NYC Date Idea: Sailing on the Hudson River

Sailing on the Hudson River makes an amazing, thrilling date. Here are some photos, if you’d like to see…

First step of any date, of course: Choosing your outfit. I decided on an Ikat tunic with jeans and flats.

We met up at an old schooner, which sails for two hours down the Hudson River around the Statue of Liberty.

The captain encourages everyone to pack a picnic, so Alex picked up two lobster rolls from Chelsea Market, along with salt-and-vinegar fries. Also, the skippers come around and offer wine or beer–I love white wine, and Alex chose Fire Island Lighthouse Ale.

Four years ago, Alex proposed on a sailboat on the Hudson, so sailing always makes us think back to that day, and we end up taking cheesy kissing photos! It cannot be helped! :)

The schooner offers a few different sailing times everyday–daytime, after dark–but I’d highly recommend the sunset sail; it’s magical to see the purple sky over Ellis Island and the Statue of Liberty. (You can double-check the exact sunset time on this handy website.) The clouds looked like cotton candy.

Do you like sailing? Would you want to go? I’d highly recommend these schooner sails. Being on the water is thrilling, with the wind in your hair and the seagulls squawking, and you feel a million miles away from the big city. My mom and her husband went this sail last summer, and they said it was one of the most romantic things they’d ever done. Hope you like it, too!

What date activities do you like? Playing games with friends? A good old-fashioned dinner + movie? I’d love to hear suggestions!! xoxo

We also sent Toby a little good-night video, so his babysitter could play it to him before he went to bed:)

P.S. How to look pretty on a first date, and 10 ways to spend an afternoon in NYC.

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  4. These are great date ideas! Dates don’t have to be always dinner outs but must be fun as well. Great post you got here. Thanks for the information that you’ve shared with your readers. :)

  5. I love that you started NYC DATES. I live in NY and love all of your ideas so far and want more for fun things for my boyfriend and I to do other than the movies!! Tonight maybe we’ll do the sail boat thing.. also if you feature more in Brooklyn that would be awesome. You guys are so adorable!! and yes thanks for keeping is well balanced as well even though you have the baby.

  6. Great post and photos as always. How are you finding the new Nokia?
    I’m contemplating between that or the iphone and since you post photos via smartphone a lot for sure I’m not alone in wondering what your thoughts are, good and bad.
    Also, I’ve been following your blog for over 4 years now and I want to say thank you for still keeping it real and well-balanced post-baby.

  7. Such a great date! I love the tunic you are wearing!

  8. Great shots! Ummm, can you tell me more about that ADORABLE ikat tunic you are wearing?!? :)

  9. Anca says...

    Oh, and if I didn’t live in Europe I would definitely try the Hudson sailing date. Maybe I’ll try it in Venice :)

  10. Anca says...

    Oh come on, you never forced anyone to buy anything. So don’t you apologize for trying on new stuff and sharing your reviews.
    I see all your posts (sponsored or otherwise) as a discussion between friends, with recommendations and advice.
    I love your blog and I’ve been checking and reading it daily for over 4 years. Thank you!

  11. Adorable photos… And a great night! Sailing is a huge part of our lives here in MI. My husband and I own a boat, got engaged on it, and sail as often as possible weather permitting. We even got married at the yacht club!

  12. Julie says...

    Oh! It was on my to do list when we came but hadn’t got the time to do it…
    Meeting you in the plane totally made up for it ;) !
    Julie xoxo

  13. I just teared up. This is the PERFECT date! If my BF planned this for me I would die… in a good way :)

  14. We chartered The Manhattan yacht from for our wedding and they were wonderful. Highly recommended for a smaller wedding in nyc.

  15. ashley says...

