Proposals & date nights

Date Night and Proposal Cruises in Jacksonville

Just the two of you, the water and the sunset. For a date night cruise, choose a private sail for two or a sailing catamaran, and your captain takes care of everything else.

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Private sail for two
Sunset timing
Picnic or restaurant stop
From $225

Best boats for proposals and date nights

Pick the right boat for a date night cruise or proposal

Every boat is private, with a USCG-licensed captain included. Each pick below says why it suits this trip. A date night cruise on a sailboat is quiet once the engine is off, and the 35 ft catamaran can add a stop at a waterfront restaurant. Most couples time the trip around the sunset.

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How to choose

If you live in Jacksonville or the beaches, the 35 ft catamaran is the closest. If you can make the drive to Fernandina Beach, the sail for two is the most romantic option we have. Planning a proposal? Call or text us before you book and we will help you plan the timing.

Just the two of you

Fernandina Beach 1 / 3

33-foot Sailboat for Couples

1 to 2 Passengers

Once the engine is off, it is just the wind, the water and the sunset.

Charter rates

2 hours$225
3 hours$299
4 hours$375
6 hours$499

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Calm and close

Under sail at sunset on the Intracoastal

Jacksonville Beach 1 / 5

35-foot Catamaran

1 to 6 Passengers

Closest to the beaches, with an optional waterfront restaurant stop.

Charter rates

2 hours$495
3 hours$695
4 hours$875
5 hours$1,075
6 hours$1,275
7 hours$1,695

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Room to stretch out

Fernandina Beach 1 / 2

37-foot Sailing Catamaran

1 to 6 Passengers

A shaded cockpit and a bow trampoline for watching the sky.

Charter rates

2 hours$399
3 hours$499
4 hours$599

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Good to know

Plan the perfect date night or proposal

A few things our captains tell every group before the trip. If your date night cruise is hiding a proposal, tell us when you book so your captain can help with the timing.

Planning a proposal?

Call or text (904) 595-9196 before you book, and we will help you plan the timing around the sunset.

Dinner by boat

Bring a picnic, or book the 35 ft catamaran with a stop at a waterfront restaurant.

Double dates

The catamarans and the 33 ft sailboat take up to 6, so couples can share and split the cost.

What to wear

Smart casual with soft-soled shoes, plus a light jacket for after the sun goes down.

Questions

Date night cruise and proposal questions, answered

Read the full guideDate night cruises in Jacksonville: ideas and prices

What is the best date night cruise in Jacksonville?

For two people, the romantic sail for two in Fernandina Beach is the favorite, from $225 for 2 hours. Closer to the beaches, the 35 ft sailing catamaran sails the Intracoastal from Palm Cove Marina, from $495 for 2 hours, and can stop at a waterfront restaurant.

How much does a private date night cruise cost?

The sail for two is $225 for 2 hours or $299 for 3 hours. The 37 ft sailing catamaran in Fernandina Beach is $399 for 2 hours, and the 35 ft catamaran in Jacksonville Beach is $495 for 2 hours. Sales tax is added.

Can we have dinner on a date night cruise?

Yes. You can bring a picnic and your own drinks, or book the 35 ft catamaran with a stop at a waterfront restaurant. If you plan to bring wine, mention it when you book so your captain can confirm the rules for your trip.

Where does a date night cruise leave from?

The sail for two and the 37 ft sailing catamaran leave from Fernandina Harbor Marina in Fernandina Beach. The 35 ft catamaran leaves from Palm Cove Marina in Jacksonville Beach and sails the Intracoastal Waterway.

Can you help plan a proposal on a date night cruise?

Yes. Call or text (904) 595-9196 before you book, and we will help you plan the timing around the sunset. The sail for two in Fernandina Beach, on Amelia Island, is the most romantic option we have.

What if the weather is bad on our date night?

Your captain makes the weather call. If we cancel for weather or safety, you get a full refund or a new date, so you can still plan the evening you had in mind. Trips cancelled by guests more than 5 days ahead are refundable, less a 3% processing fee.

Can we do a double date on a boat?

Yes. The 35 ft and 37 ft sailing catamarans and the 33 ft sailboat each take up to 6 guests, so two or three couples can share one private boat and split the cost.

What should we wear on a date night cruise?

Smart casual, with soft-soled, non-marking shoes instead of heels. Bring a light jacket or wrap, because it cools down quickly on the water after sunset.

More ideas

Other experiences

All experiences

Sunset cruisesGolden hour on the water Birthday partiesCelebrate with your crew Bachelorette partiesTiki boat or yacht Dolphin & wildlife toursCalm water, big sightings Sandbar daysSwim, float and relax Corporate & groupsTeam outings and clients Jaguars boat tailgateGame day on the river Fishing chartersInshore and nearshore Burial at seaA respectful farewell Catering on boardPrivate chefs for your trip

Testimonials

From our clients’ experience

Every trip is private, with a licensed local captain. Here is what recent guests said.

★★★★★5-star reviews on Google

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Pamela Heidelberg Posted on Google

★★★★★

“We had a grand time!! We absolutely loved our Captain, Jason.”

aarond127 Posted on Google

★★★★★

“Loved it! Great price and friendly staff”

Joshua Thompson Posted on Google

★★★★★

“Awesome experience and great captain!”

Justin Copeland Posted on Google

★★★★★

“Awesome time, good service, great experience all around. Will book again!”

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Ready to book your date night cruise?

Pick your boat and reserve online in minutes, or call or text us and we’ll help you plan.

See boats & prices (904) 595-9196