I have retired...let's travel! Help!

[+ cougar]

I have finally retired, and I have a feeling that one day—when I’m too old to travel—I’ll look back and wish I had done more of it while I could. I haven’t traveled much over the years; work always kept me tied down, and I’ve never been outside the lower 48 states. But now, with no boss breathing down my neck, I finally have the freedom to explore. The only problem is... I’m not sure where to begin.

I’ve been doing some research online, and it seems like most of the popular vacation packages are geared toward couples and families—especially those all-inclusive resorts on beautiful beaches or in secluded spots meant for relaxing and reconnecting. While that’s great for some, it’s not exactly what I’m looking for as a single traveler. That said, I have come across a few all-inclusive options that seem to offer activities and experiences that actually do interest me. Still, the typical beach resort isn’t all that exciting for someone like me—I have lived just seven miles from a famous Florida beach for over 45 years. If I want tropical weather, I just step outside!

I plan to travel to Hawaii within the next 12 months, and I’m really looking forward to it. I’ve never been on a cruise before, though several options sound exciting—like exploring the fjords of Norway. That kind of trip really appeals to me. That said, cruises are usually designed for double occupancy, and while I know some newer ships are starting to accommodate solo travelers, it still doesn’t make cruising the most budget-friendly option. I didn’t retire with a blank check—I come from a middle-class background, so I always have to keep an eye on costs when planning my travels.

I’m not interested in bringing an escort along—I’m planning to travel solo as a single man. Thankfully, my health is good, and I have no issues with mobility. I also enjoy photography, so I’m hoping to find places that offer great scenery and photo opportunities. I like architecture and urban scenes in photography.

That said, I’d love to know—what’s a place you’ve been that really surprised you with how great it was, and you’d go back in a heartbeat? And do you have a favorite “go-to” destination you always recommend?

[56harrisond]

27 minutes ago, cougar said:

That said, I’d love to know—what’s a place you’ve been that really surprised you with how great it was, and you’d go back in a heartbeat? And do you have a favorite “go-to” destination you always recommend?

Since you mentioned it, here's a discussion about overrated/underrated tourist attractions:

 

[craigville beach]

55 minutes ago, cougar said:

I have finally retired, and I have a feeling that one day—when I’m too old to travel—I’ll look back and wish I had done more of it while I could. I haven’t traveled much over the years; work always kept me tied down, and I’ve never been outside the lower 48 states. But now, with no boss breathing down my neck, I finally have the freedom to explore. The only problem is... I’m not sure where to begin.

I’ve been doing some research online, and it seems like most of the popular vacation packages are geared toward couples and families—especially those all-inclusive resorts on beautiful beaches or in secluded spots meant for relaxing and reconnecting. While that’s great for some, it’s not exactly what I’m looking for as a single traveler. That said, I have come across a few all-inclusive options that seem to offer activities and experiences that actually do interest me. Still, the typical beach resort isn’t all that exciting for someone like me—I have lived just seven miles from a famous Florida beach for over 45 years. If I want tropical weather, I just step outside!

I plan to travel to Hawaii within the next 12 months, and I’m really looking forward to it. I’ve never been on a cruise before, though several options sound exciting—like exploring the fjords of Norway. That kind of trip really appeals to me. That said, cruises are usually designed for double occupancy, and while I know some newer ships are starting to accommodate solo travelers, it still doesn’t make cruising the most budget-friendly option. I didn’t retire with a blank check—I come from a middle-class background, so I always have to keep an eye on costs when planning my travels.

I’m not interested in bringing an escort along—I’m planning to travel solo as a single man. Thankfully, my health is good, and I have no issues with mobility. I also enjoy photography, so I’m hoping to find places that offer great scenery and photo opportunities. I like architecture and urban scenes in photography.

That said, I’d love to know—what’s a place you’ve been that really surprised you with how great it was, and you’d go back in a heartbeat? And do you have a favorite “go-to” destination you always recommend?

  RoadScholar.org  has some great travel packages, some cater to solo travelers 

[+ José Soplanucas]

1 hour ago, cougar said:

I have finally retired, and I have a feeling that one day—when I’m too old to travel—I’ll look back and wish I had done more of it while I could. I haven’t traveled much over the years; work always kept me tied down, and I’ve never been outside the lower 48 states. But now, with no boss breathing down my neck, I finally have the freedom to explore. The only problem is... I’m not sure where to begin.