    I, too, am super surprised by the negativity surrounding your sponsored posts. It doesn’t bug me as I still find you to be genuine and sincere with your writing and what you provide to your readers. You clearly state that it is sponsored and it seems to me you have been forced to talk about your sponsors more as you can’t make people happy either way. I don’t think you would ever suggest or review things that you didn’t sincerely want to share or promote on your blog. I find it so disheartening to see people ‘pick on’ you for writing sponsored posts as you RARELY do such a thing. You’ve done so few and your blog is never littered with ‘c/o’ like so many other blogs out there and I truly appreciate that so much of what you put out there is not influenced by others. Just because you are a big time blogger doesn’t mean you shouldn’t be allowed to try out a cool product and get paid for it or link to your friends websites (especially if they are your sponsors!). And you should feel free to post sponsored content if you so choose. You have always been so open and so honest with your readers and I find it a shame that some of those who have previously commented don’t see it that way – they just jump on the negative. I have been a long time reader and I have never once felt taken advantage of or felt like you aren’t being open with your readers. I say keep being true to yourself and you will keep succeeding. Keep up the great work, it is why you have so many loyal followers!

    Love the photos and adorable good night message!

  16. What a fantastic pair! I love how you make spending alone time a priority. All the best!

  17. This is the best idea! I think I might need to surprise my husband with this date for his birthday later this month!

  18. i’m not sure why everyone is upset about sponsored posts,either. take things for what they’re worth. this post was worth seeing if only for the great date idea. it totally adheres to the theme of your blog, and in my opinion, there is nothing wrong with monetizing your blog however you see fit.

  19. You are so adorable! Hope to be more like you when I grow up!

  20. your family his lovely, but making family memories into an ad feels like it cheapens those. i’m sure that’s not your intention at all and i have no doubt that this was a very special time! BUT i think that’s why some readers (myself included) find sponsored posts so off-putting.

    i’m just putting the following there as part of the conversation – not saying that it applies to you: i feel the same way about sponsored posts in blogs as in magazines or other publications. i don’t mind ads being in magazines – but sponsored posts make me doubt their credibility (again, i’m not saying that these aren’t genuine, wonderful memories, it’s just a little off-putting when they’re put as ads). and it makes me question whether their content is worthwhile. also, no one would trust the new york times’ credibility, for example, if they knew that movie producers were paying them handsomely to say nice things about their movies.

  21. This comment has been removed by the author.

  22. i’ve been on a couple of yachts tours around the ny harbor, but a sailboat outing looks so much lovelier – and why do i have a feeling that leaving from chelsea piers is nicer than the east river docks? might do this for my upcoming may birthday, thanks!

  23. My first time sailing was on Lake Victoria in Tanzania. It was so amazing! I would love to have my own boat one day.

  24. What a wonderful date night idea. I don’t think my husband and I have ever done anything that exciting! You guys are seriously cute. Though I could never give up my iPhone, I do like the idea of being able to check one person’s tweets/FB updates/etc. That’s very cool.
    Ronnie xo

  25. Anonymous says...

    My fiancé and I are flying from Sweden to NYC to get married in City Hall 20th of July. For the evening we have already booked a sunset sail :) All thanks to you and your little NY guide, thanks a million!

    Hugs Jenny

  26. If I ever go to New York (fingers crossed it´s soon) I will definitely have this in mind when I plan the trip.

    When I lived in London one of my favorite things to do was just walk, walk & walk through town, for 2-3 hours at a time, the city is just different on foot.

  27. Joanna, this was just the cutest post and made me smile! After writing you almost a year ago now when I was just getting my blog up and going, I still love visiting your site everyday and hearing about your life in the Big Apple. It definitely makes me miss home…I’m looking forward to leaving Malaysia and heading off to our next adventure!
    Thanks for all your inspiration and for introducing me to this new phone and the great app. Have a great Wednesday in NY as I am getting ready to go home after work here in Kuala Lumpur. :)

    xo Grace

  28. you guys are so cute it kills me! what a fun date – and I am LOVING your ikat tunic!

  29. I always forget about this fun activity. It’s quite romantic and great to do in the summer.

  30. Jo, that looks like so much fun! Love the packed picnic and the good night video ( my son just asked me to replay it 3 times!)

