 1,250 people; three others each hold just 684) are this brand's trademark -- that, and the divine cuisine you'll experience at the gourmet Italian, Asian, and French restaurants. With cooking classes and art lessons available, and a Canyon Ranch spa, you might not want to get off at the ports of call. oceaniacruises.com
The itinerary: Ten days starting and ending in Miami, Florida. This cruise lets you explore the Latin-flavored western Caribbean, including the Cayman Islands; Belize City, Belize; Roatan, Honduras; and Costa Maya, Mexico.
The excursion worth booking: A jungle walk and cave tubing in Belize. After a 45-minute hike through the jungle, the real fun begins: floating on an inner tube down the Caves Branch River, which passes through caverns dotted with stalactites.

With two mega yachts that accommodate only 112 guests and a crew of 95, it's easy to see why you'll feel that your every need is being catered to. Prepare to be spoiled with gourmet cuisine, 24-hour room service, and toys like clear-bottom kayaks and JetSkis or WaveRunners. seadreamyachtclub.com
The itinerary: Seven days from San Juan, Puerto Rico, to St. Thomas, USVI. The coolest part of this trip is that it includes two ports rarely seen on cruises: Vieques, a charming island off Puerto Rico, and Saba, a stamp-size speck north of St. Maarten that's known for its diving.
The excursion worth booking: A trip to the Bioluminescent Bay in Vieques. You'll take a boat to this bay where the water glows like starlight, thanks to microscopic plankton that light up when they're touched.

Three tall ships (complete with impressive masts) accommodate around 200 people apiece, which means you'll have plenty of room to roam. Soak up some rays at the pools on the top deck, or catch a performance at the piano bar. starclippers.com
The itinerary: Eight days around the Grenadine Islands. The route will have you hunting out pirate haunts on Barbados, snorkeling the crystalline waters of the Tobago Cays, and practicing your French on Martinique.
The excursion worth booking: A tour of a batik workshop and a rum distillery on St. Lucia. This trip is like a behind-the-stage pass to a couple of the island's coolest companies. At Caribelle Batik, watch as artists create detailed motifs on fabric. And at the St. Lucia Distillers, you'll get an up-close look at the production of the Caribbean's favorite beverage -- rum.