I’ve been doing some research online, and it seems like most of the popular vacation packages are geared toward couples and families—especially those all-inclusive resorts on beautiful beaches or in secluded spots meant for relaxing and reconnecting. While that’s great for some, it’s not exactly what I’m looking for as a single traveler. That said, I have come across a few all-inclusive options that seem to offer activities and experiences that actually do interest me. Still, the typical beach resort isn’t all that exciting for someone like me—I have lived just seven miles from a famous Florida beach for over 45 years. If I want tropical weather, I just step outside!

I plan to travel to Hawaii within the next 12 months, and I’m really looking forward to it. I’ve never been on a cruise before, though several options sound exciting—like exploring the fjords of Norway. That kind of trip really appeals to me. That said, cruises are usually designed for double occupancy, and while I know some newer ships are starting to accommodate solo travelers, it still doesn’t make cruising the most budget-friendly option. I didn’t retire with a blank check—I come from a middle-class background, so I always have to keep an eye on costs when planning my travels.

I’m not interested in bringing an escort along—I’m planning to travel solo as a single man. Thankfully, my health is good, and I have no issues with mobility. I also enjoy photography, so I’m hoping to find places that offer great scenery and photo opportunities. I like architecture and urban scenes in photography.

That said, I’d love to know—what’s a place you’ve been that really surprised you with how great it was, and you’d go back in a heartbeat? And do you have a favorite “go-to” destination you always recommend?

My last day as an active worker is this July 3rd, and I am also thinking of traveling. But my plans are different than yours. I am selling my condo in the US and starting slow traveling for the next few years, or for as long as it is fun.

Have you consider the alternative of staying in foreign destinations for long periods instead of just a vacation?

Edited June 23 by José Soplanucas

[mike carey]

Some initial ideas while I marshall my thoughts (and reconsider my options while I'm at it).

• Where do you want to go. Europe, Asia, South America, other places in North America etc.
• How do you want to do it?
  • Solo travel by car, rail pass, work it out as you go.
  • Organised tour
  • Cruise

I've travelled on and off all my life (with significant breaks). I did a big Europe trip out of Uni, rail pass, random travel, youth hostels; a cruise to Antarctica; organised tours in South America (several days, and a two day trip from Buenos Aires to Iguazu Falls); and done city visits for a few days to a week. I'd repeat all of them, but tend towards self paced travel, but not everyone is comfortable with that.

If you want to work out the 'how to travel' rather than the 'where', you could go somewhere close at hand, even in the US and try something you hadn't done before. Two weeks in Europe might be an easy start, just in the UK if you want to try in a familiar language. Rail passes are still a thing (and good value if you want to jump on and off trains and see a lot of places), and Eurail and Britrail passes offer continuous and X days in Y period passes. Youth hostels in the UK used to be fine for people of all ages, and probably still are, although not as cheap as they were in the past. Many are in the countryside (and if you hire a car that can be good).

[Njguy2]

Congratulations on retirement!   Do you have a "bucket list" of places you want to see?   My 'bucket list' has been very helpful for me in planning and it has changed over the years.  Last year was able to visit southern Coastal Spain, Morocco and Mount Saint Michel in France.  Originally was just going to visit my best friend in Torremolinos Spain but given the cost of trans-atlantic flights, figured out I could fly through Morocco and connect to Spain on a short flight and fly back from Spain.  Morocco was for a 3 week stint and Mount Saint Michel was a two day over-night stay.  I enjoy photography and having 3 weeks in Morocco was helpful in me seeing most of the country.  Did my research and found a tour company via a professional photographer recommendation, that with a combination of 'on-my-own' travel and their driver/guide; was better than what could be done with a "package' tour with 10-20 strangers.  While in Spain another best friend and I traveled via train/taxi to some cities, (know which friends you can travel with).  Similarly when I saw what was available for quick trips from Paris to Mount Saint Michel, the tour companies would visit places/sites I had no desire to visit and didn't stay a sufficient amount of time in MSM.  Found one which stated they could do bespoke tours - reached out and we came to an agreement on a driver/guide, hotel accommodations and a schedule.    

