What Pleasant Holidays does

Pleasant Holidays is a private U.S. tour operator and travel wholesaler founded in 1959 in Point Pleasant, New Jersey, and headquartered at 2404 Townsgate Road in Westlake Village, California. Since 1999 it has operated as a wholly-owned subsidiary of the Automobile Club of Southern California (AAA), with regional offices in Westlake Village, San Diego, and Honolulu and on-island concierge/Activity Centers across Oahu, Maui, Kauai, and the Island of Hawaii. The company employs 251-500 people and serves both individual leisure travelers and B2B travel advisors via a consumer website (beta.pleasantholidays.com), a call center (1-800-742-9244), and a dedicated advisor portal (PleasantAdvisor.com).

The core offering is customizable vacation packages that combine flights, hotels, car rentals, activities, and optional travel protection, with destination coverage spanning Hawaii, Mexico, the Caribbean, Europe, Asia (including Thailand and Bali), Tahiti, Fiji, Australia, Central America, the USA, and Canada. The portfolio extends to hotel-only and car-only bookings, group travel for parties of 10-15+ rooms, and cruises via partnerships with AmaWaterways, Atlas Ocean Voyages, Norwegian Cruise Line, Scenic, Explora Journeys, Paul Gauguin, and others. Sub-brands include Pleasant Hawaiian, Pleasant Mexico Holidays, Pleasant Fiji Holidays, Pleasant Tahitian Holidays, and Pleasant Activities (an excursions platform at pleasantactivities.com). Proprietary travel protection plans are delivered through Trip Mate (a Generali brand) and underwritten by United States Fire Insurance Company, offering Cancel For Any Reason waivers with cash-back reimbursement up to $12,500 per person.

Revenue is generated predominantly on a commission and transaction-fee basis acting as a sales agent for travel suppliers, supplemented by affiliate revenue from car-rental partners (notably Hertz, with a $100 Hawaii credit promotion), travel protection plan sales, and ancillary activity bookings. Go-to-market blends direct-to-consumer online/phone sales with a channel-partner B2B advisor program supported by familiarization trips and event-driven agent training. Marketing channels include email, organic social, destination-marketing partnerships with visitor bureaus (Hawaii Visitors and Convention Bureau, Aruba Tourism Authority), and AAA affinity marketing. The company is registered as a Seller of Travel in California, Florida, Hawaii, and Washington, is a USTOA Consumer Protection Deposit Plan participant, and operates under CCPA-compliant data practices.

Name

Pleasant Holidays

Legal name

Pleasant Holidays, LLC

Website

https://pleasantholidays.com

Company type

Private

Founded year

1959

Operating status

Operating

Headcount range

251–500 employees

Short description

Pleasant Holidays is a 1959-founded, AAA-owned (since 1999) U.S. tour operator based in Westlake Village, California, selling customizable vacation packages (flights, hotels, cars, cruises, activities, travel protection) to global leisure destinations via direct-to-consumer channels and a B2B travel-advisor portal, with regional sub-brands for Hawaii, Mexico, Fiji, Tahiti, and activities.

Ownership category

akta.pro rank

Product category

Tour Operator / Vacation Package Services

NAICS

Tour Operators (561520), Travel Agencies (561510), Traveler Accommodation (7211)

akta.pro primary industry

Island, Beach & Resort Travel Agencies (THAKAFAL)

Keywords

• Vacation packages
• Travel agency services
• Tour operator
• Travel protection plans
• Travel advisor portal

Headquarters

HQ city

Westlake Village

HQ country

United States

HQ region

North America

Offices4 records

Markets served

GTM type

B2B and B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Technology or R&D, Supply Chain, Infrastructure

Revenue model

1. Vacation Package Sales: Commission-based revenue from selling bundled vacation packages including flights, hotels, car rentals, and activities. Company acts as sales agent for travel suppliers.
2. Travel Protection Plans: Revenue from selling travel protection plans including Cancel For Any Reason waivers and insurance benefits through partner Trip Mate
3. Hertz Partnership: Commission revenue from Hertz car rental bookings made through the platform

Pricing tiers

Go-to-market motion3 records

Distribution channels4 records

Marketing channels5 records

Core offering

Pleasant Holidays is a tour operator that sells customizable vacation packages — typically bundling flights, hotels, car rentals, activities, and travel protection — to global destinations with an emphasis on Hawaii, Mexico, the Caribbean, Europe, Asia, Tahiti, Fiji, and Australia. It sells direct to consumers via website and call center and also operates a B2B portal (PleasantAdvisor.com) for travel agents. It complements packages with standalone hotel, cruise, and car rental bookings and a proprietary travel protection plan offering Cancel For Any Reason waivers through partner Trip Mate.

