Sail roundtrip from San Juan aboard the 312-guest Star Pride on this 7-night Windward Islands cruise departing November 22, 2026. The itinerary visits Grenada, Bequia, Mayreau, Les Saintes, and St. Martin, with a day at sea. Book this travel deal by September 30, 2026.
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- Complimentary all-in package
- Reduced deposit
- Grand Anse beach and spice-island scenery in Grenada
- Bequia's yacht-filled Admiralty Bay
- Laid-back beaches on tiny Mayreau
- Volcanic scenery and palm-fringed beaches in Les Saintes
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Expires 9/30/2026
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Sail round-trip from Orlando (Port Canaveral) aboard Norwegian Epic on this 7-night Caribbean cruise. Ports of call include Great Stirrup Cay in the Bahamas, Ocho Rios, George Town in Grand Cayman, and Cozumel, with two days at sea. Book this travel deal by September 30, 2026.
Satisfy your wanderlust - and your wallet - by taking a look at all our top travel deals. Buy Now at ShermansTravel
- Specialty dining
- Unlimited open bar
- Wi-Fi package
- Excursion credits
Sail roundtrip from Fort Lauderdale aboard Holland America Line's Rotterdam from January 12 to 23, 2027. This Eastern Caribbean itinerary visits Philipsburg, St. Maarten; St. Johns, Antigua and Barbuda; Roseau, Dominica; Fort-de-France, Martinique; Basseterre, St. Kitts and Nevis; San Juan, Puerto Rico; and RelaxAway, Half Moon Cay, Bahamas. Taxes and fees are included. Book this travel deal by September 30, 2026.
Satisfy your wanderlust - and your wallet - by taking a look at all our top travel deals. Buy Now at Holland America Line
- Billboard Onboard, World Stage, and Rolling Stone Lounge entertainment
- Fitness center, movies, and pickleball
- Included and specialty dining options
Sail roundtrip from Piraeus (Athens), Greece, aboard Holland America Line's Oosterdam on October 14, 2026. This 10-night cruise visits Mykonos, Kusadasi (Ephesus), Kos, and Rhodes, plus an overnight stay in Istanbul. Book this travel deal by September 30, 2026.
Satisfy your wanderlust - and your wallet - by taking a look at all our top travel deals. Buy Now at Holland America Line
- Billboard Onboard, World Stage, and Rolling Stone Lounge entertainment
- Fitness center, pickleball, High Score family game room, and movies on board
- Multiple included dining options
- Taxes and fees included
Sail round-trip from Fort Lauderdale aboard Holland America Line's Eurodam on this 7-night Eastern Caribbean cruise departing December 12, 2026. The itinerary visits Nassau, Grand Turk, Amber Cove, and RelaxAway Half Moon Cay, with two days at sea. Book this travel deal by September 30, 2026.
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- Included onboard entertainment
- Fitness center
- Complimentary movies on demand
- Pickleball at sea
Sail aboard the Star Pride from Boston to San Juan on this 8-night wellness cruise departing October 20, 2026. The voyage spends two days in Hamilton and two days in St. George's, Bermuda, with wellness programming led by yoga teacher and life coach Debbie Dixon. Book this travel deal by September 30, 2026.
Satisfy your wanderlust - and your wallet - by taking a look at all our top travel deals. Buy Now at Windstar Cruises
- Complimentary all-in package
- Reduced deposit
- Meditation, breathwork, and yoga
- Wellness-focused talks and healthy food options
Sail from Santa Cruz de Tenerife to Cádiz aboard the 148-guest Wind Spirit on this 10-night cruise departing January 26, 2027. Explore the Canary Islands with stops in Las Palmas, San Sebastián, and Santa Cruz de Palma before visiting Funchal, Madeira, and continuing to Cádiz. Book this travel deal by September 30, 2026.
Satisfy your wanderlust - and your wallet - by taking a look at all our top travel deals. Buy Now at Windstar Cruises
- Complimentary all-in package
- Reduced deposit
- Four-masted Wind Spirit sailing yacht
- UNESCO-listed historic areas in Tenerife and Gran Canaria
- Terraced landscapes and views of Mount Teide from La Gomera
- Funchal stop on the island of Madeira
Explore French Polynesia aboard Windstar's Star Breeze with roundtrip airfare from Los Angeles and a pre-cruise stay at the InterContinental Tahiti Resort & Spa or similar. The voyage sails roundtrip from Papeete and visits Moorea, Raiatea, Motu Mahaea, Bora Bora, and Huahine, with an overnight stay in Bora Bora. A complimentary all-in package is included. Book this travel deal by September 30, 2026.
Satisfy your wanderlust - and your wallet - by taking a look at all our top travel deals. Buy Now at Windstar Cruises
- Roundtrip Los Angeles-Papeete airfare
- Pre-cruise Tahiti hotel stay
- Airport, hotel, and ship transfers
- Complimentary all-in package
- Windstar Destination Discovery Event in Bora Bora
- Reduced deposit
Sail from Bangkok to Phuket aboard Windstar's Star Seeker on an 11-night cruise through Thailand, Singapore, and Malaysia. The itinerary visits Ko Kut, Ko Samui, Singapore, Kuala Lumpur, Penang, Krabi, and Ko Yao Noi, with an overnight stay in Singapore. A complimentary all-in package and reduced deposit are included. Book this travel deal by September 30, 2026.
Satisfy your wanderlust - and your wallet - by taking a look at all our top travel deals. Buy Now at Windstar Cruises
- 11 nights aboard Star Seeker
- Bangkok-to-Phuket itinerary
- Visits to Thailand, Singapore, and Malaysia
- Overnight stay in Singapore
- Complimentary all-in package
- Reduced deposit
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