Vacation Packages - Wooster Street Travel

Vacation Packages

Complete Getaways, Worry-Free Travel

Experience stress-free travel with complete vacation packages featuring airfare, accommodations, and transfers all bundled together for exceptional value. We partner with the industry's leading vacation wholesalers—Funjet Vacations, Apple Vacations, Pleasant Holidays, and Travel Impressions—to bring you the best rates, widest selection, and most reliable service. Whether you're seeking all-inclusive beach resorts, city escapes, or adventure getaways, our vacation packages take care of every detail so you can simply relax and enjoy.

Our Vacation Partners

Funjet Vacations

For over 45 years, Funjet Vacations has been America's vacation expert, offering the ultimate in convenience and value. Funjet specializes in bundled packages to top beach destinations including Mexico, the Caribbean, Hawaii, and Florida, combining major airline flights with hand-selected resorts. Their exclusive FunPerks rewards program provides instant savings, and their Best Price Guarantee ensures you're getting the lowest available rate. From budget-friendly getaways to luxury all-inclusive resorts, Funjet's extensive portfolio includes over 500 hotels and resorts worldwide.

Popular Funjet Destinations: Cancun, Punta Cana, Jamaica, Aruba, Hawaii, Las Vegas, Orlando

Specialties: All-inclusive beach resorts, family vacations, couples getaways, FunPerks rewards program

Apple Vacations

As one of the nation's largest and most respected vacation companies, Apple Vacations has been delivering exceptional beach vacations for over 50 years. Apple specializes in all-inclusive resorts in Mexico and the Caribbean, featuring exclusive non-stop flights from major cities, complimentary round-trip transfers, and on-site Apple Representatives available 24/7. Their relationships with resort partners mean access to exclusive amenities, room upgrades, and special perks not available elsewhere. Apple's Worry-Free Vacation approach includes comprehensive protection plans and flexible booking options.

Popular Apple Destinations: Cancun, Riviera Maya, Los Cabos, Puerto Vallarta, Punta Cana, Jamaica

Specialties: All-inclusive resorts, non-stop charter flights, wedding packages, on-site representatives

Pleasant Holidays

With over 60 years of experience, Pleasant Holidays is the expert in Hawaiian vacations while also offering exceptional packages to Mexico, Caribbean, Europe, and beyond. Pleasant specializes in customized vacations, allowing you to mix and match flights, hotels, car rentals, and activities to create your perfect getaway. Their Pleasant Perks program provides complimentary amenities at select hotels including breakfast, resort credits, room upgrades, and early check-in. Pleasant's travel experts provide personalized service and insider knowledge to design vacations tailored to your preferences.

Popular Pleasant Destinations: Hawaii (all islands), Las Vegas, California, Mexico, Caribbean, Tahiti

Specialties: Hawaii vacations, customizable packages, Pleasant Perks amenities, multi-island trips

Travel Impressions

Travel Impressions offers the world's most comprehensive selection of vacation packages to over 1,000 destinations worldwide. From tropical beaches to European cities, African safaris to Asian adventures, Travel Impressions provides expertly crafted packages with flexibility to customize every aspect. Their extensive hotel portfolio ranges from budget-friendly to ultra-luxury properties, ensuring options for every traveler and budget. With exclusive supplier relationships, Travel Impressions delivers competitive pricing, value-added amenities, and special perks throughout your journey.

Popular Travel Impressions Destinations: Caribbean, Mexico, Hawaii, Europe, Central & South America, Asia

Specialties: Worldwide destinations, flexible customization, extensive hotel selection, honeymoon packages

Popular Vacation Destinations

Mexico

Cancun & Riviera Maya: All-inclusive beach resorts, ancient Mayan ruins, cenotes, vibrant nightlife, and pristine white-sand beaches along the Caribbean coast.

Los Cabos: Luxury resorts meeting the desert and sea, world-class golf courses, sport fishing, vibrant marina, and dramatic rock formations at Land's End.

Puerto Vallarta: Colonial charm in the Romantic Zone, adventure activities, whale watching, beautiful beaches, and authentic Mexican culture.

Caribbean

Punta Cana, Dominican Republic: Miles of pristine beaches, championship golf, all-inclusive mega-resorts, and budget-friendly luxury in the Caribbean's most popular destination.

Jamaica: Seven-mile beach in Negril, Sandals luxury couples resorts, Dunn's River Falls, reggae culture, and warm island hospitality.