Separately - sometimes on trips to see friends/family wherever they may be I tack on some time and then rent a car and explore.  Are you a traveler that has to have everything planned out to the minute or do you allow flexibility into the plan?   Do you like to travel solo or need someone to 'come along for the ride'?  Can you tolerate traveling with total strangers?  Do you like your friends enough that you could travel with them to a location?  What level of comfort do you require (Ritz Carlton, AirBnB, Roadside motel/hotel, camping tent)?  I've found several AirBnB's that have made trips so much more enjoyable given some locations may be more remote and Chain hotels may still be a long drive from where I want to visit.  Do you prefer having an active or more sedate (or combo) of a trip?

Since you mentioned photography - google local and national photography stores (B&H, Hunt's, Glazers, Dan's etc).  They typically have classes or will sponsor trips or workshops in the US and abroad.  I've been able to do shorter trips utilizing their knowledge of the locations or the subject matter and it's typically a pure photographic focus.  Saves me the time of planning all the logistics, scouting a location, and missing something and typically no surcharges for being a single traveler .  Google Photography Travel Tour (location or subject matter), there are definitely lots of those too.  If you have AAA or CAA their travel desks can be helpful and there are definitely Travel companies that accommodate for single travelers.  

Have fun traveling!  

Edited June 23 by Njguy2
Additional information

[+ cougar]

7 hours ago, 56harrisond said:

Since you mentioned it, here's a discussion about overrated/underrated tourist attractions:

 

Thank you, I missed that and will check it out now.

[+ cougar]

3 hours ago, Njguy2 said:

Congratulations on retirement!   Do you have a "bucket list" of places you want to see?   My 'bucket list' has been very helpful for me in planning and it has changed over the years.  Last year was able to visit southern Coastal Spain, Morocco and Mount Saint Michel in France.  Originally was just going to visit my best friend in Torremolinos Spain but given the cost of trans-atlantic flights, figured out I could fly through Morocco and connect to Spain on a short flight and fly back from Spain.  Morocco was for a 3 week stint and Mount Saint Michel was a two day over-night stay.  I enjoy photography and having 3 weeks in Morocco was helpful in me seeing most of the country.  Did my research and found a tour company via a professional photographer recommendation, that with a combination of 'on-my-own' travel and their driver/guide; was better than what could be done with a "package' tour with 10-20 strangers.  While in Spain another best friend and I traveled via train/taxi to some cities, (know which friends you can travel with).  Similarly when I saw what was available for quick trips from Paris to Mount Saint Michel, the tour companies would visit places/sites I had no desire to visit and didn't stay a sufficient amount of time in MSM.  Found one which stated they could do bespoke tours - reached out and we came to an agreement on a driver/guide, hotel accommodations and a schedule.    

Separately - sometimes on trips to see friends/family wherever they may be I tack on some time and then rent a car and explore.  Are you a traveler that has to have everything planned out to the minute or do you allow flexibility into the plan?   Do you like to travel solo or need someone to 'come along for the ride'?  Can you tolerate traveling with total strangers?  Do you like your friends enough that you could travel with them to a location?  What level of comfort do you require (Ritz Carlton, AirBnB, Roadside motel/hotel, camping tent)?  I've found several AirBnB's that have made trips so much more enjoyable given some locations may be more remote and Chain hotels may still be a long drive from where I want to visit.  Do you prefer having an active or more sedate (or combo) of a trip?

Since you mentioned photography - google local and national photography stores (B&H, Hunt's, Glazers, Dan's etc).  They typically have classes or will sponsor trips or workshops in the US and abroad.  I've been able to do shorter trips utilizing their knowledge of the locations or the subject matter and it's typically a pure photographic focus.  Saves me the time of planning all the logistics, scouting a location, and missing something and typically no surcharges for being a single traveler .  Google Photography Travel Tour (location or subject matter), there are definitely lots of those too.  If you have AAA or CAA their travel desks can be helpful and there are definitely Travel companies that accommodate for single travelers.  

Have fun traveling!  

Thank you! I have considered renting an Air BNB for a few weeks, probably on the US west coast so I can just explore at my own pace. That would be my base and I will probably spend a few nights in hotels as I just explore the west coast. I have been to San Francisco twice and well it was too cold for this Florida man as I really do not have any good warm clothes. I have not thought about checking out B&H or Glazers as I have purchased from them before. I haven't given much thought of traveling to Europe, I am more interested in South America for some strange reason, must be the guys there! At any rate, thanks again for helping my mind to explore.