  31. My favourite (absolute favourite) is staying at home, cuddles under a blanket, watching a nice movie. A trip to Paris would be a close second:D

  32. we go sailing a lot here in california. in fact my husband proposed to me on a sailboat too!!!! …but how great does the hudson river look?! i also love loved your night night video to toby! what cute parents!

    question for you- how did you get the Polaroid look? i love it!


  33. Anonymous says...


    I’ve been reading your blog since 2007 and it’s always been my favorite. I’ve introduced it to so many of my friends/family/coworkers. In fact, we talk about your posts everyday at work!

    The thing I’ve always admired about A Cup Of Jo is your genuine tone. These sponsored posts just don’t seem genuine yet they seem to come more and more frequently. Everyone at work today was talking about how disappointing these posts, pop-up advertisements, etc are. If it takes these sorts of ads to keep your blog running, then please by all means keep them. But it’s coming across as a bit sell-outish to us, even if that’s not totally fair for us to feel that way. To me, there is a big difference in sponsoring a company like Pinhole Press through your posts, which is something you clearly stand behind (it comes across in the way you write about it!) and a company like Nokia, which we all know you don’t use as your daily phone.

    This comment isn’t supposed to be super harsh but I just want to give you my opinion. We love your blog and it is definitely your decision to make – just wanted to give my two cents as a dedicated reader.


  34. That video was so precious! And I really love that shirt you’re wearing towards the top, so cute!

  35. goodness my, if only i could look so darling on cell phone picture. jo does it again!

  36. You and your husband are ridiculously cute! Love the photos!

  37. Sally says...

    You glow in these pictures!

  38. I LOVE sailing on date night. We live in Seattle and went last year for the first time. It was so magical! We opted for the sunset cruise and it was just amazing. Loved seeing your photos, thanks for sharing.


  39. I shouldn’t have said “everyone.” Looking back, there were only a few. I guess I got a little defensive of my favorite blog. ;)

  40. I’m not sure why everyone is so upset with the sponsored posts. Joanna, I just want you to know I think you have been very clear with your philosophy on sponsored posts. Your loyal readers should know you would never post a sponsored post on a product you don’t believe in. And if they didn’t know that it’s stated right on your blog!! Everyone wants something for nothing. I think you have found a great balance. Don’t change a thing!

    P.S. LOVE the video idea for the little munchkin! I’m going to steal it.

  41. I’ve read your blog most days for a few years now but don’t comment usually. I enjoy your lifestyle posts and don’t usually care about the advertising side of things.

    But, just to let you know, I’m thinking of buying a Nokia Lumia because of your sponsored post and I hadn’t heard of it previously. I’m not a fan of Apple and wanted to see what the competition was like, especially since I’d like to keep supporting Nokia as I’ve been buying their phones for years.

    So thank you from Australia :) Apologies for the ramble, but just wanted to let you know sponsored posts can be beneficial.

    Nothing wrong with making things a bit interesting eh? ;)

  42. I have been reading and loving your blog for years! I can’t believe it’s been four years since you became happily engaged! Congratulations! You are so lovely :)

  43. Mo says...

    This is a great idea Joanna!
    My absolute favorite date activity with the bf is apple picking. We go to a lovely orchard in Maryland and make apple crisp together afterward. They have strawberries, peaches and pumpkins too, depending on the season.

    It is the cheesiest thing ever (esp acc’d to his buddies) but one of the most romantic things we enjoy doing.

  44. lily says...

    wow – who knew a sponsored post would generate such controversy! It’s a phone people, not a nuclear bomb. It’s your blog and you should do as you feel comfortable. Personally, I am very curious to hear you thoughts on the windows phone vs. the iPhone and which you prefer after you’ve finished experimenting with both. Enjoy!

  45. Anonymous says...

    I love love love your blog! One of my daily interweb activities.

    I do feel a little taken advantage of with the blatant plugs though (especially on May Day- a day for workers).

    The blog is your special creation, and you should take it in any direction you feel comfortable. That said, the average American sees over 3,000 advertisements DAILY. I’d hate to see such a fun, personal, lifestyle blog turn into another money machine. (Of course I know you don’t want this either and it is a balance, like you said. Just want to tell you how special this site is to me and I hope it stays that way!)

