Winchester Travel
Cruises
Traveling on a cruise ship combines relaxation and adventure, making it an ideal getaway. Enjoy luxurious amenities and stunning ocean views while exploring new destinations at each port, from sun-soaked beaches to historic towns and local cultures.
Check out our Cruises!
We at Winchester Travel have sailed a combined 100 different itineraries reaching out to a varied list of countries, continents and oceans of which to advise you. We can help you plan your next cruise vacation.
Christmas Market Cruise
Nov 29 - Dec 7, 2025
per/person starting at:
$4995
Portugal River Cruise
April 16-23, 2025
per/person starting at:
$4900
Alaska Land & Sea
Aug 24 – Sep 7, 2025
per/person starting at:
$5195
Alaska Land & Sea
Aug 23 – Sept 6, 2026
per/person starting at:
$5850
Southern Caribbean Cruise
March 2026
multiple departure dates
per/person starting at:
$1745
Cruising Questions
What is required for my cruise? We've got the list: Travel Documents, Passport Requirements, Onboard Etiquette, Shore Excursions, What to bring..
River Cruising
Comfortable and convenient, River Cruising offers a greater variety of destinations than you could encounter any other way - and lets you get in-depth exposure to the culture and history of each region.
Cruise Lines
Which cruise line is best for me? We use all the best cruise lines, and each line has unique features that may appeal to you, learn more about each line.
Winchester Travel
Group Vacations
Whether it is that extra special destination wedding, or a party getaway to the Caribbean, we can set up a great group vacation.