[CuriousByNature]

Some things to think about - make sure you have travel insurance.  Getting sick in another country can get very expensive depending on the country.  If you haven't been out of the lower 48, you might want to do a foray across the northern border as a first international trip.  It's a huge country and it has a lot of diversity.  Plus we tend to be friendly and the services here are decent.  There wouldn't be as much culture shock either, though Montreal and Quebec City offer the French experience.  You could do an Alaskan cruise out of Vancouver, or a Maritimes/New England cruise that leaves from Quebec City.  

For cruising as a solo traveler, don't be wary of booking an interior stateroom unless you're claustrophobic.  You'll find you'll spend less time in your room than you might expect.  And watch for deals where the single-supplement is lower than double the double occupancy per person rate.  I've gone on cruises where I've only had to spend 10% more to have a stateroom to myself.  I've never done a single-occupancy cabin because they only have a single-sized bed in most cases, and I like to have more space.  

Financially it can make sense to get a package that includes tips, internet and drinks, because those add up over the course of a cruise.  And if for budget reasons you need to decide between an interior stateroom with the package versus an exterior stateroom without the package, I would opt for the interior with the package.  And I have never seen the point in spending for an exterior stateroom unless it has a balcony.  Having a port hole doesn't justify the additional cost to me.  And some of those rooms are so close to the waterline you can hear the waves hitting the hull all night.  That has happened to me a couple of times when I've been 'upgraded' from an interior to exterior stateroom - the interior would have been better.

Most cruises offer specialized restaurants on board for an additional charge.  I've never tried them because the food in the main dining room is usually better than what I could make myself at home, and the variety of choice is generally good depending on the cruise line.  I would advise against doing any non-cruise company shore excursions that venture far from the port because if you are not back on board by the departure time, the ship will not wait.  But they are obligated to wait if you are on a ship excursion that gets delayed for some reason.  Depending on your destination, the port might be quite far from the sights. 

Congratulations on your retirement!  

[+ Lucky]

I had travel insurance when I got sick in Bangkok, running up about $900 in bills. Travel insurance said I had to submit those claims to my health insurance. I never got a dime.

[+ Charlie]

When I was young[er], I often liked to travel by myself, so I would be free to be as sexually active and slutty as I wished. However, now that I am (much) older, I prefer to travel with a friend, because one is guaranteed companionship and support when you want it or need it. That is particularly important if you are visiting someplace exotic, especially if you don't speak the local language. Before you go, it is a good idea to do a little research about how the local medical systems work, especially if you already have any medical issues; nothing destroys the pleasure of travel like finding oneself sick or injured in a foreign hospital, where you don't know how the systems work, what will be covered by whatever travel insurance you have, or how you will get home again. However, if you are a really nervous traveler, it is probably best to look for some kind of organized group travel.

I have traveled all over the world, from Russia to New Zealand, but the only continent I have never been to is South America, so I can't give any advice about that. But if you want to ask questions about Europe, I have been to many countries there (I lived in England and Czechia, and was a student in Austria), though some of my info is bound to be outdated, because I haven't been anywhere outside the US and Canada in recent years.

[+ Vegas_Millennial]

20 hours ago, CuriousByNature said:

If you haven't been out of the lower 48, you might want to do a foray across the northern border as a first international trip.  ...There wouldn't be as much culture shock either...

When trying to describe Canada to my US friends, I often say it's like the US from 10 years ago except with more French (and I've been saying this since my first trip to Vancouver almost 15 years ago).  When they come back from their first trip to Canada, they tell me they see what I mean.  Then, I saw this on "How I Met Your Mother" and it makes sense:

 

As for Puerto Vallarta Mexico, it's like visiting southern California from 20 years ago except with more English.

Edited June 25 by Vegas_Millennial

[CuriousByNature]

1 hour ago, Vegas_Millennial said:

When trying to describe Canada to my US friends, I often say it's like the US from 10 years ago except with more French (and I've been saying this since my first trip to Vancouver almost 15 years ago).  When they come back from their first trip to Canada, they tell me they see what I mean.  Then, I saw this on "How I Met Your Mother" and it makes sense:

 

Which is why I'm still the same age I was in 2012.... lol.  As soon as I set foot south of the border I age exponentially.

[+ Vegas_Millennial]

On 6/23/2025 at 8:51 AM, cougar said:

That said, I’d love to know—what’s a place you’ve been that really surprised you with how great it was, and you’d go back in a heartbeat?

Vienna