  46. Just found your blog. So neat stuff! Love your date idea..I love anything to do with being on water – especially in the Spring/Summer. I also love the idea of sending a video “hello” back to the babysitter. Thanks for sharing.

  47. Cheryl says...

    My boyfriend and I took this same sail a few years ago on my birthday! It was such a great combo of being romantic and fun as we partied with a few other people we met on the boat! After seeing your pics I might have to go again! Thanks for sharing!

  48. Sarah says...

    What fun! The boat ride looks like a blast (I’m very land-locked in Colorado, unfortunately, no sailing near by!), and the food pics have my mouth watering. YUM! You two are adorable.

  49. This sounds like a brilliant date night, thank you! My husband is about to graduate with his Masters and this sounds like such a nice, low-key and relaxing way to celebrate. Can Alex pick up lobster rolls for us too?! ;)

  50. urbnfemme says...

    My wife surprised me with this outing last summer and it was one of my favorite this we’ve done in NYC. Your post about it is so sweet that I wanna go again right now!

  51. Tracy Gilmore says...

    I love this post – thank you for sharing such a special date with us, and thanks for the inspiration!

  52. the pic of you kissing his cheek is too sweet! you better print that :)

    and the phone does sound handy, but you’ll never get me away from my iphone, nokia, sorry ;)

  53. Oh god, you guys just kill me! Cuuuute.

  54. thanks for your email, amber! i’m glad you wrote! yes, i do have an iphone — but i’m trying out this new phone because it’s apparently the best for social media and got a glowing review in the new york times. i tried to explain that clearly in my first nokia post; maybe i should have mentioned it again here. apologies!

    i do just a few sponsored post a year — very few and far between. but thank you so much for writing, i’m definitely going to take your feedback into account. i really, really care what you (and other readers) think and i’m glad you shared. i know that i’ve gotten sick of other blogs when they do too many sponsored posts, and i’m trying to figure out a good balance of doing sponsored posts with brands i love & accepting advertising, so i can keep blogging as a business. it’s all still a bit of the wild west!

    thanks so much for writing,

  55. How fun! I met my boyfriend on a sailboat and he’s a captain so we get to go sailing a lot in the Caribbean (our backyard) sail is the best.

  56. This looks like so much fun. And I love the photos.

  57. I sooooo want to go on that boat trip! If only NYC wasn’t 3879.31 miles away (I looked it up, haha).

  58. Joanna,

    I *love* your blog, but the obviously paid adverts are getting to be a bit much — I feel like every pre-weekend post is simply links to your sponsors!

    Plus, readers know you just got an iphone not too long ago (remember the blog post you did about apps?), so it’s just disappointing to see posts like this, definitely reduces the authoritative tone your blog once held for me.

    As a dedicated reader, I feel like I have a duty to share this with you, although I do understand (financially) where you’re coming from).

    But, to thine own self be true, I suppose…

  59. y’all are too cute. i love white wine and the water too- what a perfect combo. the polaroid app is amaze-balls.

  60. that phone looks so great, and you two are extremely good-looking! rachel

  61. Leigh Tsang says...

    Looks like you two had a great date night. I’m moving out of NYC, this might be good thing to do before I leave with my husband. On a side note, I really like your lipstick, it pops with the photos.

  62. J+H, i agree–when i lived in the east village, i totally forgot that manhattan was an island. now that we’reo n the west side, we walk over to the water a lot. it’s so revitalizing. the piers around christopher/charles/w.10th are soooo lovely. you can take a picnic in the evening!

  63. ashley, you guys HAVE to go before you move!!!!! we budget 3-3.5 hours — you have to get over to chelsea, the sail takes two hours, and you can meander home. it’s amazing/wonderful/thrilling :)

  64. My boyfriend and I are always looking for new things to do in the city, I def. want to do this!

  65. I’ve done a similar cruise in Newport RI. It was so nice to be out on the water with a couple drinks on hand.

  66. You are so beautiful in all of these pictures.

  67. Those pics are lovely and that really is a very nice idea to go on a date! This kind of posts make me love your blog!

