Cruises
Ocean and river cruises, from a long weekend to a once-in-a-lifetime sailing. We match the ship and cabin to how you like to travel.
Free trip planning · Nationwide
Trips planned for you, start to finish.
Cruises, Caribbean resorts, honeymoons, group trips and crewed yacht charters. Tell us what you have in mind, and Reco and Tiffany come back with ideas and honest options.
Planning fee$0
Booked without your OKNever
Reply time1 business day
Where would you like to go?
Six kinds of trips we plan, each matched to who's going and how you like to travel.
Caribbean & all-inclusive
Beach weeks where the meals and drinks are covered, picked for the crowd you're bringing: couples, families or friends.
Honeymoons & celebrations
Honeymoons, anniversaries, milestone birthdays and destination weddings, with the details handled so you can enjoy it.
Crewed yacht charters
A week on a private boat with a captain and crew. Reco captained yachts in the Florida Keys and the Caribbean, so he knows which boats, crews and routes fit which trips.
Group trips & retreats
Family reunions, friends' getaways and company retreats. One plan, one point of contact, and everyone gets the same answers.
Florida Keys & the islands
Reco's home waters. Where to stay, what to book ahead and what to skip.
How it works
Three legs, one point of contact, and nothing booked until you say yes.
Your trip itineraryPassenger: you
- DepartureTell us your idea
Where you're thinking, roughly when, who's going and a budget range. Two minutes.
- ConnectionGet honest options
Reco or Tiffany replies by email within one business day with questions and ideas, then a short list of options that fit.
- ArrivalYou approve, then we book
Nothing is booked or charged until you approve a written quote. We stay on call until you're home.
Your planners
Real people answer every request.
President
Reco
A former travel agent who spent years as a yacht captain in the Florida Keys and the Caribbean, looking after guests, crews and every detail of the trip.
COO
Tiffany
Built call centers and back offices. She makes sure every request gets a fast, clear answer and nothing falls through the cracks.
Plan my trip
Fill in your boarding pass. Reco or Tiffany replies by email within one business day.
Travel guides
Straight, sourced advice from our team and Reco's years on the water.
When to sail the Caribbean and the Florida Keys
Caribbean and Florida Keys sailing seasons month by month: crewed charters, cruises, hurricane season, holiday weeks and how far ahead to book.
What a crewed yacht charter includes (and what costs extra)
Crewed yacht charter costs explained: base fee, APA, tax, crew gratuity, delivery fees, MYBA vs. all-inclusive terms, payment timing and what to ask.
Your first cruise: a calm, complete checklist
A first-cruise checklist: choosing a line, ship and cabin, documents, what's included vs. extra, insurance basics, packing and embarkation day.
Questions
Straight answers before you send anything.
Do you charge a planning fee?
No. Travel agencies are paid commissions by cruise lines, resorts and tour companies. Your price is usually the same as booking it yourself.
Are you open for bookings?
Upfront Travel is just opening. We're taking trip requests and planning now. Bookings are made through an established host agency (a larger agency that independent travel agents book through), and its name will be on your written quote. Nothing is booked or charged without your OK.
Where do you work?
Anywhere in the US, by email, phone and video. We plan for travelers from every state. Bookings for residents of Florida, Washington, Hawaii and Maryland open once those states' travel-seller filings are complete; trips to those places are fine for everyone else. Travelers outside the US are welcome to send a request too.
Can you help with a yacht charter?
Yes. Reco spent years as a yacht captain in the Florida Keys and the Caribbean. He'll help you choose the boat, crew and route, and explain what's included and what costs extra.
Should I send my card or passport details?
No. Never send card numbers, passport numbers or passwords through this form or by email. Traveler details are collected only when you're ready to book, through the booking system.
Who is behind Upfront Travel?
Reco and Tiffany of Upfront Consulting with Tiff & Reco LLC. Reco, our President, is a former travel agent and yacht captain. Tiffany, our COO, built call centers and back offices and makes sure every request gets a fast, clear answer.