Planning a vacation can feel like navigating uncharted waters, but with our 10 easy steps to plan your next cruise vacation, you'll be off to the high seas in style when you book early!
Whether you're a first-time cruiser or a seasoned Sailor looking to upgrade your next adventure, this comprehensive guide will help you plan the perfect cruise vacation that matches your dreams, budget, and travel style.
How to Plan a Cruise Vacation for 2026-2027
Between financial concerns, choosing a destination, figuring out what to pack, and decision paralysis, it might start sounding more tantalizing to simply stay home on the couch. But planning a cruise trip doesn’t have to look like a labyrinth of multiple web browser tabs and Excel budget spreadsheets. Planning a cruise can even be easier than trying to choose a movie on Netflix (and certainly less contentious for your family). One of the reasons we love planning cruise vacations is because they’re not just more straightforward than your typical vacation – they’re more fun too!
This step-by-step guide walks you through exactly how to plan a cruise for 2026 or 2027. We’ll cover everything from picking a destination and cruise cabin to finding the right season and locking in a good deal. Whether you’re dreaming of the Caribbean or the Mediterranean, this is the place to start.
Reasons to Plan your 2026 and 2027 Cruise Vacation
You'll want to plan and book your next cruise early to get the best prices. That’s especially true with our lineup of 2026 cruises to stunning destinations. We’ve got plenty of new voyages on deck for the next two years, sailing to new destinations… the decisions can seem endless for exciting destinations around the world. But we’re making it as easy as possible to book adults-only cruises for 2026 and 2027. Whether you're sailing to tropical Caribbean waters for a Caribbean cruise or venturing to the Med, for breathtaking views and rich culture, here are ten essential steps to help you plan your next cruise.
10 Pro Tips for Planning a Cruise
Planning a cruise vacation involves several key decisions that will shape your entire experience. Virgin Voyages makes this process seamless with all-inclusive pricing value that includes dining, essential drinks, WiFi, group fitness classes, and entertainment—eliminating the guesswork of hidden costs.No matter which of our cruise itineraries piques your interest, there’s a pretty simple blueprint for planning your trip:
1. Why Do you want to Take a Cruise? Choosing the Right Type of Cruise
Asking yourself “why?” when planning a vacation might sound like a stupid question, because… duh, everyone deserves a fun getaway, and planning ahead will help you meet your vacation goals. But are you celebrating a bachelorette party? An anniversary? A family reunion? Or maybe you’re just looking for a relaxing solo escape, a much needed couples getaway, or a special themed cruise vacation. No matter what your reason for celebrating with a cruise, we make the occasion more special with our intimate and elevated eateries, adventurous Shore Excursions, shipwide activities and events, and Manor nightclub brimming with party vibes.
2. Set a Travel and Spending Budget:
This doesn’t have to be the scary part of booking a cruise vacation. Setting a budget is actually pretty easy when you take an always included luxury cruise, because unlike a typical vacation, your expenses aren’t a moving target. With this always included cruise package, food at our 20+ eateries, WiFi, group workout classes, entertainment, and basic beverages are all included in your booking fare. Of course, you can always splurge on alcoholic drinks or Shore Things (both totally worth it, in our opinion) but otherwise, there are no hidden costs lying in wait to break your budget.
3. Research the Destinations You Want to Cruise to:
Explore where you want to travel and activities you’d like to do: The hardest part about planning a cruise trip is choosing where to go. With over 100 dreamy destinations around the world, it’s tough to go wrong finding the best cruise vacation. Start by asking yourself a basic question: “What do I want to do?” Zipline through a jungle? Relax at a beach club? See exotic wildlife?
Your cruise destination sets the tone for your entire vacation experience. Consider factors like weather preferences, cultural interests, activity levels, and travel distance from your home port.
Popular Cruise Regions and When to Go
Caribbean Cruises: Perfect year-round, with peak season from December to April offering the best weather. Virgin Voyages sails to the Eastern and Southern Caribbean from Miami and San Juan, featuring destinations like:
- Bimini Beach Club - Our private beach paradise in the Bahamas
- Puerto Rico - Rich culture and vibrant nightlife
- Dominican Republic - Beautiful beaches and adventure activities
- Jamaica - Waterfalls, beaches, and reggae culture
Europe Cruises: Best from May to October, with summer months offering the warmest weather. Cruise from Athens or Barcelona to explore:
- Greek Islands - Santorini, Mykonos, and ancient history
- Mediterranean - Rich culture, cuisine, and coastal beauty
Alaska Cruises: Available May through August, offering spectacular glacier views and wildlife encounters. Virgin Voyages' Brilliant Lady sails from Seattle to:
- Inside Passage - Breathtaking fjords and glaciers
- Ketchikan and Sitka - Native culture and salmon fishing
- Juneau - Glacier hiking and whale watching
4. What's the Best Cruise Length for My Vacation?
Cruise length depends on your available time, budget, and desired destination coverage. First-time cruisers often prefer 4-5 night cruises for the perfect balance of relaxation and adventure, while experienced cruisers might choose longer 7+ night cruises for deeper destination immersion.
Choosing Your Ideal Cruise Duration
4-5 Night Cruises: Perfect for weekend getaways or first time cruisers. Virgin Voyages offers short Caribbean escapes featuring Key West and our Beach Club at Bimini.
7 Night Cruises: The sweet spot for most cruisers, allowing time to unwind while visiting 3-4 destinations. Our week-long Caribbean and Mediterranean itineraries provide excellent variety.
9+ Night Cruises: Ideal for exploring multiple regions or enjoying extended relaxation. Our longer Caribbean voyages reach the Southern Caribbean's most pristine islands.