  68. I know this is going to make me sound like the ultimate “one-upper,” which I hate, but because it’s relevant (and I’m so excited about it), I’m actually building a boat!! It’s just a small dinghy but it’s mine, made by me, and totally awesome.

    On a completely different note, I hope you and Alex never take for granted the amazing love you have for each other. I know we (readers) only see what you (bloggers) want us to see, but it appears as though you two are incredibly lucky. I’ve very happy for you.

  69. I did a Hudson River sail about 12 or so years ago, and it was wonderful–such a different take on the city.

    I like the Circle Line tours for the same reason, even if they’re touristy. Seeing the city from the water is a really different perspective and experience. When I get back to New York, I’ll have to do something like this again.

  70. Those lobster rolls look amazing!!


  71. I surprised Ed with this for his birthday last year. I picked up cheese and crackers from Zabars….. of course, it was a hit!

  72. I love my Windows Phone. Exciting to see that you’re enjoying it too. :)

    And now I want to go sailing. :)

  73. I love ‘date night’ we try and do various things each week such as dinner and a movie (old school), watching a jazz band, wandering around London eating pancakes. I really love the idea of meeting up at the venue rather than going together, so much more exciting and a little bit of a reminder of the real ‘dating’ days.

    I think it’s great that you make time to spend just the two of you, I’ve just posted a question about how parents do it. I’d love to hear your thoughts.

    C x

  74. Awww you and your hubby are just so adorable!! I lov the video! My hubby and i havent gone on a date alone since our baby was born and its been 14months! :(. We totally need one soon!!

  75. You guys are TOO CUTE! Love the video! Toby is a lucky kid :)

    xxo, vanessa

  76. ahhh i love it! i’ve been thinking about fun summer date ideas in NYC… 2 lovebirds can only feel “so” romantic in the tiny “intimate” restaurants of manhattan. we always end up talking to our dinner neighbors, considering they are only inches away, haha. NYC is surrounded by water, and sometimes i think we all forget that lovely fact being ALSO surrounded by the concrete jungle :D

  77. Thanks for the recommendation! I just bought my dad and his wife a night-time cruise on a schooner for his birthday.

  78. My fiance and I like to walk around the French Quarter and look at the art, finishing with beignets at cafe du monde (New Orleans) for Sunday afternoon dates. This schooner trip looks like so much fun, we’ll have to look into something similar on the Mississippi!

  79. this looks like such a perfect date night idea. glad you guys had fun!

  80. Oh! My boyfriend and I are spending a weekend in the City in July. When I ran the idea by him he just loved it as much as I did! Thanks so much! xoxo

  81. Aw, this looked like a lot of fun! I’ve always wanted to go sailing on the Charles River in Boston. I feel like it’s a fun date idea in the spring/summer. So glad you had fun :)

    Minestrone Soup For the Teenage Soul

  82. Those pictures of the skyline and clouds are INCREDIBLE! What a fun date! You have totally inspired me to take my husband on a sailing date!

  83. susan, that is awesome! you’re going to love it:)

  84. My uncle teaches sailing on the Hudson! It’s so fun to go out with him when we visit from Canada. Last time we went it was October and we got super cold and wet – but it was still so much fun.

  85. I am hoping so much that I will be going on this very cruise with someone new this summer. We’ll see. But I wanted to say thank you because upon your advice I sent a friend & her visiting mother (from west coast) & they loved it, Joanna. A big hit. So one needn’t take their true love. However…as I said: hope.


  86. the goodnight video is so cute. what a great date night-i would love it…if it wasn’t too choppy that day!

  87. You two are so cute! I love the sailing pictures. That just looks so romantic and sweet! How fun of a trip !

  88. Oh I used to live on an old wooden sailboat down at Pier 25 in the late 90’s… commuting by dinghy and sunset sails with friends was magical! There was a whole community of eccentric characters!