Our Services

With Out There with Jake, you get honest, transparent, and truly curated travel planning. No hidden agendas. No affiliate schemes. Just real recommendations and a relentless focus on what’s actually worth your time and money.

  • Luxury hotel room with a bed, a beige upholstered bench, a bedside lamp, a living area with a sofa, ottoman, and chairs near large windows with a view of the sky and balcony railing.

    ACCOMMODATION BOOKING - Complimentary

    Handpicked hotels. No hype. Just what's worth it.

    I handle your hotel booking at no cost to you—you get the best available rates, priority access, and exclusive perks at select properties. I earn commission directly from hotels, so my service costs you nothing. You'll receive up to 20 vetted recommendations until we find the perfect match for your style and standards.

    Best for: Travelers who already have their plans but want expert hotel selection.

  • Balcony with rattan lounge chairs and small tables overlooking the ocean under partly cloudy sky

    CUSTOM ITINERARIES - $149 per trip

    Your trip, curated. No generic listicles. No wasted time.

    I build a fully tailored itinerary based on your taste, pace, and priorities—cutting out tourist traps and filler. You'll get day-by-day recommendations for design-forward experiences, local favorites, hidden gems, and restaurant picks that actually deliver. Includes hotel booking (up to 20 recommendations), tour and activity bookings, and up to 3 rounds of revisions.

    What's not included: Ground transportation (airport transfers, private drivers), private guides, or white-glove concierge coordination.

  • Modern luxury hotel entrance with lush tropical landscaping, a vintage white Rolls-Royce, and dramatic architectural lines at sunrise—greenery and understated opulence.

    VIP CONCIERGE - $349 per trip

    The full experience—everything planned, everything handled.

    Everything in Custom Itineraries, plus I partner with trusted local specialists to arrange private guides, ground transportation, and exclusive experiences you can't book yourself. Airport transfers, private drivers, hard-to-get reservations—fully coordinated. You show up, everything's handled.

    This is the complete package with on-the-ground support—ideal for travelers who want zero logistics to manage.

  • Rooftop terrace bar with minimalist marble counter, contemporary wooden seating, and panoramic ocean views—sleek design, open-air ambiance, and elegant details.

    GROUPS & EVENTS - Starting at $499

    Big moments, handled. No stress, no generic group travel.

    Perfect for destination weddings, curated group getaways, and family reunions. I coordinate every detail for groups up to 10 people. Need a hotel block (8+ rooms)? I'll negotiate rates and secure perks. Larger groups require custom pricing—let's talk.

    Includes: Venue sourcing, room block coordination, group itinerary planning, and on-site logistics.

    Contact me for groups larger than 10 or complex multi-day events.

Private hotel pool and terrace with wicker loungers, minimalist landscaping, and panoramic Atlantic Ocean views in Funchal, Madeira—serene, modern, and uncluttered.
Modern infinity pool with sleek tile steps, sculptural metal arch, and unobstructed Atlantic Ocean views—contemporary design and tranquil setting in Funchal, Madeira.

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OUR PROCESS

  • Share your travel goals, must-haves, deal-breakers, budget, timeline, and dream destinations.

    We’ll chat briefly—no endless forms.

  • You’ll receive a clear quote and overview of what I’ll deliver, based on your needs and service tier.

  • Once you’re happy with the plan and pricing, you make payment and I get to work.

  • You review your personalized recommendations or itinerary. Need tweaks? I’ll revise until it’s right—no surprises, just clarity.

  • I handle booking your accommodations and experiences (you book your own flights).

    Once confirmed, you get a final itinerary and all the details you need.

  • Pack your bags and enjoy! I’m available for questions before and during your trip.

    After you return, I’ll check in for feedback to make your next trip even better.