12-15 Night Cruises: Perfect for special occasions or comprehensive regional exploration, like our Alaska expeditions, Mediterranean grand cruises, and transatlantic cruises.
5. Consider a Seasonal Cruise
Seasonal timing affects weather, pricing, crowds, and available activities. Each season offers unique advantages for different types of cruise experiences.
Spring Cruise Planning (March-May)
Advantages: Moderate temperatures, fewer crowds, good pricing, blooming destinations
Best For: Europe repositioning cruises, early Caribbean season, Mediterranean shoulder season
Virgin Voyages Tip: Spring Mediterranean cruises offer perfect weather with fewer tourists at popular Greek islands
Summer Cruise Planning (June-August)
Advantages: Peak weather conditions, longest days, best for families (though Virgin Voyages is adults-only), all destinations accessible
Best For: Alaska cruises, Northern Europe, peak Mediterranean season
Virgin Voyages Tip: Our Alaska cruises from Seattle offer the best wildlife viewing and warmest weather
Fall Cruise Planning (September-November)
Advantages: Lower prices, fewer crowds, comfortable temperatures, beautiful autumn colors
Best For: Caribbean hurricane season deals, Mediterranean shoulder season, repositioning cruises
Virgin Voyages Tip: Fall Caribbean cruises offer excellent value with warm waters and fewer crowds
Winter Cruise Planning (December-February)
Advantages: Escape cold weather, holiday and New Year celebrations, peak Caribbean season
Best For: Caribbean escapes, holiday-themed cruises, avoiding winter weather
Virgin Voyages Tip: Our holiday cruises feature special celebrations and festive entertainment
6. How Do I Find the Best Cruise Deals?
If you're planning to cruise in 2026 or 2027, don’t wait until the last minute. Booking early gives you the best shot at low prices, better cabin choices, and early-booking perks like free drinks and instant savings.
Discover deals and payment plans for your trip: Everyone loves a deal. Including us. Whether it’s special romance packages or our 2026-2027 cruise deals are here to make it even easier to stay within your budget when you plan and book your next cruise. The best cruise deals combine early booking discounts, seasonal promotions, and value-added cruise packages. You can even finance your cruise with monthly payments and $0 down. There are also additional ways to save on cruises:
Book Early: Book your cruise 6-12 months ahead for the best cabin selection and early booking bonuses. Virgin Voyages offers cruise financing options to make early booking more accessible.
Wave Season: January through March typically features the year's best cruise deals and promotions.
Last-Minute Deals: 60-90 days before sailing can yield significant savings, though cabin and dining preferences may be limited.
Shoulder Season: Travel during less popular months for better pricing while still enjoying excellent weather and experiences.
7. Picking a Cruise Add-On Package
Strategic add-on selection enhances your cruise experience while helping you manage costs. Virgin Voyages' all-inclusive pricing eliminates many traditional cruise extras, but some upgrades can enhance your voyage.
Essential Virgin Voyages Cruise Add-Ons
Bar Tab: Prepaid beverage credits for cocktails, wine, and premium drinks
Shore Excursions: Curated local experiences and adventures
Spa Services: Relaxation and wellness treatments
Internet Upgrades: Faster connectivity for streaming and video calls
8. Pick the Perfect Cruise Cabin
Cruise cabin selection impacts your comfort, budget, and overall cruise experience. Consider factors like location, size, view, and special amenities when making your choice.
Virgin Voyages Cabin Categories
Interior Cabins: Budget-friendly options with modern design and mood lighting
Sea View Cabins: Ocean views with innovative design features
Sea Terrace Cabins: Private balconies with convertible spaces
Suites: Spacious luxury with premium amenities and priority services
Location Tips:
- Midship cabins offer the most stability
- Lower decksprovide easier access to dining and entertainment
- Higher decks offer better views but more elevator traffic
9. Pick Shore Excursions that Fit Your Vibe
Consider Ship-Sponsored Tours: Guaranteed return timing and quality assurance
Book Early: Popular excursions sell out, especially in destinations like Santorini or Alaska
Research Independently: Local tour operators often offer more personalized experiences
Weather Backup Plans: Have indoor alternatives for outdoor activities
10. Pack Your Bags and Prepare Your Travel Documents for Your Next Cruise
Once your cruise is booked, it's time to handle the paperwork. Make sure your passport is valid for at least six months beyond your return date — even if your cruise departs and returns from the same port. Some countries also require visas, so check the rules for every port you'll visit.
The more unknowns in your trip, the heavier you need to pack. Cruising doesn’t come with many unknowns. You know exactly what amenities to expect, how long you’ll be on shore, and what restaurants are at your fingertips. That means you can pack much lighter than you would for a traditional vacation. We live by a “come as you are” mentality, so there’s no need to bring any fancy attire (unless you wish). If you want, every day can be spent entirely in flip flops and a bathing suit. And since you won’t exactly be roughing it in Arctic conditions, there’s no need for many layers beyond a rain jacket, just in case of rain. Certain Shore Things might have specific packing tips, which you should always follow, but other than that – a minimalist packing philosophy is a safe bet on Virgin Voyages.
Get help planning from our AI chatbot and friends at Sailor Services
The other great thing about planning a cruise is that you don’t have to go at it alone, nor do you have to enlist the help of an outside travel agent. Vivi, our Generative AI-powered chatbot, is here to answer your questions. If you need something more in-depth, reach out to our Sailor Services team, who’s ready to provide end-to-end support and answer any questions you may have for planning a cruise – from destination and cabin selection to booking Shore Things once you’re onboard. Contact Sailor Services via our online portal, email, or by phone.
Put our vacation planning tips to the test and find your perfect vacation spot for 2026 and 2027.
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How to Plan a Cruise Trip
