Cruise Vacations - Windstar
Cruise Vacations - Mississippi River Cruise
Cruise Vacations - River Cruise
Cruise Vacations - Hawaii Cruise

Pleasant Holidays Cruise Vacations

Pleasant Holidays makes it easy and affordable to plan and book 2018, 2019 & 2020 river and ocean cruises at top destinations worldwide including Alaska, Europe, Hawaii, Mexico, Tahiti, Iceland, Central America, Caribbean, Asia plus U.S River Cruises on the Mississippi, Columbia and Snake Rivers in the Pacific Northwest.

We partner with the world's top cruise lines including AMA Waterways, Norwegian NCL, Windstar, Paul Gauguin, Iceland ProCruises, Un-Cruise Adventures, Aranui and the American Queen Steamboat Company for the best deals and best prices. Many cruise packages include onboard meals, beverages, entertainment, guest lecturers, premium shore excursions and the Pleasant Holidays exclusive onboard credit. One-stop shopping includes flights, cruises, pre and post cruise hotel packages.

    • International & Domestic Flights▾

      • Let the air travel experts at Pleasant Holidays or Air By Pleasant book flights for the cruise vacation on a preferred airline. We offer over 80 airlines to destinations worldwide with service in first class, business class and premium economy for more spacious seating and amenities on overseas flights.
    • U.S. & Europe Airport Hotels▾

      • Pleasant Holidays offers convenient locations and well-appointed accommodations at many U.S. and Europe Airports for early flight departures or late arriving flights with complimentary shuttles available. Ask about affordable rates at top U.S. Airports in Boston (BOS), Chicago (ORD), Denver (DEN), Las Vegas (LAS), Los Angeles (LAX), Miami (MIA), New York (JFK) and Seattle (SEA).

        In Europe, stay close to Amsterdam (AMS), Athens (ATH), Copenhagen (CPH), Frankfurt (FRA), London Heathrow (LHR), London Gatwick (LGW), Munich (MUC), Paris (CDG) and Rome (FCO). Sheraton Hotel CDG is located inside Terminal 2 near the train station.
    • Extend Your Trip Pre & Post Cruise Packages▾

      • Extend your cruise vacation of a lifetime and maximize the value of your overseas flight with a pre or post land package in Europe, Hawaii, Tahiti, Mexico, Central America or the U.S. Pleasant Holidays partners with the best hotel brands including Marriott, Hilton, Westin, Sheraton, W Hotels, Hyatt, Fairmont, Four Seasons, St. Regis and Ritz-Carlton with real-time rates and instant reservation confirmations.
    • Cruise Protection Plans▾

      • Enjoy peace of mind with comprehensive pre- and post-travel coverage. Safeguard your vacation investment with price protection, change coverage, trip cancellation and interruption benefits and more.

Call Our Dedicated Cruise Desk at 877-287-2835

  • Hawaii

    Experience the very best of Hawaii on a seven night cruise from Honolulu sailing each Saturday year-round visiting Oahu, Kauai, Maui and Hawaii Island with an award-winning itinerary that gives you the most time in port – nearly 100 hours to explore the Aloha Spirit and Soul of Hawaii.  Explore the Hawaiian Islands on a small luxury ship aboard the 36-guest yacht Safari Explorer from Molokai or Hawaii Island.

  • Alaska and U.S. River Cruises

    Explore America’s last frontier on an Alaskan cruise with Norwegian from Seattle sailing May – September.

    Cruise the Mississippi and rivers of the Pacific Northwest on the largest and most elegant paddlewheel steamboats including our exclusive $140 onboard credit.  New for 2017, the American Duchess, first all-suite river cruise ship.

  • Europe

    Explore Europe’s most fascinating cities aboard a luxury Windstar yacht including Rome, Venice, Greece and Barcelona.

    Cruise the rivers of Europe on luxury AMA Waterways including Paris & Normandy, Bordeaux, the Romantic Danube, Gems of Southeast Europe, The Rhine and more.

    NCL Cruises depart from 10 European cities visiting 24 countries.

  • Iceland

    Iceland and Greenland

    A unique and unforgettable experience of the breathtaking nature of Iceland and Greenland aboard the super yacht, Ocean Diamond, with 107 outside staterooms and suites. Explore this mystic land of rugged volcanic landscapes, steeped in Viking traditions, with shore excursions designed to interact with Iceland’s culture, history and people. Sailing May – September only.

  • Caribbean

    Cruise the sunny Caribbean year-round aboard NCL’s award-winning fleet sailing from Miami, New York, New Orleans and Orlando visiting the top islands including the Bahamas, Belize, Honduras, U.S. Virgin Islands and more.

  • South Pacific – Tahiti, French Polynesia & Fiji

    Explore the islands of the South Pacific Islands of Tahiti, French Polynesia, Fiji and Cook Islands aboard the luxurious Paul Gauguin with all oceanview staterooms accommodating only 332 guests with airfare included from Los Angeles.

    Cruise Tahiti’s most spectacular Islands of Moorea, Bora Bora, Tahaa, Raiatea and Huahine on Windstar’s Dreams of Tahiti.  Papeete to Papeete on Wind Spirit accommodating 148 guests in all oceanview staterooms.

  • Costa Rica & Panama Canal

    Explore the exotic beauty of Costa Rica and transit The Panama Canal on Windstar’s Star Breeze all-suite yacht with only 212 guests in 106 oceanview suites.

  • Galapagos Islands Cruises

    Uncover New World marvels and Darwin’s archipelago wonderland on this magnificent cruise adventure.  Explore two UNESCO World Heritage sites - the Galapagos Islands and Quito’s Colonial City. Visit seven islands and islets and view nesting birds and wildlife in their natural habitat.  Each day of your voyage will be filled with the promise of adventure and the joy of discovery.

  • Mexico

    Cruise along the Mexican Riviera for a festive 7-Night vacation from Los Angeles on Norwegian visiting Puerto Vallarta, Mazatlán and Cabo San Lucas.

    A small ship cruise exploration in Mexico’s Sea of Cortes on the Un-Cruise Safari Endeavor featuring 42 cabins and 84 guests.

  • Vietnam, Cambodia & Riches of the Mekong

    One of the most unique and exotic journeys available on the Mekong River in Southeast Asia visiting Vietnam and Cambodia. This deluxe river cruise features regionally-inspired cuisine, ancient temples, life enriching tours, entertainment and more.