Product overview

Pleasant Holidays is a tour operator and subsidiary of AAA (Automobile Club of Southern California) offering a comprehensive portfolio of vacation products and services. The core offering centers on customizable vacation packages combining flights, hotels, car rentals, cruises, activities, and travel protection coverage. The portfolio includes the main Vacation Packages platform (with optional airfare), Hotel Bookings, Car Rental through Hertz and partners, and Cruises via multiple cruise lines. Add-on protection is provided through Travel Protection Plan Plus and Cruise Vacation Protection Plan Plus (offered via Trip Mate). The company operates regional sub-brands including Pleasant Hawaiian, Pleasant Mexico Holidays, Pleasant Fiji Holidays, and Pleasant Tahitian Holidays for destination-specific offerings. A dedicated travel agent portal (PleasantAgent.com) serves advisors, while Pleasant Activities handles excursion and experience bookings. The company was founded in 1959, became a subsidiary of AAA in 1999, and maintains headquarters in Westlake Village, California.

Differentiator

Problem solved

Functional benefit

Products and services

• Vacation Packages Customizable vacation packages to global destinations, available with or without airfare, combining hotel accommodations, flight reservations with seat assignments, airport transfers or car rentals, activities, and travel protection coverage. Sold direct to consumers online and via call center.
• Hotel Bookings Hotel-only bookings across a global portfolio spanning Hawaii, Mexico, Caribbean, Europe, Asia, Tahiti, Fiji, Australia, and other destinations, featuring properties from luxury brands to all-inclusive resorts.
• Car Rental Car rental packages through Hertz and other providers, available as standalone hotel-and-car packages or bundled with flight and hotel bookings, with options for non-airport pickup locations.
• Cruises Cruise vacation packages and bookings through partnered cruise lines including AmaWaterways, Atlas Ocean Voyages, Celestyal Cruises, Norwegian Cruise Line, Scenic Luxury Cruises, Emerald Cruises, Explora Journeys, Windstar Cruises, Paul Gauguin Cruises, and Victory Cruise Lines.
• Group Travel Group travel services for parties requiring a minimum of 10-15 rooms, with dedicated group booking support and customized travel arrangements for reunions, corporate retreats, and destination weddings.
• Travel Protection Plan Plus Comprehensive travel protection plan offered through Trip Mate featuring a Cancel For Any Reason Waiver (Part A non-insurance benefit) and post-departure travel insurance benefits underwritten by United States Fire Insurance Company (Part B), including trip interruption, trip delay, accident and sickness medical expense, baggage protection, and medical evacuation up to $50,000.
• Cruise Vacation Protection Plan Plus Cruise-specific protection plan through Trip Mate offering Cancel For Any Reason Waiver with reimbursement options (cash or Future Travel Credit up to $12,500 per person), plus cruise vacation insurance benefits including trip interruption, trip delay, accident and sickness medical expense ($25,000), baggage protection ($1,000), and medical evacuation ($50,000).
• Pleasant Activities Activity booking platform for tours, excursions, and experiences at destinations worldwide, operated at pleasantactivities.com as a wholly-owned subsidiary.
• PleasantAdvisor.com Travel Agent Portal Dedicated B2B portal for travel agents and advisors to access inventory, book packages for clients, and track commissions; the principal distribution channel for the company's travel advisor program.
• Hawaii Concierge Service On-island concierge support at Activity Centers, hotel concierge locations, and island briefing sessions across Oahu, Maui, Kauai, and Island of Hawaii, assisting visitors with activity selection and reservations.
• Global Hotel Collection Expansion (2026) Expanded hotel portfolio of nearly 60 new global properties added since the start of 2026, including luxury additions such as Waldorf Astoria Bangkok, Hotel de l'Opera Hanoi, Waldorf Astoria Helsinki, and a Ritz-Carlton Reserve property on Mexico's Pacific Coast, intended to provide travel advisor partners with more options to create customized vacations.
• Pleasant Hawaiian Specialized sub-brand focused on Hawaii travel packages and vacations, operating at pleasanthawaiian.com.
• Pleasant Mexico Holidays Specialized wholly-owned subsidiary brand for Mexico travel packages and vacations.
• Pleasant Fiji Holidays Specialized wholly-owned subsidiary brand for Fiji and South Pacific travel packages and vacations.
• Pleasant Tahitian Holidays Specialized wholly-owned subsidiary brand for Tahiti and South Pacific travel packages and vacations.

Quantifiable outcome

• Travel protection reimbursement up to $12,500 per person for cancelled trips
• +1 more outcomes

Named customers4 records

Segments4 records

Ideal customer profiles3 records

Technology focussed Yes

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Feature3 records

Partnerships

Seven partnerships are on record, tiered core and minor.

