Itinerary Specialist

About Simply Select

Simply Select is a premier luxury travel and lifestyle group with over 30 years of expertise crafting extraordinary experiences for discerning individuals and families worldwide. Operating across two complementary divisions — Simply Select and Simply Select Yachts — we deliver curated travel itineraries, exclusive hotel and villa arrangements, private aviation, and world-class yacht charters across the globe's most coveted destinations.

Our reputation is built on discretion, attention to detail, and an unwavering commitment to excellence. From sun-drenched Mediterranean escapes aboard cutting-edge sailing yachts to bespoke cultural journeys through Asia and the Americas, Simply Select brings the world to those who expect nothing less than the extraordinary.

Position Overview

The Itinerary Specialist is the creative force behind every client experience, responsible for designing bespoke, client-facing itineraries that seamlessly blend dining, activities, and cultural moments into cohesive narratives. Working behind the scenes, you will source and vet restaurants and experiences, intelligently sequence activities to create optimal flow, and present polished, beautifully designed itineraries that reflect both the client's preferences and Simply Select's uncompromising standards. This role demands refined taste, discernment, and an acute understanding of ultra-high-net-worth clientele across diverse demographics and nationalities. 

 Key Responsibilities

• Research, identify, and vet restaurants and activities for client itineraries based on specific client profiles and preferences
• Build and design custom, client-facing itineraries that thoughtfully sequence experiences and dining reservations with attention to pacing and flow
• Source and book restaurant reservations and activity experiences, confirming availability and accommodations with vendors
• Maintain and update dining and activity guides for popular destinations, identifying and evaluating new openings and experiences
• Conduct vendor outreach via phone and research to confirm details, availability, and fit for client itineraries
• Coordinate with the executive team to vet recommendations and ensure alignment with Simply Select standards
• Write compelling experience and restaurant descriptions, maintaining the brand voice
• Present itineraries with thoughtful aesthetic design and professional formatting using design tools
• Manage tight deadlines and fast-turnaround itinerary requests while maintaining quality standards
• Develop and maintain institutional knowledge of destinations, vendors, and emerging dining/experience trends
• Understand and respond to nuanced client needs based on group composition (families, couples, friend groups), age demographics, and lifestyle preferences

Requirements

Essential

• Refined taste and discernment with the ability to identify restaurants and activities that appeal to ultra-high-net-worth clientele
• Strong understanding of how client composition impacts experience curation (families vs. couples vs. friend groups; age differences; cultural and national preferences)
• Exceptional attention to detail and design sensibility—client-facing itineraries must be aesthetically polished and professionally presented
• Excellent writing ability with the capacity to craft compelling, brief descriptions of experiences and activities
• Proficiency with G Suite (Gmail, Google Calendar, Google Docs, Google Sheets)
• Proficiency with Canva or similar design tools for creating visually appealing itineraries
• Familiarity with AI tools and platforms, including Claude
• Comfort working under tight deadlines and managing fast-turnaround requests
• Strong research skills and ability to quickly learn new destinations and identify quality vendors
• Intellectual curiosity and ability to stay current with new restaurant openings, activity trends, and cultural developments
• Ability to thoughtfully sequence experiences—understanding optimal timing, pacing, and flow 
• Excellent communication skills and ability to engage confidently with vendors and internal teams
• Strong organizational skills and ability to manage multiple itineraries simultaneously

Beneficial but not Required

• Bachelor's degree in hospitality, business, travel & tourism, fine arts, or related field
• Demonstrated passion for travel and personal travel experience
• Genuine interest in food, culinary arts, and fine dining
• Experience with destination research and travel planning
• Familiarity with additional design software (Adobe Creative Suite, Figma, etc.)
• Background in event planning, curation, or creative industries

Why Join Simply Select?

• Be part of a prestigious company with over 30 years of industry excellence
• Work with a global network of luxury vendors and exclusive destinations
• Develop expertise in luxury travel and yacht experiences
• Collaborate with a team committed to delivering extraordinary experiences
• Enjoy a role that combines strategic thinking with direct client engagement