Proposal & Engagement Trips
The best out of 797 Proposal & Engagement Trips deals - enter destination and dates to check availability.
Nearest Proposal & Engagement Trips
Nearest Proposal & Engagement Trips
Boat Chicago Charters – Dolce Mare
Chicago, Illinois+2Instant ConfirmationTrips fromUS $800Pura Vida Boat Charters
Chicago, Illinois+3Trips fromUS $1,750- +1Instant ConfirmationTrips fromUS $3,500
Captained 37’ Sea Ray Sundancer: Navy Pier
Chicago, Illinois+4Trips fromUS $1,0503rd Coast Cruising – Lagoon 380
Chicago, Illinois+3Instant ConfirmationTrips fromUS $1,200- +2Instant ConfirmationTrips fromUS $500
- +3Trips fromUS $550
Blackhawk Boat Tours, LLC
Chicago, IllinoisInstant ConfirmationTrips fromUS $170Toronto Breeze Yachts
Toronto, Ontario+4Instant ConfirmationTrips fromUS $2,400- Instant ConfirmationTrips fromUS $848
Nearest Proposal & Engagement Trips destinations
Top Proposal & Engagement Trips worldwide
- 6 Hour – Private Boat Tour (AM) - 10:00 AM+8Instant ConfirmationPrice for up to 8 peopleUS $1,100
- Private Sunset Cruise+6Instant ConfirmationPrice for up to 6 peopleUS $250
- Full Adventure Day I BEST VALUE!+7Instant ConfirmationPrice for up to 6 peopleUS $799
- 1 hour Blue Lagoon Quick Escape+1Instant ConfirmationPrice for up to 10 peopleUS $57
- 2 HR - Sunset Cruise+1Instant ConfirmationPrice for up to 6 peopleUS $750
- Private Islamorada Sunset Cruise+10Instant ConfirmationPrice for up to 6 peopleUS $300
- Half Day Afternoon/, Sunset+4Instant ConfirmationPrice for up to 6 peopleUS $499
- Island Excursion Topsail - 4:00 PM+6Instant ConfirmationPrice for up to 6 peopleUS $450
- 2H - Sunset tour+3Instant ConfirmationPrice for up to 9 peopleUS $251
- 2 Hour – Little River Sunset Tour+4Instant ConfirmationPrice for up to 10 peopleUS $200
Popular Proposal & Engagement Trips destinations worldwide
What boaters say about Proposal & Engagement Trips
- 5.0/5(Fall 4H PM (Su-Th))
Had a blast!
Amazing boat and captains! We had such a great day cruising around, hitting beaches and a bar, and even saw a dolphin!
- 5.0/5(4 Hour – Private Boat Tour (AM))
So much fun!
We went to swim with the pigs and went to two different snorkel spots! Great day!
- 5.0/5(4 Hour – Little River Boat Tour - 1:00 PM)
Fun trip with friends!
Trent was friendly and took us to a sandbar for swimming. We had so much fun on the water!
- 5.0/5(2 Hour – Sunset Adventure)
So much fun!
Exactly what we wanted out of this trip - immaculate boat, super fun Captain John & great music too! It was easy booking & great communication prior to leaving. As locals, who have done the bigger sightseeing cruises with our guests, we have now found the best way to enjoy the water! Definitely recommend :-)
- 5.0/5(2 Hour – Little River Sunset Tour)
Awesome Outing!!!
We had a wonderful sunset cruise from Little River up to Bird Island and back. Captain Trent was personable, entertaining, and accommodating of our group of 4 life-long friends. He’s willing to adapt the trip to meet the preferences of your group. We’re planning on another trip nect year! Highly recommended!!
About Proposal & Engagement Trips
Proposal & Engagement Trips turn a big life moment into a calm, private time on the water. You get a quiet setting, open views, and a relaxed pace. It is simple, romantic, and easy to plan.
Expect a short safety chat, then a smooth cast off from the dock. Your captain will cruise to a scenic spot, often at sunset. The bow, which is the front of the boat, makes a great place for photos.
Trips are run by licensed captains who know how to time the moment. Tell them your plan, music, and any surprise details. Many offer extras like a chilled toast, flowers, or a photo stop at anchor.
This experience suits first-time boaters, couples, small families, and close friends. Wear soft, non-marking shoes and bring layers, sunscreen, and a camera. If anyone gets seasick, choose a calm bay or larger vessel like a catamaran for a steadier ride.
Regulations vary by location, so check local licenses, permits, and operating rules before you go. Follow your captain’s safety briefing, know the capacity rating, and keep life jackets, also called PFDs, ready for all guests. Always respect USCG rules, no open containers for the captain, and local laws on drones and celebrations.