• A | T CollectivecoreStrategic or Co-development Partner · 15 May 2026According to A | T Collective CEO David Hu, partnership expansion aims to provide travel advisor partners with more options to create customized vacations and strengthen client loyalty through new luxury property additions including Waldorf Astoria Bangkok, Hotel de l'Opera Hanoi, Waldorf Astoria Helsinki, and Ritz-Carlton Reserve properties.
• Trip MatecoreTechnology or IntegrationPartnership with Trip Mate, a Generali Global Assistance & Insurance Services brand, to offer travel protection plans including Cancel For Any Reason waivers and insurance benefits. Trip Mate markets travel insurance on behalf of United States Fire Insurance Company.
• HertzcoreGTM or Marketing PartnerHertz car rental partnership offering $100 car rental credits on Hawaii bookings. Partnership includes cancellation policy integration with $100 fee for cancellations within 48 hours.
• Hawaii Visitors and Convention BureaucoreGTM or Marketing PartnerMarketing partnership with Hawaii Visitors and Convention Bureau (HVCB) promoting Hawaii tourism with co-branded offers and exclusive rates for Hawaii destinations.
• AAA (Automobile Club of Southern California)coreOthersPleasant Holidays is a subsidiary of AAA (Automobile Club of Southern California) since 1999. AAA membership provides customer acquisition through affinity marketing.
• Aruba Tourism AuthorityminorGTM or Marketing PartnerCo-marketing partnership featuring Aruba destination promotions with tagline 'One Happy Island' and promotional offers.
• United States Fire Insurance CompanycoreTechnology or IntegrationInsurance underwriter for travel protection plans offered through Trip Mate. Part B of travel protection is underwritten under form series T7000 et al and TP-401 et al.

Scale indicators3 records

Recent moves6 records

Expansion highlights4 records

Direct peers

• Classic Vacations: Long-standing upscale tour operator packaging flights, hotels, and car rentals to Hawaii, Mexico, Caribbean, Europe, and Fiji. Closest analogue to Pleasant Holidays' focus on beach/resort destinations with a travel-advisor channel and similar supplier relationships.
• ALG Vacations: Hyatt-owned (formerly Apple Leisure Group) vacation wholesaler focused on Mexico and Caribbean all-inclusive package vacations sold through travel agents. Directly competes with Pleasant Holidays' Mexico and Caribbean product set and shared B2B distribution model.
• Delta Vacations: Airline-owned tour operator packaging flights on Delta with hotels, car rentals, cruises, and activities globally. Comparable bundle structure and travel-advisor platform; Pleasant Holidays operates as airline-agnostic so Delta Vacations is the natural direct competitor on air-inclusive packages.
• Apple Leisure Group: Hyatt subsidiary that owns AMResorts (all-inclusive resort brands) and ALG Vacations distribution. Overlaps with Pleasant Holidays on hotel sourcing into Mexico/Caribbean and competes for the same travel-agent bookings through overlapping inventory.
• Journese: Luxury tour operator (formerly Travel Solutions International / ALG brand) selling curated upscale vacations with Hawaii, Mexico, and Europe focus. Targets the same affluent travel-advisor segment via commissions and luxury hotel partnerships.
• Funjet Vacations: Mid-market package tour operator specializing in Mexico, Caribbean, and Hawaii vacations sold through travel agents with charter air options. Direct competitor on volume leisure packages with overlapping destination and supplier set.
• Travel Impressions: Long-established tour operator under ALG selling resort vacations to Mexico, Caribbean, Hawaii, and Europe through travel advisors. Competes head-to-head with Pleasant Holidays on travel-agent commission economics and resort supplier allocations.
• Gate 1 Travel: Mid-market escorted tour and independent vacation package operator covering Europe, Asia, Hawaii, and South Pacific. Overlaps with Pleasant Holidays on multi-component package construction and global destination breadth, though leans more escorted-vs-independent.
• American Express Travel: Premium-cardholder tour operator packaging luxury and upscale vacations with hotel, cruise, and air components through travel counselors and digital channels. Targets the same AAA-adjacent affluent segment with comparable vacation-package structures.

Broad incumbents

• Expedia Group: Largest online travel agency conglomerate operating Expedia, Hotels.com, Vrbo, and B2B partner programs. While not a like-for-like tour operator, Expedia's B2B partner network and broad leisure packages compete with the supplier-commission layer Pleasant Holidays depends on.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat5 records

Key risks6 records

Key highlights7 records

Customer concentration

• Facebookfacebook.com/pleasantholidays
• Instagraminstagram.com/pleasantholidays
• Xx.com/pleasantholiday
• LinkedInlinkedin.com/company/pleasant-holidays

Compliance7 records

Revenue estimate

Valuation estimate

Number of profiles

Subsidiaries5 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Pleasant Holidays