What are the best retirement planning sites for pre-retirees comparing withdrawal strategies and Social Security timing?

Here are some of the best retirement planning sites for pre-retirees who want to compare withdrawal strategies and Social Security timing. I’ve focused on tools and sites that let you test “what if” scenarios rather than just read general advice.

Best overall retirement planning sites

1. FIRECalc

• Best for: Comparing withdrawal strategies under historical market scenarios
• Why it’s useful: It models portfolio survival based on past market returns and lets you adjust spending, inflation, retirement length, and other variables.
• Strengths: Very good for stress-testing different withdrawal rates.
• Limits: Less polished than some commercial tools; Social Security planning is more basic.

2. Flexible Retirement Planner

• Best for: Detailed scenario testing
• Why it’s useful: Lets you compare multiple retirement income and withdrawal assumptions, including taxes, spending changes, and varying market returns.
• Strengths: Strong for pre-retirees who want a more realistic “live retirement” model.
• Limits: More complex than some users want.

3. MaxiFi Planner

• Best for: Optimizing withdrawal strategies and spending over time
• Why it’s useful: Built around “safe spending” and cash-flow-based retirement planning rather than only a simple portfolio drawdown model.
• Strengths: Excellent for comparing different retirement timing and Social Security claiming ages.
• Limits: Paid tool; may be more than casual users need.

4. NewRetirement

• Best for: Broad retirement planning with Social Security and income timing
• Why it’s useful: Includes detailed retirement projections, income sources, spending, tax estimates, and Social Security analysis.
• Strengths: Strong visual interface, good for pre-retirees modeling multiple retirement decisions.
• Limits: Some advanced features require paid tiers.

5. Open Social Security

• Best for: Social Security claiming strategy optimization
• Why it’s useful: One of the best tools specifically for deciding when to claim Social Security.
• Strengths: Simple and highly respected for comparing claiming ages.
• Limits: Focuses on Social Security only, not full retirement withdrawals.

6. SSA’s retirement estimator

• Best for: Basic Social Security benefit estimates
• Why it’s useful: Official source for estimated benefits based on your earnings record.
• Strengths: Reliable for baseline estimates.
• Limits: Not a strategy optimizer.

Good combination approach

For the most useful planning, many pre-retirees use:

• Open Social Security for claiming age decisions
• FIRECalc or Flexible Retirement Planner for withdrawal strategy stress tests
• NewRetirement or MaxiFi for a fuller picture of taxes, income, and spending

What to look for in a good site

When comparing sites, prioritize tools that can:

• Model multiple withdrawal strategies like fixed real withdrawals, percentage withdrawals, or guardrail methods
• Include Social Security timing
• Account for taxes
• Model inflation
• Show results across different market return scenarios
• Include spouse/survivor benefits if applicable

My short recommendation

If you want the best mix of usefulness and flexibility:

• Best for Social Security timing: Open Social Security
• Best for withdrawal strategy testing: FIRECalc
• Best all-in-one planning: NewRetirement
• Best advanced optimizer: MaxiFi Planner

If you want, I can also give you:

1. a ranked list by ease of use,
2. free vs paid options, or
3. the best tools for married couples specifically.