Aruba: Guaranteed sunshine with desert landscapes meeting turquoise waters, Dutch Caribbean culture, and safe, welcoming atmosphere.

Hawaii

Maui: Road to Hana scenic drive, Haleakala volcano sunrise, snorkeling at Molokini Crater, luxury resorts, and world-famous beaches.

Oahu: Waikiki Beach, Pearl Harbor, Diamond Head hiking, North Shore surf, and blend of Hawaiian culture with modern Honolulu.

Kauai: Garden Isle with Na Pali Coast, Waimea Canyon, lush landscapes, waterfalls, and peaceful island atmosphere.

Types of Vacation Packages

All-Inclusive Beach Resorts

Everything included in one upfront price: accommodations, all meals and snacks, unlimited drinks including premium alcohol, water sports, entertainment, and activities. No wristbands, no worries—just relax and indulge without reaching for your wallet. Popular with couples and families seeking hassle-free beach vacations where everything is taken care of.

Air + Hotel Packages

Bundled flights and accommodations offering significant savings compared to booking separately. Choose your hotel category from budget to luxury, select your flight times and airline preferences, and customize with optional car rentals, transfers, and activities. Flexibility to explore destinations at your own pace while benefiting from package pricing.

City Getaways

Urban vacation packages to vibrant cities combining flights, centrally-located hotels, and optional tours and activities. Perfect for weekend escapes, shopping trips, cultural exploration, and experiencing world-class dining and entertainment. Popular destinations include Las Vegas, New York, San Francisco, and European capitals.

Family Vacation Packages

Family-friendly resorts featuring kids' clubs, water parks, supervised activities, and accommodations with multiple bedrooms or suites. Many include complimentary stays and meals for children, making family vacations more affordable. Destinations like Orlando theme parks, Caribbean resorts, and Hawaii combine fun for kids with relaxation for parents.

Honeymoon & Romance Packages

Romantic getaways designed for couples featuring luxury accommodations, private dinners, couples' spa treatments, champagne and amenities, and adults-only resorts. From tropical overwater bungalows to European cities of romance, these packages create unforgettable experiences for newlyweds and anniversary celebrations.

Why Book Vacation Packages

Exceptional Value

Vacation packages bundle flights, hotels, and transfers at rates significantly lower than booking components separately. Our supplier relationships provide access to deeply discounted airfares and hotel rates not available to individual travelers. Additional perks like resort credits, complimentary upgrades, and free nights add even more value.

Convenience & Simplicity

One booking, one confirmation, one price—everything coordinated and confirmed together. No need to research flights, compare hotels, arrange transfers, or worry about logistics. Simply choose your destination, select your preferences, pack your bags, and go. We handle all the details from departure to return.

Protection & Support

Comprehensive travel protection plans available covering cancellations, interruptions, medical emergencies, and more. Supplier guarantees and protections ensure your vacation investment is secure. Our agency provides personalized support before, during, and after your trip with 24/7 emergency assistance available.

Expert Guidance

Our travel advisors bring firsthand knowledge of resorts, destinations, and suppliers. We match you with the perfect vacation based on your preferences, budget, and travel style. We share insider tips, recommend optimal travel dates, suggest room categories, and ensure you're aware of all available perks and amenities.

Planning Your Vacation Package

When to Book

Book 3-6 months in advance for best selection and pricing, especially for peak travel periods including winter holidays, spring break, and summer vacations. Last-minute deals available 2-6 weeks before departure for flexible travelers with open dates. Early booking bonuses often include reduced deposits, free nights, and complimentary upgrades.

What's Included

Vacation packages typically include round-trip airfare, hotel accommodations for specified nights, and round-trip airport transfers. All-inclusive packages additionally include all meals, drinks, activities, and entertainment. Always review what's included versus optional add-ons when comparing packages to understand true value.

Travel Documentation

U.S. citizens need valid passports for international travel, with expiration dates at least 6 months beyond return date recommended. Some destinations require visas or entry fees. We provide complete documentation requirements when you book and remind you of important deadlines and procedures.

Start Planning Your Getaway

Ready to escape to paradise? Let us create your perfect vacation package combining the best rates, ideal accommodations, and convenient flights. Whether you're dreaming of Caribbean beaches, Hawaiian sunsets, Mexican adventures, or distant destinations, our vacation packages deliver exceptional value and worry-free travel. Contact us today to explore current specials, compare options, and book your next unforgettable getaway.