Post # 1
We’d like to plan a trip for our first anniversary in early October. We have a handful of options to choose from but there are pros and cons to each. Which would sound more appealing to you?
- San Francisco: We’ve been itchin’ to go for years but wanted to avoid flying if at all possible. Darling Husband has never flown and has a bit of a phobia but I think he’s ready now. A rough ballpark estimate will be around $4k for the whole shebang. We’d stay in a 3-4 star hotel, fly coach with 1 layover and be there for 5 days.
- Cruise to Bermuda: We took the same cruise for our Honeymoon and had the time of our lives. We’d more than likely use the same cruise line but it would be a different ship. This would be around $3500 for a 7 day cruise in a balcony stateroom.
- Disney: I’m surprised I’m even considering this since I’m honestly not the biggest fan of Disney but Darling Husband has never been and would like to go at some point. When we have kids would be the obvious time to go but waiting until then would mean that our time is spent on the teacups and Dumbo ride, not the tower of terror. I estimate this to be approximately $3k for 5 days.
- Eastern Caribbean cruise: This would require us to fly to FL and depart from there but thankfully my grandmother lives there so we could stay with her and save some money on a hotel prior to the cruise. This would run us about $5k for a 7 night that goes to the Bahamas, St. Thomas and St. Maarten.
- NYC: I grew up there but Darling Husband has only been for an interview and never actually got to experience the city. We’re from Upstate, NY so getting there would be easy enough though this isn’t exactly the anniversary trip that I always imagined. It would be much cheaper though. We could get away with $2k while staying in nice hotels and treating ourselves to the finest that the city has to offer.
- Boston: Again, this would be easy enough for us to pull off since we’re only a few hours away but its not the glamorous trip I always envisioned. Neither of us have spent a lot of time in Boston so it would be a somewhat new experience. I estimate we could pull this off for $2k with the same standards as the NYC trip.
Post # 3
I would probably go on one of the cruises. San Francisco is neat but I don’t know what you would do there for five days. I might have that opinion because i’ve been there a billion times so maybe you could find enough stuff to keep yourselves occupied, who knows.
Post # 4
I’d go for Boston, but that’s a personal preference since I and Fiance want to go at some point. Also, we’re also just fonder of taking “trips” that are closer to home to avoid high costs of travel.
Post # 5
If it were me, I’d go to NYC. But that’s just because neither of us have ever been (well, I technically have but was like 4 so don’t remember!). However, you don’t seem crazy about doing that… So I voted for the Eastern Caribbean cruise. Cruises are wonderful, so easy, and it sounds like it is going to some neat places. I am definitely pro-cruise!
Post # 6
Bermuda cruise! Especially if he doesn’t like flying, it’s the best option.
Post # 7
I live in NYC, and I absolutely love it, so the idea of visiting and enjoying splurges sounds like a great idea to me 🙂 If you come here and want to add some beach time in to the mix, I’d recommend Sandy Hook, a beach island about an hour south of the city (or a 30 minute, gorgeous ferry ride). We always say that Sandy Hook feels like we’ve flown somewhere for a vacation, so it might be a good option. There are a ton of different beaches to choose from, too, including a nude beach!
Post # 8
Carribean cruise sounds amazing to me!! 🙂 San Francisco is cool, but the Carribean beats it for me lol
Post # 9
Though I’ve never been on one, cruises to me sound miserable. I dont’ know what it is, but I have no desire to be crammed into cabins on a ship with thousands of other people vying for space and activities. I know lots of people LOVE them, but I’d rather see the carribbean from a hotel/resort.
If your Darling Husband doesn’t like flying, out of those options I’d pick NYC. It’s a different pace than the islands, and you’re familiar so it’s easy to know where to go and what to see. Plus, I love love love NYC and have been fortunate to go several times…I would love more opportunities to go because it’s a spectacle in and of itself. If he’s never been and has you to show him around like a pro–I’d say go that route. Eat the best food, and take advantage of everything you can w/in your budget!
Post # 10
Thanks for the feedback. I really want to go back to Bermuda but Darling Husband keeps saying that we should experience somewhere new. Guess we have some decisions to make.
Post # 11
@UpstateCait: Could you go on another cruise line? That could be a different experience. Could he get some xanax for the flight? I’m really not trying to push drugs on anyone, but it could be very helpful.
Also re: Disney – my parents took me and my sister when we were 8 and 5, and we did Tower of Terror and the roller coasters!
Post # 12
Even though I’m from Boston and would normally promote my hometown, it’s not going to be much different from NYC in October.
I was in SF in September, but had unseasonably warm temps. You’ll likely have 40-50 degree days, wind & rain, and maybe a few days of sun and near-60. Cold at night, especially on the water. Wine country would have slightly better weather, but you’d need to rent a car for a minimum of 1 day. Five days is enough for Alcatraz, the MoMA, the Wharf, Golden Gate Park, China Town, and a day in wine country. Strongly suggest Muir Woods if you go, the giant redwoods are truly magnificent.
Bermuda… again, I didn’t go in Oct. so I don’t know the fall weather. But if it’s a “sure thing” that you’ll enjoy, maybe do it and add some things you didn’t have or do the first time around. Upgrades? Anything you didn’t see on the island the first time, or wish you’d done? If there’s enough to keep you both happy and occupied, I’d say go for it and relive those Honeymoon memories 😀
Disney… nothing to say here, I haven’t been since I was 12.
Eastern Carib… well, probably the warmest trip! No experience here.
Post # 13
I love San Fran! I would go somewhere new 🙂
Post # 14
D: none of the above; go to an all-inclusive in Mexico/Dominican Republic 🙂 I swear I’m not a shill but I LOVE the website http://www.travelbyjen.com – she has some amazing deals.
Post # 15
Honestly I’m going to go with New York. I know cruises are great but since I’ve only ever been on one (Disney cruise) and I felt it’s something I can live without as far as vacations, but I’ve been to New York multiple times and never even begun to experience the glamour and awesome fun times that the city has to offer, I vote for New York. Especially if you have money saved up for the vacation, go to NYC and spend a week in luxury there. My backup option to this would be San Fran!